TY  - JOUR
AU  - Čobeljić, Božidar
AU  - Živković, Marijana B.
AU  - Matić, Ivana Z.
AU  - Novaković, Irena T.
AU  - Sladić, Dušan
AU  - Anđelković, Katarina K.
AU  - Krstić, Natalija M.
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4788
AB  - In this work, Pt(II) complexes of previously synthesized steroidal thiosemicarbazones were synthesized and characterized. The ligands and their metal complexes were studied by analytical and spectroscopic data (elemental analysis, IR, 1D-NMR and 2D-NMR, HSQC, HMBC, NOESY, COSY), the analysis of which enabled complete 1H and 13C assignments of each compound including E and Z isomers. All the synthesized ligands and complexes were screened for their cytotoxic and antimicrobial activity. The results demonstrate that the new steroidal thiosemicarbazone complexes were significantly less cytotoxic than the corresponding steroidal thiosemicarbazones. In addition, complexes showed lower antimicrobial activity than the standard drugs, similar to the activity of the starting thiosemicarbazones.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones
VL  - 86
IS  - 5
SP  - 459
EP  - 468
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4788
ER  - 

@article{
author = "Čobeljić, Božidar and Živković, Marijana B. and Matić, Ivana Z. and Novaković, Irena T. and Sladić, Dušan and Anđelković, Katarina K. and Krstić, Natalija M.",
year = "2021",
abstract = "In this work, Pt(II) complexes of previously synthesized steroidal thiosemicarbazones were synthesized and characterized. The ligands and their metal complexes were studied by analytical and spectroscopic data (elemental analysis, IR, 1D-NMR and 2D-NMR, HSQC, HMBC, NOESY, COSY), the analysis of which enabled complete 1H and 13C assignments of each compound including E and Z isomers. All the synthesized ligands and complexes were screened for their cytotoxic and antimicrobial activity. The results demonstrate that the new steroidal thiosemicarbazone complexes were significantly less cytotoxic than the corresponding steroidal thiosemicarbazones. In addition, complexes showed lower antimicrobial activity than the standard drugs, similar to the activity of the starting thiosemicarbazones.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones",
volume = "86",
number = "5",
pages = "459-468",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4788"
}

Čobeljić, B., Živković, M. B., Matić, I. Z., Novaković, I. T., Sladić, D., Anđelković, K. K.,& Krstić, N. M.. (2021). Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 86(5), 459-468.
https://hdl.handle.net/21.15107/rcub_cherry_4788

Čobeljić B, Živković MB, Matić IZ, Novaković IT, Sladić D, Anđelković KK, Krstić NM. Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones. in Journal of the Serbian Chemical Society. 2021;86(5):459-468.
https://hdl.handle.net/21.15107/rcub_cherry_4788 .

Čobeljić, Božidar, Živković, Marijana B., Matić, Ivana Z., Novaković, Irena T., Sladić, Dušan, Anđelković, Katarina K., Krstić, Natalija M., "Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones" in Journal of the Serbian Chemical Society, 86, no. 5 (2021):459-468,
https://hdl.handle.net/21.15107/rcub_cherry_4788 .

TY  - JOUR
AU  - Živković, Marijana B.
AU  - Novaković, Irena T.
AU  - Matić, Ivana Z.
AU  - Sladić, Dušan
AU  - Krstić, Natalija M.
PY  - 2019
UR  - http://www.sciencedirect.com/science/article/pii/S0039128X19300893
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3082
AB  - Eleven new steroidal mono- and bis(semicarbazones)2a–e, 4d and 3a–e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a–e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a-e were obtained. The structures of all synthesized compounds and identification of each E/Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro of the new compounds has been conducted against three cancer cell lines, K562, Jurkat and HeLa cells. HeLa cells were the most sensitive while K562 cells were the least sensitive to the cytotoxic action of the novel steroid derivatives. Compounds 2e, 3c and 5e were found to have the best but still moderate cytotoxic effects. All tested compounds showed very weak antimicrobial activities. These results demonstrate that the replacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.
T2  - Steroids
T1  - Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives
VL  - 148
SP  - 36
EP  - 46
DO  - 10.1016/j.steroids.2019.04.010
ER  - 

@article{
author = "Živković, Marijana B. and Novaković, Irena T. and Matić, Ivana Z. and Sladić, Dušan and Krstić, Natalija M.",
year = "2019",
abstract = "Eleven new steroidal mono- and bis(semicarbazones)2a–e, 4d and 3a–e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a–e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a-e were obtained. The structures of all synthesized compounds and identification of each E/Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro of the new compounds has been conducted against three cancer cell lines, K562, Jurkat and HeLa cells. HeLa cells were the most sensitive while K562 cells were the least sensitive to the cytotoxic action of the novel steroid derivatives. Compounds 2e, 3c and 5e were found to have the best but still moderate cytotoxic effects. All tested compounds showed very weak antimicrobial activities. These results demonstrate that the replacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.",
journal = "Steroids",
title = "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives",
volume = "148",
pages = "36-46",
doi = "10.1016/j.steroids.2019.04.010"
}

Živković, M. B., Novaković, I. T., Matić, I. Z., Sladić, D.,& Krstić, N. M.. (2019). Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids, 148, 36-46.
https://doi.org/10.1016/j.steroids.2019.04.010

Živković MB, Novaković IT, Matić IZ, Sladić D, Krstić NM. Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids. 2019;148:36-46.
doi:10.1016/j.steroids.2019.04.010 .

Živković, Marijana B., Novaković, Irena T., Matić, Ivana Z., Sladić, Dušan, Krstić, Natalija M., "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives" in Steroids, 148 (2019):36-46,
https://doi.org/10.1016/j.steroids.2019.04.010 . .

TY  - DATA
AU  - Živković, Marijana B.
AU  - Novaković, Irena T.
AU  - Matić, Ivana Z.
AU  - Sladić, Dušan
AU  - Krstić, Natalija M.
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3083
T2  - Steroids
T1  - Supplementary data for article: Živković, M. B.; Novaković, I. T.; Matić, I. Z.; Sladić, D. M.; Krstić, N. M. Synthesis and Preliminary Screening for the Biological Activity of Some Steroidal Δ4-Unsaturated Semicarbazone Derivatives. Steroids 2019, 148, 36–46. https://doi.org/10.1016/j.steroids.2019.04.010
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3083
ER  - 

@misc{
author = "Živković, Marijana B. and Novaković, Irena T. and Matić, Ivana Z. and Sladić, Dušan and Krstić, Natalija M.",
year = "2019",
journal = "Steroids",
title = "Supplementary data for article: Živković, M. B.; Novaković, I. T.; Matić, I. Z.; Sladić, D. M.; Krstić, N. M. Synthesis and Preliminary Screening for the Biological Activity of Some Steroidal Δ4-Unsaturated Semicarbazone Derivatives. Steroids 2019, 148, 36–46. https://doi.org/10.1016/j.steroids.2019.04.010",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3083"
}

Živković, M. B., Novaković, I. T., Matić, I. Z., Sladić, D.,& Krstić, N. M.. (2019). Supplementary data for article: Živković, M. B.; Novaković, I. T.; Matić, I. Z.; Sladić, D. M.; Krstić, N. M. Synthesis and Preliminary Screening for the Biological Activity of Some Steroidal Δ4-Unsaturated Semicarbazone Derivatives. Steroids 2019, 148, 36–46. https://doi.org/10.1016/j.steroids.2019.04.010. in Steroids.
https://hdl.handle.net/21.15107/rcub_cherry_3083

Živković MB, Novaković IT, Matić IZ, Sladić D, Krstić NM. Supplementary data for article: Živković, M. B.; Novaković, I. T.; Matić, I. Z.; Sladić, D. M.; Krstić, N. M. Synthesis and Preliminary Screening for the Biological Activity of Some Steroidal Δ4-Unsaturated Semicarbazone Derivatives. Steroids 2019, 148, 36–46. https://doi.org/10.1016/j.steroids.2019.04.010. in Steroids. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3083 .

Živković, Marijana B., Novaković, Irena T., Matić, Ivana Z., Sladić, Dušan, Krstić, Natalija M., "Supplementary data for article: Živković, M. B.; Novaković, I. T.; Matić, I. Z.; Sladić, D. M.; Krstić, N. M. Synthesis and Preliminary Screening for the Biological Activity of Some Steroidal Δ4-Unsaturated Semicarbazone Derivatives. Steroids 2019, 148, 36–46. https://doi.org/10.1016/j.steroids.2019.04.010" in Steroids (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3083 .

TY  - JOUR
AU  - Živković, Marijana B.
AU  - Novaković, Irena T.
AU  - Matić, Ivana Z.
AU  - Sladić, Dušan
AU  - Krstić, Natalija M.
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3084
AB  - Eleven new steroidal mono- and bis(semicarbazones)2a–e, 4d and 3a–e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a–e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a-e were obtained. The structures of all synthesized compounds and identification of each E/Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro of the new compounds has been conducted against three cancer cell lines, K562, Jurkat and HeLa cells. HeLa cells were the most sensitive while K562 cells were the least sensitive to the cytotoxic action of the novel steroid derivatives. Compounds 2e, 3c and 5e were found to have the best but still moderate cytotoxic effects. All tested compounds showed very weak antimicrobial activities. These results demonstrate that the replacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.
T2  - Steroids
T1  - Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives
VL  - 148
SP  - 36
EP  - 46
DO  - 10.1016/j.steroids.2019.04.010
ER  - 

@article{
author = "Živković, Marijana B. and Novaković, Irena T. and Matić, Ivana Z. and Sladić, Dušan and Krstić, Natalija M.",
year = "2019",
abstract = "Eleven new steroidal mono- and bis(semicarbazones)2a–e, 4d and 3a–e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a–e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a-e were obtained. The structures of all synthesized compounds and identification of each E/Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro of the new compounds has been conducted against three cancer cell lines, K562, Jurkat and HeLa cells. HeLa cells were the most sensitive while K562 cells were the least sensitive to the cytotoxic action of the novel steroid derivatives. Compounds 2e, 3c and 5e were found to have the best but still moderate cytotoxic effects. All tested compounds showed very weak antimicrobial activities. These results demonstrate that the replacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.",
journal = "Steroids",
title = "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives",
volume = "148",
pages = "36-46",
doi = "10.1016/j.steroids.2019.04.010"
}

Živković, M. B., Novaković, I. T., Matić, I. Z., Sladić, D.,& Krstić, N. M.. (2019). Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids, 148, 36-46.
https://doi.org/10.1016/j.steroids.2019.04.010

Živković MB, Novaković IT, Matić IZ, Sladić D, Krstić NM. Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids. 2019;148:36-46.
doi:10.1016/j.steroids.2019.04.010 .

Živković, Marijana B., Novaković, Irena T., Matić, Ivana Z., Sladić, Dušan, Krstić, Natalija M., "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives" in Steroids, 148 (2019):36-46,
https://doi.org/10.1016/j.steroids.2019.04.010 . .

TY  - JOUR
AU  - Živković, Marijana B.
AU  - Matić, Ivana Z.
AU  - Rodić, Marko
AU  - Novaković, Irena T.
AU  - Krivokuća, Ana M.
AU  - Sladić, Dušan
AU  - Krstić, Natalija M.
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3191
AB  - The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Journal of Steroid Biochemistry and Molecular Biology
T1  - Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro
VL  - 174
SP  - 72
EP  - 85
DO  - 10.1016/j.jsbmb.2017.07.031
ER  - 

@article{
author = "Živković, Marijana B. and Matić, Ivana Z. and Rodić, Marko and Novaković, Irena T. and Krivokuća, Ana M. and Sladić, Dušan and Krstić, Natalija M.",
year = "2017",
abstract = "The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Journal of Steroid Biochemistry and Molecular Biology",
title = "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro",
volume = "174",
pages = "72-85",
doi = "10.1016/j.jsbmb.2017.07.031"
}

Živković, M. B., Matić, I. Z., Rodić, M., Novaković, I. T., Krivokuća, A. M., Sladić, D.,& Krstić, N. M.. (2017). Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology
Pergamon-Elsevier Science Ltd, Oxford., 174, 72-85.
https://doi.org/10.1016/j.jsbmb.2017.07.031

Živković MB, Matić IZ, Rodić M, Novaković IT, Krivokuća AM, Sladić D, Krstić NM. Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology. 2017;174:72-85.
doi:10.1016/j.jsbmb.2017.07.031 .

Živković, Marijana B., Matić, Ivana Z., Rodić, Marko, Novaković, Irena T., Krivokuća, Ana M., Sladić, Dušan, Krstić, Natalija M., "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro" in Journal of Steroid Biochemistry and Molecular Biology, 174 (2017):72-85,
https://doi.org/10.1016/j.jsbmb.2017.07.031 . .

TY  - DATA
AU  - Živković, Marijana B.
AU  - Matić, Ivana Z.
AU  - Rodić, Marko
AU  - Novaković, Irena T.

AU  - Krivokuća, Ana M.
AU  - Sladić, Dušan
AU  - Krstić, Natalija M.
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3192
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Journal of Steroid Biochemistry and Molecular Biology
T1  - Supplementary material for the article:         Živković, M. B.; Matić, I. Z.; Rodić, M. V.; Novaković, I. T.; Krivokuća, A. M.; Sladić, D. M.; Krstić, N. M. Anticancer Potential of New Steroidal Thiazolidin-4-One Derivatives. Mechanisms of Cytotoxic Action and Effects on Angiogenesis in Vitro. Journal of Steroid Biochemistry and Molecular Biology 2017, 174, 72–85. https://doi.org/10.1016/j.jsbmb.2017.07.031
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3192
ER  - 

@misc{
author = "Živković, Marijana B. and Matić, Ivana Z. and Rodić, Marko and Novaković, Irena T.
 and Krivokuća, Ana M. and Sladić, Dušan and Krstić, Natalija M.",
year = "2017",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Journal of Steroid Biochemistry and Molecular Biology",
title = "Supplementary material for the article:         Živković, M. B.; Matić, I. Z.; Rodić, M. V.; Novaković, I. T.; Krivokuća, A. M.; Sladić, D. M.; Krstić, N. M. Anticancer Potential of New Steroidal Thiazolidin-4-One Derivatives. Mechanisms of Cytotoxic Action and Effects on Angiogenesis in Vitro. Journal of Steroid Biochemistry and Molecular Biology 2017, 174, 72–85. https://doi.org/10.1016/j.jsbmb.2017.07.031",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3192"
}

Živković, M. B., Matić, I. Z., Rodić, M., Novaković, I. T., Krivokuća, A. M., Sladić, D.,& Krstić, N. M.. (2017). Supplementary material for the article:         Živković, M. B.; Matić, I. Z.; Rodić, M. V.; Novaković, I. T.; Krivokuća, A. M.; Sladić, D. M.; Krstić, N. M. Anticancer Potential of New Steroidal Thiazolidin-4-One Derivatives. Mechanisms of Cytotoxic Action and Effects on Angiogenesis in Vitro. Journal of Steroid Biochemistry and Molecular Biology 2017, 174, 72–85. https://doi.org/10.1016/j.jsbmb.2017.07.031. in Journal of Steroid Biochemistry and Molecular Biology
Pergamon-Elsevier Science Ltd, Oxford..
https://hdl.handle.net/21.15107/rcub_cherry_3192

Živković MB, Matić IZ, Rodić M, Novaković IT, Krivokuća AM, Sladić D, Krstić NM. Supplementary material for the article:         Živković, M. B.; Matić, I. Z.; Rodić, M. V.; Novaković, I. T.; Krivokuća, A. M.; Sladić, D. M.; Krstić, N. M. Anticancer Potential of New Steroidal Thiazolidin-4-One Derivatives. Mechanisms of Cytotoxic Action and Effects on Angiogenesis in Vitro. Journal of Steroid Biochemistry and Molecular Biology 2017, 174, 72–85. https://doi.org/10.1016/j.jsbmb.2017.07.031. in Journal of Steroid Biochemistry and Molecular Biology. 2017;.
https://hdl.handle.net/21.15107/rcub_cherry_3192 .

Živković, Marijana B., Matić, Ivana Z., Rodić, Marko, Novaković, Irena T.
, Krivokuća, Ana M., Sladić, Dušan, Krstić, Natalija M., "Supplementary material for the article:         Živković, M. B.; Matić, I. Z.; Rodić, M. V.; Novaković, I. T.; Krivokuća, A. M.; Sladić, D. M.; Krstić, N. M. Anticancer Potential of New Steroidal Thiazolidin-4-One Derivatives. Mechanisms of Cytotoxic Action and Effects on Angiogenesis in Vitro. Journal of Steroid Biochemistry and Molecular Biology 2017, 174, 72–85. https://doi.org/10.1016/j.jsbmb.2017.07.031" in Journal of Steroid Biochemistry and Molecular Biology (2017),
https://hdl.handle.net/21.15107/rcub_cherry_3192 .

TY  - JOUR
AU  - Živković, Marijana B.
AU  - Matić, Ivana Z.
AU  - Rodić, Marko
AU  - Novaković, Irena T.
AU  - Krivokuća, Ana M.
AU  - Sladić, Dušan
AU  - Krstić, Natalija M.
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2550
AB  - The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Journal of Steroid Biochemistry and Molecular Biology
T1  - Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro
VL  - 174
SP  - 72
EP  - 85
DO  - 10.1016/j.jsbmb.2017.07.031
ER  - 

@article{
author = "Živković, Marijana B. and Matić, Ivana Z. and Rodić, Marko and Novaković, Irena T. and Krivokuća, Ana M. and Sladić, Dušan and Krstić, Natalija M.",
year = "2017",
abstract = "The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Journal of Steroid Biochemistry and Molecular Biology",
title = "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro",
volume = "174",
pages = "72-85",
doi = "10.1016/j.jsbmb.2017.07.031"
}

Živković, M. B., Matić, I. Z., Rodić, M., Novaković, I. T., Krivokuća, A. M., Sladić, D.,& Krstić, N. M.. (2017). Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology
Pergamon-Elsevier Science Ltd, Oxford., 174, 72-85.
https://doi.org/10.1016/j.jsbmb.2017.07.031

Živković MB, Matić IZ, Rodić M, Novaković IT, Krivokuća AM, Sladić D, Krstić NM. Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology. 2017;174:72-85.
doi:10.1016/j.jsbmb.2017.07.031 .

Živković, Marijana B., Matić, Ivana Z., Rodić, Marko, Novaković, Irena T., Krivokuća, Ana M., Sladić, Dušan, Krstić, Natalija M., "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro" in Journal of Steroid Biochemistry and Molecular Biology, 174 (2017):72-85,
https://doi.org/10.1016/j.jsbmb.2017.07.031 . .

TY  - DATA
AU  - Živković, Marijana B.
AU  - Matić, Ivana Z.
AU  - Rodić, Marko
AU  - Novaković, Irena T.
AU  - Sladić, Dušan
AU  - Krstić, Natalija M.
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3645
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Supplementary material for the article: Živković, M. B.; Matić, I. Z.; Rodić, M. V.; Novaković, I. T.; Sladić, D. M.; Krstić, N. M. Synthesis, Characterization and in Vitro Cytotoxic Activities of New Steroidal Thiosemicarbazones and Thiadiazolines. RSC Advances 2016, 6 (41), 34312–34333. https://doi.org/10.1039/c6ra01516f
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3645
ER  - 

@misc{
author = "Živković, Marijana B. and Matić, Ivana Z. and Rodić, Marko and Novaković, Irena T. and Sladić, Dušan and Krstić, Natalija M.",
year = "2016",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Supplementary material for the article: Živković, M. B.; Matić, I. Z.; Rodić, M. V.; Novaković, I. T.; Sladić, D. M.; Krstić, N. M. Synthesis, Characterization and in Vitro Cytotoxic Activities of New Steroidal Thiosemicarbazones and Thiadiazolines. RSC Advances 2016, 6 (41), 34312–34333. https://doi.org/10.1039/c6ra01516f",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3645"
}

Živković, M. B., Matić, I. Z., Rodić, M., Novaković, I. T., Sladić, D.,& Krstić, N. M.. (2016). Supplementary material for the article: Živković, M. B.; Matić, I. Z.; Rodić, M. V.; Novaković, I. T.; Sladić, D. M.; Krstić, N. M. Synthesis, Characterization and in Vitro Cytotoxic Activities of New Steroidal Thiosemicarbazones and Thiadiazolines. RSC Advances 2016, 6 (41), 34312–34333. https://doi.org/10.1039/c6ra01516f. in RSC Advances
Royal Soc Chemistry, Cambridge..
https://hdl.handle.net/21.15107/rcub_cherry_3645

Živković MB, Matić IZ, Rodić M, Novaković IT, Sladić D, Krstić NM. Supplementary material for the article: Živković, M. B.; Matić, I. Z.; Rodić, M. V.; Novaković, I. T.; Sladić, D. M.; Krstić, N. M. Synthesis, Characterization and in Vitro Cytotoxic Activities of New Steroidal Thiosemicarbazones and Thiadiazolines. RSC Advances 2016, 6 (41), 34312–34333. https://doi.org/10.1039/c6ra01516f. in RSC Advances. 2016;.
https://hdl.handle.net/21.15107/rcub_cherry_3645 .

Živković, Marijana B., Matić, Ivana Z., Rodić, Marko, Novaković, Irena T., Sladić, Dušan, Krstić, Natalija M., "Supplementary material for the article: Živković, M. B.; Matić, I. Z.; Rodić, M. V.; Novaković, I. T.; Sladić, D. M.; Krstić, N. M. Synthesis, Characterization and in Vitro Cytotoxic Activities of New Steroidal Thiosemicarbazones and Thiadiazolines. RSC Advances 2016, 6 (41), 34312–34333. https://doi.org/10.1039/c6ra01516f" in RSC Advances (2016),
https://hdl.handle.net/21.15107/rcub_cherry_3645 .

TY  - JOUR
AU  - Živković, Marijana B.
AU  - Matić, Ivana Z.
AU  - Rodić, Marko
AU  - Novaković, Irena T.
AU  - Sladić, Dušan
AU  - Krstić, Natalija M.
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1913
AB  - A series of new steroidal mono- and bis(thiosemicarbazones) (2a-e and 3a-e) and corresponding mono- and bis(1,3,4-thiadiazolines) (4a-e and 5a-e) was synthesized, characterized and evaluated for their anticancer activity. Detailed NMR analysis of the mono-and bis(thiosemicarbazones) revealed the presence of two stereoisomers (Z and E) with different configurations in the hydrazone moiety at the C-3 position, where the substituents on the C(3)]=N double bond in the main isomers adopted the E configuration. The configurations at C-3 and C-17 in thiadiazolines 4a-e and 5a-e were deduced by detailed NMR analysis as well as by the examination of Dreiding molecular models and X-ray analysis of 3-thiadiazoline 4a, which confirmed the structure and absolute configuration at C-3. The synthesized compounds were tested against six cancer cell lines (HeLa, K562, MDA-MB-361, MDA-MB-453, LS174 and A549), the normal human cell line MRC-5 and peripheral blood mononuclear cells (PBMC) isolated from healthy donors. The best activity was exhibited by 3-thiosemicarbazones 2a, 2b, 2c and 2e and 3,17-bis(thiadiazolines) 5a and 5d. Examination of the mechanisms of cytotoxicity on cervical adenocarcinoma HeLa cells revealed the pro-apoptotic action of these compounds, which triggered both extrinsic and intrinsic apoptotic pathways. These compounds also showed the ability to decrease angiogenesis in vitro. In addition, 3,17-bis(thiadiazolines) 5a and 5d showed high selectivity in anticancer activity against all the examined malignant cell lines. Compound 5a displayed prominent anticancer potential. The tested compounds showed poor antimicrobial activity.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines
VL  - 6
IS  - 41
SP  - 34312
EP  - 34333
DO  - 10.1039/c6ra01516f
ER  - 

@article{
author = "Živković, Marijana B. and Matić, Ivana Z. and Rodić, Marko and Novaković, Irena T. and Sladić, Dušan and Krstić, Natalija M.",
year = "2016",
abstract = "A series of new steroidal mono- and bis(thiosemicarbazones) (2a-e and 3a-e) and corresponding mono- and bis(1,3,4-thiadiazolines) (4a-e and 5a-e) was synthesized, characterized and evaluated for their anticancer activity. Detailed NMR analysis of the mono-and bis(thiosemicarbazones) revealed the presence of two stereoisomers (Z and E) with different configurations in the hydrazone moiety at the C-3 position, where the substituents on the C(3)]=N double bond in the main isomers adopted the E configuration. The configurations at C-3 and C-17 in thiadiazolines 4a-e and 5a-e were deduced by detailed NMR analysis as well as by the examination of Dreiding molecular models and X-ray analysis of 3-thiadiazoline 4a, which confirmed the structure and absolute configuration at C-3. The synthesized compounds were tested against six cancer cell lines (HeLa, K562, MDA-MB-361, MDA-MB-453, LS174 and A549), the normal human cell line MRC-5 and peripheral blood mononuclear cells (PBMC) isolated from healthy donors. The best activity was exhibited by 3-thiosemicarbazones 2a, 2b, 2c and 2e and 3,17-bis(thiadiazolines) 5a and 5d. Examination of the mechanisms of cytotoxicity on cervical adenocarcinoma HeLa cells revealed the pro-apoptotic action of these compounds, which triggered both extrinsic and intrinsic apoptotic pathways. These compounds also showed the ability to decrease angiogenesis in vitro. In addition, 3,17-bis(thiadiazolines) 5a and 5d showed high selectivity in anticancer activity against all the examined malignant cell lines. Compound 5a displayed prominent anticancer potential. The tested compounds showed poor antimicrobial activity.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines",
volume = "6",
number = "41",
pages = "34312-34333",
doi = "10.1039/c6ra01516f"
}

Živković, M. B., Matić, I. Z., Rodić, M., Novaković, I. T., Sladić, D.,& Krstić, N. M.. (2016). Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines. in RSC Advances
Royal Soc Chemistry, Cambridge., 6(41), 34312-34333.
https://doi.org/10.1039/c6ra01516f

Živković MB, Matić IZ, Rodić M, Novaković IT, Sladić D, Krstić NM. Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines. in RSC Advances. 2016;6(41):34312-34333.
doi:10.1039/c6ra01516f .

Živković, Marijana B., Matić, Ivana Z., Rodić, Marko, Novaković, Irena T., Sladić, Dušan, Krstić, Natalija M., "Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines" in RSC Advances, 6, no. 41 (2016):34312-34333,
https://doi.org/10.1039/c6ra01516f . .

TY  - JOUR
AU  - Milenković, Milica
AU  - Pevec, Andrej
AU  - Turel, Iztok
AU  - Milenković, Marina
AU  - Čobeljić, Božidar
AU  - Sladić, Dušan
AU  - Krstić, Natalija M.
AU  - Anđelković, Katarina K.
PY  - 2015
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5692
AB  - Square-planar isocyanate and chloride Ni(II) complexes with tridentate PNO condensation
product of 2-(diphenylphosphino)benzaldehyde and Girard’s T reagent have been synthesized
and their crystal structures determined. These Ni(II) complexes with different monodentate
ligands, chloride, cyanate and thiocyanate, were tested for their antimicrobial activities
against pathogenic microorganisms. The ligand and Ni(II) complexes were active not only
against laboratory control strains of bacteria and yeast, but also on clinical isolates of E. coli
and P. aeruginosa strains resistant to most of the clinically used antibiotics.
PB  - Taylor and Francis
T2  - J. Coord. Chem.
T1  - Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard’s T reagent
VL  - 68
IS  - 16
SP  - 2858
EP  - 2870
DO  - 10.1080/00958972.2015.1055260
ER  - 

@article{
author = "Milenković, Milica and Pevec, Andrej and Turel, Iztok and Milenković, Marina and Čobeljić, Božidar and Sladić, Dušan and Krstić, Natalija M. and Anđelković, Katarina K.",
year = "2015",
abstract = "Square-planar isocyanate and chloride Ni(II) complexes with tridentate PNO condensation
product of 2-(diphenylphosphino)benzaldehyde and Girard’s T reagent have been synthesized
and their crystal structures determined. These Ni(II) complexes with different monodentate
ligands, chloride, cyanate and thiocyanate, were tested for their antimicrobial activities
against pathogenic microorganisms. The ligand and Ni(II) complexes were active not only
against laboratory control strains of bacteria and yeast, but also on clinical isolates of E. coli
and P. aeruginosa strains resistant to most of the clinically used antibiotics.",
publisher = "Taylor and Francis",
journal = "J. Coord. Chem.",
title = "Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard’s T reagent",
volume = "68",
number = "16",
pages = "2858-2870",
doi = "10.1080/00958972.2015.1055260"
}

Milenković, M., