TY  - JOUR
AU  - Marić, Aleksandar
AU  - Jovanov, Pavle
AU  - Gadžurić, Slobodan
AU  - Trtić-Petrović, Tatjana
AU  - Sakač, Marijana
AU  - Tot, Aleksandar
AU  - Bertić, Marko
AU  - Vraneš, Milan
PY  - 2023
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/12042
AB  - 5-Hydroxymethylfurfural (HMF), a Maillard reaction product, can be formed when honey is subjected to heat treatment or a long storage time, becoming volatile and toxic depending on its concentration. The fact that, until today, there is no literature data on the extraction of 5-hydroxymethylfurfural (HMF) from honey using ionic liquids directed the investigation of the influence of biodegradable cholinium ionic liquids on the formation of aqueous biphasic systems and the application of these systems for the extraction of HMF from honey. The influence of anions of synthesised ionic liquids on the construction of biphasic systems in which an inorganic salt was used as a salting agent was investigated. Then, the extraction of HMF in these systems was examined, and the mechanisms of HMF extraction using ionic liquids were explained using computer simulations. Examining the effect of cholinium ionic liquids (choline chloride ([Ch][Cl]), cholinium nicotinate ([Ch][Nic]), cholinium propionate ([Ch][Prop]), and cholinium butyrate ([Ch][But])) on the formation of aqueous biphasic systems by comparing the phase diagrams, it was concluded that the ability of ionic liquids to form an aqueous biphasic system with tripotassium phosphate (K3PO4) decreases in the following order: [Ch][But] z [Ch][Prop] > [Ch][Nic] > [Ch][Cl]. By applying all tested aqueous biphasic systems for the extraction of HMF from honey, an extraction efficiency of more than 89% was achieved. Complete extraction was achieved using the extraction system with [Ch][But], while the weakest ability to extract HMF was exhibited by the system with [Ch][Cl]. The mechanisms of HMF extraction using ionic liquids are explained on the basis of the optimised structures of the ionic liquid systems with HMF, together with the visualisation of noncovalent interactions, and on the basis of the calculated binding energies DGbin, which can be used as a good predictor of the extraction potential of newly synthesised ionic liquids
T2  - RSC Advances
T1  - Application of biodegradable cholinium ionic liquids for the extraction of 5-hydroxymethylfurfural (HMF) from honey
VL  - 13
IS  - 46
SP  - 32714
EP  - 32721
DO  - 10.1039/D3RA06077B
ER  - 

@article{
author = "Marić, Aleksandar and Jovanov, Pavle and Gadžurić, Slobodan and Trtić-Petrović, Tatjana and Sakač, Marijana and Tot, Aleksandar and Bertić, Marko and Vraneš, Milan",
year = "2023",
abstract = "5-Hydroxymethylfurfural (HMF), a Maillard reaction product, can be formed when honey is subjected to heat treatment or a long storage time, becoming volatile and toxic depending on its concentration. The fact that, until today, there is no literature data on the extraction of 5-hydroxymethylfurfural (HMF) from honey using ionic liquids directed the investigation of the influence of biodegradable cholinium ionic liquids on the formation of aqueous biphasic systems and the application of these systems for the extraction of HMF from honey. The influence of anions of synthesised ionic liquids on the construction of biphasic systems in which an inorganic salt was used as a salting agent was investigated. Then, the extraction of HMF in these systems was examined, and the mechanisms of HMF extraction using ionic liquids were explained using computer simulations. Examining the effect of cholinium ionic liquids (choline chloride ([Ch][Cl]), cholinium nicotinate ([Ch][Nic]), cholinium propionate ([Ch][Prop]), and cholinium butyrate ([Ch][But])) on the formation of aqueous biphasic systems by comparing the phase diagrams, it was concluded that the ability of ionic liquids to form an aqueous biphasic system with tripotassium phosphate (K3PO4) decreases in the following order: [Ch][But] z [Ch][Prop] > [Ch][Nic] > [Ch][Cl]. By applying all tested aqueous biphasic systems for the extraction of HMF from honey, an extraction efficiency of more than 89% was achieved. Complete extraction was achieved using the extraction system with [Ch][But], while the weakest ability to extract HMF was exhibited by the system with [Ch][Cl]. The mechanisms of HMF extraction using ionic liquids are explained on the basis of the optimised structures of the ionic liquid systems with HMF, together with the visualisation of noncovalent interactions, and on the basis of the calculated binding energies DGbin, which can be used as a good predictor of the extraction potential of newly synthesised ionic liquids",
journal = "RSC Advances",
title = "Application of biodegradable cholinium ionic liquids for the extraction of 5-hydroxymethylfurfural (HMF) from honey",
volume = "13",
number = "46",
pages = "32714-32721",
doi = "10.1039/D3RA06077B"
}

Marić, A., Jovanov, P., Gadžurić, S., Trtić-Petrović, T., Sakač, M., Tot, A., Bertić, M.,& Vraneš, M.. (2023). Application of biodegradable cholinium ionic liquids for the extraction of 5-hydroxymethylfurfural (HMF) from honey. in RSC Advances, 13(46), 32714-32721.
https://doi.org/10.1039/D3RA06077B

Marić A, Jovanov P, Gadžurić S, Trtić-Petrović T, Sakač M, Tot A, Bertić M, Vraneš M. Application of biodegradable cholinium ionic liquids for the extraction of 5-hydroxymethylfurfural (HMF) from honey. in RSC Advances. 2023;13(46):32714-32721.
doi:10.1039/D3RA06077B .

Marić, Aleksandar, Jovanov, Pavle, Gadžurić, Slobodan, Trtić-Petrović, Tatjana, Sakač, Marijana, Tot, Aleksandar, Bertić, Marko, Vraneš, Milan, "Application of biodegradable cholinium ionic liquids for the extraction of 5-hydroxymethylfurfural (HMF) from honey" in RSC Advances, 13, no. 46 (2023):32714-32721,
https://doi.org/10.1039/D3RA06077B . .

TY  - JOUR
AU  - Jocić, Ana
AU  - Marić, Slađana
AU  - Dimitrijević, Aleksandra
AU  - Tot, Aleksandar
AU  - Gadžurić, Slobodan
AU  - Vraneš, Milan
AU  - Trtić-Petrović, Tatjana M.
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8835
AB  - This work addresses use of a set of 2-hydroxypropylammonium based protic ionic liquids (PILs) as adjuvants in the aqueous biphasic system (ABS) composed of polyethylene glycol, with molecular weight 2000 g/mol (PEG 2000) and potassium carbonate. The phase diagrams were determined at 25 °C for ABS without and with the addition of 5 wt% of PIL. Comparative analysis of solubility curves indicates that PILs influence liquid-liquid equilibria of PEG 2000-K2CO3 ABS by heightening the hydrophilicity of a PEG-rich phase in various degrees. The compositions of the phases (tie lines) were determined for the selected ABS mixture composition, 26 wt% of PEG 2000 + 10 wt% of K2CO3, without and with 5 wt% of PILs, that is further used for the separation studies. The distribution of PILs between two phases is mainly dependent on specific PEG-PIL interactions and on the PIL content in ABS mixture. The experimental results are supported by molecular simulations that contributed to a broader picture of underlying effects of PILs as adjuvants on ABS formation. The partition of four dye compounds, Remazol Brilliant Blue R (RBBR), Orange II (OII), Rhodamine B (RB) and Congo Red (CR), as probe molecules with different intrinsic properties, was investigated. Obtained results show that the addition of PILs can improve the extraction of hydrophilic and charged compounds as OII, RBBR and CR in PEG-rich phase. On the other hand, it promotes the extraction of hydrophobic and neutral solutes as RB in salt-rich phase. By the addition of the most hydrophilic 3-chloropropanoate based PIL in the PEG 2000-K2CO3 ABS 12 times higher separation factor for OII and RB was achieved. © 2020 Elsevier B.V.
T2  - Journal of Molecular Liquids
T1  - Protic ionic liquids as adjuvants to enhance extraction and separation performance of diverse polarity compounds in PEG-salt based aqueous biphasic system
VL  - 303
SP  - 112484
DO  - 10.1016/j.molliq.2020.112484
ER  - 

@article{
author = "Jocić, Ana and Marić, Slađana and Dimitrijević, Aleksandra and Tot, Aleksandar and Gadžurić, Slobodan and Vraneš, Milan and Trtić-Petrović, Tatjana M.",
year = "2020",
abstract = "This work addresses use of a set of 2-hydroxypropylammonium based protic ionic liquids (PILs) as adjuvants in the aqueous biphasic system (ABS) composed of polyethylene glycol, with molecular weight 2000 g/mol (PEG 2000) and potassium carbonate. The phase diagrams were determined at 25 °C for ABS without and with the addition of 5 wt% of PIL. Comparative analysis of solubility curves indicates that PILs influence liquid-liquid equilibria of PEG 2000-K2CO3 ABS by heightening the hydrophilicity of a PEG-rich phase in various degrees. The compositions of the phases (tie lines) were determined for the selected ABS mixture composition, 26 wt% of PEG 2000 + 10 wt% of K2CO3, without and with 5 wt% of PILs, that is further used for the separation studies. The distribution of PILs between two phases is mainly dependent on specific PEG-PIL interactions and on the PIL content in ABS mixture. The experimental results are supported by molecular simulations that contributed to a broader picture of underlying effects of PILs as adjuvants on ABS formation. The partition of four dye compounds, Remazol Brilliant Blue R (RBBR), Orange II (OII), Rhodamine B (RB) and Congo Red (CR), as probe molecules with different intrinsic properties, was investigated. Obtained results show that the addition of PILs can improve the extraction of hydrophilic and charged compounds as OII, RBBR and CR in PEG-rich phase. On the other hand, it promotes the extraction of hydrophobic and neutral solutes as RB in salt-rich phase. By the addition of the most hydrophilic 3-chloropropanoate based PIL in the PEG 2000-K2CO3 ABS 12 times higher separation factor for OII and RB was achieved. © 2020 Elsevier B.V.",
journal = "Journal of Molecular Liquids",
title = "Protic ionic liquids as adjuvants to enhance extraction and separation performance of diverse polarity compounds in PEG-salt based aqueous biphasic system",
volume = "303",
pages = "112484",
doi = "10.1016/j.molliq.2020.112484"
}

Jocić, A., Marić, S., Dimitrijević, A., Tot, A., Gadžurić, S., Vraneš, M.,& Trtić-Petrović, T. M.. (2020). Protic ionic liquids as adjuvants to enhance extraction and separation performance of diverse polarity compounds in PEG-salt based aqueous biphasic system. in Journal of Molecular Liquids, 303, 112484.
https://doi.org/10.1016/j.molliq.2020.112484

Jocić A, Marić S, Dimitrijević A, Tot A, Gadžurić S, Vraneš M, Trtić-Petrović TM. Protic ionic liquids as adjuvants to enhance extraction and separation performance of diverse polarity compounds in PEG-salt based aqueous biphasic system. in Journal of Molecular Liquids. 2020;303:112484.
doi:10.1016/j.molliq.2020.112484 .

Jocić, Ana, Marić, Slađana, Dimitrijević, Aleksandra, Tot, Aleksandar, Gadžurić, Slobodan, Vraneš, Milan, Trtić-Petrović, Tatjana M., "Protic ionic liquids as adjuvants to enhance extraction and separation performance of diverse polarity compounds in PEG-salt based aqueous biphasic system" in Journal of Molecular Liquids, 303 (2020):112484,
https://doi.org/10.1016/j.molliq.2020.112484 . .

