TY  - JOUR
AU  - Burmudžija, Adrijana
AU  - Muškinja, Jovana
AU  - Ratković, Zoran R.
AU  - Kosanić, Marijana
AU  - Ranković, Branislav
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
PY  - 2018
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1910
AB  - A series of ferrocenyl ketones were synthesized in reaction with ferrocene and corresponding substituted acryloyl chlorides, following previously described procedure. Synthesized products have conjugated enone system, which is suitable for further transformations. In a reaction with hydrazine in acidic medium (acetic acid) new pyrazoline derivatives were obtained. Their antimicrobial properties have been tested. Synthesized pyrazoline derivatives demonstrated expressed in vitro antimicrobial activity towards 12 strains of microorganisms inhibiting all tested bacteria and fungi. The most potent compound in all cases was sorbyl derivative; for bacteria activity was very close to streptomycin, and for fungi in one case the same as ketoconazole. It is established that this compound can be a new, potential antimicrobial agent with minimum inhibitory concentrations from 0.039 to 0.312 mg/mL. One of the starting compounds and two products were crystal substances, suitable for the single crystal X-ray diffraction analysis, which confirmed undoubtedly their structures. (C) 2017 Elsevier B.V. All rights reserved.
T2  - Inorganica Chimica Acta
T1  - Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties
VL  - 471
SP  - 570
EP  - 576
DO  - 10.1016/j.ica.2017.11.061
ER  - 

@article{
author = "Burmudžija, Adrijana and Muškinja, Jovana and Ratković, Zoran R. and Kosanić, Marijana and Ranković, Branislav and Novaković, Slađana B. and Bogdanović, Goran A.",
year = "2018",
abstract = "A series of ferrocenyl ketones were synthesized in reaction with ferrocene and corresponding substituted acryloyl chlorides, following previously described procedure. Synthesized products have conjugated enone system, which is suitable for further transformations. In a reaction with hydrazine in acidic medium (acetic acid) new pyrazoline derivatives were obtained. Their antimicrobial properties have been tested. Synthesized pyrazoline derivatives demonstrated expressed in vitro antimicrobial activity towards 12 strains of microorganisms inhibiting all tested bacteria and fungi. The most potent compound in all cases was sorbyl derivative; for bacteria activity was very close to streptomycin, and for fungi in one case the same as ketoconazole. It is established that this compound can be a new, potential antimicrobial agent with minimum inhibitory concentrations from 0.039 to 0.312 mg/mL. One of the starting compounds and two products were crystal substances, suitable for the single crystal X-ray diffraction analysis, which confirmed undoubtedly their structures. (C) 2017 Elsevier B.V. All rights reserved.",
journal = "Inorganica Chimica Acta",
title = "Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties",
volume = "471",
pages = "570-576",
doi = "10.1016/j.ica.2017.11.061"
}

Burmudžija, A., Muškinja, J., Ratković, Z. R., Kosanić, M., Ranković, B., Novaković, S. B.,& Bogdanović, G. A.. (2018). Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties. in Inorganica Chimica Acta, 471, 570-576.
https://doi.org/10.1016/j.ica.2017.11.061

Burmudžija A, Muškinja J, Ratković ZR, Kosanić M, Ranković B, Novaković SB, Bogdanović GA. Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties. in Inorganica Chimica Acta. 2018;471:570-576.
doi:10.1016/j.ica.2017.11.061 .

Burmudžija, Adrijana, Muškinja, Jovana, Ratković, Zoran R., Kosanić, Marijana, Ranković, Branislav, Novaković, Slađana B., Bogdanović, Goran A., "Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties" in Inorganica Chimica Acta, 471 (2018):570-576,
https://doi.org/10.1016/j.ica.2017.11.061 . .

