Mechanistic studies of the reactions of transition metal ion complexes with biologically relevant molecules

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Mechanistic studies of the reactions of transition metal ion complexes with biologically relevant molecules (en)
Испитивање механизма реакција комплекса јона прелазних метала са биолошки значајним молекулима (sr)
Ispitivanje mehanizma reakcija kompleksa jona prelaznih metala sa biološki značajnim molekulima (sr_RS)
Authors

Publications

Synthesis, Characterization, Antioxidant Activity of β-diketonates, and Effects of Coordination to Copper(II) Ion on their Activity: DNA, BSA Interactions and Molecular Docking Study

Joksimović, Nenad; Petronijević, Jelena; Janković, Nenad; Kosanić, Marijana; Milivojević, Dušan; Vraneš, Milan; Tot, Aleksandar; Bugarčić, Zorica

(2021)

TY  - JOUR
AU  - Joksimović, Nenad
AU  - Petronijević, Jelena
AU  - Janković, Nenad
AU  - Kosanić, Marijana
AU  - Milivojević, Dušan
AU  - Vraneš, Milan
AU  - Tot, Aleksandar
AU  - Bugarčić, Zorica
PY  - 2021
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9156
AB  - Background: In order to make some progress in discovering the more effective way to eliminate ROS which cause the oxidative stress in organism in humans and bearing in mind the fact that ethyl-2-hydroxy-4-aryl(alkyl)-4-oxo-2-butenoates (β-diketonates) belong to a class of biologically active compounds, series of β-diketonates were synthesized, characterized, and tested to evaluate there antioxidant activity. Further, to investigate how coordination to copper(II) ion affects the activity of β-diketonates, appropriate complexes were synthesized and characterized. Methods: All complexes were characterized by UV-Vis, IR, and EPR spectroscopy, MS spectrometry, and elemental analysis. Fluorescence spectroscopic method was used for investigations of the interactions between biomacromolecules (DNA or BSA) and compound 2E. Viscosity measurements and molecular docking study were performed to confirm the mode of interactions between DNA and BSA and compound 2E. Results: Scavenging activity on DPPH radical revealed that compounds 2A, 2B, and 2E possess largest free radical scavenging, comparable to standard while results of superoxide anion scavenging activities of tested samples showed that maximum scavenging activity (IC50=168.92 µg/mL) was found for 2E, very similar to standard ascorbic acid, followed by 2B and 2G. Results of the interactions between biomacromolecules and 2E indicated that 2E has the affinity to displace EB from the EB-DNA complex through intercalation [Ksv = (3.7 ± 0.1) × 103 M-1], while Ka value obtained via titration of BSA with 2E [Ka = (4.2 ± 0.2) × 105 M-1], support the fact that the significant amount of the drug could be transported and distributed through the cells. Conclusions: All β-diketonates exhibited better scavenging activities than their corresponding copper complexes. Among all the tested compounds, 2E gave the highest reducing power, even higher than standard ascorbic acid, while reducing power for compounds 2A and 2B was also good but lower than standard. DNA and BSA binding study for 2E showed that this compound has the potential to be used as medicament. © 2021 Bentham Science Publishers.
T2  - Medicinal Chemistry
T1  - Synthesis, Characterization, Antioxidant Activity of β-diketonates, and Effects of Coordination to Copper(II) Ion on their Activity: DNA, BSA Interactions and Molecular Docking Study
VL  - 17
IS  - 5
SP  - 519
EP  - 532
DO  - 10.2174/1573406415666191024102520
ER  - 
@article{
author = "Joksimović, Nenad and Petronijević, Jelena and Janković, Nenad and Kosanić, Marijana and Milivojević, Dušan and Vraneš, Milan and Tot, Aleksandar and Bugarčić, Zorica",
year = "2021",
abstract = "Background: In order to make some progress in discovering the more effective way to eliminate ROS which cause the oxidative stress in organism in humans and bearing in mind the fact that ethyl-2-hydroxy-4-aryl(alkyl)-4-oxo-2-butenoates (β-diketonates) belong to a class of biologically active compounds, series of β-diketonates were synthesized, characterized, and tested to evaluate there antioxidant activity. Further, to investigate how coordination to copper(II) ion affects the activity of β-diketonates, appropriate complexes were synthesized and characterized. Methods: All complexes were characterized by UV-Vis, IR, and EPR spectroscopy, MS spectrometry, and elemental analysis. Fluorescence spectroscopic method was used for investigations of the interactions between biomacromolecules (DNA or BSA) and compound 2E. Viscosity measurements and molecular docking study were performed to confirm the mode of interactions between DNA and BSA and compound 2E. Results: Scavenging activity on DPPH radical revealed that compounds 2A, 2B, and 2E possess largest free radical scavenging, comparable to standard while results of superoxide anion scavenging activities of tested samples showed that maximum scavenging activity (IC50=168.92 µg/mL) was found for 2E, very similar to standard ascorbic acid, followed by 2B and 2G. Results of the interactions between biomacromolecules and 2E indicated that 2E has the affinity to displace EB from the EB-DNA complex through intercalation [Ksv = (3.7 ± 0.1) × 103 M-1], while Ka value obtained via titration of BSA with 2E [Ka = (4.2 ± 0.2) × 105 M-1], support the fact that the significant amount of the drug could be transported and distributed through the cells. Conclusions: All β-diketonates exhibited better scavenging activities than their corresponding copper complexes. Among all the tested compounds, 2E gave the highest reducing power, even higher than standard ascorbic acid, while reducing power for compounds 2A and 2B was also good but lower than standard. DNA and BSA binding study for 2E showed that this compound has the potential to be used as medicament. © 2021 Bentham Science Publishers.",
journal = "Medicinal Chemistry",
title = "Synthesis, Characterization, Antioxidant Activity of β-diketonates, and Effects of Coordination to Copper(II) Ion on their Activity: DNA, BSA Interactions and Molecular Docking Study",
volume = "17",
number = "5",
pages = "519-532",
doi = "10.2174/1573406415666191024102520"
}
Joksimović, N., Petronijević, J., Janković, N., Kosanić, M., Milivojević, D., Vraneš, M., Tot, A.,& Bugarčić, Z.. (2021). Synthesis, Characterization, Antioxidant Activity of β-diketonates, and Effects of Coordination to Copper(II) Ion on their Activity: DNA, BSA Interactions and Molecular Docking Study. in Medicinal Chemistry, 17(5), 519-532.
https://doi.org/10.2174/1573406415666191024102520
Joksimović N, Petronijević J, Janković N, Kosanić M, Milivojević D, Vraneš M, Tot A, Bugarčić Z. Synthesis, Characterization, Antioxidant Activity of β-diketonates, and Effects of Coordination to Copper(II) Ion on their Activity: DNA, BSA Interactions and Molecular Docking Study. in Medicinal Chemistry. 2021;17(5):519-532.
doi:10.2174/1573406415666191024102520 .
Joksimović, Nenad, Petronijević, Jelena, Janković, Nenad, Kosanić, Marijana, Milivojević, Dušan, Vraneš, Milan, Tot, Aleksandar, Bugarčić, Zorica, "Synthesis, Characterization, Antioxidant Activity of β-diketonates, and Effects of Coordination to Copper(II) Ion on their Activity: DNA, BSA Interactions and Molecular Docking Study" in Medicinal Chemistry, 17, no. 5 (2021):519-532,
https://doi.org/10.2174/1573406415666191024102520 . .
1
1

Performances of ionic liquid matrices with butyl ammonium counterion for matrix-assisted laser desorption/ionization mass spectrometric detection and analysis of sucralfate

Petković, Marijana; Leopold, Jenny; Popović, Iva A.; Dimić, Dušan; Ilić, Jelica; Nenadović, Miloš; Rakočević, Zlatko Lj.; Schiller, Jürgen

(2020)

TY  - JOUR
AU  - Petković, Marijana
AU  - Leopold, Jenny
AU  - Popović, Iva A.
AU  - Dimić, Dušan
AU  - Ilić, Jelica
AU  - Nenadović, Miloš
AU  - Rakočević, Zlatko Lj.
AU  - Schiller, Jürgen
PY  - 2020
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/8623
AB  - In this work, the performances of two ionic liquid matrices (ILMs) with the same ammonium counterpart for mass spectrometric analysis of the insoluble and soluble sucralfate were compared. Matrix-assisted laser desorption/ionization mass spectrometry (MALDI MS) was performed assisted by the butylammonium salts of α-cyano-hydroxycinnamic acid (CHCAB) and 2,5-dihydroxybenzoic acid (DHBB). CHCAB has a higher IE than DHBB, but better optical properties. CHCAB is more suitable for the analysis of sucralfate, although molecular ions of both compounds were detectable only with low intensities. Thus, optical properties of ILMs are crucial to enhance the sensitivity of MALDI MS detection of polysulfated oligosaccharides. © 2019, © 2019 Taylor & Francis Group, LLC.
T2  - Journal of Carbohydrate Chemistry
T1  - Performances of ionic liquid matrices with butyl ammonium counterion for matrix-assisted laser desorption/ionization mass spectrometric detection and analysis of sucralfate
VL  - 39
IS  - 1
SP  - 1
EP  - 23
DO  - 10.1080/07328303.2019.1669633
ER  - 
@article{
author = "Petković, Marijana and Leopold, Jenny and Popović, Iva A. and Dimić, Dušan and Ilić, Jelica and Nenadović, Miloš and Rakočević, Zlatko Lj. and Schiller, Jürgen",
year = "2020",
abstract = "In this work, the performances of two ionic liquid matrices (ILMs) with the same ammonium counterpart for mass spectrometric analysis of the insoluble and soluble sucralfate were compared. Matrix-assisted laser desorption/ionization mass spectrometry (MALDI MS) was performed assisted by the butylammonium salts of α-cyano-hydroxycinnamic acid (CHCAB) and 2,5-dihydroxybenzoic acid (DHBB). CHCAB has a higher IE than DHBB, but better optical properties. CHCAB is more suitable for the analysis of sucralfate, although molecular ions of both compounds were detectable only with low intensities. Thus, optical properties of ILMs are crucial to enhance the sensitivity of MALDI MS detection of polysulfated oligosaccharides. © 2019, © 2019 Taylor & Francis Group, LLC.",
journal = "Journal of Carbohydrate Chemistry",
title = "Performances of ionic liquid matrices with butyl ammonium counterion for matrix-assisted laser desorption/ionization mass spectrometric detection and analysis of sucralfate",
volume = "39",
number = "1",
pages = "1-23",
doi = "10.1080/07328303.2019.1669633"
}
Petković, M., Leopold, J., Popović, I. A., Dimić, D., Ilić, J., Nenadović, M., Rakočević, Z. Lj.,& Schiller, J.. (2020). Performances of ionic liquid matrices with butyl ammonium counterion for matrix-assisted laser desorption/ionization mass spectrometric detection and analysis of sucralfate. in Journal of Carbohydrate Chemistry, 39(1), 1-23.
https://doi.org/10.1080/07328303.2019.1669633
Petković M, Leopold J, Popović IA, Dimić D, Ilić J, Nenadović M, Rakočević ZL, Schiller J. Performances of ionic liquid matrices with butyl ammonium counterion for matrix-assisted laser desorption/ionization mass spectrometric detection and analysis of sucralfate. in Journal of Carbohydrate Chemistry. 2020;39(1):1-23.
doi:10.1080/07328303.2019.1669633 .
Petković, Marijana, Leopold, Jenny, Popović, Iva A., Dimić, Dušan, Ilić, Jelica, Nenadović, Miloš, Rakočević, Zlatko Lj., Schiller, Jürgen, "Performances of ionic liquid matrices with butyl ammonium counterion for matrix-assisted laser desorption/ionization mass spectrometric detection and analysis of sucralfate" in Journal of Carbohydrate Chemistry, 39, no. 1 (2020):1-23,
https://doi.org/10.1080/07328303.2019.1669633 . .
4
4

Biocompatibility of TiO2 prolate nanospheroids as a potential photosenzitizer in therapy of cancer

Matijević, Milica; Nakarada, Đura; Liang, Xinyue; Korićanac, Lela; Rajsiglova, Lenka; Vannucci, Luca; Nešić, Maja D.; Vranješ, Mila; Mojović, Miloš D.; Mi, Lan; Estrela-Lopis, Irina; Böttner, Julia; Šaponjić, Zoran; Petković, Marijana; Stepić, Milutin

(2020)

TY  - JOUR
AU  - Matijević, Milica
AU  - Nakarada, Đura
AU  - Liang, Xinyue
AU  - Korićanac, Lela
AU  - Rajsiglova, Lenka
AU  - Vannucci, Luca
AU  - Nešić, Maja D.
AU  - Vranješ, Mila
AU  - Mojović, Miloš D.
AU  - Mi, Lan
AU  - Estrela-Lopis, Irina
AU  - Böttner, Julia
AU  - Šaponjić, Zoran
AU  - Petković, Marijana
AU  - Stepić, Milutin
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9058
AB  - TiO2 prolatenanospheroids (PNSs) may be photosensitizers (PSs), which act by catalyzation of hydroxyl radical (∙OH) formation upon light illumination. ∙OH might, in turn, contribute to killing of cancer cells. On the other hand, there is great concern about toxicity in the dark of TiO2 nanoparticles in general. In this work, we have investigated the biocompatibility of TiO2 PNSs of the anatase crystal form (length between 100 and 300 nm and width 50 nm) in the dark with immune cells and light-induced cytotoxicity on several cancer cell lines. The effects of the treatment of different cell lines with several concentrations of TiO2 PNSs suspensions showed the specifics of cells’ viability and the intracellular localization. The results of in vitro studies obtained by cytotoxicity assays adjusted to individual cell lines’ metabolism point towards the biocompatibility of TiO2 PNSs at low and moderate concentrations in the dark, which neither kill the cells, nor induce activation of the immune system cells. Laser scanning confocal microscopy revealed that PNSs are taken up by cells, and insight into the intracellular distribution was obtained in this study.
T2  - Journal of Nanoparticle Research
T1  - Biocompatibility of TiO2 prolate nanospheroids as a potential photosenzitizer in therapy of cancer
VL  - 22
IS  - 7
SP  - 175
DO  - 10.1007/s11051-020-04899-3
ER  - 
@article{
author = "Matijević, Milica and Nakarada, Đura and Liang, Xinyue and Korićanac, Lela and Rajsiglova, Lenka and Vannucci, Luca and Nešić, Maja D. and Vranješ, Mila and Mojović, Miloš D. and Mi, Lan and Estrela-Lopis, Irina and Böttner, Julia and Šaponjić, Zoran and Petković, Marijana and Stepić, Milutin",
year = "2020",
abstract = "TiO2 prolatenanospheroids (PNSs) may be photosensitizers (PSs), which act by catalyzation of hydroxyl radical (∙OH) formation upon light illumination. ∙OH might, in turn, contribute to killing of cancer cells. On the other hand, there is great concern about toxicity in the dark of TiO2 nanoparticles in general. In this work, we have investigated the biocompatibility of TiO2 PNSs of the anatase crystal form (length between 100 and 300 nm and width 50 nm) in the dark with immune cells and light-induced cytotoxicity on several cancer cell lines. The effects of the treatment of different cell lines with several concentrations of TiO2 PNSs suspensions showed the specifics of cells’ viability and the intracellular localization. The results of in vitro studies obtained by cytotoxicity assays adjusted to individual cell lines’ metabolism point towards the biocompatibility of TiO2 PNSs at low and moderate concentrations in the dark, which neither kill the cells, nor induce activation of the immune system cells. Laser scanning confocal microscopy revealed that PNSs are taken up by cells, and insight into the intracellular distribution was obtained in this study.",
journal = "Journal of Nanoparticle Research",
title = "Biocompatibility of TiO2 prolate nanospheroids as a potential photosenzitizer in therapy of cancer",
volume = "22",
number = "7",
pages = "175",
doi = "10.1007/s11051-020-04899-3"
}
Matijević, M., Nakarada, Đ., Liang, X., Korićanac, L., Rajsiglova, L., Vannucci, L., Nešić, M. D., Vranješ, M., Mojović, M. D., Mi, L., Estrela-Lopis, I., Böttner, J., Šaponjić, Z., Petković, M.,& Stepić, M.. (2020). Biocompatibility of TiO2 prolate nanospheroids as a potential photosenzitizer in therapy of cancer. in Journal of Nanoparticle Research, 22(7), 175.
https://doi.org/10.1007/s11051-020-04899-3
Matijević M, Nakarada Đ, Liang X, Korićanac L, Rajsiglova L, Vannucci L, Nešić MD, Vranješ M, Mojović MD, Mi L, Estrela-Lopis I, Böttner J, Šaponjić Z, Petković M, Stepić M. Biocompatibility of TiO2 prolate nanospheroids as a potential photosenzitizer in therapy of cancer. in Journal of Nanoparticle Research. 2020;22(7):175.
doi:10.1007/s11051-020-04899-3 .
Matijević, Milica, Nakarada, Đura, Liang, Xinyue, Korićanac, Lela, Rajsiglova, Lenka, Vannucci, Luca, Nešić, Maja D., Vranješ, Mila, Mojović, Miloš D., Mi, Lan, Estrela-Lopis, Irina, Böttner, Julia, Šaponjić, Zoran, Petković, Marijana, Stepić, Milutin, "Biocompatibility of TiO2 prolate nanospheroids as a potential photosenzitizer in therapy of cancer" in Journal of Nanoparticle Research, 22, no. 7 (2020):175,
https://doi.org/10.1007/s11051-020-04899-3 . .
1
1
1

Interactions of binuclear copper(II) complexes with S-substituted thiosalicylate derivatives with some relevant biomolecules

Jovanović, Snežana; Bogojeski, Jovana V.; Nikolić, Miloš V.; Mijajlović, Marina Ž.; Tomović, Dušan Lj.; Bukonjić, Andriana M.; Knežević Rangelov, Sanja M.; Mijailović, Nataša R.; Ratković, Zoran; Jevtić, Verica V.; Petrović, Biljana V.; Trifunović, Srećko R.; Novaković, Slađana B.; Bogdanović, Goran A.; Radić, Gordana P.

(2019)

TY  - JOUR
AU  - Jovanović, Snežana
AU  - Bogojeski, Jovana V.
AU  - Nikolić, Miloš V.
AU  - Mijajlović, Marina Ž.
AU  - Tomović, Dušan Lj.
AU  - Bukonjić, Andriana M.
AU  - Knežević Rangelov, Sanja M.
AU  - Mijailović, Nataša R.
AU  - Ratković, Zoran
AU  - Jevtić, Verica V.
AU  - Petrović, Biljana V.
AU  - Trifunović, Srećko R.
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Radić, Gordana P.
PY  - 2019
UR  - https://www.tandfonline.com/doi/full/10.1080/00958972.2019.1610561
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/8196
AB  - Interactions of copper(II) complexes which contain S-alkyl derivatives of thiosalicylic acid (alkyl = methyl, ethyl, propyl and butyl; aryl = benzyl), marked as 1–5, with guanosine-5′-monophosphate (5′-GMP) and calf thymus DNA (CT-DNA) were studied. Kinetics of substitution reactions of 1–5 with 5′-GMP and CT-DNA were investigated under pseudo-first-order conditions at 310 K and pH = 7.2 in 25 mM Hepes buffer using stopped-flow method. All complexes have high affinity toward studied bio-molecules. Additionally, interactions with CT-DNA were followed by absorption spectroscopy and fluorescence quenching measurements. The results indicate that complexes bind to DNA exhibiting high binding constants (Kb = 104 M−1). During the examination of competitive reactions with ethidium bromide (EB), results showed that complexes can replace EB-bound DNA. In addition, a new crystal structure of the binuclear Cu(II) complex with S-substituted thiosalicylate derivative has been reported. In the present series of Cu(II) complexes the crystal structure is the first example of a complex comprising an S-aryl derivative of thiosalicylate ligand. Through comparative study of structural properties of six molecules from four crystal structures we examined the structural variations, potentially important for biological activity of these complexes. © 2019, © 2019 Informa UK Limited, trading as Taylor & Francis Group.
T2  - Journal of Coordination Chemistry
T1  - Interactions of binuclear copper(II) complexes with S-substituted thiosalicylate derivatives with some relevant biomolecules
VL  - 72
IS  - 10
SP  - 1603
EP  - 1620
DO  - 10.1080/00958972.2019.1610561
ER  - 
@article{
author = "Jovanović, Snežana and Bogojeski, Jovana V. and Nikolić, Miloš V. and Mijajlović, Marina Ž. and Tomović, Dušan Lj. and Bukonjić, Andriana M. and Knežević Rangelov, Sanja M. and Mijailović, Nataša R. and Ratković, Zoran and Jevtić, Verica V. and Petrović, Biljana V. and Trifunović, Srećko R. and Novaković, Slađana B. and Bogdanović, Goran A. and Radić, Gordana P.",
year = "2019",
abstract = "Interactions of copper(II) complexes which contain S-alkyl derivatives of thiosalicylic acid (alkyl = methyl, ethyl, propyl and butyl; aryl = benzyl), marked as 1–5, with guanosine-5′-monophosphate (5′-GMP) and calf thymus DNA (CT-DNA) were studied. Kinetics of substitution reactions of 1–5 with 5′-GMP and CT-DNA were investigated under pseudo-first-order conditions at 310 K and pH = 7.2 in 25 mM Hepes buffer using stopped-flow method. All complexes have high affinity toward studied bio-molecules. Additionally, interactions with CT-DNA were followed by absorption spectroscopy and fluorescence quenching measurements. The results indicate that complexes bind to DNA exhibiting high binding constants (Kb = 104 M−1). During the examination of competitive reactions with ethidium bromide (EB), results showed that complexes can replace EB-bound DNA. In addition, a new crystal structure of the binuclear Cu(II) complex with S-substituted thiosalicylate derivative has been reported. In the present series of Cu(II) complexes the crystal structure is the first example of a complex comprising an S-aryl derivative of thiosalicylate ligand. Through comparative study of structural properties of six molecules from four crystal structures we examined the structural variations, potentially important for biological activity of these complexes. © 2019, © 2019 Informa UK Limited, trading as Taylor & Francis Group.",
journal = "Journal of Coordination Chemistry",
title = "Interactions of binuclear copper(II) complexes with S-substituted thiosalicylate derivatives with some relevant biomolecules",
volume = "72",
number = "10",
pages = "1603-1620",
doi = "10.1080/00958972.2019.1610561"
}
Jovanović, S., Bogojeski, J. V., Nikolić, M. V., Mijajlović, M. Ž., Tomović, D. Lj., Bukonjić, A. M., Knežević Rangelov, S. M., Mijailović, N. R., Ratković, Z., Jevtić, V. V., Petrović, B. V., Trifunović, S. R., Novaković, S. B., Bogdanović, G. A.,& Radić, G. P.. (2019). Interactions of binuclear copper(II) complexes with S-substituted thiosalicylate derivatives with some relevant biomolecules. in Journal of Coordination Chemistry, 72(10), 1603-1620.
https://doi.org/10.1080/00958972.2019.1610561
Jovanović S, Bogojeski JV, Nikolić MV, Mijajlović MŽ, Tomović DL, Bukonjić AM, Knežević Rangelov SM, Mijailović NR, Ratković Z, Jevtić VV, Petrović BV, Trifunović SR, Novaković SB, Bogdanović GA, Radić GP. Interactions of binuclear copper(II) complexes with S-substituted thiosalicylate derivatives with some relevant biomolecules. in Journal of Coordination Chemistry. 2019;72(10):1603-1620.
doi:10.1080/00958972.2019.1610561 .
Jovanović, Snežana, Bogojeski, Jovana V., Nikolić, Miloš V., Mijajlović, Marina Ž., Tomović, Dušan Lj., Bukonjić, Andriana M., Knežević Rangelov, Sanja M., Mijailović, Nataša R., Ratković, Zoran, Jevtić, Verica V., Petrović, Biljana V., Trifunović, Srećko R., Novaković, Slađana B., Bogdanović, Goran A., Radić, Gordana P., "Interactions of binuclear copper(II) complexes with S-substituted thiosalicylate derivatives with some relevant biomolecules" in Journal of Coordination Chemistry, 72, no. 10 (2019):1603-1620,
https://doi.org/10.1080/00958972.2019.1610561 . .

Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study

Joksimović, Nenad; Petronijević, Jelena; Janković, Nenad Ž.; Baskić, Dejan; Popović, Suzana Lj.; Todorović, Danijela V.; Matić, Sanja Lj.; Bogdanović, Goran A.; Vraneš, Milan; Tot, Aleksandar; Bugarčić, Zorica M.

(2019)

TY  - JOUR
AU  - Joksimović, Nenad
AU  - Petronijević, Jelena
AU  - Janković, Nenad Ž.
AU  - Baskić, Dejan
AU  - Popović, Suzana Lj.
AU  - Todorović, Danijela V.
AU  - Matić, Sanja Lj.
AU  - Bogdanović, Goran A.
AU  - Vraneš, Milan
AU  - Tot, Aleksandar
AU  - Bugarčić, Zorica M.
PY  - 2019
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/8186
AB  - In order to make a progress in discovering a new agents for chemotherapy with improved properties and bearing in mind the fact that substituted 3-hydroxy-3-pyrrolin-2-ones belong to a class of biologically active compounds, series of novel 1,5-diaryl-4-(2-thienylcarbonyl)-3-hydroxy-3-pyrrolin-2-ones were synthesized and characterized by spectral (UV–Vis, IR, NMR, ESI-MS), X-ray and elemental analysis. All compounds were examined for their cytotoxic effect on human cancer cell lines HeLa and MDA-MB 231 and normal fibroblasts (MRC-5). Four compounds, 3-hydroxy-1-(p-tolyl)-4-(2-thienylcarbonyl)-5-(4-chlorophenyl)-2,5-dihydro-1H-pyrrol-2-one (D10), 3-hydroxy-1-(3-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D13), 3-hydroxy-1-(4-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D14), and 3-hydroxy-1-(4-chlorophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D15), that showed the highest cytotoxicity against malignant cells and the best selectivity towards normal cells were selected for further experiments. Results obtained by investigating mechanisms of cytotoxic activity suggest that selected 3-hydroxy-3-pyrrolin-2-one derivatives in HeLa cells induce apoptosis that is associated with S phase arrest (D13, D15, and D10) or unrelated to cell cycle distribution (D14). Additionally, to better understand their suitability for potential use as anticancer medicaments we studied the interactions between biomacromolecules (DNA or BSA) and D13 and D15. The results indicated that D13 and D15 have great affinity to displace EB from the EB-DNA complex through intercalation [K sv = (3.7 ± 0.1) and (3.4 ± 0.1) × 10 3 M −1 , respectively], an intercalative mode also confirmed through viscosity measurements. K a values, obtained as result of fluorescence titration of BSA with D13 and D15 [K a = (4.2 ± 0.2) and (2.6 ± 0.2) × 10 5 M, respectively], support the fact that a significant amount of the tested compounds could be transported and distributed through the cells. In addition, by DNA and BSA molecular docking study for D13, D14 and D15 is determined and predicted the binding mode and the interaction region. © 2019 Elsevier Inc.
T2  - Bioorganic Chemistry
T1  - Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study
VL  - 88
SP  - 102954
DO  - 10.1016/j.bioorg.2019.102954
ER  - 
@article{
author = "Joksimović, Nenad and Petronijević, Jelena and Janković, Nenad Ž. and Baskić, Dejan and Popović, Suzana Lj. and Todorović, Danijela V. and Matić, Sanja Lj. and Bogdanović, Goran A. and Vraneš, Milan and Tot, Aleksandar and Bugarčić, Zorica M.",
year = "2019",
abstract = "In order to make a progress in discovering a new agents for chemotherapy with improved properties and bearing in mind the fact that substituted 3-hydroxy-3-pyrrolin-2-ones belong to a class of biologically active compounds, series of novel 1,5-diaryl-4-(2-thienylcarbonyl)-3-hydroxy-3-pyrrolin-2-ones were synthesized and characterized by spectral (UV–Vis, IR, NMR, ESI-MS), X-ray and elemental analysis. All compounds were examined for their cytotoxic effect on human cancer cell lines HeLa and MDA-MB 231 and normal fibroblasts (MRC-5). Four compounds, 3-hydroxy-1-(p-tolyl)-4-(2-thienylcarbonyl)-5-(4-chlorophenyl)-2,5-dihydro-1H-pyrrol-2-one (D10), 3-hydroxy-1-(3-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D13), 3-hydroxy-1-(4-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D14), and 3-hydroxy-1-(4-chlorophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D15), that showed the highest cytotoxicity against malignant cells and the best selectivity towards normal cells were selected for further experiments. Results obtained by investigating mechanisms of cytotoxic activity suggest that selected 3-hydroxy-3-pyrrolin-2-one derivatives in HeLa cells induce apoptosis that is associated with S phase arrest (D13, D15, and D10) or unrelated to cell cycle distribution (D14). Additionally, to better understand their suitability for potential use as anticancer medicaments we studied the interactions between biomacromolecules (DNA or BSA) and D13 and D15. The results indicated that D13 and D15 have great affinity to displace EB from the EB-DNA complex through intercalation [K sv = (3.7 ± 0.1) and (3.4 ± 0.1) × 10 3 M −1 , respectively], an intercalative mode also confirmed through viscosity measurements. K a values, obtained as result of fluorescence titration of BSA with D13 and D15 [K a = (4.2 ± 0.2) and (2.6 ± 0.2) × 10 5 M, respectively], support the fact that a significant amount of the tested compounds could be transported and distributed through the cells. In addition, by DNA and BSA molecular docking study for D13, D14 and D15 is determined and predicted the binding mode and the interaction region. © 2019 Elsevier Inc.",
journal = "Bioorganic Chemistry",
title = "Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study",
volume = "88",
pages = "102954",
doi = "10.1016/j.bioorg.2019.102954"
}
Joksimović, N., Petronijević, J., Janković, N. Ž., Baskić, D., Popović, S. Lj., Todorović, D. V., Matić, S. Lj., Bogdanović, G. A., Vraneš, M., Tot, A.,& Bugarčić, Z. M.. (2019). Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study. in Bioorganic Chemistry, 88, 102954.
https://doi.org/10.1016/j.bioorg.2019.102954
Joksimović N, Petronijević J, Janković NŽ, Baskić D, Popović SL, Todorović DV, Matić SL, Bogdanović GA, Vraneš M, Tot A, Bugarčić ZM. Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study. in Bioorganic Chemistry. 2019;88:102954.
doi:10.1016/j.bioorg.2019.102954 .
Joksimović, Nenad, Petronijević, Jelena, Janković, Nenad Ž., Baskić, Dejan, Popović, Suzana Lj., Todorović, Danijela V., Matić, Sanja Lj., Bogdanović, Goran A., Vraneš, Milan, Tot, Aleksandar, Bugarčić, Zorica M., "Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study" in Bioorganic Chemistry, 88 (2019):102954,
https://doi.org/10.1016/j.bioorg.2019.102954 . .
1
5
6
6

Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study

Joksimović, Nenad; Petronijević, Jelena; Janković, Nenad Ž.; Baskić, Dejan; Popović, Suzana Lj.; Todorović, Danijela V.; Matić, Sanja Lj.; Bogdanović, Goran A.; Vraneš, Milan; Tot, Aleksandar; Bugarčić, Zorica M.

(2019)

TY  - JOUR
AU  - Joksimović, Nenad
AU  - Petronijević, Jelena
AU  - Janković, Nenad Ž.
AU  - Baskić, Dejan
AU  - Popović, Suzana Lj.
AU  - Todorović, Danijela V.
AU  - Matić, Sanja Lj.
AU  - Bogdanović, Goran A.
AU  - Vraneš, Milan
AU  - Tot, Aleksandar
AU  - Bugarčić, Zorica M.
PY  - 2019
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/8173
AB  - In order to make a progress in discovering a new agents for chemotherapy with improved properties and bearing in mind the fact that substituted 3-hydroxy-3-pyrrolin-2-ones belong to a class of biologically active compounds, series of novel 1,5-diaryl-4-(2-thienylcarbonyl)-3-hydroxy-3-pyrrolin-2-ones were synthesized and characterized by spectral (UV–Vis, IR, NMR, ESI-MS), X-ray and elemental analysis. All compounds were examined for their cytotoxic effect on human cancer cell lines HeLa and MDA-MB 231 and normal fibroblasts (MRC-5). Four compounds, 3-hydroxy-1-(p-tolyl)-4-(2-thienylcarbonyl)-5-(4-chlorophenyl)-2,5-dihydro-1H-pyrrol-2-one (D10), 3-hydroxy-1-(3-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D13), 3-hydroxy-1-(4-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D14), and 3-hydroxy-1-(4-chlorophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D15), that showed the highest cytotoxicity against malignant cells and the best selectivity towards normal cells were selected for further experiments. Results obtained by investigating mechanisms of cytotoxic activity suggest that selected 3-hydroxy-3-pyrrolin-2-one derivatives in HeLa cells induce apoptosis that is associated with S phase arrest (D13, D15, and D10) or unrelated to cell cycle distribution (D14). Additionally, to better understand their suitability for potential use as anticancer medicaments we studied the interactions between biomacromolecules (DNA or BSA) and D13 and D15. The results indicated that D13 and D15 have great affinity to displace EB from the EB-DNA complex through intercalation [K sv = (3.7 ± 0.1) and (3.4 ± 0.1) × 10 3 M −1 , respectively], an intercalative mode also confirmed through viscosity measurements. K a values, obtained as result of fluorescence titration of BSA with D13 and D15 [K a = (4.2 ± 0.2) and (2.6 ± 0.2) × 10 5 M, respectively], support the fact that a significant amount of the tested compounds could be transported and distributed through the cells. In addition, by DNA and BSA molecular docking study for D13, D14 and D15 is determined and predicted the binding mode and the interaction region. © 2019 Elsevier Inc.
T2  - Bioorganic Chemistry
T1  - Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study
VL  - 88
SP  - 102954
DO  - 10.1016/j.bioorg.2019.102954
ER  - 
@article{
author = "Joksimović, Nenad and Petronijević, Jelena and Janković, Nenad Ž. and Baskić, Dejan and Popović, Suzana Lj. and Todorović, Danijela V. and Matić, Sanja Lj. and Bogdanović, Goran A. and Vraneš, Milan and Tot, Aleksandar and Bugarčić, Zorica M.",
year = "2019",
abstract = "In order to make a progress in discovering a new agents for chemotherapy with improved properties and bearing in mind the fact that substituted 3-hydroxy-3-pyrrolin-2-ones belong to a class of biologically active compounds, series of novel 1,5-diaryl-4-(2-thienylcarbonyl)-3-hydroxy-3-pyrrolin-2-ones were synthesized and characterized by spectral (UV–Vis, IR, NMR, ESI-MS), X-ray and elemental analysis. All compounds were examined for their cytotoxic effect on human cancer cell lines HeLa and MDA-MB 231 and normal fibroblasts (MRC-5). Four compounds, 3-hydroxy-1-(p-tolyl)-4-(2-thienylcarbonyl)-5-(4-chlorophenyl)-2,5-dihydro-1H-pyrrol-2-one (D10), 3-hydroxy-1-(3-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D13), 3-hydroxy-1-(4-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D14), and 3-hydroxy-1-(4-chlorophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D15), that showed the highest cytotoxicity against malignant cells and the best selectivity towards normal cells were selected for further experiments. Results obtained by investigating mechanisms of cytotoxic activity suggest that selected 3-hydroxy-3-pyrrolin-2-one derivatives in HeLa cells induce apoptosis that is associated with S phase arrest (D13, D15, and D10) or unrelated to cell cycle distribution (D14). Additionally, to better understand their suitability for potential use as anticancer medicaments we studied the interactions between biomacromolecules (DNA or BSA) and D13 and D15. The results indicated that D13 and D15 have great affinity to displace EB from the EB-DNA complex through intercalation [K sv = (3.7 ± 0.1) and (3.4 ± 0.1) × 10 3 M −1 , respectively], an intercalative mode also confirmed through viscosity measurements. K a values, obtained as result of fluorescence titration of BSA with D13 and D15 [K a = (4.2 ± 0.2) and (2.6 ± 0.2) × 10 5 M, respectively], support the fact that a significant amount of the tested compounds could be transported and distributed through the cells. In addition, by DNA and BSA molecular docking study for D13, D14 and D15 is determined and predicted the binding mode and the interaction region. © 2019 Elsevier Inc.",
journal = "Bioorganic Chemistry",
title = "Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study",
volume = "88",
pages = "102954",
doi = "10.1016/j.bioorg.2019.102954"
}
Joksimović, N., Petronijević, J., Janković, N. Ž., Baskić, D., Popović, S. Lj., Todorović, D. V., Matić, S. Lj., Bogdanović, G. A., Vraneš, M., Tot, A.,& Bugarčić, Z. M.. (2019). Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study. in Bioorganic Chemistry, 88, 102954.
https://doi.org/10.1016/j.bioorg.2019.102954
Joksimović N, Petronijević J, Janković NŽ, Baskić D, Popović SL, Todorović DV, Matić SL, Bogdanović GA, Vraneš M, Tot A, Bugarčić ZM. Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study. in Bioorganic Chemistry. 2019;88:102954.
doi:10.1016/j.bioorg.2019.102954 .
Joksimović, Nenad, Petronijević, Jelena, Janković, Nenad Ž., Baskić, Dejan, Popović, Suzana Lj., Todorović, Danijela V., Matić, Sanja Lj., Bogdanović, Goran A., Vraneš, Milan, Tot, Aleksandar, Bugarčić, Zorica M., "Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study" in Bioorganic Chemistry, 88 (2019):102954,
https://doi.org/10.1016/j.bioorg.2019.102954 . .
1
5
6
6

Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes

Radisavljević, Snežana; Ćoćić, Dušan; Jovanović, Snežana; Šmit, Biljana; Petković, Marijana; Milivojević, Nevena; Planojević, Nevena; Marković, Snežana D.; Petrović, Biljana V.