TY  - JOUR
AU  - Dimitrijević, Aleksandra
AU  - Мilićević, Jelena
AU  - Jocić, Ana
AU  - Marić, Slađana
AU  - Trtić-Petrović, Tatjana M.
AU  - Papović, Snežana
AU  - Tot, Aleksandar
AU  - Gadžurić, Slobodan
AU  - Vraneš, Milan
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8833
AB  - Despite a large collection of publications dealing with the characterization of ionic liquid-based aqueous biphasic systems (IL-ABS), a gap still exists regarding the impact of functionalized alkyl side branches and IL positional isomers on phase equilibria. Therefore, this work addresses the investigation of the ability of different methyl substituted pyridinium based ILs on the formation of ABSs with K3PO4. We evaluated the impact of (i) functional groups (hydroxyl or ether) embed in side alkyl chains of pyridinium cations, (ii) positional isomerism of methyl group (ortho, meta and para) and (iii) the IL cation core. Ternary phase diagrams of the ABSs formed by these ILs and K3PO4 and the appropriate tie lines were determined and presented. It is shown that the presence of functionalized alkyl chain largely affects the salting-in behavior of ILs (ILs with the oxygen groups are more difficult to form ABS) while more subtle differences were observed among positional isomers. Based on the obtained results it is concluded that change of biphasic area of ABS is the manifestation of the altered affinity of ILs for water as a consequence of cation structure. Moreover, aiming at gathering a broader picture of the relationship between ILs structure and ABS properties, molecular simulations were performed, and it was showed that the obtained results are consistent with the experimental results. © 2020 Elsevier B.V.
T2  - Fluid Phase Equilibria
T1  - Further insight into the influence of functionalization and positional isomerism of pyridinium ionic liquids on the aqueous two-phase system equilibria
VL  - 512
SP  - 112520
DO  - 10.1016/j.fluid.2020.112520
ER  - 

@article{
author = "Dimitrijević, Aleksandra and Мilićević, Jelena and Jocić, Ana and Marić, Slađana and Trtić-Petrović, Tatjana M. and Papović, Snežana and Tot, Aleksandar and Gadžurić, Slobodan and Vraneš, Milan",
year = "2020",
abstract = "Despite a large collection of publications dealing with the characterization of ionic liquid-based aqueous biphasic systems (IL-ABS), a gap still exists regarding the impact of functionalized alkyl side branches and IL positional isomers on phase equilibria. Therefore, this work addresses the investigation of the ability of different methyl substituted pyridinium based ILs on the formation of ABSs with K3PO4. We evaluated the impact of (i) functional groups (hydroxyl or ether) embed in side alkyl chains of pyridinium cations, (ii) positional isomerism of methyl group (ortho, meta and para) and (iii) the IL cation core. Ternary phase diagrams of the ABSs formed by these ILs and K3PO4 and the appropriate tie lines were determined and presented. It is shown that the presence of functionalized alkyl chain largely affects the salting-in behavior of ILs (ILs with the oxygen groups are more difficult to form ABS) while more subtle differences were observed among positional isomers. Based on the obtained results it is concluded that change of biphasic area of ABS is the manifestation of the altered affinity of ILs for water as a consequence of cation structure. Moreover, aiming at gathering a broader picture of the relationship between ILs structure and ABS properties, molecular simulations were performed, and it was showed that the obtained results are consistent with the experimental results. © 2020 Elsevier B.V.",
journal = "Fluid Phase Equilibria",
title = "Further insight into the influence of functionalization and positional isomerism of pyridinium ionic liquids on the aqueous two-phase system equilibria",
volume = "512",
pages = "112520",
doi = "10.1016/j.fluid.2020.112520"
}

Dimitrijević, A., Мilićević, J., Jocić, A., Marić, S., Trtić-Petrović, T. M., Papović, S., Tot, A., Gadžurić, S.,& Vraneš, M.. (2020). Further insight into the influence of functionalization and positional isomerism of pyridinium ionic liquids on the aqueous two-phase system equilibria. in Fluid Phase Equilibria, 512, 112520.
https://doi.org/10.1016/j.fluid.2020.112520

Dimitrijević A, Мilićević J, Jocić A, Marić S, Trtić-Petrović TM, Papović S, Tot A, Gadžurić S, Vraneš M. Further insight into the influence of functionalization and positional isomerism of pyridinium ionic liquids on the aqueous two-phase system equilibria. in Fluid Phase Equilibria. 2020;512:112520.
doi:10.1016/j.fluid.2020.112520 .

Dimitrijević, Aleksandra, Мilićević, Jelena, Jocić, Ana, Marić, Slađana, Trtić-Petrović, Tatjana M., Papović, Snežana, Tot, Aleksandar, Gadžurić, Slobodan, Vraneš, Milan, "Further insight into the influence of functionalization and positional isomerism of pyridinium ionic liquids on the aqueous two-phase system equilibria" in Fluid Phase Equilibria, 512 (2020):112520,
https://doi.org/10.1016/j.fluid.2020.112520 . .

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  - https://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 . .

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  - https://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 . .

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  - https://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 . .

TY  - JOUR
AU  - Dimitrijević, Aleksandra
AU  - Jocić, Ana
AU  - Zec, Nebojša
AU  - Tot, Aleksandar
AU  - Papović, Snežana
AU  - Gadžurić, Slobodan
AU  - Vraneš, Milan
AU  - Trtić-Petrović, Tatjana M.
PY  - 2019
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8157
AB  - The novel aqueous biphasic systems based on symmetric imidazolium ionic liquids (IL-ABSs)for the extraction of toxic and resistive dyes from water was studied. The cation symmetricity of ILs strongly influence the outstanding ability of 1,3-dibutylimidazolium dicyanamide, [bbim][dca], to generate ABS with the exceptionally low amount of eco-friendly citrate salt. A remarkable potential of [bbim][dca]/citrate based ABS to remove Orange II from wastewater with concentration up to 1000 fold and efficiency above 99.4% in a single step was achieved. The improved safety of proposed method nominates it as promising future strategy for pollution prevention. © 2019 The Korean Society of Industrial and Engineering Chemistry
T2  - Journal of Industrial and Engineering Chemistry
T1  - Improved single-step extraction performance of aqueous biphasic systems using novel symmetric ionic liquids for the decolorisation of toxic dye effluents
VL  - 76
SP  - 500
EP  - 507
DO  - 10.1016/j.jiec.2019.04.017
ER  - 

@article{
author = "Dimitrijević, Aleksandra and Jocić, Ana and Zec, Nebojša and Tot, Aleksandar and Papović, Snežana and Gadžurić, Slobodan and Vraneš, Milan and Trtić-Petrović, Tatjana M.",
year = "2019",
abstract = "The novel aqueous biphasic systems based on symmetric imidazolium ionic liquids (IL-ABSs)for the extraction of toxic and resistive dyes from water was studied. The cation symmetricity of ILs strongly influence the outstanding ability of 1,3-dibutylimidazolium dicyanamide, [bbim][dca], to generate ABS with the exceptionally low amount of eco-friendly citrate salt. A remarkable potential of [bbim][dca]/citrate based ABS to remove Orange II from wastewater with concentration up to 1000 fold and efficiency above 99.4% in a single step was achieved. The improved safety of proposed method nominates it as promising future strategy for pollution prevention. © 2019 The Korean Society of Industrial and Engineering Chemistry",
journal = "Journal of Industrial and Engineering Chemistry",
title = "Improved single-step extraction performance of aqueous biphasic systems using novel symmetric ionic liquids for the decolorisation of toxic dye effluents",
volume = "76",
pages = "500-507",
doi = "10.1016/j.jiec.2019.04.017"
}

Dimitrijević, A., Jocić, A., Zec, N., Tot, A., Papović, S., Gadžurić, S., Vraneš, M.,& Trtić-Petrović, T. M.. (2019). Improved single-step extraction performance of aqueous biphasic systems using novel symmetric ionic liquids for the decolorisation of toxic dye effluents. in Journal of Industrial and Engineering Chemistry, 76, 500-507.
https://doi.org/10.1016/j.jiec.2019.04.017

Dimitrijević A, Jocić A, Zec N, Tot A, Papović S, Gadžurić S, Vraneš M, Trtić-Petrović TM. Improved single-step extraction performance of aqueous biphasic systems using novel symmetric ionic liquids for the decolorisation of toxic dye effluents. in Journal of Industrial and Engineering Chemistry. 2019;76:500-507.
doi:10.1016/j.jiec.2019.04.017 .

Dimitrijević, Aleksandra, Jocić, Ana, Zec, Nebojša, Tot, Aleksandar, Papović, Snežana, Gadžurić, Slobodan, Vraneš, Milan, Trtić-Petrović, Tatjana M., "Improved single-step extraction performance of aqueous biphasic systems using novel symmetric ionic liquids for the decolorisation of toxic dye effluents" in Journal of Industrial and Engineering Chemistry, 76 (2019):500-507,
https://doi.org/10.1016/j.jiec.2019.04.017 . .

TY  - JOUR
AU  - Dimitrijević, Aleksandra
AU  - Jocić, Ana
AU  - Zec, Nebojša
AU  - Tot, Aleksandar
AU  - Papović, Snežana
AU  - Gadžurić, Slobodan
AU  - Vraneš, Milan
AU  - Trtić-Petrović, Tatjana M.
PY  - 2019
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8168
AB  - The novel aqueous biphasic systems based on symmetric imidazolium ionic liquids (IL-ABSs)for the extraction of toxic and resistive dyes from water was studied. The cation symmetricity of ILs strongly influence the outstanding ability of 1,3-dibutylimidazolium dicyanamide, [bbim][dca], to generate ABS with the exceptionally low amount of eco-friendly citrate salt. A remarkable potential of [bbim][dca]/citrate based ABS to remove Orange II from wastewater with concentration up to 1000 fold and efficiency above 99.4% in a single step was achieved. The improved safety of proposed method nominates it as promising future strategy for pollution prevention.
T2  - Journal of Industrial and Engineering Chemistry
T1  - Improved single-step extraction performance of aqueous biphasic systems using novel symmetric ionic liquids for the decolorisation of toxic dye effluents
VL  - 76
SP  - 500
EP  - 507
DO  - 10.1016/j.jiec.2019.04.017
ER  - 

@article{
author = "Dimitrijević, Aleksandra and Jocić, Ana and Zec, Nebojša and Tot, Aleksandar and Papović, Snežana and Gadžurić, Slobodan and Vraneš, Milan and Trtić-Petrović, Tatjana M.",
year = "2019",
abstract = "The novel aqueous biphasic systems based on symmetric imidazolium ionic liquids (IL-ABSs)for the extraction of toxic and resistive dyes from water was studied. The cation symmetricity of ILs strongly influence the outstanding ability of 1,3-dibutylimidazolium dicyanamide, [bbim][dca], to generate ABS with the exceptionally low amount of eco-friendly citrate salt. A remarkable potential of [bbim][dca]/citrate based ABS to remove Orange II from wastewater with concentration up to 1000 fold and efficiency above 99.4% in a single step was achieved. The improved safety of proposed method nominates it as promising future strategy for pollution prevention.",
journal = "Journal of Industrial and Engineering Chemistry",
title = "Improved single-step extraction performance of aqueous biphasic systems using novel symmetric ionic liquids for the decolorisation of toxic dye effluents",
volume = "76",
pages = "500-507",
doi = "10.1016/j.jiec.2019.04.017"
}

Dimitrijević, A., Jocić, A., Zec, N., Tot, A., Papović, S., Gadžurić, S., Vraneš, M.,& Trtić-Petrović, T. M.. (2019). Improved single-step extraction performance of aqueous biphasic systems using novel symmetric ionic liquids for the decolorisation of toxic dye effluents. in Journal of Industrial and Engineering Chemistry, 76, 500-507.
https://doi.org/10.1016/j.jiec.2019.04.017

Dimitrijević A, Jocić A, Zec N, Tot A, Papović S, Gadžurić S, Vraneš M, Trtić-Petrović TM. Improved single-step extraction performance of aqueous biphasic systems using novel symmetric ionic liquids for the decolorisation of toxic dye effluents. in Journal of Industrial and Engineering Chemistry. 2019;76:500-507.
doi:10.1016/j.jiec.2019.04.017 .

Dimitrijević, Aleksandra, Jocić, Ana, Zec, Nebojša, Tot, Aleksandar, Papović, Snežana, Gadžurić, Slobodan, Vraneš, Milan, Trtić-Petrović, Tatjana M., "Improved single-step extraction performance of aqueous biphasic systems using novel symmetric ionic liquids for the decolorisation of toxic dye effluents" in Journal of Industrial and Engineering Chemistry, 76 (2019):500-507,
https://doi.org/10.1016/j.jiec.2019.04.017 . .

TY  - JOUR
AU  - Vraneš, Milan
AU  - Panić, Jovana
AU  - Tot, Aleksandar
AU  - Popsavin, Mirjana
AU  - Jocić, Ana
AU  - Gadžurić, Slobodan
PY  - 2019
UR  - https://linkinghub.elsevier.com/retrieve/pii/S0021961418307808
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7943
AB  - In this paper, physicochemical characterization of newly synthesized choline based ionic liquids with five different chelating anions were examined. The ionic liquids (ILs): cholinium-L-lactate, [Ch][Lac], cholinium-picolinate, [Ch][Pic], cholinium-anthranilate, [Ch][Ant], cholinium-oxyquinolinate, [Ch][oQ], and cholinium-diethylenetriaminepentaacetate, [Ch]3[DTPA], were prepared for the first time and their structures were confirmed by IR and 1H and 13C NMR spectra. Also, thermogravimetric analysis (TGA) was applied to determine their thermal stabilities. Based on the measured density values and viscosity in the temperature range from (293.15 to 323.15) K and calculated values of thermal expansion coefficients and activation energy of viscous flow, as well as of computational simulations, the interactions and structures of the investigated ionic liquids were discussed. © 2018 Elsevier Ltd
T2  - The Journal of Chemical Thermodynamics
T1  - Physicochemical characterization of choline based ionic liquids with chelating anions
VL  - 131
SP  - 80
EP  - 87
DO  - 10.1016/j.jct.2018.10.026
ER  - 

@article{
author = "Vraneš, Milan and Panić, Jovana and Tot, Aleksandar and Popsavin, Mirjana and Jocić, Ana and Gadžurić, Slobodan",
year = "2019",
abstract = "In this paper, physicochemical characterization of newly synthesized choline based ionic liquids with five different chelating anions were examined. The ionic liquids (ILs): cholinium-L-lactate, [Ch][Lac], cholinium-picolinate, [Ch][Pic], cholinium-anthranilate, [Ch][Ant], cholinium-oxyquinolinate, [Ch][oQ], and cholinium-diethylenetriaminepentaacetate, [Ch]3[DTPA], were prepared for the first time and their structures were confirmed by IR and 1H and 13C NMR spectra. Also, thermogravimetric analysis (TGA) was applied to determine their thermal stabilities. Based on the measured density values and viscosity in the temperature range from (293.15 to 323.15) K and calculated values of thermal expansion coefficients and activation energy of viscous flow, as well as of computational simulations, the interactions and structures of the investigated ionic liquids were discussed. © 2018 Elsevier Ltd",
journal = "The Journal of Chemical Thermodynamics",
title = "Physicochemical characterization of choline based ionic liquids with chelating anions",
volume = "131",
pages = "80-87",
doi = "10.1016/j.jct.2018.10.026"
}

Vraneš, M., Panić, J., Tot, A., Popsavin, M., Jocić, A.,& Gadžurić, S.. (2019). Physicochemical characterization of choline based ionic liquids with chelating anions. in The Journal of Chemical Thermodynamics, 131, 80-87.
https://doi.org/10.1016/j.jct.2018.10.026

Vraneš M, Panić J, Tot A, Popsavin M, Jocić A, Gadžurić S. Physicochemical characterization of choline based ionic liquids with chelating anions. in The Journal of Chemical Thermodynamics. 2019;131:80-87.
doi:10.1016/j.jct.2018.10.026 .

Vraneš, Milan, Panić, Jovana, Tot, Aleksandar, Popsavin, Mirjana, Jocić, Ana, Gadžurić, Slobodan, "Physicochemical characterization of choline based ionic liquids with chelating anions" in The Journal of Chemical Thermodynamics, 131 (2019):80-87,
https://doi.org/10.1016/j.jct.2018.10.026 . .

TY  - JOUR
AU  - Trtić-Petrović, Tatjana M.
AU  - Dimitrijević, Aleksandra
AU  - Zdolšek, Nikola
AU  - Đorđević, Jelena S.
AU  - Tot, Aleksandar
AU  - Vraneš, Milan
AU  - Gadžurić, Slobodan
PY  - 2018
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1891
AB  - In this study, four hydrophilic ionic liquids (ILs) containing 1-alkyl-3-methylimidazolim cation and either salicylate or chloride anions were synthetized and studied as new task-specific ionic liquids (TSILs) suitable for aqueous biphasic system (ABS) formation and selective one-step extraction of copper(II). TSILs are designed so that the anion is responsible for forming the complex with metal(II) and preventing hydrolysis of metal cations at very strong alkaline pH, whereas the cation is responsible for selective extraction of metal(II)-salicylate complexes. It was found that 1-butyl-3-methylimidazolium salicylate could be used for selective extraction of Cu(II) in the presence of Zn(II), Cd(II), and Pb(II) at very alkaline solution without metal hydroxide formation. It was assumed that formation of metal(II)-salicylate complexes prevents the hydrolysis of the metal ions in alkaline solutions. The determined stability constants for Cu(II)-salicylate complexes, where salicylate was derived from different ionic liquids, indicated that there was no significant influence of the cation of the ionic liquid on the stability of the complexes. The ABS based on 1-butyl-3-methylimidazolium salicylate has been applied as the sample preparation step prior to voltammetric determination of Cu(II). The effect of volume of aqueous sample and IL and extraction time were investigated and optimum extraction conditions were determined. The obtained detection limits were 8 ng dm(-3). The optimized method was applied for the determination of Cu(II) in tap water, wastewater, and urine. The study indicated that application of the ABS based on 1-butyl-3-methylimidazolium salicylate ionic liquid could be successfully applied as the sample preparation method for the determination of Cu(II) from various environmental samples.
T2  - Analytical and Bioanalytical Chemistry
T1  - New sample preparation method based on task-specific ionic liquids for extraction and determination of copper in urine and wastewater
VL  - 410
IS  - 1
SP  - 155
EP  - 166
DO  - 10.1007/s00216-017-0705-z
ER  - 

@article{
author = "Trtić-Petrović, Tatjana M. and Dimitrijević, Aleksandra and Zdolšek, Nikola and Đorđević, Jelena S. and Tot, Aleksandar and Vraneš, Milan and Gadžurić, Slobodan",
year = "2018",
abstract = "In this study, four hydrophilic ionic liquids (ILs) containing 1-alkyl-3-methylimidazolim cation and either salicylate or chloride anions were synthetized and studied as new task-specific ionic liquids (TSILs) suitable for aqueous biphasic system (ABS) formation and selective one-step extraction of copper(II). TSILs are designed so that the anion is responsible for forming the complex with metal(II) and preventing hydrolysis of metal cations at very strong alkaline pH, whereas the cation is responsible for selective extraction of metal(II)-salicylate complexes. It was found that 1-butyl-3-methylimidazolium salicylate could be used for selective extraction of Cu(II) in the presence of Zn(II), Cd(II), and Pb(II) at very alkaline solution without metal hydroxide formation. It was assumed that formation of metal(II)-salicylate complexes prevents the hydrolysis of the metal ions in alkaline solutions. The determined stability constants for Cu(II)-salicylate complexes, where salicylate was derived from different ionic liquids, indicated that there was no significant influence of the cation of the ionic liquid on the stability of the complexes. The ABS based on 1-butyl-3-methylimidazolium salicylate has been applied as the sample preparation step prior to voltammetric determination of Cu(II). The effect of volume of aqueous sample and IL and extraction time were investigated and optimum extraction conditions were determined. The obtained detection limits were 8 ng dm(-3). The optimized method was applied for the determination of Cu(II) in tap water, wastewater, and urine. The study indicated that application of the ABS based on 1-butyl-3-methylimidazolium salicylate ionic liquid could be successfully applied as the sample preparation method for the determination of Cu(II) from various environmental samples.",
journal = "Analytical and Bioanalytical Chemistry",
title = "New sample preparation method based on task-specific ionic liquids for extraction and determination of copper in urine and wastewater",
volume = "410",
number = "1",
pages = "155-166",
doi = "10.1007/s00216-017-0705-z"
}

Trtić-Petrović, T. M., Dimitrijević, A., Zdolšek, N., Đorđević, J. S., Tot, A., Vraneš, M.,& Gadžurić, S.. (2018). New sample preparation method based on task-specific ionic liquids for extraction and determination of copper in urine and wastewater. in Analytical and Bioanalytical Chemistry, 410(1), 155-166.
https://doi.org/10.1007/s00216-017-0705-z

Trtić-Petrović TM, Dimitrijević A, Zdolšek N, Đorđević JS, Tot A, Vraneš M, Gadžurić S. New sample preparation method based on task-specific ionic liquids for extraction and determination of copper in urine and wastewater. in Analytical and Bioanalytical Chemistry. 2018;410(1):155-166.
doi:10.1007/s00216-017-0705-z .

Trtić-Petrović, Tatjana M., Dimitrijević, Aleksandra, Zdolšek, Nikola, Đorđević, Jelena S., Tot, Aleksandar, Vraneš, Milan, Gadžurić, Slobodan, "New sample preparation method based on task-specific ionic liquids for extraction and determination of copper in urine and wastewater" in Analytical and Bioanalytical Chemistry, 410, no. 1 (2018):155-166,
https://doi.org/10.1007/s00216-017-0705-z . .

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  - https://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 . .

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  - https://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 . .

TY  - JOUR
AU  - Dimitrijević, Aleksandra
AU  - Ignjatović, Ljubiša M.
AU  - Tot, Aleksandar
AU  - Vraneš, Milan
AU  - Zec, Nebojša
AU  - Gadžurić, Slobodan
AU  - Trtić-Petrović, Tatjana M.
PY  - 2017
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1776
AB  - In this paper we report a simultaneous one-step extraction of five pesticides (acetamiprid, imidaclopride, simazine, linuron and tebufenozide) of different polarity using aqueous biphasic system based on 1-butyl-3(methyl or ethyl) substituted imidazolium or pyrrolidinium ionic liquids with bromide or dicyanamide anion and potassium carbonate as a salting-out agent. Experimentally data obtained for the ternary system (ionic liquid + K2CO3 + H2O) were fitted and correlated by Merchuk equation with satisfactory high correlation factor. The effect of the cation alkyl chain length and the variation of anions of the ionic liquid on the aqueous biphasic system formation and the efficiency of pesticide extraction were investigated. Complete extraction of all studied pesticides was obtained applying aqueous biphasic system based on 1-butyl-3-ethyl imidazolium dicyanamide. It was shown that simultaneous extraction of the different polarity pesticides is achieved in a single-step procedure applying properly tailored ionic liquids in the aqueous biphasic system formulation. In order to explain excellent extraction of the polar pesticides in the studied aqueous biphasic systems, molecular dynamics was applied and the binding energies and non-covalent interactions were calculated. It was found that 1-butyl-3-ethyl imidazolium dicyanamide achieves the strongest interactions with the polar pesticides (acetamiprid and imidaclopride) leading to the highest partition coefficients. It was shown that combination of experimental and computational approach can be successfully applied for the selection and design of suitable ionic liquids for efficient extraction of various polarity pesticides using simple aqueous biphasic ionic liquid based systems. (C) 2017 Elsevier B.V. All rights reserved.
T2  - Journal of Molecular Liquids
T1  - Simultaneous extraction of pesticides of different polarity applying aqueous biphasic systems based on ionic liquids
VL  - 243
SP  - 646
EP  - 653
DO  - 10.1016/j.molliq.2017.08.077
ER  - 

@article{
author = "Dimitrijević, Aleksandra and Ignjatović, Ljubiša M. and Tot, Aleksandar and Vraneš, Milan and Zec, Nebojša and Gadžurić, Slobodan and Trtić-Petrović, Tatjana M.",
year = "2017",
abstract = "In this paper we report a simultaneous one-step extraction of five pesticides (acetamiprid, imidaclopride, simazine, linuron and tebufenozide) of different polarity using aqueous biphasic system based on 1-butyl-3(methyl or ethyl) substituted imidazolium or pyrrolidinium ionic liquids with bromide or dicyanamide anion and potassium carbonate as a salting-out agent. Experimentally data obtained for the ternary system (ionic liquid + K2CO3 + H2O) were fitted and correlated by Merchuk equation with satisfactory high correlation factor. The effect of the cation alkyl chain length and the variation of anions of the ionic liquid on the aqueous biphasic system formation and the efficiency of pesticide extraction were investigated. Complete extraction of all studied pesticides was obtained applying aqueous biphasic system based on 1-butyl-3-ethyl imidazolium dicyanamide. It was shown that simultaneous extraction of the different polarity pesticides is achieved in a single-step procedure applying properly tailored ionic liquids in the aqueous biphasic system formulation. In order to explain excellent extraction of the polar pesticides in the studied aqueous biphasic systems, molecular dynamics was applied and the binding energies and non-covalent interactions were calculated. It was found that 1-butyl-3-ethyl imidazolium dicyanamide achieves the strongest interactions with the polar pesticides (acetamiprid and imidaclopride) leading to the highest partition coefficients. It was shown that combination of experimental and computational approach can be successfully applied for the selection and design of suitable ionic liquids for efficient extraction of various polarity pesticides using simple aqueous biphasic ionic liquid based systems. (C) 2017 Elsevier B.V. All rights reserved.",
journal = "Journal of Molecular Liquids",
title = "Simultaneous extraction of pesticides of different polarity applying aqueous biphasic systems based on ionic liquids",
volume = "243",
pages = "646-653",
doi = "10.1016/j.molliq.2017.08.077"
}