TY  - JOUR
AU  - Muškinja, Jovana
AU  - Burmudžija, Adrijana
AU  - Ratković, Zoran R.
AU  - Ranković, Branislav
AU  - Kosanić, Marijana
AU  - Bogdanović, Goran A.
AU  - Novaković, Slađana B.
PY  - 2016
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1268
AB  - O-alkylated vanillin derivatives 2a-f and acetylferrocene react under Claisen-Schmidt conditions, resulting in good-to-high yields of the corresponding ferrocene chalcones 3a-f. None of the resultant compounds 3b-f has been previously described in the literature. All synthesized compounds were characterized by spectral and physical data, whereas two of them, 1-ferrocenyl-3-(4-ethoxy-3-methoxyphenyl)-prop-2-en-1-one (3b) and 1-ferrocenyl-3-(4-buthoxy-3-methoxy-phenyl)-prop-2-en-1-one (3e), were crystalline substances, suitable for single-crystal X-ray analysis, which confirmed undoubtedly their structures. Chalcones 3a-f were tested for their biological activity and demonstrated relatively good in vitro antimicrobial activity towards different strains of bacteria and fungi. The best antibacterial activity is expressed by compounds 3b and 3c, while compound 3d shows the best antifungal activity.
T2  - Medicinal Chemistry Research
T1  - Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis
VL  - 25
IS  - 9
SP  - 1744
EP  - 1753
DO  - 10.1007/s00044-016-1609-8
ER  - 

@article{
author = "Muškinja, Jovana and Burmudžija, Adrijana and Ratković, Zoran R. and Ranković, Branislav and Kosanić, Marijana and Bogdanović, Goran A. and Novaković, Slađana B.",
year = "2016",
abstract = "O-alkylated vanillin derivatives 2a-f and acetylferrocene react under Claisen-Schmidt conditions, resulting in good-to-high yields of the corresponding ferrocene chalcones 3a-f. None of the resultant compounds 3b-f has been previously described in the literature. All synthesized compounds were characterized by spectral and physical data, whereas two of them, 1-ferrocenyl-3-(4-ethoxy-3-methoxyphenyl)-prop-2-en-1-one (3b) and 1-ferrocenyl-3-(4-buthoxy-3-methoxy-phenyl)-prop-2-en-1-one (3e), were crystalline substances, suitable for single-crystal X-ray analysis, which confirmed undoubtedly their structures. Chalcones 3a-f were tested for their biological activity and demonstrated relatively good in vitro antimicrobial activity towards different strains of bacteria and fungi. The best antibacterial activity is expressed by compounds 3b and 3c, while compound 3d shows the best antifungal activity.",
journal = "Medicinal Chemistry Research",
title = "Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis",
volume = "25",
number = "9",
pages = "1744-1753",
doi = "10.1007/s00044-016-1609-8"
}

Muškinja, J., Burmudžija, A., Ratković, Z. R., Ranković, B., Kosanić, M., Bogdanović, G. A.,& Novaković, S. B.. (2016). Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis. in Medicinal Chemistry Research, 25(9), 1744-1753.
https://doi.org/10.1007/s00044-016-1609-8

Muškinja J, Burmudžija A, Ratković ZR, Ranković B, Kosanić M, Bogdanović GA, Novaković SB. Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis. in Medicinal Chemistry Research. 2016;25(9):1744-1753.
doi:10.1007/s00044-016-1609-8 .

Muškinja, Jovana, Burmudžija, Adrijana, Ratković, Zoran R., Ranković, Branislav, Kosanić, Marijana, Bogdanović, Goran A., Novaković, Slađana B., "Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis" in Medicinal Chemistry Research, 25, no. 9 (2016):1744-1753,
https://doi.org/10.1007/s00044-016-1609-8 . .