(2019)

TY  - JOUR
AU  - Radisavljević, Snežana
AU  - Ćoćić, Dušan
AU  - Jovanović, Snežana
AU  - Šmit, Biljana
AU  - Petković, Marijana
AU  - Milivojević, Nevena
AU  - Planojević, Nevena
AU  - Marković, Snežana D.
AU  - Petrović, Biljana V.
PY  - 2019
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/8592
AB  - Abstract: In this study, we have synthesized a series of dinuclear and trinuclear gold(III) complexes of the general formula [Au2(N–N)Cl6] (1–3) for dinuclear and [Au3(N–N)2Cl8]+ (4–6) for trinuclear compounds, respectively, in which N–N is a bidentate ligand (1,4-diaminobutane; 1,6-diaminohexane or 1,8-diaminooctane). These complexes were characterized by elemental analysis, molar conductivity, and spectroscopic techniques (IR, UV–Vis, 1H NMR, ESI–MS). We performed DFT calculations to get insight into the geometry of the studies complexes. DNA-binding studies were performed by UV–Vis spectrophotometry and fluorescence spectroscopy. The results of competitive reactions between gold(III) complexes and ethidium bromide (EB) towards DNA have shown that selected complexes can displace EB from DNA-EB adduct. In addition, these experiments confirm that polynuclear gold(III) complexes interact with DNA covalently or via intercalation. Furthermore, high values of binding constants of gold(III) complexes towards bovine serum albumin (BSA) protein indicate good binding affinity. In addition, redox stability of complexes in the presence of DNA/BSA was confirmed by cyclic voltammetry. Results of the interactions between gold(III) complexes with DNA/BSA were discussed in reference to molecular docking data obtain by Molegro virtual docker. The cytotoxic activity of synthesized gold(III) complexes was evaluated on human breast cancer cell line (MDA-MB-231), human colorectal cancer cell line (HCT-116), and normal human lung fibroblast cell line (MRC-5). All complexes dose-dependently reduced cancer and normal cells viabilities, with significant cytotoxic effects (IC50 < 25 μM) for trinuclear gold(III) complexes (4, 5) on HCT-116 cells. Graphic abstract: [Figure not available: see fulltext.].
T2  - JBIC Journal of Biological Inorganic Chemistry
T1  - Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes
VL  - 24
IS  - 7
SP  - 1057
EP  - 1076
DO  - 10.1007/s00775-019-01716-8
ER  - 
@article{
author = "Radisavljević, Snežana and Ćoćić, Dušan and Jovanović, Snežana and Šmit, Biljana and Petković, Marijana and Milivojević, Nevena and Planojević, Nevena and Marković, Snežana D. and Petrović, Biljana V.",
year = "2019",
abstract = "Abstract: In this study, we have synthesized a series of dinuclear and trinuclear gold(III) complexes of the general formula [Au2(N–N)Cl6] (1–3) for dinuclear and [Au3(N–N)2Cl8]+ (4–6) for trinuclear compounds, respectively, in which N–N is a bidentate ligand (1,4-diaminobutane; 1,6-diaminohexane or 1,8-diaminooctane). These complexes were characterized by elemental analysis, molar conductivity, and spectroscopic techniques (IR, UV–Vis, 1H NMR, ESI–MS). We performed DFT calculations to get insight into the geometry of the studies complexes. DNA-binding studies were performed by UV–Vis spectrophotometry and fluorescence spectroscopy. The results of competitive reactions between gold(III) complexes and ethidium bromide (EB) towards DNA have shown that selected complexes can displace EB from DNA-EB adduct. In addition, these experiments confirm that polynuclear gold(III) complexes interact with DNA covalently or via intercalation. Furthermore, high values of binding constants of gold(III) complexes towards bovine serum albumin (BSA) protein indicate good binding affinity. In addition, redox stability of complexes in the presence of DNA/BSA was confirmed by cyclic voltammetry. Results of the interactions between gold(III) complexes with DNA/BSA were discussed in reference to molecular docking data obtain by Molegro virtual docker. The cytotoxic activity of synthesized gold(III) complexes was evaluated on human breast cancer cell line (MDA-MB-231), human colorectal cancer cell line (HCT-116), and normal human lung fibroblast cell line (MRC-5). All complexes dose-dependently reduced cancer and normal cells viabilities, with significant cytotoxic effects (IC50 < 25 μM) for trinuclear gold(III) complexes (4, 5) on HCT-116 cells. Graphic abstract: [Figure not available: see fulltext.].",
journal = "JBIC Journal of Biological Inorganic Chemistry",
title = "Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes",
volume = "24",
number = "7",
pages = "1057-1076",
doi = "10.1007/s00775-019-01716-8"
}
Radisavljević, S., Ćoćić, D., Jovanović, S., Šmit, B., Petković, M., Milivojević, N., Planojević, N., Marković, S. D.,& Petrović, B. V.. (2019). Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes. in JBIC Journal of Biological Inorganic Chemistry, 24(7), 1057-1076.
https://doi.org/10.1007/s00775-019-01716-8
Radisavljević S, Ćoćić D, Jovanović S, Šmit B, Petković M, Milivojević N, Planojević N, Marković SD, Petrović BV. Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes. in JBIC Journal of Biological Inorganic Chemistry. 2019;24(7):1057-1076.
doi:10.1007/s00775-019-01716-8 .
Radisavljević, Snežana, Ćoćić, Dušan, Jovanović, Snežana, Šmit, Biljana, Petković, Marijana, Milivojević, Nevena, Planojević, Nevena, Marković, Snežana D., Petrović, Biljana V., "Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes" in JBIC Journal of Biological Inorganic Chemistry, 24, no. 7 (2019):1057-1076,
https://doi.org/10.1007/s00775-019-01716-8 . .
10
10
11

Discovery of the Biginelli hybrids as novel caspase-9 activators in apoptotic machines: Lipophilicity, molecular docking study, influence on angiogenesis gene and miR-21 expression levels

Janković, Nenad Ž.; Trifunović Ristovski, Jovana; Vraneš, Milan; Tot, Aleksandar; Petronijević, Jelena; Joksimović, Nenad; Stanojković, Tatjana P.; Đorđić Crnogorac, Marija; Petrović, Nina; Boljević, Ivana; Matić, Ivana Z.; Bogdanović, Goran A.; Mikov, Momir; Bugarčić, Zorica M.

(2019)

TY  - JOUR
AU  - Janković, Nenad Ž.
AU  - Trifunović Ristovski, Jovana
AU  - Vraneš, Milan
AU  - Tot, Aleksandar
AU  - Petronijević, Jelena
AU  - Joksimović, Nenad
AU  - Stanojković, Tatjana P.
AU  - Đorđić Crnogorac, Marija
AU  - Petrović, Nina
AU  - Boljević, Ivana
AU  - Matić, Ivana Z.
AU  - Bogdanović, Goran A.
AU  - Mikov, Momir
AU  - Bugarčić, Zorica M.
PY  - 2019
UR  - https://linkinghub.elsevier.com/retrieve/pii/S0045206818312598
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/8071
AB  - In order to investigate potential therapeutically agents, novel products of Biginelli reaction (4a-l) were synthesized and exposed to cytotoxic and caspase activities, angiogenesis, cell cycle distribution, gene and microRNA expression levels, lipophilicity assessment and docking study. Among the twelve novel compounds (4a-l) evaluated for the cytotoxic activity, five of them (4c, 4d, 4f, 4k and 4l) that showed excellent activity on the tested cell lines (HeLa, LS174 and A549) were selected for further evaluation. Interestingly, compound 4f has up to three times higher selectivity index (SI) towards cancer cells than cisplatin (on HeLa, LS174 and A549 SI = 18.2, 13.5 and 11.2, respectively). The obtained results from cell cycle distribution and caspase activity indicate that tested compounds (4c, 4d, 4f, 4k and 4l) promoted caspase-9 activation, implicated in the intrinsic pathway of apoptosis. Lipophilicity of 4a-l was determinate by using reversed-phase high-performance liquid chromatography. © 2019 Elsevier Inc.
T2  - Bioorganic Chemistry
T1  - Discovery of the Biginelli hybrids as novel caspase-9 activators in apoptotic machines: Lipophilicity, molecular docking study, influence on angiogenesis gene and miR-21 expression levels
VL  - 86
SP  - 569
EP  - 582
DO  - 10.1016/j.bioorg.2019.02.026
ER  - 
@article{
author = "Janković, Nenad Ž. and Trifunović Ristovski, Jovana and Vraneš, Milan and Tot, Aleksandar and Petronijević, Jelena and Joksimović, Nenad and Stanojković, Tatjana P. and Đorđić Crnogorac, Marija and Petrović, Nina and Boljević, Ivana and Matić, Ivana Z. and Bogdanović, Goran A. and Mikov, Momir and Bugarčić, Zorica M.",
year = "2019",
abstract = "In order to investigate potential therapeutically agents, novel products of Biginelli reaction (4a-l) were synthesized and exposed to cytotoxic and caspase activities, angiogenesis, cell cycle distribution, gene and microRNA expression levels, lipophilicity assessment and docking study. Among the twelve novel compounds (4a-l) evaluated for the cytotoxic activity, five of them (4c, 4d, 4f, 4k and 4l) that showed excellent activity on the tested cell lines (HeLa, LS174 and A549) were selected for further evaluation. Interestingly, compound 4f has up to three times higher selectivity index (SI) towards cancer cells than cisplatin (on HeLa, LS174 and A549 SI = 18.2, 13.5 and 11.2, respectively). The obtained results from cell cycle distribution and caspase activity indicate that tested compounds (4c, 4d, 4f, 4k and 4l) promoted caspase-9 activation, implicated in the intrinsic pathway of apoptosis. Lipophilicity of 4a-l was determinate by using reversed-phase high-performance liquid chromatography. © 2019 Elsevier Inc.",
journal = "Bioorganic Chemistry",
title = "Discovery of the Biginelli hybrids as novel caspase-9 activators in apoptotic machines: Lipophilicity, molecular docking study, influence on angiogenesis gene and miR-21 expression levels",
volume = "86",
pages = "569-582",
doi = "10.1016/j.bioorg.2019.02.026"
}
Janković, N. Ž., Trifunović Ristovski, J., Vraneš, M., Tot, A., Petronijević, J., Joksimović, N., Stanojković, T. P., Đorđić Crnogorac, M., Petrović, N., Boljević, I., Matić, I. Z., Bogdanović, G. A., Mikov, M.,& Bugarčić, Z. M.. (2019). Discovery of the Biginelli hybrids as novel caspase-9 activators in apoptotic machines: Lipophilicity, molecular docking study, influence on angiogenesis gene and miR-21 expression levels. in Bioorganic Chemistry, 86, 569-582.
https://doi.org/10.1016/j.bioorg.2019.02.026
Janković NŽ, Trifunović Ristovski J, Vraneš M, Tot A, Petronijević J, Joksimović N, Stanojković TP, Đorđić Crnogorac M, Petrović N, Boljević I, Matić IZ, Bogdanović GA, Mikov M, Bugarčić ZM. Discovery of the Biginelli hybrids as novel caspase-9 activators in apoptotic machines: Lipophilicity, molecular docking study, influence on angiogenesis gene and miR-21 expression levels. in Bioorganic Chemistry. 2019;86:569-582.
doi:10.1016/j.bioorg.2019.02.026 .
Janković, Nenad Ž., Trifunović Ristovski, Jovana, Vraneš, Milan, Tot, Aleksandar, Petronijević, Jelena, Joksimović, Nenad, Stanojković, Tatjana P., Đorđić Crnogorac, Marija, Petrović, Nina, Boljević, Ivana, Matić, Ivana Z., Bogdanović, Goran A., Mikov, Momir, Bugarčić, Zorica M., "Discovery of the Biginelli hybrids as novel caspase-9 activators in apoptotic machines: Lipophilicity, molecular docking study, influence on angiogenesis gene and miR-21 expression levels" in Bioorganic Chemistry, 86 (2019):569-582,
https://doi.org/10.1016/j.bioorg.2019.02.026 . .
5
5
5

Chemistry and reactivity of ruthenium(II) complexes: DNA/protein binding mode and anticancer activity are related to the complex structure

Rilak Simović, Ana; Masnikosa, Romana; Bratsos, Ioannis; Alessio, Enzo

(2019)

TY  - JOUR
AU  - Rilak Simović, Ana
AU  - Masnikosa, Romana
AU  - Bratsos, Ioannis
AU  - Alessio, Enzo
PY  - 2019
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/8433
AB  - In this review we summarize our work on development of Ru complexes with potential antitumor activity, which was performed over the last few years. In order to establish the structure-activity relationship for Ru(II) compounds, we have designed, synthesized and thoroughly studied several Ru(II) complexes, which were divided in three main groups: i) organometallic Ru(II)-arene complexes, ii) Ru(II) half-sandwich coordination complexes bearing neutral face-capping macrocyclic ligands, such as 1,4,7-trithiacyclononane ([9]aneS3) and 1,4,7-triazacyclononane ([9]aneN3), and iii) Ru(II)-polypyridyl complexes. Our most recent experiments moved toward synthesis, chemistry and reactivity of the heteronuclear ruthenium(II)/ferrocene complexes. The first part of the present review gives a brief overview of the structural features and anticancer activity of ruthenium complexes. The second part is focused mainly on the results obtained from the kinetic and mechanistic studies of the reactions between Ru(II) complexes and guanine derivatives, such as 9-methylguanine (9MeG), guanosine (Guo) and guanosine-5′-monophosphate (5′-GMP), as well as on structural characterization of the final products of these reactions. In the final part we deal with the reactions of Ru(II) complexes with DNA, which is widely accepted as a potential target for cytotoxic ruthenium compounds. We have also described the interactions of Ru(II) compounds with the most abundant transport proteins from human serum: human serum albumin (HSA) and transferrin (Tf). We believe that a systematic review of the aforementioned studies will not only contribute to the future development of ruthenium complexes as potential antitumor agents, but will also help to understand the potential toxicity of ruthenium-based drugs. © 2019 Elsevier B.V.
T2  - Coordination Chemistry Reviews
T1  - Chemistry and reactivity of ruthenium(II) complexes: DNA/protein binding mode and anticancer activity are related to the complex structure
VL  - 398
SP  - 113011
DO  - 10.1016/j.ccr.2019.07.008
ER  - 
@article{
author = "Rilak Simović, Ana and Masnikosa, Romana and Bratsos, Ioannis and Alessio, Enzo",
year = "2019",
abstract = "In this review we summarize our work on development of Ru complexes with potential antitumor activity, which was performed over the last few years. In order to establish the structure-activity relationship for Ru(II) compounds, we have designed, synthesized and thoroughly studied several Ru(II) complexes, which were divided in three main groups: i) organometallic Ru(II)-arene complexes, ii) Ru(II) half-sandwich coordination complexes bearing neutral face-capping macrocyclic ligands, such as 1,4,7-trithiacyclononane ([9]aneS3) and 1,4,7-triazacyclononane ([9]aneN3), and iii) Ru(II)-polypyridyl complexes. Our most recent experiments moved toward synthesis, chemistry and reactivity of the heteronuclear ruthenium(II)/ferrocene complexes. The first part of the present review gives a brief overview of the structural features and anticancer activity of ruthenium complexes. The second part is focused mainly on the results obtained from the kinetic and mechanistic studies of the reactions between Ru(II) complexes and guanine derivatives, such as 9-methylguanine (9MeG), guanosine (Guo) and guanosine-5′-monophosphate (5′-GMP), as well as on structural characterization of the final products of these reactions. In the final part we deal with the reactions of Ru(II) complexes with DNA, which is widely accepted as a potential target for cytotoxic ruthenium compounds. We have also described the interactions of Ru(II) compounds with the most abundant transport proteins from human serum: human serum albumin (HSA) and transferrin (Tf). We believe that a systematic review of the aforementioned studies will not only contribute to the future development of ruthenium complexes as potential antitumor agents, but will also help to understand the potential toxicity of ruthenium-based drugs. © 2019 Elsevier B.V.",
journal = "Coordination Chemistry Reviews",
title = "Chemistry and reactivity of ruthenium(II) complexes: DNA/protein binding mode and anticancer activity are related to the complex structure",
volume = "398",
pages = "113011",
doi = "10.1016/j.ccr.2019.07.008"
}
Rilak Simović, A., Masnikosa, R., Bratsos, I.,& Alessio, E.. (2019). Chemistry and reactivity of ruthenium(II) complexes: DNA/protein binding mode and anticancer activity are related to the complex structure. in Coordination Chemistry Reviews, 398, 113011.
https://doi.org/10.1016/j.ccr.2019.07.008
Rilak Simović A, Masnikosa R, Bratsos I, Alessio E. Chemistry and reactivity of ruthenium(II) complexes: DNA/protein binding mode and anticancer activity are related to the complex structure. in Coordination Chemistry Reviews. 2019;398:113011.
doi:10.1016/j.ccr.2019.07.008 .
Rilak Simović, Ana, Masnikosa, Romana, Bratsos, Ioannis, Alessio, Enzo, "Chemistry and reactivity of ruthenium(II) complexes: DNA/protein binding mode and anticancer activity are related to the complex structure" in Coordination Chemistry Reviews, 398 (2019):113011,
https://doi.org/10.1016/j.ccr.2019.07.008 . .
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Highly water-soluble ruthenium(II) terpyridine coordination compounds form stable adducts with blood-borne metal transporting proteins

Nišavić, Marija; Stoiljković, Milovan; Crnolatac, Ivo; Milošević, Maja; Rilak, Ana; Masnikosa, Romana

(2018)

TY  - JOUR
AU  - Nišavić, Marija
AU  - Stoiljković, Milovan
AU  - Crnolatac, Ivo
AU  - Milošević, Maja
AU  - Rilak, Ana
AU  - Masnikosa, Romana
PY  - 2018
UR  - http://linkinghub.elsevier.com/retrieve/pii/S1878535216301198
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/7665
AB  - Three coordination compounds of ruthenium(II), belonging to a recently synthesised series of water-soluble compounds of general formula mer-{[}Ru(L3)(N-N) Cl] Cl, where L3 = 4'-chloro2,2': 6', 200-terpyridine (Cl-tpy), N-N= ethylenediamine (en), 1,2-diaminocyclohexane (dach) or 2,2'bipyridine (bpy), have shown strong binding to calf thymus DNA and moderate in vitro cytotoxicity towards cancer cell lines. Knowing that serum proteins play a crucial role in the transport and deactivation of ruthenium drugs, we have conducted a detailed study of their interactions with two major metal-transporting serum proteins, albumin and transferrin, and it is presented herein. Ruthenated protein adducts were formed with various concentrations of the three compounds and then separated from the unbound portions by ultrafiltration through 10 kDa cut-off centrifugal filter units. The stoichiometry of binding was determined using inductively coupled plasma optical emission spectrometry. One mol of albumin bound up to 7, 8.5 and 1.5 mol of compound 1 ({[}Ru(Cltpy)(en) Cl]{[}Cl]), 2 ({[}Ru(Cl-tpy)(dach) Cl]{[}Cl] and 3 ({[}Ru(Cl-tpy)(bpy) Cl]{[}Cl]), respectively. One mol of transferrin bound up to 3, 3.5 and 0.4 mol of 1, 2 and 3, respectively. The affinity of albumin and transferrin for the three ruthenium compounds was evaluated using fluorescence quenching. The binding constants for 1 and 2 lay within the range 10(4) -10(5) M - 1, suggesting moderate-to-strong attachment to albumin. Both compounds showed much lower affinity for transferrin (10(2) -10(3) M - 1). Compound 3 bound weakly to each studied protein. High resolution ESI qTOF mass spectra of albumin before and after binding of 1 revealed the high stoichiometry of binding. Although the binding of the compounds 1-3 to albumin and transferrin did not affect proteins' secondary structure much, their tertiary structures underwent some alterations, as deduced from the circular dichroism study. Changes in the stability of albumin, after binding to compounds 1-3 were examined by differential scanning calorimetry. (C) 2016 The Authors. Production and hosting by Elsevier B. V. on behalf of King Saud University. This is an open access article under theCCBY-NC-NDlicense.
T2  - Arabian Journal of Chemistry
T1  - Highly water-soluble ruthenium(II) terpyridine coordination compounds form stable adducts with blood-borne metal transporting proteins
VL  - 11
IS  - 3
SP  - 291
EP  - 304
DO  - 10.1016/j.arabjc.2016.07.021
ER  - 
@article{
author = "Nišavić, Marija and Stoiljković, Milovan and Crnolatac, Ivo and Milošević, Maja and Rilak, Ana and Masnikosa, Romana",
year = "2018",
abstract = "Three coordination compounds of ruthenium(II), belonging to a recently synthesised series of water-soluble compounds of general formula mer-{[}Ru(L3)(N-N) Cl] Cl, where L3 = 4'-chloro2,2': 6', 200-terpyridine (Cl-tpy), N-N= ethylenediamine (en), 1,2-diaminocyclohexane (dach) or 2,2'bipyridine (bpy), have shown strong binding to calf thymus DNA and moderate in vitro cytotoxicity towards cancer cell lines. Knowing that serum proteins play a crucial role in the transport and deactivation of ruthenium drugs, we have conducted a detailed study of their interactions with two major metal-transporting serum proteins, albumin and transferrin, and it is presented herein. Ruthenated protein adducts were formed with various concentrations of the three compounds and then separated from the unbound portions by ultrafiltration through 10 kDa cut-off centrifugal filter units. The stoichiometry of binding was determined using inductively coupled plasma optical emission spectrometry. One mol of albumin bound up to 7, 8.5 and 1.5 mol of compound 1 ({[}Ru(Cltpy)(en) Cl]{[}Cl]), 2 ({[}Ru(Cl-tpy)(dach) Cl]{[}Cl] and 3 ({[}Ru(Cl-tpy)(bpy) Cl]{[}Cl]), respectively. One mol of transferrin bound up to 3, 3.5 and 0.4 mol of 1, 2 and 3, respectively. The affinity of albumin and transferrin for the three ruthenium compounds was evaluated using fluorescence quenching. The binding constants for 1 and 2 lay within the range 10(4) -10(5) M - 1, suggesting moderate-to-strong attachment to albumin. Both compounds showed much lower affinity for transferrin (10(2) -10(3) M - 1). Compound 3 bound weakly to each studied protein. High resolution ESI qTOF mass spectra of albumin before and after binding of 1 revealed the high stoichiometry of binding. Although the binding of the compounds 1-3 to albumin and transferrin did not affect proteins' secondary structure much, their tertiary structures underwent some alterations, as deduced from the circular dichroism study. Changes in the stability of albumin, after binding to compounds 1-3 were examined by differential scanning calorimetry. (C) 2016 The Authors. Production and hosting by Elsevier B. V. on behalf of King Saud University. This is an open access article under theCCBY-NC-NDlicense.",
journal = "Arabian Journal of Chemistry",
title = "Highly water-soluble ruthenium(II) terpyridine coordination compounds form stable adducts with blood-borne metal transporting proteins",
volume = "11",
number = "3",
pages = "291-304",
doi = "10.1016/j.arabjc.2016.07.021"
}
Nišavić, M., Stoiljković, M., Crnolatac, I., Milošević, M., Rilak, A.,& Masnikosa, R.. (2018). Highly water-soluble ruthenium(II) terpyridine coordination compounds form stable adducts with blood-borne metal transporting proteins. in Arabian Journal of Chemistry, 11(3), 291-304.
https://doi.org/10.1016/j.arabjc.2016.07.021
Nišavić M, Stoiljković M, Crnolatac I, Milošević M, Rilak A, Masnikosa R. Highly water-soluble ruthenium(II) terpyridine coordination compounds form stable adducts with blood-borne metal transporting proteins. in Arabian Journal of Chemistry. 2018;11(3):291-304.
doi:10.1016/j.arabjc.2016.07.021 .
Nišavić, Marija, Stoiljković, Milovan, Crnolatac, Ivo, Milošević, Maja, Rilak, Ana, Masnikosa, Romana, "Highly water-soluble ruthenium(II) terpyridine coordination compounds form stable adducts with blood-borne metal transporting proteins" in Arabian Journal of Chemistry, 11, no. 3 (2018):291-304,
https://doi.org/10.1016/j.arabjc.2016.07.021 . .
3
14
15
16

Inorganic Nanoparticles In Biology: Drug Carriers And Auxiliary Tools In Bioimaging And Bioanalytics

Matijević, Milica; Popović, Iva A.; Stepić, Milutin; Nešić, Maja D.; Radoičić, Marija B.; Stanković, Maja; Šaponjić, Zoran; Petković, Marijana

(2018)

TY  - JOUR
AU  - Matijević, Milica
AU  - Popović, Iva A.
AU  - Stepić, Milutin
AU  - Nešić, Maja D.
AU  - Radoičić, Marija B.
AU  - Stanković, Maja
AU  - Šaponjić, Zoran
AU  - Petković, Marijana
PY  - 2018
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9062
AB  - Among various nano-scaled materials composed from a spectrum of chemical compounds, inorganic nanoparticles are very attractive due to their physico-chemical properties, as well as their availability, simplicity, possibility of modifications, stability and biocompatibility. They are, on the one hand, an useful tool in advanced analytical chemistry, in particular for studying of biologically-relevant processes, but also important as functional parts of the systems designed for controlled and targeted delivery of medicaments for treatment of a variety of diseases and for imaging. So far, thousands of compounds and systems have been developed for the above-mentioned purposes, but there are only a few reviews dealing with these topics. The aim of this review is, thus, to summarize recent applications of nano-structured inorganic materials in the field of drug delivery, bioimaging and bioanalytics, and to give a prospective from the standpoint of biology-related applications.
T2  - Biologica Nyssana
T1  - Inorganic Nanoparticles In Biology: Drug Carriers And Auxiliary Tools In Bioimaging And Bioanalytics
VL  - 9
IS  - 1
SP  - 1
EP  - 19
DO  - 10.5281/zenodo.1470841
ER  - 
@article{
author = "Matijević, Milica and Popović, Iva A. and Stepić, Milutin and Nešić, Maja D. and Radoičić, Marija B. and Stanković, Maja and Šaponjić, Zoran and Petković, Marijana",
year = "2018",
abstract = "Among various nano-scaled materials composed from a spectrum of chemical compounds, inorganic nanoparticles are very attractive due to their physico-chemical properties, as well as their availability, simplicity, possibility of modifications, stability and biocompatibility. They are, on the one hand, an useful tool in advanced analytical chemistry, in particular for studying of biologically-relevant processes, but also important as functional parts of the systems designed for controlled and targeted delivery of medicaments for treatment of a variety of diseases and for imaging. So far, thousands of compounds and systems have been developed for the above-mentioned purposes, but there are only a few reviews dealing with these topics. The aim of this review is, thus, to summarize recent applications of nano-structured inorganic materials in the field of drug delivery, bioimaging and bioanalytics, and to give a prospective from the standpoint of biology-related applications.",
journal = "Biologica Nyssana",
title = "Inorganic Nanoparticles In Biology: Drug Carriers And Auxiliary Tools In Bioimaging And Bioanalytics",
volume = "9",
number = "1",
pages = "1-19",
doi = "10.5281/zenodo.1470841"
}
Matijević, M., Popović, I. A., Stepić, M., Nešić, M. D., Radoičić, M. B., Stanković, M., Šaponjić, Z.,& Petković, M.. (2018). Inorganic Nanoparticles In Biology: Drug Carriers And Auxiliary Tools In Bioimaging And Bioanalytics. in Biologica Nyssana, 9(1), 1-19.
https://doi.org/10.5281/zenodo.1470841
Matijević M, Popović IA, Stepić M, Nešić MD, Radoičić MB, Stanković M, Šaponjić Z, Petković M. Inorganic Nanoparticles In Biology: Drug Carriers And Auxiliary Tools In Bioimaging And Bioanalytics. in Biologica Nyssana. 2018;9(1):1-19.
doi:10.5281/zenodo.1470841 .
Matijević, Milica, Popović, Iva A., Stepić, Milutin, Nešić, Maja D., Radoičić, Marija B., Stanković, Maja, Šaponjić, Zoran, Petković, Marijana, "Inorganic Nanoparticles In Biology: Drug Carriers And Auxiliary Tools In Bioimaging And Bioanalytics" in Biologica Nyssana, 9, no. 1 (2018):1-19,
https://doi.org/10.5281/zenodo.1470841 . .

Newly Synthesized Heteronuclear Ruthenium(II)/Ferrocene Complexes Suppress the Growth of Mammary Carcinoma in 4T1-Treated BALB/c Mice by Promoting Activation of Antitumor Immunity

Milutinović, Milan M.; Čanović, Petar P.; Stevanović, Dragana D.; Masnikosa, Romana; Vraneš, Milan; Tot, Aleksandar; Zarić, Milan M.; Marković-Simović, Bojana; Misirkić-Marjanović, Maja; Vučićević, Ljubica; Savić, Maja; Jakovljević, Vladimir Lj.; Trajković, Vladimir S.; Volarević, Vladislav; Kanjevac, Tatjana; Rilak Simović, Ana

(2018)

TY  - JOUR
AU  - Milutinović, Milan M.
AU  - Čanović, Petar P.
AU  - Stevanović, Dragana D.
AU  - Masnikosa, Romana
AU  - Vraneš, Milan
AU  - Tot, Aleksandar
AU  - Zarić, Milan M.
AU  - Marković-Simović, Bojana
AU  - Misirkić-Marjanović, Maja
AU  - Vučićević, Ljubica
AU  - Savić, Maja
AU  - Jakovljević, Vladimir Lj.
AU  - Trajković, Vladimir S.
AU  - Volarević, Vladislav
AU  - Kanjevac, Tatjana
AU  - Rilak Simović, Ana
PY  - 2018
UR  - http://pubs.acs.org/doi/10.1021/acs.organomet.8b00604
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/7967
AB  - The two new heterometallic Ru(II)-tpy/ferrocene complexes [Ru(tpy)Cl2(mtefc)] (1) and [Ru(tpy)Cl2(mtpfc)] (2) (where tpy = 2,2′:6′,2′′-terpyridine, mtefc = (2-(methylthio)ethyl)ferrocene, and mtpfc = (3-(methylthio)propyl)ferrocene) have been synthesized and then characterized through elemental analysis, followed by various spectroscopic (IR, UV-vis, 1D and 2D NMR) and mass spectrometric techniques (MALDI TOF and ESI Q-TOF MS). UV-vis and fluorescence spectroscopy and viscometry were employed to study the interactions of the complexes 1 and 2 with calf thymus DNA. Both 1 and 2 expelled ethidium bromide (EB) from the EB/DNA complex (Ksv = (1.5-1.8) × 104 M-1), which suggested that the complexes intercalated into the double helix of DNA. Both complexes strongly quenched the fluorescence of tryptophan residues in serum albumin through both static and dynamic quenching. Molecular docking confirmed the intercalative mode of complex interaction with DNA. The docking results implied that 1 and 2 interacted with hydrophobic residues of albumin, particularly with those lying in the proximity of Tyr 160. We here demonstrate the high cytotoxic potential of complexes 1 and 2 against the breast cancer cells that originated either from humans (MDA-MB-231) or from mice (4T1), with apoptosis being the main mechanism of complex-induced cell death. It is worth noting that both complexes promoted activation of innate and acquired antitumor immunity, which contributed to the reduced growth and progression of mammary carcinoma in vivo. Copyright © 2018 American Chemical Society.
T2  - Organometallics
T1  - Newly Synthesized Heteronuclear Ruthenium(II)/Ferrocene Complexes Suppress the Growth of Mammary Carcinoma in 4T1-Treated BALB/c Mice by Promoting Activation of Antitumor Immunity
VL  - 37
IS  - 22
SP  - 4250
EP  - 4266
DO  - 10.1021/acs.organomet.8b00604
ER  - 
@article{
author = "Milutinović, Milan M. and Čanović, Petar P. and Stevanović, Dragana D. and Masnikosa, Romana and Vraneš, Milan and Tot, Aleksandar and Zarić, Milan M. and Marković-Simović, Bojana and Misirkić-Marjanović, Maja and Vučićević, Ljubica and Savić, Maja and Jakovljević, Vladimir Lj. and Trajković, Vladimir S. and Volarević, Vladislav and Kanjevac, Tatjana and Rilak Simović, Ana",
year = "2018",
abstract = "The two new heterometallic Ru(II)-tpy/ferrocene complexes [Ru(tpy)Cl2(mtefc)] (1) and [Ru(tpy)Cl2(mtpfc)] (2) (where tpy = 2,2′:6′,2′′-terpyridine, mtefc = (2-(methylthio)ethyl)ferrocene, and mtpfc = (3-(methylthio)propyl)ferrocene) have been synthesized and then characterized through elemental analysis, followed by various spectroscopic (IR, UV-vis, 1D and 2D NMR) and mass spectrometric techniques (MALDI TOF and ESI Q-TOF MS). UV-vis and fluorescence spectroscopy and viscometry were employed to study the interactions of the complexes 1 and 2 with calf thymus DNA. Both 1 and 2 expelled ethidium bromide (EB) from the EB/DNA complex (Ksv = (1.5-1.8) × 104 M-1), which suggested that the complexes intercalated into the double helix of DNA. Both complexes strongly quenched the fluorescence of tryptophan residues in serum albumin through both static and dynamic quenching. Molecular docking confirmed the intercalative mode of complex interaction with DNA. The docking results implied that 1 and 2 interacted with hydrophobic residues of albumin, particularly with those lying in the proximity of Tyr 160. We here demonstrate the high cytotoxic potential of complexes 1 and 2 against the breast cancer cells that originated either from humans (MDA-MB-231) or from mice (4T1), with apoptosis being the main mechanism of complex-induced cell death. It is worth noting that both complexes promoted activation of innate and acquired antitumor immunity, which contributed to the reduced growth and progression of mammary carcinoma in vivo. Copyright © 2018 American Chemical Society.",
journal = "Organometallics",
title = "Newly Synthesized Heteronuclear Ruthenium(II)/Ferrocene Complexes Suppress the Growth of Mammary Carcinoma in 4T1-Treated BALB/c Mice by Promoting Activation of Antitumor Immunity",
volume = "37",
number = "22",
pages = "4250-4266",
doi = "10.1021/acs.organomet.8b00604"
}
Milutinović, M. M., Čanović, P. P., Stevanović, D. D., Masnikosa, R., Vraneš, M., Tot, A., Zarić, M. M., Marković-Simović, B., Misirkić-Marjanović, M., Vučićević, L., Savić, M., Jakovljević, V. Lj., Trajković, V. S., Volarević, V., Kanjevac, T.,& Rilak Simović, A.. (2018). Newly Synthesized Heteronuclear Ruthenium(II)/Ferrocene Complexes Suppress the Growth of Mammary Carcinoma in 4T1-Treated BALB/c Mice by Promoting Activation of Antitumor Immunity. in Organometallics, 37(22), 4250-4266.
https://doi.org/10.1021/acs.organomet.8b00604
Milutinović MM, Čanović PP, Stevanović DD, Masnikosa R, Vraneš M, Tot A, Zarić MM, Marković-Simović B, Misirkić-Marjanović M, Vučićević L, Savić M, Jakovljević VL, Trajković VS, Volarević V, Kanjevac T, Rilak Simović A. Newly Synthesized Heteronuclear Ruthenium(II)/Ferrocene Complexes Suppress the Growth of Mammary Carcinoma in 4T1-Treated BALB/c Mice by Promoting Activation of Antitumor Immunity. in Organometallics. 2018;37(22):4250-4266.
doi:10.1021/acs.organomet.8b00604 .
Milutinović, Milan M., Čanović, Petar P., Stevanović, Dragana D., Masnikosa, Romana, Vraneš, Milan, Tot, Aleksandar, Zarić, Milan M., Marković-Simović, Bojana, Misirkić-Marjanović, Maja, Vučićević, Ljubica, Savić, Maja, Jakovljević, Vladimir Lj., Trajković, Vladimir S., Volarević, Vladislav, Kanjevac, Tatjana, Rilak Simović, Ana, "Newly Synthesized Heteronuclear Ruthenium(II)/Ferrocene Complexes Suppress the Growth of Mammary Carcinoma in 4T1-Treated BALB/c Mice by Promoting Activation of Antitumor Immunity" in Organometallics, 37, no. 22 (2018):4250-4266,
https://doi.org/10.1021/acs.organomet.8b00604 . .
4
13
13
11

Light controllable TiO2-Ru nanocomposite system encapsulated in phospholipid unilamellar vesicles for anti-cancer photodynamic therapy

Matijević, Milica; Nešić, Maja A.; Stepić, Milutin; Radoičić, Marija B.; Šaponjić, Zoran; Petković, Marijana

(2018)

TY  - JOUR
AU  - Matijević, Milica
AU  - Nešić, Maja A.
AU  - Stepić, Milutin
AU  - Radoičić, Marija B.
AU  - Šaponjić, Zoran
AU  - Petković, Marijana
PY  - 2018
UR  - http://link.springer.com/10.1007/s11082-018-1495-z
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/7697
AB  - Photodynamic therapy implies a combined use of a photosensitizing medicament and low-intensity light to cause selective damage to the target tissue—tumor. As potential medicament, we use Ru(II)(dcbpy)2Cl2complex, and in order to achieve better photosensitization properties, the Ru complex was attached to the nano carrier—TiO2nanoparticles. Additionally, this nanocomposite system was encapsulated in the phospholipid vesicles, which could be classified as small unilamellar vesicles, based on the technique of production. The complex-release tests were performed under light illumination, at pH 5, characteristic for tumor cells` interior and compared with the release pattern at pH 7, characteristic for the serum, i.e. physiological solution.
T2  - Optical and Quantum Electronics
T1  - Light controllable TiO2-Ru nanocomposite system encapsulated in phospholipid unilamellar vesicles for anti-cancer photodynamic therapy
VL  - 50
IS  - 6
SP  - 232
DO  - 10.1007/s11082-018-1495-z
ER  - 
@article{
author = "Matijević, Milica and Nešić, Maja A. and Stepić, Milutin and Radoičić, Marija B. and Šaponjić, Zoran and Petković, Marijana",
year = "2018",
abstract = "Photodynamic therapy implies a combined use of a photosensitizing medicament and low-intensity light to cause selective damage to the target tissue—tumor. As potential medicament, we use Ru(II)(dcbpy)2Cl2complex, and in order to achieve better photosensitization properties, the Ru complex was attached to the nano carrier—TiO2nanoparticles. Additionally, this nanocomposite system was encapsulated in the phospholipid vesicles, which could be classified as small unilamellar vesicles, based on the technique of production. The complex-release tests were performed under light illumination, at pH 5, characteristic for tumor cells` interior and compared with the release pattern at pH 7, characteristic for the serum, i.e. physiological solution.",
journal = "Optical and Quantum Electronics",
title = "Light controllable TiO2-Ru nanocomposite system encapsulated in phospholipid unilamellar vesicles for anti-cancer photodynamic therapy",
volume = "50",
number = "6",
pages = "232",
doi = "10.1007/s11082-018-1495-z"
}
Matijević, M., Nešić, M. A., Stepić, M., Radoičić, M. B., Šaponjić, Z.,& Petković, M.. (2018). Light controllable TiO2-Ru nanocomposite system encapsulated in phospholipid unilamellar vesicles for anti-cancer photodynamic therapy. in Optical and Quantum Electronics, 50(6), 232.
https://doi.org/10.1007/s11082-018-1495-z
Matijević M, Nešić MA, Stepić M, Radoičić MB, Šaponjić Z, Petković M. Light controllable TiO2-Ru nanocomposite system encapsulated in phospholipid unilamellar vesicles for anti-cancer photodynamic therapy. in Optical and Quantum Electronics. 2018;50(6):232.
doi:10.1007/s11082-018-1495-z .
Matijević, Milica, Nešić, Maja A., Stepić, Milutin, Radoičić, Marija B., Šaponjić, Zoran, Petković, Marijana, "Light controllable TiO2-Ru nanocomposite system encapsulated in phospholipid unilamellar vesicles for anti-cancer photodynamic therapy" in Optical and Quantum Electronics, 50, no. 6 (2018):232,
https://doi.org/10.1007/s11082-018-1495-z . .
2
1
1

Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins

Nišavić, Marija; Janjić, Goran V.; Hozić, Amela; Petković, Marijana; Milčić, Miloš K.; Vujčić, Zoran; Cindrić, Mario

(2018)

TY  - JOUR
AU  - Nišavić, Marija
AU  - Janjić, Goran V.
AU  - Hozić, Amela
AU  - Petković, Marijana
AU  - Milčić, Miloš K.
AU  - Vujčić, Zoran
AU  - Cindrić, Mario
PY  - 2018
UR  - http://xlink.rsc.org/?DOI=C7MT00330G
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/7615
AB  - Binding of three ruthenium(ii) compounds of general formula mer-[Ru(L3)(N-N)X][Y] (where L3 = 4-chloro-2,2:6,2-terpyridine (Cl-tpy); N-N = 1,2-diaminoethane (en), 1,2-diaminocyclohexane (dach) or 2,2-bipyridine (bipy); X = Cl; Y = Cl) to human serum albumin (HSA) has been investigated by nano-LC/nano-ESI MS and docking studies. A bottom-up proteomics approach has been applied for the structural characterization of metallated proteins and the data were analyzed in both the positive and negative ion mode. The negative ion mode was achieved after the post-column addition of an isopropanol solution of formaldehyde that enabled sample ionization at micro-flow rates. The negative ion mode MS has been proved to be beneficial for the analysis of binding sites on ruthenated protein in terms of ion charge reduction and consequent simplification of target sequence identification based on isotopic differences between ruthenated and non-ruthenated peptides. Moreover, the negative ion mode ESI MS shows the advantage of singly charged ion formation and, unlike MALDI MS, it does not cause complete ligand fragmentation, merging the benefits of each method into a single experiment. Six target sequences were identified for the binding of en and dach compounds, and four sequences for the binding of bipy. All compounds have been found to bind histidine and one aspartate residue. Docking studies showed that the identified sequences are the constituents of five distinct binding sites for en and dach, or two sites for the bipy complex. The selection of binding sites seems to be dependent on the chelate ligand and the form of the complex prior or after hydrolysis of the leaving chloride ligand.
T2  - Metallomics
T1  - Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins
VL  - 10
IS  - 4
SP  - 587
EP  - 594
DO  - 10.1039/C7MT00330G
ER  - 
@article{
author = "Nišavić, Marija and Janjić, Goran V. and Hozić, Amela and Petković, Marijana and Milčić, Miloš K. and Vujčić, Zoran and Cindrić, Mario",
year = "2018",
abstract = "Binding of three ruthenium(ii) compounds of general formula mer-[Ru(L3)(N-N)X][Y] (where L3 = 4-chloro-2,2:6,2-terpyridine (Cl-tpy); N-N = 1,2-diaminoethane (en), 1,2-diaminocyclohexane (dach) or 2,2-bipyridine (bipy); X = Cl; Y = Cl) to human serum albumin (HSA) has been investigated by nano-LC/nano-ESI MS and docking studies. A bottom-up proteomics approach has been applied for the structural characterization of metallated proteins and the data were analyzed in both the positive and negative ion mode. The negative ion mode was achieved after the post-column addition of an isopropanol solution of formaldehyde that enabled sample ionization at micro-flow rates. The negative ion mode MS has been proved to be beneficial for the analysis of binding sites on ruthenated protein in terms of ion charge reduction and consequent simplification of target sequence identification based on isotopic differences between ruthenated and non-ruthenated peptides. Moreover, the negative ion mode ESI MS shows the advantage of singly charged ion formation and, unlike MALDI MS, it does not cause complete ligand fragmentation, merging the benefits of each method into a single experiment. Six target sequences were identified for the binding of en and dach compounds, and four sequences for the binding of bipy. All compounds have been found to bind histidine and one aspartate residue. Docking studies showed that the identified sequences are the constituents of five distinct binding sites for en and dach, or two sites for the bipy complex. The selection of binding sites seems to be dependent on the chelate ligand and the form of the complex prior or after hydrolysis of the leaving chloride ligand.",
journal = "Metallomics",
title = "Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins",
volume = "10",
number = "4",
pages = "587-594",
doi = "10.1039/C7MT00330G"
}
Nišavić, M., Janjić, G. V., Hozić, A., Petković, M., Milčić, M. K., Vujčić, Z.,& Cindrić, M.. (2018). Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins. in Metallomics, 10(4), 587-594.
https://doi.org/10.1039/C7MT00330G
Nišavić M, Janjić GV, Hozić A, Petković M, Milčić MK, Vujčić Z, Cindrić M. Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins. in Metallomics. 2018;10(4):587-594.
doi:10.1039/C7MT00330G .
Nišavić, Marija, Janjić, Goran V., Hozić, Amela, Petković, Marijana, Milčić, Miloš K., Vujčić, Zoran, Cindrić, Mario, "Positive and negative nano-electrospray mass spectrometry of ruthenated serum albumin supported by docking studies: an integrated approach towards defining metallodrug binding sites on proteins" in Metallomics, 10, no. 4 (2018):587-594,
https://doi.org/10.1039/C7MT00330G . .
1
6
6
7

New gold pincer-type complexes: synthesis, characterization, DNA binding studies and cytotoxicity

Radisavljević, Snežana; Bratsos, Ioannis; Scheurer, Andreas; Korzekwa, Jana; Masnikosa, Romana; Tot, Aleksandar; Gligorijević, Nevenka N.; Radulović, Siniša S.; Rilak Simović, Ana

(2018)

TY  - JOUR
AU  - Radisavljević, Snežana
AU  - Bratsos, Ioannis
AU  - Scheurer, Andreas
AU  - Korzekwa, Jana
AU  - Masnikosa, Romana
AU  - Tot, Aleksandar
AU  - Gligorijević, Nevenka N.
AU  - Radulović, Siniša S.
AU  - Rilak Simović, Ana
PY  - 2018
UR  - http://xlink.rsc.org/?DOI=C8DT02903B
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/7894
AB  - With the aim of assessing whether Au(iii) compounds with pincer type ligands might be utilized as potential antitumor agents, three new monofunctional Au(iii) complexes of the general formula [Au(N-N'-N)Cl]Cl-2, where N-N'-N = 2,6-bis(5-tert-butyl-1H-pyrazol-3-yl)pyridine (H2LtBu, 1), 2,6-bis(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)pyridine (Me2LtBu, 2) or 2,6-bis((4S,7R)-1,7,8,8-tetramethyl-4,5,6,7-tetrahydro-1H-4,7-methanoindazol-3-yl)pyridine (Me-2*L, 3) were synthesized. All complexes were characterized by elemental analysis, spectroscopic techniques (IR, UV-Vis, 1D and 2D NMR) and mass spectrometry (MALDI TOF MS). The chemical behavior of the complexes under physiological conditions was studied by UV-Vis spectroscopy, which showed that all compounds were remarkably stable and that the gold center remained in the 3+ oxidation state. The kinetics and the mechanism of the reaction of complexes 1-3 with guanine derivatives (i.e. guanosine (Guo) and guanosine-5-monophosphate (5-GMP)) and calf thymus DNA (CT DNA) were studied by stopped-flow spectroscopy. The three complexes displayed moderately different rate constants in their reactions with Guo, 5-GMP and CT DNA, which can be explained by the steric hindrance and sigma-donicity of the methyl substituent on the bis-pyrazolylpyridine fragment in complexes 2 and 3. The measured enthalpies and entropies of activation (Delta H-not equal > 0, Delta S-not equal < 0) supported an associative mechanism for the substitution process. The interaction of the newly synthesized complexes 1-3 with CT DNA was investigated by UV-Vis and fluorescence spectroscopy, and also by viscosity measurements, which all indicated that complexes 1-3 bound to CT DNA with moderate binding affinity (K-b = 1.6-5.7 x 10(3) M-1) and stabilized the duplex of CT DNA. Molecular docking indicated that complexes 1-3 interacted with DNA via intercalation. Complex 1 reduced the cell survival of all the investigated cell lines (A549, A375, and LS-174) with IC50 values being up to 20 mu M. We have shown that 1 induced perturbations of the cell cycle and led to apoptosis in human melanoma A375 cells. Complex 1 also affected the level of reactive oxygen species (ROS) in the same cells. However, pre-treatment of A375 cells with NAC (ROS scavenger) reversed the effect of 1 on their survival.
T2  - Dalton Transactions
T1  - New gold pincer-type complexes: synthesis, characterization, DNA binding studies and cytotoxicity
VL  - 47
IS  - 38
SP  - 13696
EP  - 13712
DO  - 10.1039/C8DT02903B
ER  - 
@article{
author = "Radisavljević, Snežana and Bratsos, Ioannis and Scheurer, Andreas and Korzekwa, Jana and Masnikosa, Romana and Tot, Aleksandar and Gligorijević, Nevenka N. and Radulović, Siniša S. and Rilak Simović, Ana",
year = "2018",
abstract = "With the aim of assessing whether Au(iii) compounds with pincer type ligands might be utilized as potential antitumor agents, three new monofunctional Au(iii) complexes of the general formula [Au(N-N'-N)Cl]Cl-2, where N-N'-N = 2,6-bis(5-tert-butyl-1H-pyrazol-3-yl)pyridine (H2LtBu, 1), 2,6-bis(5-tert-butyl-1-methyl-1H-pyrazol-3-yl)pyridine (Me2LtBu, 2) or 2,6-bis((4S,7R)-1,7,8,8-tetramethyl-4,5,6,7-tetrahydro-1H-4,7-methanoindazol-3-yl)pyridine (Me-2*L, 3) were synthesized. All complexes were characterized by elemental analysis, spectroscopic techniques (IR, UV-Vis, 1D and 2D NMR) and mass spectrometry (MALDI TOF MS). The chemical behavior of the complexes under physiological conditions was studied by UV-Vis spectroscopy, which showed that all compounds were remarkably stable and that the gold center remained in the 3+ oxidation state. The kinetics and the mechanism of the reaction of complexes 1-3 with guanine derivatives (i.e. guanosine (Guo) and guanosine-5-monophosphate (5-GMP)) and calf thymus DNA (CT DNA) were studied by stopped-flow spectroscopy. The three complexes displayed moderately different rate constants in their reactions with Guo, 5-GMP and CT DNA, which can be explained by the steric hindrance and sigma-donicity of the methyl substituent on the bis-pyrazolylpyridine fragment in complexes 2 and 3. The measured enthalpies and entropies of activation (Delta H-not equal > 0, Delta S-not equal < 0) supported an associative mechanism for the substitution process. The interaction of the newly synthesized complexes 1-3 with CT DNA was investigated by UV-Vis and fluorescence spectroscopy, and also by viscosity measurements, which all indicated that complexes 1-3 bound to CT DNA with moderate binding affinity (K-b = 1.6-5.7 x 10(3) M-1) and stabilized the duplex of CT DNA. Molecular docking indicated that complexes 1-3 interacted with DNA via intercalation. Complex 1 reduced the cell survival of all the investigated cell lines (A549, A375, and LS-174) with IC50 values being up to 20 mu M. We have shown that 1 induced perturbations of the cell cycle and led to apoptosis in human melanoma A375 cells. Complex 1 also affected the level of reactive oxygen species (ROS) in the same cells. However, pre-treatment of A375 cells with NAC (ROS scavenger) reversed the effect of 1 on their survival.",
journal = "Dalton Transactions",
title = "New gold pincer-type complexes: synthesis, characterization, DNA binding studies and cytotoxicity",
volume = "47",
number = "38",
pages = "13696-13712",
doi = "10.1039/C8DT02903B"
}
Radisavljević, S., Bratsos, I., Scheurer, A., Korzekwa, J., Masnikosa, R., Tot, A., Gligorijević, N. N., Radulović, S. S.,& Rilak Simović, A.. (2018). New gold pincer-type complexes: synthesis, characterization, DNA binding studies and cytotoxicity. in Dalton Transactions, 47(38), 13696-13712.
https://doi.org/10.1039/C8DT02903B
Radisavljević S, Bratsos I, Scheurer A, Korzekwa J, Masnikosa R, Tot A, Gligorijević NN, Radulović SS, Rilak Simović A. New gold pincer-type complexes: synthesis, characterization, DNA binding studies and cytotoxicity. in Dalton Transactions. 2018;47(38):13696-13712.
doi:10.1039/C8DT02903B .
Radisavljević, Snežana, Bratsos, Ioannis, Scheurer, Andreas, Korzekwa, Jana, Masnikosa, Romana, Tot, Aleksandar, Gligorijević, Nevenka N., Radulović, Siniša S., Rilak Simović, Ana, "New gold pincer-type complexes: synthesis, characterization, DNA binding studies and cytotoxicity" in Dalton Transactions, 47, no. 38 (2018):13696-13712,
https://doi.org/10.1039/C8DT02903B . .
1
15
17
17

Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry

Janković, Nenad Ž.; Stefanović, Srđan M.; Petronijević, Jelena; Joksimović, Nenad; Novaković, Slađana B.; Bogdanović, Goran A.; Muškinja, Jovana; Vraneš, Milan; Ratković, Zoran; Bugarčić, Zorica M.

(2018)

TY  - JOUR
AU  - Janković, Nenad Ž.
AU  - Stefanović, Srđan M.
AU  - Petronijević, Jelena
AU  - Joksimović, Nenad
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Muškinja, Jovana
AU  - Vraneš, Milan
AU  - Ratković, Zoran
AU  - Bugarčić, Zorica M.
PY  - 2018
UR  - http://pubs.acs.org/doi/10.1021/acssuschemeng.8b03127
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/7886
AB  - The selective synthesis of 5,6-dihydropyrimidin-4(3H)-one scaffold (precursor of dihydrouracil) was a very difficult synthetic challenge that, so far, has not been achieved. For the first time, in this paper, green, selective and high-yields approach to 40 novel 5,6-dihydropyrimidin-4(3H)-ones (DHPMs) by one-pot reaction of aldehydes, Meldrum's acid and isothioureas under solvent-free conditions, in the presence of water, since an additive is presented. In the majority of cases, introduced methodology gave an unprecedented tautomer-selective fashion toward targeted compounds with excellent tautomeric purity (>99.9%), which reached 100% in few cases. The molecular structure of the five compounds has been determined by X-ray crystallography. In each one of them, very short length for the corresponding N2-C1 bond was noticed, making them especially interesting from a structural standpoint. This experimental fact can imply a highly localized electron π density in this part of each heterocyclic ring. The obtained experimental results, which are determined from NMR and ESI-MS study, indicate that this Biginelli-type reaction smoothly proceeds in a one-pot mode, pointing to the three-step tandem process, proceeding via the Knoevenagel, aza-Michael, and retro-Diels-Alder reactions. The presented strategy also had the following advantages: reduction amount of waste, excellent values of green chemistry metrics (cEF, EcoScale and GCIS), and it is the first eco-friendly strategy toward the DHPMs scaffold. © Copyright 2018 American Chemical Society.
T2  - ACS Sustainable Chemistry & Engineering
T1  - Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry
VL  - 6
IS  - 10
SP  - 13358
EP  - 13366
DO  - 10.1021/acssuschemeng.8b03127
ER  - 
@article{
author = "Janković, Nenad Ž. and Stefanović, Srđan M. and Petronijević, Jelena and Joksimović, Nenad and Novaković, Slađana B. and Bogdanović, Goran A. and Muškinja, Jovana and Vraneš, Milan and Ratković, Zoran and Bugarčić, Zorica M.",
year = "2018",
abstract = "The selective synthesis of 5,6-dihydropyrimidin-4(3H)-one scaffold (precursor of dihydrouracil) was a very difficult synthetic challenge that, so far, has not been achieved. For the first time, in this paper, green, selective and high-yields approach to 40 novel 5,6-dihydropyrimidin-4(3H)-ones (DHPMs) by one-pot reaction of aldehydes, Meldrum's acid and isothioureas under solvent-free conditions, in the presence of water, since an additive is presented. In the majority of cases, introduced methodology gave an unprecedented tautomer-selective fashion toward targeted compounds with excellent tautomeric purity (>99.9%), which reached 100% in few cases. The molecular structure of the five compounds has been determined by X-ray crystallography. In each one of them, very short length for the corresponding N2-C1 bond was noticed, making them especially interesting from a structural standpoint. This experimental fact can imply a highly localized electron π density in this part of each heterocyclic ring. The obtained experimental results, which are determined from NMR and ESI-MS study, indicate that this Biginelli-type reaction smoothly proceeds in a one-pot mode, pointing to the three-step tandem process, proceeding via the Knoevenagel, aza-Michael, and retro-Diels-Alder reactions. The presented strategy also had the following advantages: reduction amount of waste, excellent values of green chemistry metrics (cEF, EcoScale and GCIS), and it is the first eco-friendly strategy toward the DHPMs scaffold. © Copyright 2018 American Chemical Society.",
journal = "ACS Sustainable Chemistry & Engineering",
title = "Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry",
volume = "6",
number = "10",
pages = "13358-13366",
doi = "10.1021/acssuschemeng.8b03127"
}
Janković, N. Ž., Stefanović, S. M., Petronijević, J., Joksimović, N., Novaković, S. B., Bogdanović, G. A., Muškinja, J., Vraneš, M., Ratković, Z.,& Bugarčić, Z. M.. (2018). Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry. in ACS Sustainable Chemistry & Engineering, 6(10), 13358-13366.
https://doi.org/10.1021/acssuschemeng.8b03127
Janković NŽ, Stefanović SM, Petronijević J, Joksimović N, Novaković SB, Bogdanović GA, Muškinja J, Vraneš M, Ratković Z, Bugarčić ZM. Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry. in ACS Sustainable Chemistry & Engineering. 2018;6(10):13358-13366.
doi:10.1021/acssuschemeng.8b03127 .
Janković, Nenad Ž., Stefanović, Srđan M., Petronijević, Jelena, Joksimović, Nenad, Novaković, Slađana B., Bogdanović, Goran A., Muškinja, Jovana, Vraneš, Milan, Ratković, Zoran, Bugarčić, Zorica M., "Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry" in ACS Sustainable Chemistry & Engineering, 6, no. 10 (2018):13358-13366,
https://doi.org/10.1021/acssuschemeng.8b03127 . .
5
5

Supporting information for: Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry

Janković, Nenad Ž.; Stefanović, Srđan M.; Petronijević, Jelena; Joksimović, Nenad; Novaković, Slađana B.; Bogdanović, Goran A.; Muškinja, Jovana; Vraneš, Milan; Ratković, Zoran; Bugarčić, Zorica M.

(2018)

TY  - GEN
AU  - Janković, Nenad Ž.
AU  - Stefanović, Srđan M.
AU  - Petronijević, Jelena
AU  - Joksimović, Nenad
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Muškinja, Jovana
AU  - Vraneš, Milan
AU  - Ratković, Zoran
AU  - Bugarčić, Zorica M.
PY  - 2018
UR  - http://pubs.acs.org/doi/10.1021/acssuschemeng.8b03127
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/7886
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/7888
AB  - The selective synthesis of 5,6-dihydropyrimidin-4(3H)-one scaffold (precursor of dihydrouracil) was a very difficult synthetic challenge that, so far, has not been achieved. For the first time, in this paper, green, selective and high-yields approach to 40 novel 5,6-dihydropyrimidin-4(3H)-ones (DHPMs) by one-pot reaction of aldehydes, Meldrum's acid and isothioureas under solvent-free conditions, in the presence of water, since an additive is presented. In the majority of cases, introduced methodology gave an unprecedented tautomer-selective fashion toward targeted compounds with excellent tautomeric purity (>99.9%), which reached 100% in few cases. The molecular structure of the five compounds has been determined by X-ray crystallography. In each one of them, very short length for the corresponding N2-C1 bond was noticed, making them especially interesting from a structural standpoint. This experimental fact can imply a highly localized electron π density in this part of each heterocyclic ring. The obtained experimental results, which are determined from NMR and ESI-MS study, indicate that this Biginelli-type reaction smoothly proceeds in a one-pot mode, pointing to the three-step tandem process, proceeding via the Knoevenagel, aza-Michael, and retro-Diels-Alder reactions. The presented strategy also had the following advantages: reduction amount of waste, excellent values of green chemistry metrics (cEF, EcoScale and GCIS), and it is the first eco-friendly strategy toward the DHPMs scaffold. © Copyright 2018 American Chemical Society.
T2  - ACS Sustainable Chemistry & Engineering
T1  - Supporting information for: Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry
VL  - 6
IS  - 10
SP  - 13358
EP  - 13366
DO  - 10.1021/acssuschemeng.8b03127.s006
ER  - 
@misc{
author = "Janković, Nenad Ž. and Stefanović, Srđan M. and Petronijević, Jelena and Joksimović, Nenad and Novaković, Slađana B. and Bogdanović, Goran A. and Muškinja, Jovana and Vraneš, Milan and Ratković, Zoran and Bugarčić, Zorica M.",
year = "2018",
abstract = "The selective synthesis of 5,6-dihydropyrimidin-4(3H)-one scaffold (precursor of dihydrouracil) was a very difficult synthetic challenge that, so far, has not been achieved. For the first time, in this paper, green, selective and high-yields approach to 40 novel 5,6-dihydropyrimidin-4(3H)-ones (DHPMs) by one-pot reaction of aldehydes, Meldrum's acid and isothioureas under solvent-free conditions, in the presence of water, since an additive is presented. In the majority of cases, introduced methodology gave an unprecedented tautomer-selective fashion toward targeted compounds with excellent tautomeric purity (>99.9%), which reached 100% in few cases. The molecular structure of the five compounds has been determined by X-ray crystallography. In each one of them, very short length for the corresponding N2-C1 bond was noticed, making them especially interesting from a structural standpoint. This experimental fact can imply a highly localized electron π density in this part of each heterocyclic ring. The obtained experimental results, which are determined from NMR and ESI-MS study, indicate that this Biginelli-type reaction smoothly proceeds in a one-pot mode, pointing to the three-step tandem process, proceeding via the Knoevenagel, aza-Michael, and retro-Diels-Alder reactions. The presented strategy also had the following advantages: reduction amount of waste, excellent values of green chemistry metrics (cEF, EcoScale and GCIS), and it is the first eco-friendly strategy toward the DHPMs scaffold. © Copyright 2018 American Chemical Society.",
journal = "ACS Sustainable Chemistry & Engineering",
title = "Supporting information for: Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry",
volume = "6",
number = "10",
pages = "13358-13366",
doi = "10.1021/acssuschemeng.8b03127.s006"
}
Janković, N. Ž., Stefanović, S. M., Petronijević, J., Joksimović, N., Novaković, S. B., Bogdanović, G. A., Muškinja, J., Vraneš, M., Ratković, Z.,& Bugarčić, Z. M.. (2018). Supporting information for: Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry. in ACS Sustainable Chemistry & Engineering, 6(10), 13358-13366.
https://doi.org/10.1021/acssuschemeng.8b03127.s006
Janković NŽ, Stefanović SM, Petronijević J, Joksimović N, Novaković SB, Bogdanović GA, Muškinja J, Vraneš M, Ratković Z, Bugarčić ZM. Supporting information for: Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry. in ACS Sustainable Chemistry & Engineering. 2018;6(10):13358-13366.
doi:10.1021/acssuschemeng.8b03127.s006 .
Janković, Nenad Ž., Stefanović, Srđan M., Petronijević, Jelena, Joksimović, Nenad, Novaković, Slađana B., Bogdanović, Goran A., Muškinja, Jovana, Vraneš, Milan, Ratković, Zoran, Bugarčić, Zorica M., "Supporting information for: Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry" in ACS Sustainable Chemistry & Engineering, 6, no. 10 (2018):13358-13366,
https://doi.org/10.1021/acssuschemeng.8b03127.s006 . .
5
2

High-Efficiency Microflow and Nanoflow Negative Electrospray Ionization of Peptides Induced by Gas-Phase Proton Transfer Reactions

Nišavić, Marija; Hozic, Amela; Hamersak, Zdenko; Radić, Martina; Butorac, Ana; Duvnjak, Marija; Cindrić, Mario

(2017)

TY  - JOUR
AU  - Nišavić, Marija
AU  - Hozic, Amela
AU  - Hamersak, Zdenko
AU  - Radić, Martina
AU  - Butorac, Ana
AU  - Duvnjak, Marija
AU  - Cindrić, Mario
PY  - 2017
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/1552
AB  - Liquid chromatography coupled with electrospray ionization mass spectrometry (ESI-MS) is routinely used in proteomics research. Mass spectrometry-based peptide analysis is performed de facto in positive-ion mode, except for the analysis of some post-translationally modified peptides (e.g., phosphorylation and glycosylation). Collected mass spectrometry data after peptide negative ionization analysis is scarce, because of a lack of negatively charged amino acid side-chain residues that would enable efficient ionization (i.e., on average, every 10th amino acid residue is negatively charged). Also, several phenomena linked to negative ionization, such as corona discharge, arcing, and electrospray destabilization, because of the presence of polar mobile-phase solutions or acidic mobile-phase additives (e.g., formic or trifluoroacetic acid), reduce its use. Named phenomena influence microflow and nanoflow electrospray ionization (ESI) of peptides in a way that prevents the formation of negatively charged peptide ions. In this work, we have investigated the effects of post-column addition of isopropanol solutions of formaldehyde, 2,2-dimethylpropanal, ethyl methanoate, and 2-phenyl-2-oxoethanal as the negative-ion-mode mobile-phase modifiers for the analysis of peptides. According to the obtained data, all four modifiers exhibited significant enhancement of peptide negative ionization, while ethyl methanoate showed the best results. The proposed mechanism of action of the modifiers includes proton transfer reactions through oxonium ion formation. In this way, mobile phase protons are prevented from interfering with the process of negative ionization. To the best of our knowledge, this is the first study that describes the use and reaction mechanism of aforementioned modifiers for enhancement of peptide negative ionization.
T2  - Analytical Chemistry
T1  - High-Efficiency Microflow and Nanoflow Negative Electrospray Ionization of Peptides Induced by Gas-Phase Proton Transfer Reactions
VL  - 89
IS  - 9
SP  - 4847
EP  - 4854
DO  - 10.1021/acs.analchem.6b04466
ER  - 
@article{
author = "Nišavić, Marija and Hozic, Amela and Hamersak, Zdenko and Radić, Martina and Butorac, Ana and Duvnjak, Marija and Cindrić, Mario",
year = "2017",
abstract = "Liquid chromatography coupled with electrospray ionization mass spectrometry (ESI-MS) is routinely used in proteomics research. Mass spectrometry-based peptide analysis is performed de facto in positive-ion mode, except for the analysis of some post-translationally modified peptides (e.g., phosphorylation and glycosylation). Collected mass spectrometry data after peptide negative ionization analysis is scarce, because of a lack of negatively charged amino acid side-chain residues that would enable efficient ionization (i.e., on average, every 10th amino acid residue is negatively charged). Also, several phenomena linked to negative ionization, such as corona discharge, arcing, and electrospray destabilization, because of the presence of polar mobile-phase solutions or acidic mobile-phase additives (e.g., formic or trifluoroacetic acid), reduce its use. Named phenomena influence microflow and nanoflow electrospray ionization (ESI) of peptides in a way that prevents the formation of negatively charged peptide ions. In this work, we have investigated the effects of post-column addition of isopropanol solutions of formaldehyde, 2,2-dimethylpropanal, ethyl methanoate, and 2-phenyl-2-oxoethanal as the negative-ion-mode mobile-phase modifiers for the analysis of peptides. According to the obtained data, all four modifiers exhibited significant enhancement of peptide negative ionization, while ethyl methanoate showed the best results. The proposed mechanism of action of the modifiers includes proton transfer reactions through oxonium ion formation. In this way, mobile phase protons are prevented from interfering with the process of negative ionization. To the best of our knowledge, this is the first study that describes the use and reaction mechanism of aforementioned modifiers for enhancement of peptide negative ionization.",
journal = "Analytical Chemistry",
title = "High-Efficiency Microflow and Nanoflow Negative Electrospray Ionization of Peptides Induced by Gas-Phase Proton Transfer Reactions",
volume = "89",
number = "9",
pages = "4847-4854",
doi = "10.1021/acs.analchem.6b04466"
}
Nišavić, M., Hozic, A., Hamersak, Z., Radić, M., Butorac, A., Duvnjak, M.,& Cindrić, M.. (2017). High-Efficiency Microflow and Nanoflow Negative Electrospray Ionization of Peptides Induced by Gas-Phase Proton Transfer Reactions. in Analytical Chemistry, 89(9), 4847-4854.
https://doi.org/10.1021/acs.analchem.6b04466
Nišavić M, Hozic A, Hamersak Z, Radić M, Butorac A, Duvnjak M, Cindrić M. High-Efficiency Microflow and Nanoflow Negative Electrospray Ionization of Peptides Induced by Gas-Phase Proton Transfer Reactions. in Analytical Chemistry. 2017;89(9):4847-4854.
doi:10.1021/acs.analchem.6b04466 .
Nišavić, Marija, Hozic, Amela, Hamersak, Zdenko, Radić, Martina, Butorac, Ana, Duvnjak, Marija, Cindrić, Mario, "High-Efficiency Microflow and Nanoflow Negative Electrospray Ionization of Peptides Induced by Gas-Phase Proton Transfer Reactions" in Analytical Chemistry, 89, no. 9 (2017):4847-4854,
https://doi.org/10.1021/acs.analchem.6b04466 . .
4
5
4
5

Experimental design for optimizing MALDI-TOF-MS analysis of palladium complexes

Rakić-Kostić, Tijana M.; Bogojeski, Jovana V.; Popović, Iva A.; Nešić, Maja D.; Rajčić, Boris; Nišavić, Marija; Petković, Marijana; Veličković, Suzana

(2017)

TY  - JOUR
AU  - Rakić-Kostić, Tijana M.
AU  - Bogojeski, Jovana V.
AU  - Popović, Iva A.
AU  - Nešić, Maja D.
AU  - Rajčić, Boris
AU  - Nišavić, Marija
AU  - Petković, Marijana
AU  - Veličković, Suzana
PY  - 2017
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/1362
AB  - This paper presents optimization of matrix-assisted laser desorption/ionization (MALDI) time-of-flight (TOF) mass spectrometer (MS) instrumental parameters for the analysis of chloro(2,2 , 2 -terpyridine) palladium(II) chloride dihydrate complex applying design of experiments methodology (DoE). This complex is of interest for potential use in the cancer therapy. DoE methodology was proved to succeed in optimization of many complex analytical problems. However, it has been poorly used for MALDI-TOF-MS optimization up to now. The theoretical mathematical relationships which explain the influence of important experimental factors (laser energy, grid voltage and number of laser shots) on the selected responses (signal to noise - S/N ratio and the resolution - R of the leading peak) is established. The optimal instrumental settings providing maximal S/N and R are identified and experimentally verified.
T2  - Hemijska industrija
T1  - Experimental design for optimizing MALDI-TOF-MS analysis of palladium complexes
VL  - 71
IS  - 4
SP  - 281
EP  - 288
DO  - 10.2298/HEMIND160614038R
ER  - 
@article{
author = "Rakić-Kostić, Tijana M. and Bogojeski, Jovana V. and Popović, Iva A. and Nešić, Maja D. and Rajčić, Boris and Nišavić, Marija and Petković, Marijana and Veličković, Suzana",
year = "2017",
abstract = "This paper presents optimization of matrix-assisted laser desorption/ionization (MALDI) time-of-flight (TOF) mass spectrometer (MS) instrumental parameters for the analysis of chloro(2,2 , 2 -terpyridine) palladium(II) chloride dihydrate complex applying design of experiments methodology (DoE). This complex is of interest for potential use in the cancer therapy. DoE methodology was proved to succeed in optimization of many complex analytical problems. However, it has been poorly used for MALDI-TOF-MS optimization up to now. The theoretical mathematical relationships which explain the influence of important experimental factors (laser energy, grid voltage and number of laser shots) on the selected responses (signal to noise - S/N ratio and the resolution - R of the leading peak) is established. The optimal instrumental settings providing maximal S/N and R are identified and experimentally verified.",
journal = "Hemijska industrija",
title = "Experimental design for optimizing MALDI-TOF-MS analysis of palladium complexes",
volume = "71",
number = "4",
pages = "281-288",
doi = "10.2298/HEMIND160614038R"
}
Rakić-Kostić, T. M., Bogojeski, J. V., Popović, I. A., Nešić, M. D., Rajčić, B., Nišavić, M., Petković, M.,& Veličković, S.. (2017). Experimental design for optimizing MALDI-TOF-MS analysis of palladium complexes. in Hemijska industrija, 71(4), 281-288.
https://doi.org/10.2298/HEMIND160614038R
Rakić-Kostić TM, Bogojeski JV, Popović IA, Nešić MD, Rajčić B, Nišavić M, Petković M, Veličković S. Experimental design for optimizing MALDI-TOF-MS analysis of palladium complexes. in Hemijska industrija. 2017;71(4):281-288.
doi:10.2298/HEMIND160614038R .
Rakić-Kostić, Tijana M., Bogojeski, Jovana V., Popović, Iva A., Nešić, Maja D., Rajčić, Boris, Nišavić, Marija, Petković, Marijana, Veličković, Suzana, "Experimental design for optimizing MALDI-TOF-MS analysis of palladium complexes" in Hemijska industrija, 71, no. 4 (2017):281-288,
https://doi.org/10.2298/HEMIND160614038R . .

New dinuclear palladium(II) complexes: Studies of the nucleophilic substitution reactions, DNA/BSA interactions and cytotoxic activity

Cocic, Dugan; Jovanović, Snežana; Nišavić, Marija; Baskic, Dejan; Todorović, Danijela V.; Popovic, Suzana; Bugarčić, Živadin D.; Petrović, Biljana

(2017)

TY  - JOUR
AU  - Cocic, Dugan
AU  - Jovanović, Snežana
AU  - Nišavić, Marija
AU  - Baskic, Dejan
AU  - Todorović, Danijela V.
AU  - Popovic, Suzana
AU  - Bugarčić, Živadin D.
AU  - Petrović, Biljana
PY  - 2017
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/1758
AB  - Six new dinuclear Pd(II) complexes, [{Pd(2,2-bipy)Cl}(2)(mu-pz)](ClO4)2 (Pd1), [{Pd(dach)Cl}(2)(mu-pz)](ClO4)(2) (Pd2), [{Pd(en)Cl}(2)(mu-pz)] (ClO4)(2) (Pd3), [{Pd(2,2-bipy)Cl}(2)(mu-4,4-bipy)](ClO4)(2) (Pd4), [{Pd(dach)Cl}(2)(mu-4,4-bipy)] (ClO4)(2) (Pd5) and [{Pd(en)Cl-2(mu-4,4-bipy)](ClO4)(2) (Pd6) (where 2,2-bipy = 2,2-bipyridyl, pz = pyrazine, dach = trans-(+/-)-1,2-diaminocyclohexane, en = ethylenediamine, 4,4-bipy = 4,4-bipyridyl) have been synthesized and characterized by elemental microanalysis, IR, H-1 NMR and MALDI-TOF mass spectrometry. The pK(a) values of corresponding diaqua complexes were determined by spectrophotometric pH titration. Substitution reactions with thiourea (Tu), L-methionine (L-Met), L-cysteine (L-Cys), L-histidine (L-His) and guanosine-5-monophosphate (5-GMP) were studied under the pseudo-first order conditions at pH 7.2. Reactions of Pdl with Tu, L-Met and L-Cys were followed by decomposition of complexes, while structures of dinuclear complexes were preserved during the substitution with nitrogen donors. Interactions with calf-thymus DNA (CT DNA) were followed by absorption spectroscopy and fluorescence quenching measurements. All complexes can bind to CT-DNA exhibiting high intrinsic binding constants (K-b = 10(4)-10(5) M-1). Competitive studies with ethidium bromide (EB) have shown that complexes can displace DNA-bound EB. High values of binding constants towards bovine serum albumin protein (BSA) indicate good binding affinity. Finally, all complexes showed moderate to high cytotoxic activity against HeLa (human cervical epithelial carcinoma cell lines) and MDA-MB-231 (human breast epithelial carcinoma cell lines) tumor cell lines inducing apoptotic type cell death, whereas normal fibroblasts were significantly less sensitive. The impact on cell cycle of these cells was distinctive, where Pd4, Pd5 and Pd6 showed the most prominent effect arresting MDA-MB-231 (human lung fibroblast cell lines) cell in G1/S phase of cell cycle.
T2  - Journal of Inorganic Biochemistry
T1  - New dinuclear palladium(II) complexes: Studies of the nucleophilic substitution reactions, DNA/BSA interactions and cytotoxic activity
VL  - 175
SP  - 67
EP  - 79
DO  - 10.1016/j.jinorgbio.2017.07.009
ER  - 
@article{
author = "Cocic, Dugan and Jovanović, Snežana and Nišavić, Marija and Baskic, Dejan and Todorović, Danijela V. and Popovic, Suzana and Bugarčić, Živadin D. and Petrović, Biljana",
year = "2017",
abstract = "Six new dinuclear Pd(II) complexes, [{Pd(2,2-bipy)Cl}(2)(mu-pz)](ClO4)2 (Pd1), [{Pd(dach)Cl}(2)(mu-pz)](ClO4)(2) (Pd2), [{Pd(en)Cl}(2)(mu-pz)] (ClO4)(2) (Pd3), [{Pd(2,2-bipy)Cl}(2)(mu-4,4-bipy)](ClO4)(2) (Pd4), [{Pd(dach)Cl}(2)(mu-4,4-bipy)] (ClO4)(2) (Pd5) and [{Pd(en)Cl-2(mu-4,4-bipy)](ClO4)(2) (Pd6) (where 2,2-bipy = 2,2-bipyridyl, pz = pyrazine, dach = trans-(+/-)-1,2-diaminocyclohexane, en = ethylenediamine, 4,4-bipy = 4,4-bipyridyl) have been synthesized and characterized by elemental microanalysis, IR, H-1 NMR and MALDI-TOF mass spectrometry. The pK(a) values of corresponding diaqua complexes were determined by spectrophotometric pH titration. Substitution reactions with thiourea (Tu), L-methionine (L-Met), L-cysteine (L-Cys), L-histidine (L-His) and guanosine-5-monophosphate (5-GMP) were studied under the pseudo-first order conditions at pH 7.2. Reactions of Pdl with Tu, L-Met and L-Cys were followed by decomposition of complexes, while structures of dinuclear complexes were preserved during the substitution with nitrogen donors. Interactions with calf-thymus DNA (CT DNA) were followed by absorption spectroscopy and fluorescence quenching measurements. All complexes can bind to CT-DNA exhibiting high intrinsic binding constants (K-b = 10(4)-10(5) M-1). Competitive studies with ethidium bromide (EB) have shown that complexes can displace DNA-bound EB. High values of binding constants towards bovine serum albumin protein (BSA) indicate good binding affinity. Finally, all complexes showed moderate to high cytotoxic activity against HeLa (human cervical epithelial carcinoma cell lines) and MDA-MB-231 (human breast epithelial carcinoma cell lines) tumor cell lines inducing apoptotic type cell death, whereas normal fibroblasts were significantly less sensitive. The impact on cell cycle of these cells was distinctive, where Pd4, Pd5 and Pd6 showed the most prominent effect arresting MDA-MB-231 (human lung fibroblast cell lines) cell in G1/S phase of cell cycle.",
journal = "Journal of Inorganic Biochemistry",
title = "New dinuclear palladium(II) complexes: Studies of the nucleophilic substitution reactions, DNA/BSA interactions and cytotoxic activity",
volume = "175",
pages = "67-79",
doi = "10.1016/j.jinorgbio.2017.07.009"
}
Cocic, D., Jovanović, S., Nišavić, M., Baskic, D., Todorović, D. V., Popovic, S., Bugarčić, Ž. D.,& Petrović, B.. (2017). New dinuclear palladium(II) complexes: Studies of the nucleophilic substitution reactions, DNA/BSA interactions and cytotoxic activity. in Journal of Inorganic Biochemistry, 175, 67-79.
https://doi.org/10.1016/j.jinorgbio.2017.07.009
Cocic D, Jovanović S, Nišavić M, Baskic D, Todorović DV, Popovic S, Bugarčić ŽD, Petrović B. New dinuclear palladium(II) complexes: Studies of the nucleophilic substitution reactions, DNA/BSA interactions and cytotoxic activity. in Journal of Inorganic Biochemistry. 2017;175:67-79.
doi:10.1016/j.jinorgbio.2017.07.009 .
Cocic, Dugan, Jovanović, Snežana, Nišavić, Marija, Baskic, Dejan, Todorović, Danijela V., Popovic, Suzana, Bugarčić, Živadin D., Petrović, Biljana, "New dinuclear palladium(II) complexes: Studies of the nucleophilic substitution reactions, DNA/BSA interactions and cytotoxic activity" in Journal of Inorganic Biochemistry, 175 (2017):67-79,
https://doi.org/10.1016/j.jinorgbio.2017.07.009 . .
23
26
27

Determination of isotopic distribution of lead by a matrix assisted laser desorption/ionization versus a laser desorption/ionization time of flight mass spectrometry

Kamceva, Tina T.; Nešić, Maja D.; Stoiljković, Milovan; Popović, Iva A.; Miletić, Jadranka; Rajčić, Boris; Petković, Marijana; Veličković, Suzana

(2017)

TY  - JOUR
AU  - Kamceva, Tina T.
AU  - Nešić, Maja D.
AU  - Stoiljković, Milovan
AU  - Popović, Iva A.
AU  - Miletić, Jadranka
AU  - Rajčić, Boris
AU  - Petković, Marijana
AU  - Veličković, Suzana
PY  - 2017
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/1471
AB  - In this work it has been shown that both the laser desorption/ionization mass spectrometry (LDI MS) and the matrix assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI TOF MS) are the simple and quick methods for determination of relative natural isotopic distribution of lead. The analysis of metal salts with these approaches does not require any time-consuming preparation of samples: a single run can take only a minute, and numerous information can be obtained. Results obtained in this work show that chosen matrix has no negative effect on quantitative determination of lead isotopes and support once more the applicability of MALDI TOF MS for lead isotope distribution determination in the sample and accurate data are obtained. Additionally, the generation of PbnOn and PbnOn-1 (n: 2-6) clusters have been successfully achieved in the positive mode, using the both LDI and MALDI methods. All stoichiometries were confirmed using isotopic pattern modelling.
T2  - Hemijska industrija
T1  - Determination of isotopic distribution of lead by a matrix assisted laser desorption/ionization versus a laser desorption/ionization time of flight mass spectrometry
VL  - 71
IS  - 1
SP  - 19
EP  - 26
DO  - 10.2298/HEMIND151218013K
ER  - 
@article{
author = "Kamceva, Tina T. and Nešić, Maja D. and Stoiljković, Milovan and Popović, Iva A. and Miletić, Jadranka and Rajčić, Boris and Petković, Marijana and Veličković, Suzana",
year = "2017",
abstract = "In this work it has been shown that both the laser desorption/ionization mass spectrometry (LDI MS) and the matrix assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI TOF MS) are the simple and quick methods for determination of relative natural isotopic distribution of lead. The analysis of metal salts with these approaches does not require any time-consuming preparation of samples: a single run can take only a minute, and numerous information can be obtained. Results obtained in this work show that chosen matrix has no negative effect on quantitative determination of lead isotopes and support once more the applicability of MALDI TOF MS for lead isotope distribution determination in the sample and accurate data are obtained. Additionally, the generation of PbnOn and PbnOn-1 (n: 2-6) clusters have been successfully achieved in the positive mode, using the both LDI and MALDI methods. All stoichiometries were confirmed using isotopic pattern modelling.",
journal = "Hemijska industrija",
title = "Determination of isotopic distribution of lead by a matrix assisted laser desorption/ionization versus a laser desorption/ionization time of flight mass spectrometry",
volume = "71",
number = "1",
pages = "19-26",
doi = "10.2298/HEMIND151218013K"
}
Kamceva, T. T., Nešić, M. D., Stoiljković, M., Popović, I. A., Miletić, J., Rajčić, B., Petković, M.,& Veličković, S.. (2017). Determination of isotopic distribution of lead by a matrix assisted laser desorption/ionization versus a laser desorption/ionization time of flight mass spectrometry. in Hemijska industrija, 71(1), 19-26.
https://doi.org/10.2298/HEMIND151218013K
Kamceva TT, Nešić MD, Stoiljković M, Popović IA, Miletić J, Rajčić B, Petković M, Veličković S. Determination of isotopic distribution of lead by a matrix assisted laser desorption/ionization versus a laser desorption/ionization time of flight mass spectrometry. in Hemijska industrija. 2017;71(1):19-26.
doi:10.2298/HEMIND151218013K .
Kamceva, Tina T., Nešić, Maja D., Stoiljković, Milovan, Popović, Iva A., Miletić, Jadranka, Rajčić, Boris, Petković, Marijana, Veličković, Suzana, "Determination of isotopic distribution of lead by a matrix assisted laser desorption/ionization versus a laser desorption/ionization time of flight mass spectrometry" in Hemijska industrija, 71, no. 1 (2017):19-26,
https://doi.org/10.2298/HEMIND151218013K . .
1
1

Light controlled metallo-drug delivery system based on the TiO(2-)nanoparticles and Ru-complex

Nešić, Maja A.; Žakula, Jelena; Korićanac, Lela; Stepić, Milutin; Radoičić, Marija B.; Popović, Iva A.; Šaponjić, Zoran; Petković, Marijana

(2017)

TY  - JOUR
AU  - Nešić, Maja A.
AU  - Žakula, Jelena
AU  - Korićanac, Lela
AU  - Stepić, Milutin
AU  - Radoičić, Marija B.
AU  - Popović, Iva A.
AU  - Šaponjić, Zoran
AU  - Petković, Marijana
PY  - 2017
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/1747
AB  - We studied the colloidal TiO2 nanoparticles as a carrier for controlled delivery of the ruthenium complex to the melanoma cell line. The system demonstrated slower complex release upon visible and increased release rate upon UV light illumination. Accordingly, the light-dependent cytotoxicity of the system was demonstrated on amelanotic melanoma cancer line. The cell death is enhanced by UV and reduced by red light in the presence of investigated nanocomposite system. Both components of the system may act as photosensitizers, by generating reactive oxygen species, which promote cell death. Thus, the system might act dually, as photodynamic therapeutic agent and as the light tunable system for metallo-drug delivery and it might be of interest for development of new more efficient drug delivery approaches by using a light as external stimulus. (C) 2017 Elsevier B.V. All rights reserved.
T2  - Journal of Photochemistry and Photobiology. A: Chemistry
T1  - Light controlled metallo-drug delivery system based on the TiO(2-)nanoparticles and Ru-complex
VL  - 347
SP  - 55
EP  - 66
DO  - 10.1016/jjphotochem.2017.06.045
ER  - 
@article{
author = "Nešić, Maja A. and Žakula, Jelena and Korićanac, Lela and Stepić, Milutin and Radoičić, Marija B. and Popović, Iva A. and Šaponjić, Zoran and Petković, Marijana",
year = "2017",
abstract = "We studied the colloidal TiO2 nanoparticles as a carrier for controlled delivery of the ruthenium complex to the melanoma cell line. The system demonstrated slower complex release upon visible and increased release rate upon UV light illumination. Accordingly, the light-dependent cytotoxicity of the system was demonstrated on amelanotic melanoma cancer line. The cell death is enhanced by UV and reduced by red light in the presence of investigated nanocomposite system. Both components of the system may act as photosensitizers, by generating reactive oxygen species, which promote cell death. Thus, the system might act dually, as photodynamic therapeutic agent and as the light tunable system for metallo-drug delivery and it might be of interest for development of new more efficient drug delivery approaches by using a light as external stimulus. (C) 2017 Elsevier B.V. All rights reserved.",
journal = "Journal of Photochemistry and Photobiology. A: Chemistry",
title = "Light controlled metallo-drug delivery system based on the TiO(2-)nanoparticles and Ru-complex",
volume = "347",
pages = "55-66",
doi = "10.1016/jjphotochem.2017.06.045"
}
Nešić, M. A., Žakula, J., Korićanac, L., Stepić, M., Radoičić, M. B., Popović, I. A., Šaponjić, Z.,& Petković, M.. (2017). Light controlled metallo-drug delivery system based on the TiO(2-)nanoparticles and Ru-complex. in Journal of Photochemistry and Photobiology. A: Chemistry, 347, 55-66.
https://doi.org/10.1016/jjphotochem.2017.06.045
Nešić MA, Žakula J, Korićanac L, Stepić M, Radoičić MB, Popović IA, Šaponjić Z, Petković M. Light controlled metallo-drug delivery system based on the TiO(2-)nanoparticles and Ru-complex. in Journal of Photochemistry and Photobiology. A: Chemistry. 2017;347:55-66.
doi:10.1016/jjphotochem.2017.06.045 .
Nešić, Maja A., Žakula, Jelena, Korićanac, Lela, Stepić, Milutin, Radoičić, Marija B., Popović, Iva A., Šaponjić, Zoran, Petković, Marijana, "Light controlled metallo-drug delivery system based on the TiO(2-)nanoparticles and Ru-complex" in Journal of Photochemistry and Photobiology. A: Chemistry, 347 (2017):55-66,
https://doi.org/10.1016/jjphotochem.2017.06.045 . .
9

Ispitivanje primene neorganskih supstrata na bazi nanokristala TiO2 za detekciju i kvantifikaciju malih molekula SALDI TOF masenom spektrometrijom

Popović, Iva A.

(Универзитет у Крагујевцу, Природно-математички факултет, 2017)

TY  - THES
AU  - Popović, Iva A.
PY  - 2017
UR  - http://eteze.kg.ac.rs/application/showtheses?thesesId=4617
UR  - https://fedorakg.kg.ac.rs/fedora/get/o:752/bdef:Content/download
UR  - http://nardus.mpn.gov.rs/123456789/7630
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/7310
AB  - Izvod: MALDI TOF (Matrix Assisted Laser Desorption and Ionization Time-Of-Flight) masenaspektrometrija je meka jonizaciona tehnika koja se prvenstveno koristi za analizubiomolekula (proteina i nukleinskih kiselina) i omogućava detekciju molekula uzveoma nizak stepen fragmentacije. Kako bi se sprečila/ublažila fragmentacijaizazvana direktnom ekscitacijom laserom, uzorak se meša sa matricama koje imajuvisok apsorpcioni koeficijent u oblasti u kojoj laser emituje. Primarno su sekoristile organske, „tradicionalne“ matrice. Pored brojnih prednosti, organskematrice pokazuju i značajne mane koje onemogućavaju primenu MALDI masenespektrometrije za kvantitativnu analizu molekula i sprečavaju detekciju molekulamalih masa manjih od 1000 Da. Kako se u ovoj grupi molekula nalaze i različitibiološki značajni molekuli (metaboliti) postoji potreba za prevazilaženjemnedostataka organskih matrica.Jedan od najranije primenjenih načina je zamena organskih matrica neorganskimjedinjenjima i/ili nanočesticama (supstratima). Koriste se različiti supstrati nabazi ugljeničnih polimera i sol-gel polimerne strukture na bazi silicijum dioksida.Upotreba nanostrukturnih supstrata u metodi koja je nazvana SALDI (Surface AssistedLaser Desorption and Ionization) u poslednjoj deceniji je predmet velikog brojapublikovanih radova. Međutim, nanočestice od metala i oksida metala, kao što su Au,Pt, Ag, ZnO, Fe i MnO2/MnO3, nude prednost u odnosu na ostale materijale - stabilnijesu u vazduhu i poseduju visoku provodljivost. Prednost nanočestica je apsorpcijaenergije lasera i efikasan prenos energije do uzorka. Istakle su se nanočestice odtitan(IV)-oksida zbog svoje dostupnosti, netoksičnosti i niske cene, što je takođepredmet mnogih publikovanih radova. Osim navedenih osobina, titan(IV)-oksid jepoluprovodnik sa dobrom UV apsorpcijom. Generalno, TiO2 snažno apsorbuje UVsvetlost (ima znatnu širinu energetske barijere, 3,2 eV) azotnog lasera koji se koristiu MALDI TOF masenoj spektrometriji, ali proces pripreme nanočestica TiO2verovatno ima snažan uticaj na apsorpciju jer ona zavisi od veličine, oblika i sastavačestica. Površina, a posredno i veličina i oblik kristala utiču na analitičkeperformanse i jonizacionu efikasnost u SALDI masenoj spektrometriji.U ovoj doktorskoj disertaciji korišćeni su nanokristali TiO2 različite veličinei oblika: koloidne nanočestice TiO2 (TiO2 NČ) prosečnog dijametra 5 nm, elipsoidnenanočestice TiO2 (TiO2 ENČ) dužine 40-50 nm, lateralne dimenzije 14-16 nm inanotube TiO2 (TiO2 NT) dužine od 100 do 150 nm i prosečnog dijametra od 11 nm.Molekuli na kojima je bila testirana potencijalna primena nanokristala su biološkiaktivni molekuli malih masa: amino-kiseline (L-cistein, L-alanin, DL-metionin),tripeptid glutation, polni steroidni hormoni (estradiol, testosteron, progesteron),ugljeni hidrati (D-(+)-glukoza, D-(+)-maltoza, rafinoza, arabinoza, β-ciklodekstrin),limunska kiselina, deksametazon (deksazon), vitamini (vitamin A i vitamin E).
AB  - Summary:MALDI TOF (Matrix-Assisted Laser Desorption and Ionization Time-Of-Flight) massspectrometry is soft ionization technique. Primarily, this technique was used for the analysis ofbiomolecules such as proteins and nucleic acids with low level of their fragmentation. In orderto prevent/reduce fragmentation of analyzed molecules, induced with direct excitation withlaser, samples are mixed with matrix molecules. Matrix has high absorption coefficient in therange of the laser emission. In spite of numerous advantages, there are serious drawbacks ofthe matrices, and because of that they cannot be used for quantitative MALDI massspectrometric analysis and for the detection of small molecules (molecular mass less than 1000Da). In this group of molecules (mass less than 1000 Da) there are various biologically activemolecules (metabolites), so there is a great need to overcome disadvantages of the applicationof organic matrices.Considerable efforts have been made to overcome the above mention problems andseveral alternative approaches have been developed: an organic-matrix-free approach in whichthe substrates, usually nanoparticles act as a matrix. Many are in use: graphite, silica gel, carbonpowder, activated carbon, graphene, porous silicon, and many more.The term SALDI (Surface-Assisted Laser Desorption and Ionization) was coined todesignate the techniques that use nanostructured substrates. The use of various nanoparticlesas substrates in SALDI MS has attracted a lot of attention in the last decade. Nanoparticlesabsorb the laser energy and then rapidly transfer to analyzed molecule. However, the substratesprepared from materials based on metal-oxides (Аu, Pt, Ag, ZnO, Fe and MnO2/MnO3) aremore stable in the air and have a high conductivity. Titanium(IV)-oxide (TiO2) is consideredto be a good candidate for SALDI substrate since it is readily available, chemically stable, nontoxicand inexpensive material. Titanium(IV)-oxide is a semiconductor with high absorptivityof UV light of nitrogen laser (have a large band gap 3.2 eV) which is used in MALDI TOFmass spectrometry, but the method of synthesis of TiO2 nanocrystal have a great impact onabsorption because this phenomena depends on size, shape and composition of nanoparticles.In this doctoral thesis, the applicability of TiO2 nanocrystals of different size and shape wastested. Colloidal TiO2 nanoparticles (NPs, average diameter ~ 5 nm), TiO2 prolatenanospheroids (PNSs, length: 40–50 nm, the lateral dimension: 14–16 nm) and TiO2 nanotubes(NTs, length: 100-150 nm, average diameter 11 nm) were used as substrates for potentialSALDI TOF MS quantitative analysis of low mass molecules. The analyzed molecules werebiologically active molecules with small molecule mass (Mm less than 1000 Da): amino acids(L-cysteine, L-alanine, DL-methionine), tripeptide glutathione, sex steroid hormones (estradiol,testosterone, progesterone), carbohydrates (D-(+)-glucose, D-(+)-maltose, raffinose, arabinose,β-cyclodextrin), citric acid, dexamethasone (dexasone), vitamins (vitamin А and vitamin Е).
PB  - Универзитет у Крагујевцу, Природно-математички факултет
T2  - Универзитет у Крагујевцу
T1  - Ispitivanje primene neorganskih supstrata na bazi nanokristala TiO2 za detekciju i kvantifikaciju malih molekula SALDI TOF masenom spektrometrijom
ER  - 
@phdthesis{
author = "Popović, Iva A.",
year = "2017",
abstract = "Izvod: MALDI TOF (Matrix Assisted Laser Desorption and Ionization Time-Of-Flight) masenaspektrometrija je meka jonizaciona tehnika koja se prvenstveno koristi za analizubiomolekula (proteina i nukleinskih kiselina) i omogućava detekciju molekula uzveoma nizak stepen fragmentacije. Kako bi se sprečila/ublažila fragmentacijaizazvana direktnom ekscitacijom laserom, uzorak se meša sa matricama koje imajuvisok apsorpcioni koeficijent u oblasti u kojoj laser emituje. Primarno su sekoristile organske, „tradicionalne“ matrice. Pored brojnih prednosti, organskematrice pokazuju i značajne mane koje onemogućavaju primenu MALDI masenespektrometrije za kvantitativnu analizu molekula i sprečavaju detekciju molekulamalih masa manjih od 1000 Da. Kako se u ovoj grupi molekula nalaze i različitibiološki značajni molekuli (metaboliti) postoji potreba za prevazilaženjemnedostataka organskih matrica.Jedan od najranije primenjenih načina je zamena organskih matrica neorganskimjedinjenjima i/ili nanočesticama (supstratima). Koriste se različiti supstrati nabazi ugljeničnih polimera i sol-gel polimerne strukture na bazi silicijum dioksida.Upotreba nanostrukturnih supstrata u metodi koja je nazvana SALDI (Surface AssistedLaser Desorption and Ionization) u poslednjoj deceniji je predmet velikog brojapublikovanih radova. Međutim, nanočestice od metala i oksida metala, kao što su Au,Pt, Ag, ZnO, Fe i MnO2/MnO3, nude prednost u odnosu na ostale materijale - stabilnijesu u vazduhu i poseduju visoku provodljivost. Prednost nanočestica je apsorpcijaenergije lasera i efikasan prenos energije do uzorka. Istakle su se nanočestice odtitan(IV)-oksida zbog svoje dostupnosti, netoksičnosti i niske cene, što je takođepredmet mnogih publikovanih radova. Osim navedenih osobina, titan(IV)-oksid jepoluprovodnik sa dobrom UV apsorpcijom. Generalno, TiO2 snažno apsorbuje UVsvetlost (ima znatnu širinu energetske barijere, 3,2 eV) azotnog lasera koji se koristiu MALDI TOF masenoj spektrometriji, ali proces pripreme nanočestica TiO2verovatno ima snažan uticaj na apsorpciju jer ona zavisi od veličine, oblika i sastavačestica. Površina, a posredno i veličina i oblik kristala utiču na analitičkeperformanse i jonizacionu efikasnost u SALDI masenoj spektrometriji.U ovoj doktorskoj disertaciji korišćeni su nanokristali TiO2 različite veličinei oblika: koloidne nanočestice TiO2 (TiO2 NČ) prosečnog dijametra 5 nm, elipsoidnenanočestice TiO2 (TiO2 ENČ) dužine 40-50 nm, lateralne dimenzije 14-16 nm inanotube TiO2 (TiO2 NT) dužine od 100 do 150 nm i prosečnog dijametra od 11 nm.Molekuli na kojima je bila testirana potencijalna primena nanokristala su biološkiaktivni molekuli malih masa: amino-kiseline (L-cistein, L-alanin, DL-metionin),tripeptid glutation, polni steroidni hormoni (estradiol, testosteron, progesteron),ugljeni hidrati (D-(+)-glukoza, D-(+)-maltoza, rafinoza, arabinoza, β-ciklodekstrin),limunska kiselina, deksametazon (deksazon), vitamini (vitamin A i vitamin E)., Summary:MALDI TOF (Matrix-Assisted Laser Desorption and Ionization Time-Of-Flight) massspectrometry is soft ionization technique. Primarily, this technique was used for the analysis ofbiomolecules such as proteins and nucleic acids with low level of their fragmentation. In orderto prevent/reduce fragmentation of analyzed molecules, induced with direct excitation withlaser, samples are mixed with matrix molecules. Matrix has high absorption coefficient in therange of the laser emission. In spite of numerous advantages, there are serious drawbacks ofthe matrices, and because of that they cannot be used for quantitative MALDI massspectrometric analysis and for the detection of small molecules (molecular mass less than 1000Da). In this group of molecules (mass less than 1000 Da) there are various biologically activemolecules (metabolites), so there is a great need to overcome disadvantages of the applicationof organic matrices.Considerable efforts have been made to overcome the above mention problems andseveral alternative approaches have been developed: an organic-matrix-free approach in whichthe substrates, usually nanoparticles act as a matrix. Many are in use: graphite, silica gel, carbonpowder, activated carbon, graphene, porous silicon, and many more.The term SALDI (Surface-Assisted Laser Desorption and Ionization) was coined todesignate the techniques that use nanostructured substrates. The use of various nanoparticlesas substrates in SALDI MS has attracted a lot of attention in the last decade. Nanoparticlesabsorb the laser energy and then rapidly transfer to analyzed molecule. However, the substratesprepared from materials based on metal-oxides (Аu, Pt, Ag, ZnO, Fe and MnO2/MnO3) aremore stable in the air and have a high conductivity. Titanium(IV)-oxide (TiO2) is consideredto be a good candidate for SALDI substrate since it is readily available, chemically stable, nontoxicand inexpensive material. Titanium(IV)-oxide is a semiconductor with high absorptivityof UV light of nitrogen laser (have a large band gap 3.2 eV) which is used in MALDI TOFmass spectrometry, but the method of synthesis of TiO2 nanocrystal have a great impact onabsorption because this phenomena depends on size, shape and composition of nanoparticles.In this doctoral thesis, the applicability of TiO2 nanocrystals of different size and shape wastested. Colloidal TiO2 nanoparticles (NPs, average diameter ~ 5 nm), TiO2 prolatenanospheroids (PNSs, length: 40–50 nm, the lateral dimension: 14–16 nm) and TiO2 nanotubes(NTs, length: 100-150 nm, average diameter 11 nm) were used as substrates for potentialSALDI TOF MS quantitative analysis of low mass molecules. The analyzed molecules werebiologically active molecules with small molecule mass (Mm less than 1000 Da): amino acids(L-cysteine, L-alanine, DL-methionine), tripeptide glutathione, sex steroid hormones (estradiol,testosterone, progesterone), carbohydrates (D-(+)-glucose, D-(+)-maltose, raffinose, arabinose,β-cyclodextrin), citric acid, dexamethasone (dexasone), vitamins (vitamin А and vitamin Е).",
publisher = "Универзитет у Крагујевцу, Природно-математички факултет",
journal = "Универзитет у Крагујевцу",
title = "Ispitivanje primene neorganskih supstrata na bazi nanokristala TiO2 za detekciju i kvantifikaciju malih molekula SALDI TOF masenom spektrometrijom"
}
Popović, I. A.. (2017). Ispitivanje primene neorganskih supstrata na bazi nanokristala TiO2 za detekciju i kvantifikaciju malih molekula SALDI TOF masenom spektrometrijom. in Универзитет у Крагујевцу
Универзитет у Крагујевцу, Природно-математички факултет..
Popović IA. Ispitivanje primene neorganskih supstrata na bazi nanokristala TiO2 za detekciju i kvantifikaciju malih molekula SALDI TOF masenom spektrometrijom. in Универзитет у Крагујевцу. 2017;..
Popović, Iva A., "Ispitivanje primene neorganskih supstrata na bazi nanokristala TiO2 za detekciju i kvantifikaciju malih molekula SALDI TOF masenom spektrometrijom" in Универзитет у Крагујевцу (2017).

An enolate ion as a synthon in biocatalytic synthesis of 3,4-dihydro-2(1H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones: lemon juice as an alternative to hazardous solvents and catalysts

Petronijević, Jelena; Bugarcic, Zorica; Bogdanović, Goran A.; Stefanovic, Srdan; Jankovic, Nenad

(2017)

TY  - JOUR
AU  - Petronijević, Jelena
AU  - Bugarcic, Zorica
AU  - Bogdanović, Goran A.
AU  - Stefanovic, Srdan
AU  - Jankovic, Nenad
PY  - 2017
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/1444
AB  - Innovative, efficient, clean, experimentally simple and environmentally friendly one-pot biocatalytic synthesis of two small libraries of 3,4-dihydro-2(1H)-quinoxalinones (4a-m) and 3,4-dihydro-1,4-benzoxazin-2-ones (5a, 5b, 5f and 5k-o) by heterocyclization of ethyl 2-hydroxy-4-alkyl(aryl)-4-oxo-2-butenoates (1a-o) or their corresponding salts (1a-o) with o-phenylenediamine (2) or o-aminophenol (3) in lemon juice as a solvent and a catalyst is presented. In all reactions where esters 1a-o are used for 24 h, very good-to-excellent yields were achieved, but the best yield was realized in the synthesis of 5a (97%) from 3 and 1a. The use of enolate salts (1a-o) instead of the corresponding esters 1a-o significantly reduced the reaction time (up to 6 h) and good-to-excellent yields were achieved. Groups with electron-donating or -withdrawing effects at the aromatic ring of the ester did not have significant influences on the yield of targeted products. In addition, several selected 3,4-dihydro-2(1H)-quinoxalinones and 3,4dihydro-1,4-benzoxazin-2-ones on a gram-scale in the yields up to 92% were synthesized. The presented synthetic strategy has produced smaller amount of waste without by-products and with excellent values of green chemistry metrics (atom efficiency, reaction mass efficiency, E-factor and EcoScale).
T2  - Green Chemistry
T1  - An enolate ion as a synthon in biocatalytic synthesis of 3,4-dihydro-2(1H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones: lemon juice as an alternative to hazardous solvents and catalysts
VL  - 19
IS  - 3
SP  - 707
EP  - 715
DO  - 10.1039/c6gc02893d
ER  - 
@article{
author = "Petronijević, Jelena and Bugarcic, Zorica and Bogdanović, Goran A. and Stefanovic, Srdan and Jankovic, Nenad",
year = "2017",
abstract = "Innovative, efficient, clean, experimentally simple and environmentally friendly one-pot biocatalytic synthesis of two small libraries of 3,4-dihydro-2(1H)-quinoxalinones (4a-m) and 3,4-dihydro-1,4-benzoxazin-2-ones (5a, 5b, 5f and 5k-o) by heterocyclization of ethyl 2-hydroxy-4-alkyl(aryl)-4-oxo-2-butenoates (1a-o) or their corresponding salts (1a-o) with o-phenylenediamine (2) or o-aminophenol (3) in lemon juice as a solvent and a catalyst is presented. In all reactions where esters 1a-o are used for 24 h, very good-to-excellent yields were achieved, but the best yield was realized in the synthesis of 5a (97%) from 3 and 1a. The use of enolate salts (1a-o) instead of the corresponding esters 1a-o significantly reduced the reaction time (up to 6 h) and good-to-excellent yields were achieved. Groups with electron-donating or -withdrawing effects at the aromatic ring of the ester did not have significant influences on the yield of targeted products. In addition, several selected 3,4-dihydro-2(1H)-quinoxalinones and 3,4dihydro-1,4-benzoxazin-2-ones on a gram-scale in the yields up to 92% were synthesized. The presented synthetic strategy has produced smaller amount of waste without by-products and with excellent values of green chemistry metrics (atom efficiency, reaction mass efficiency, E-factor and EcoScale).",
journal = "Green Chemistry",
title = "An enolate ion as a synthon in biocatalytic synthesis of 3,4-dihydro-2(1H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones: lemon juice as an alternative to hazardous solvents and catalysts",
volume = "19",
number = "3",
pages = "707-715",
doi = "10.1039/c6gc02893d"
}
Petronijević, J., Bugarcic, Z., Bogdanović, G. A., Stefanovic, S.,& Jankovic, N.. (2017). An enolate ion as a synthon in biocatalytic synthesis of 3,4-dihydro-2(1H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones: lemon juice as an alternative to hazardous solvents and catalysts. in Green Chemistry, 19(3), 707-715.
https://doi.org/10.1039/c6gc02893d
Petronijević J, Bugarcic Z, Bogdanović GA, Stefanovic S, Jankovic N. An enolate ion as a synthon in biocatalytic synthesis of 3,4-dihydro-2(1H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones: lemon juice as an alternative to hazardous solvents and catalysts. in Green Chemistry. 2017;19(3):707-715.
doi:10.1039/c6gc02893d .
Petronijević, Jelena, Bugarcic, Zorica, Bogdanović, Goran A., Stefanovic, Srdan, Jankovic, Nenad, "An enolate ion as a synthon in biocatalytic synthesis of 3,4-dihydro-2(1H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones: lemon juice as an alternative to hazardous solvents and catalysts" in Green Chemistry, 19, no. 3 (2017):707-715,
https://doi.org/10.1039/c6gc02893d . .
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Structure analysis of geopolymers synthesized from clay originated from Serbia

Nenadović, Snežana S.; Kljajević, Ljiljana M.; Nešić, Maja A.; Petković, Marijana; Trivunac, Katarina V.; Pavlović, Vladimir B.

(2017)

TY  - JOUR
AU  - Nenadović, Snežana S.
AU  - Kljajević, Ljiljana M.
AU  - Nešić, Maja A.
AU  - Petković, Marijana
AU  - Trivunac, Katarina V.
AU  - Pavlović, Vladimir B.
PY  - 2017
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/1407
AB  - The paper presents chemical and structural analysis of geopolymer materials which are obtained by alkali-activated calcined clay (metakaolin) originated from Serbia under strictly defined conditions. Characterization of the metakaolin and geopolymers molecular structure has been done using X-ray diffraction, scanning electron microscope, Fourier transform infrared spectroscopy and matrix-assisted laser desorption ionization time-of-flight mass spectrometry. The paper presents the possibility of obtaining geopolymer structure and differences in chemical and structural characterization of these materials taking into account the concentration of NaOH as a variable parameter. The results of MALDI analysis of metakaolin and synthesized geopolymer structures using various matrix system: 2,4,6 trihydroxyacetophenone (THAP), alpha-cyano-4-hydroxycinnamic, 2,6 dihydroxyacetophenone and laser desorption/ionization, have shown that THAP matrix is the most appropriate for analysing these aluminosilicate materials.
T2  - Environmental Earth Sciences
T1  - Structure analysis of geopolymers synthesized from clay originated from Serbia
VL  - 76
IS  - 2
DO  - 10.1007/s12665-016-6360-4
ER  - 
@article{
author = "Nenadović, Snežana S. and Kljajević, Ljiljana M. and Nešić, Maja A. and Petković, Marijana and Trivunac, Katarina V. and Pavlović, Vladimir B.",
year = "2017",
abstract = "The paper presents chemical and structural analysis of geopolymer materials which are obtained by alkali-activated calcined clay (metakaolin) originated from Serbia under strictly defined conditions. Characterization of the metakaolin and geopolymers molecular structure has been done using X-ray diffraction, scanning electron microscope, Fourier transform infrared spectroscopy and matrix-assisted laser desorption ionization time-of-flight mass spectrometry. The paper presents the possibility of obtaining geopolymer structure and differences in chemical and structural characterization of these materials taking into account the concentration of NaOH as a variable parameter. The results of MALDI analysis of metakaolin and synthesized geopolymer structures using various matrix system: 2,4,6 trihydroxyacetophenone (THAP), alpha-cyano-4-hydroxycinnamic, 2,6 dihydroxyacetophenone and laser desorption/ionization, have shown that THAP matrix is the most appropriate for analysing these aluminosilicate materials.",
journal = "Environmental Earth Sciences",
title = "Structure analysis of geopolymers synthesized from clay originated from Serbia",
volume = "76",
number = "2",
doi = "10.1007/s12665-016-6360-4"
}
Nenadović, S. S., Kljajević, L. M., Nešić, M. A., Petković, M., Trivunac, K. V.,& Pavlović, V. B.. (2017). Structure analysis of geopolymers synthesized from clay originated from Serbia. in Environmental Earth Sciences, 76(2).
https://doi.org/10.1007/s12665-016-6360-4
Nenadović SS, Kljajević LM, Nešić MA, Petković M, Trivunac KV, Pavlović VB. Structure analysis of geopolymers synthesized from clay originated from Serbia. in Environmental Earth Sciences. 2017;76(2).
doi:10.1007/s12665-016-6360-4 .
Nenadović, Snežana S., Kljajević, Ljiljana M., Nešić, Maja A., Petković, Marijana, Trivunac, Katarina V., Pavlović, Vladimir B., "Structure analysis of geopolymers synthesized from clay originated from Serbia" in Environmental Earth Sciences, 76, no. 2 (2017),
https://doi.org/10.1007/s12665-016-6360-4 . .
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