Dimitrijević, A., Ignjatović, L. M., Tot, A., Vraneš, M., Zec, N., Gadžurić, S.,& Trtić-Petrović, T. M.. (2017). Simultaneous extraction of pesticides of different polarity applying aqueous biphasic systems based on ionic liquids. in Journal of Molecular Liquids, 243, 646-653.
https://doi.org/10.1016/j.molliq.2017.08.077

Dimitrijević A, Ignjatović LM, Tot A, Vraneš M, Zec N, Gadžurić S, Trtić-Petrović TM. Simultaneous extraction of pesticides of different polarity applying aqueous biphasic systems based on ionic liquids. in Journal of Molecular Liquids. 2017;243:646-653.
doi:10.1016/j.molliq.2017.08.077 .

Dimitrijević, Aleksandra, Ignjatović, Ljubiša M., Tot, Aleksandar, Vraneš, Milan, Zec, Nebojša, Gadžurić, Slobodan, Trtić-Petrović, Tatjana M., "Simultaneous extraction of pesticides of different polarity applying aqueous biphasic systems based on ionic liquids" in Journal of Molecular Liquids, 243 (2017):646-653,
https://doi.org/10.1016/j.molliq.2017.08.077 . .

TY  - JOUR
AU  - Dimitrijević, Aleksandra
AU  - Trtić-Petrović, Tatjana M.
AU  - Vraneš, Milan
AU  - Papović, Snežana
AU  - Tot, Aleksandar
AU  - Dožić, Sanja
AU  - Gadžurić, Slobodan
PY  - 2016
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/899
AB  - In this work, novel phase diagrams for aqueous solutions of 1-alkyl-3-methylimidazolium- and 1-butyl-3-ethylimidazolium-based ILs combined with phosphate-based salts, namely, K3PO4 or K2HPO4, are reported and discussed. To correlate the binodal data, the Merchuk equation is applied. The tie lines and tie-line lengths are also presented. The anion influence on the ability to form aqueous biphasic system (ABS) is investigated for the IL with the same1-butyl-3-methylimidazolium cation, [bmim](+), and various anions, for example, salicylate, [SAL](-); trifluoromethanesulfonate, [TFS](-); dicyanamide, [DCA](-); and chloride, [Cl](-). The order of studied anions to form ABS is [TFS](-) GT [SAL](-) GT [DCA](-) GT [Cl](-). The effect of alkyl chain length on imidazolium ion on liquidliquid equilibrium is discussed in terms of increasing ionic liquid hydrophobicity and poorer affinity for water. It is shown that 1-hexyl-3-methylimidazolium chloride ionic liquid has a better ability to form ABS comparing to ionic liquid with butyl chain and the same anion. Newly synthesized ionic-liquid-containing ethyl group 1-butyl-3-ethylimidazolium bromide was also investigated, showing the influence of both ethyl group and bromide anion on the ability of ABS formation.
T2  - Journal of Chemical and Engineering Data
T1  - Liquid-Liquid Equilibria in Aqueous 1-Alkyl-3-methylimidazolium- and 1-Butyl-3-ethylimidazolium-Based Ionic Liquids
VL  - 61
IS  - 1
SP  - 549
EP  - 555
DO  - 10.1021/acs.jced.5b00697
ER  - 

@article{
author = "Dimitrijević, Aleksandra and Trtić-Petrović, Tatjana M. and Vraneš, Milan and Papović, Snežana and Tot, Aleksandar and Dožić, Sanja and Gadžurić, Slobodan",
year = "2016",
abstract = "In this work, novel phase diagrams for aqueous solutions of 1-alkyl-3-methylimidazolium- and 1-butyl-3-ethylimidazolium-based ILs combined with phosphate-based salts, namely, K3PO4 or K2HPO4, are reported and discussed. To correlate the binodal data, the Merchuk equation is applied. The tie lines and tie-line lengths are also presented. The anion influence on the ability to form aqueous biphasic system (ABS) is investigated for the IL with the same1-butyl-3-methylimidazolium cation, [bmim](+), and various anions, for example, salicylate, [SAL](-); trifluoromethanesulfonate, [TFS](-); dicyanamide, [DCA](-); and chloride, [Cl](-). The order of studied anions to form ABS is [TFS](-) GT [SAL](-) GT [DCA](-) GT [Cl](-). The effect of alkyl chain length on imidazolium ion on liquidliquid equilibrium is discussed in terms of increasing ionic liquid hydrophobicity and poorer affinity for water. It is shown that 1-hexyl-3-methylimidazolium chloride ionic liquid has a better ability to form ABS comparing to ionic liquid with butyl chain and the same anion. Newly synthesized ionic-liquid-containing ethyl group 1-butyl-3-ethylimidazolium bromide was also investigated, showing the influence of both ethyl group and bromide anion on the ability of ABS formation.",
journal = "Journal of Chemical and Engineering Data",
title = "Liquid-Liquid Equilibria in Aqueous 1-Alkyl-3-methylimidazolium- and 1-Butyl-3-ethylimidazolium-Based Ionic Liquids",
volume = "61",
number = "1",
pages = "549-555",
doi = "10.1021/acs.jced.5b00697"
}

Dimitrijević, A., Trtić-Petrović, T. M., Vraneš, M., Papović, S., Tot, A., Dožić, S.,& Gadžurić, S.. (2016). Liquid-Liquid Equilibria in Aqueous 1-Alkyl-3-methylimidazolium- and 1-Butyl-3-ethylimidazolium-Based Ionic Liquids. in Journal of Chemical and Engineering Data, 61(1), 549-555.
https://doi.org/10.1021/acs.jced.5b00697

Dimitrijević A, Trtić-Petrović TM, Vraneš M, Papović S, Tot A, Dožić S, Gadžurić S. Liquid-Liquid Equilibria in Aqueous 1-Alkyl-3-methylimidazolium- and 1-Butyl-3-ethylimidazolium-Based Ionic Liquids. in Journal of Chemical and Engineering Data. 2016;61(1):549-555.
doi:10.1021/acs.jced.5b00697 .

Dimitrijević, Aleksandra, Trtić-Petrović, Tatjana M., Vraneš, Milan, Papović, Snežana, Tot, Aleksandar, Dožić, Sanja, Gadžurić, Slobodan, "Liquid-Liquid Equilibria in Aqueous 1-Alkyl-3-methylimidazolium- and 1-Butyl-3-ethylimidazolium-Based Ionic Liquids" in Journal of Chemical and Engineering Data, 61, no. 1 (2016):549-555,
https://doi.org/10.1021/acs.jced.5b00697 . .

TY  - JOUR
AU  - Dimitrijević, Aleksandra
AU  - Zec, Nebojša
AU  - Zdolšek, Nikola
AU  - Dožić, Sanja
AU  - Tot, Aleksandar
AU  - Gadžurić, Slobodan
AU  - Vraneš, Milan
AU  - Trtić-Petrović, Tatjana M.
PY  - 2016
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1213
AB  - In this work three 1-alkyl-3-ethylimidazolium bromide ionic liquids (alkyl = ethyl, hexyl and octyl) were synthesized applying both, conventional and microwave assisted synthetic paths. The phase diagrams for aqueous solutions of 1-alkyl-3-ethylimidazolium bromide ionic liquids as novel extractants combined with phosphate-based salts are reported and discussed in terms of aqueous biphasic system (ABS) formation. Merchuk equation was applied in order to correlate the,experimental binodal data. The liquid-liquid equilibrium data (tie-line compositions and tie-line length) were also experimentally determined by a gravimetric method. The influence of the alkyl chain length on ABS formation ability was investigated. It was found that ability to form ABS increases with the increase of the alkyl chain length on the imidazolium cation. Also, it was found that ionic liquids with ethyl group in the N-3 position better form ABS compared to those with methyl substituent. This was discussed in terms of increasing ionic liquid hydrophobicity and poor affinity for water. In order to better understand the impact of the alkyl side chain of the imidazolium ion and the efficiency of ABS formation, computer simulations were performed using investigated ionic liquids with the ethyl group in the position N-3 of the cation and different alkyl substituents in the position N-1. Also, extraction of selected organic dyes was performed to demonstrate application of studied ionic liquids as novel extractants. (C) 2016 The Korean Society of Industrial and Engineering Chemistry. Published by Elsevier B.V. All rights reserved.
T2  - Journal of Industrial and Engineering Chemistry
T1  - Aqueous biphasic system formation using 1-alkyl-3-ethylimidazolium bromide ionic liquids as new extractants
VL  - 40
SP  - 152
EP  - 160
DO  - 10.1016/j.jiec.2016.06.017
ER  - 

@article{
author = "Dimitrijević, Aleksandra and Zec, Nebojša and Zdolšek, Nikola and Dožić, Sanja and Tot, Aleksandar and Gadžurić, Slobodan and Vraneš, Milan and Trtić-Petrović, Tatjana M.",
year = "2016",
abstract = "In this work three 1-alkyl-3-ethylimidazolium bromide ionic liquids (alkyl = ethyl, hexyl and octyl) were synthesized applying both, conventional and microwave assisted synthetic paths. The phase diagrams for aqueous solutions of 1-alkyl-3-ethylimidazolium bromide ionic liquids as novel extractants combined with phosphate-based salts are reported and discussed in terms of aqueous biphasic system (ABS) formation. Merchuk equation was applied in order to correlate the,experimental binodal data. The liquid-liquid equilibrium data (tie-line compositions and tie-line length) were also experimentally determined by a gravimetric method. The influence of the alkyl chain length on ABS formation ability was investigated. It was found that ability to form ABS increases with the increase of the alkyl chain length on the imidazolium cation. Also, it was found that ionic liquids with ethyl group in the N-3 position better form ABS compared to those with methyl substituent. This was discussed in terms of increasing ionic liquid hydrophobicity and poor affinity for water. In order to better understand the impact of the alkyl side chain of the imidazolium ion and the efficiency of ABS formation, computer simulations were performed using investigated ionic liquids with the ethyl group in the position N-3 of the cation and different alkyl substituents in the position N-1. Also, extraction of selected organic dyes was performed to demonstrate application of studied ionic liquids as novel extractants. (C) 2016 The Korean Society of Industrial and Engineering Chemistry. Published by Elsevier B.V. All rights reserved.",
journal = "Journal of Industrial and Engineering Chemistry",
title = "Aqueous biphasic system formation using 1-alkyl-3-ethylimidazolium bromide ionic liquids as new extractants",
volume = "40",
pages = "152-160",
doi = "10.1016/j.jiec.2016.06.017"
}

Dimitrijević, A., Zec, N., Zdolšek, N., Dožić, S., Tot, A., Gadžurić, S., Vraneš, M.,& Trtić-Petrović, T. M.. (2016). Aqueous biphasic system formation using 1-alkyl-3-ethylimidazolium bromide ionic liquids as new extractants. in Journal of Industrial and Engineering Chemistry, 40, 152-160.
https://doi.org/10.1016/j.jiec.2016.06.017

Dimitrijević A, Zec N, Zdolšek N, Dožić S, Tot A, Gadžurić S, Vraneš M, Trtić-Petrović TM. Aqueous biphasic system formation using 1-alkyl-3-ethylimidazolium bromide ionic liquids as new extractants. in Journal of Industrial and Engineering Chemistry. 2016;40:152-160.
doi:10.1016/j.jiec.2016.06.017 .

Dimitrijević, Aleksandra, Zec, Nebojša, Zdolšek, Nikola, Dožić, Sanja, Tot, Aleksandar, Gadžurić, Slobodan, Vraneš, Milan, Trtić-Petrović, Tatjana M., "Aqueous biphasic system formation using 1-alkyl-3-ethylimidazolium bromide ionic liquids as new extractants" in Journal of Industrial and Engineering Chemistry, 40 (2016):152-160,
https://doi.org/10.1016/j.jiec.2016.06.017 . .