TY  - JOUR
AU  - Ratković, Zoran R.
AU  - Muškinja, Jovana
AU  - Burmudžija, Adrijana
AU  - Ranković, Branislav
AU  - Kosanić, Marijana
AU  - Bogdanović, Goran A.
AU  - Marković-Simović, Bojana
AU  - Nikolić, Aleksandar
AU  - Arsenijević, Nebojša N.
AU  - Đorđević, Snežana
AU  - Vukićević, Rastko D.
PY  - 2016
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1127
AB  - A small series of 1-acetyl-5-aryl-4,5-dihydro-1H-pyrazoles (aryl = 4-hydroxy-3-methoxyphenyl and 4-alkoxy-3-methoxyphenyl) was prepared, starting from 4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one, dehydrozingerone, and its alkyl derivatives. Their in vitro cytotoxic activity against some cancer cell lines was tested, showing significant anticancer activity. All the new compounds were well characterized by IR, H-1, C-13 NMR and ESI-MS spectroscopy and physical data, whereas structures of two of them were determined by single crystal X-ray analysis. (C) 2016 Elsevier B.V. All rights reserved.
T2  - Journal of Molecular Structure
T1  - Dehydrozingerone based 1-acetyl-5-aryl-4,5-dihydro-1H-pyrazoles: Synthesis, characterization and anticancer activity
VL  - 1109
SP  - 82
EP  - 88
DO  - 10.1016/j.molstruc.2015.12.079
ER  - 

@article{
author = "Ratković, Zoran R. and Muškinja, Jovana and Burmudžija, Adrijana and Ranković, Branislav and Kosanić, Marijana and Bogdanović, Goran A. and Marković-Simović, Bojana and Nikolić, Aleksandar and Arsenijević, Nebojša N. and Đorđević, Snežana and Vukićević, Rastko D.",
year = "2016",
abstract = "A small series of 1-acetyl-5-aryl-4,5-dihydro-1H-pyrazoles (aryl = 4-hydroxy-3-methoxyphenyl and 4-alkoxy-3-methoxyphenyl) was prepared, starting from 4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one, dehydrozingerone, and its alkyl derivatives. Their in vitro cytotoxic activity against some cancer cell lines was tested, showing significant anticancer activity. All the new compounds were well characterized by IR, H-1, C-13 NMR and ESI-MS spectroscopy and physical data, whereas structures of two of them were determined by single crystal X-ray analysis. (C) 2016 Elsevier B.V. All rights reserved.",
journal = "Journal of Molecular Structure",
title = "Dehydrozingerone based 1-acetyl-5-aryl-4,5-dihydro-1H-pyrazoles: Synthesis, characterization and anticancer activity",
volume = "1109",
pages = "82-88",
doi = "10.1016/j.molstruc.2015.12.079"
}

Ratković, Z. R., Muškinja, J., Burmudžija, A., Ranković, B., Kosanić, M., Bogdanović, G. A., Marković-Simović, B., Nikolić, A., Arsenijević, N. N., Đorđević, S.,& Vukićević, R. D.. (2016). Dehydrozingerone based 1-acetyl-5-aryl-4,5-dihydro-1H-pyrazoles: Synthesis, characterization and anticancer activity. in Journal of Molecular Structure, 1109, 82-88.
https://doi.org/10.1016/j.molstruc.2015.12.079

Ratković ZR, Muškinja J, Burmudžija A, Ranković B, Kosanić M, Bogdanović GA, Marković-Simović B, Nikolić A, Arsenijević NN, Đorđević S, Vukićević RD. Dehydrozingerone based 1-acetyl-5-aryl-4,5-dihydro-1H-pyrazoles: Synthesis, characterization and anticancer activity. in Journal of Molecular Structure. 2016;1109:82-88.
doi:10.1016/j.molstruc.2015.12.079 .

Ratković, Zoran R., Muškinja, Jovana, Burmudžija, Adrijana, Ranković, Branislav, Kosanić, Marijana, Bogdanović, Goran A., Marković-Simović, Bojana, Nikolić, Aleksandar, Arsenijević, Nebojša N., Đorđević, Snežana, Vukićević, Rastko D., "Dehydrozingerone based 1-acetyl-5-aryl-4,5-dihydro-1H-pyrazoles: Synthesis, characterization and anticancer activity" in Journal of Molecular Structure, 1109 (2016):82-88,
https://doi.org/10.1016/j.molstruc.2015.12.079 . .

TY  - JOUR
AU  - Joksimović, Nenad
AU  - Baskic, Dejan
AU  - Popovic, Suzana
AU  - Zarić, Milan
AU  - Kosanić, Marijana
AU  - Ranković, Branislav
AU  - Stanojković, Tatjana P.
AU  - Novaković, Slađana B.
AU  - Davidovic, Goran
AU  - Bugarčič, Zorica M.
AU  - Janković, Nenad
PY  - 2016
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1269
AB  - A serie of novel square pyramidal copper(II) complexes [Cu(L)(2)H2O] (3a-d) with O,O-bidentate ligands [L = ethyl-2-hydroxy-4-aryl-4-oxo-2-butenoate; aryl = 3-methoxyphenyl-2a, (E)-2-phenylvinyl-2b, (E)-2-(4-hydroxy-3-methoxyphenyl)vinyl-2c, 3-nitrophenyl-2d, 2-thienyl-2e] were synthesized and characterized by spectral (UV-Vis, IR, ESI-MS and EPR), elemental and X-ray analysis. The antimicrobial activity was estimated by the determination of the minimal inhibitory concentration (MIC) using the broth micro-dilution method. The most active antibacterial compounds were 3c and 3d, while the best antifungal activity was showed by complexes 3b and 3e. The lowest MIC value (0.048 mg mL(-1)) was measured for 3c against Proteus mirabilis. The cytotoxic activity was tested using the MTT method on human epithelial carcinoma HeLa cells, human lung carcinoma A549 cells and human colon carcinoma LS174 cells. All complexes showed extremely better cytotoxic activity compared to cisplatin at all tested concentrations. Compound 3d expressed the best activity against all tested cell lines with IC50 values ranging from 7.45 to 7.91 mu g mL(-1). The type of cell death and the impact on the cell cycle for 3d and 3e were evaluated by flow cytometry. Both compounds induced apoptosis and S phase cell cycle arrest. The interactions between selected complexes (3d and 3e) and CT-DNA or bovine serum albumin (BSA) were investigated by the fluorescence spectroscopic method. Competitive experiments with ethidium bromide (EB) indicated that 3d and 3e have a propensity to displace EB from the EB-DNA complex through intercalation suggesting strong competition with EB [K-sv = (1.4 +/- 0.2) and (2.9 +/- 0.1) x 10(4) M-1, respectively]. K-sv values indicate that these complexes bind to DNA covalently and non-covalently. The achieved results in the fluorescence titration of BSA with 3d and 3e [K-a = (2.9 +/- 0.2) x 10(6) and (2.5 +/- 0.2) x 10(5) M, respectively] showed that the fluorescence quenching of BSA is a result of the formation of the 3d- and 3e-BSA complexes. The obtained K-a values are high enough to ensure that a significant amount of 3d and 3e gets transported and distributed through the cells.
T2  - Dalton Transactions
T1  - Synthesis, characterization, biological activity, DNA and BSA binding study: novel copper(II) complexes with 2-hydroxy-4-aryl-4-oxo-2-butenoate
VL  - 45
IS  - 38
SP  - 15067
EP  - 15077
DO  - 10.1039/c6dt02257j
ER  - 

@article{
author = "Joksimović, Nenad and Baskic, Dejan and Popovic, Suzana and Zarić, Milan and Kosanić, Marijana and Ranković, Branislav and Stanojković, Tatjana P. and Novaković, Slađana B. and Davidovic, Goran and Bugarčič, Zorica M. and Janković, Nenad",
year = "2016",
abstract = "A serie of novel square pyramidal copper(II) complexes [Cu(L)(2)H2O] (3a-d) with O,O-bidentate ligands [L = ethyl-2-hydroxy-4-aryl-4-oxo-2-butenoate; aryl = 3-methoxyphenyl-2a, (E)-2-phenylvinyl-2b, (E)-2-(4-hydroxy-3-methoxyphenyl)vinyl-2c, 3-nitrophenyl-2d, 2-thienyl-2e] were synthesized and characterized by spectral (UV-Vis, IR, ESI-MS and EPR), elemental and X-ray analysis. The antimicrobial activity was estimated by the determination of the minimal inhibitory concentration (MIC) using the broth micro-dilution method. The most active antibacterial compounds were 3c and 3d, while the best antifungal activity was showed by complexes 3b and 3e. The lowest MIC value (0.048 mg mL(-1)) was measured for 3c against Proteus mirabilis. The cytotoxic activity was tested using the MTT method on human epithelial carcinoma HeLa cells, human lung carcinoma A549 cells and human colon carcinoma LS174 cells. All complexes showed extremely better cytotoxic activity compared to cisplatin at all tested concentrations. Compound 3d expressed the best activity against all tested cell lines with IC50 values ranging from 7.45 to 7.91 mu g mL(-1). The type of cell death and the impact on the cell cycle for 3d and 3e were evaluated by flow cytometry. Both compounds induced apoptosis and S phase cell cycle arrest. The interactions between selected complexes (3d and 3e) and CT-DNA or bovine serum albumin (BSA) were investigated by the fluorescence spectroscopic method. Competitive experiments with ethidium bromide (EB) indicated that 3d and 3e have a propensity to displace EB from the EB-DNA complex through intercalation suggesting strong competition with EB [K-sv = (1.4 +/- 0.2) and (2.9 +/- 0.1) x 10(4) M-1, respectively]. K-sv values indicate that these complexes bind to DNA covalently and non-covalently. The achieved results in the fluorescence titration of BSA with 3d and 3e [K-a = (2.9 +/- 0.2) x 10(6) and (2.5 +/- 0.2) x 10(5) M, respectively] showed that the fluorescence quenching of BSA is a result of the formation of the 3d- and 3e-BSA complexes. The obtained K-a values are high enough to ensure that a significant amount of 3d and 3e gets transported and distributed through the cells.",
journal = "Dalton Transactions",
title = "Synthesis, characterization, biological activity, DNA and BSA binding study: novel copper(II) complexes with 2-hydroxy-4-aryl-4-oxo-2-butenoate",
volume = "45",
number = "38",
pages = "15067-15077",
doi = "10.1039/c6dt02257j"
}

Joksimović, N., Baskic, D., Popovic, S., Zarić, M., Kosanić, M., Ranković, B., Stanojković, T. P., Novaković, S. B., Davidovic, G., Bugarčič, Z. M.,& Janković, N.. (2016). Synthesis, characterization, biological activity, DNA and BSA binding study: novel copper(II) complexes with 2-hydroxy-4-aryl-4-oxo-2-butenoate. in Dalton Transactions, 45(38), 15067-15077.
https://doi.org/10.1039/c6dt02257j

Joksimović N, Baskic D, Popovic S, Zarić M, Kosanić M, Ranković B, Stanojković TP, Novaković SB, Davidovic G, Bugarčič ZM, Janković N. Synthesis, characterization, biological activity, DNA and BSA binding study: novel copper(II) complexes with 2-hydroxy-4-aryl-4-oxo-2-butenoate. in Dalton Transactions. 2016;45(38):15067-15077.
doi:10.1039/c6dt02257j .

Joksimović, Nenad, Baskic, Dejan, Popovic, Suzana, Zarić, Milan, Kosanić, Marijana, Ranković, Branislav, Stanojković, Tatjana P., Novaković, Slađana B., Davidovic, Goran, Bugarčič, Zorica M., Janković, Nenad, "Synthesis, characterization, biological activity, DNA and BSA binding study: novel copper(II) complexes with 2-hydroxy-4-aryl-4-oxo-2-butenoate" in Dalton Transactions, 45, no. 38 (2016):15067-15077,
https://doi.org/10.1039/c6dt02257j . .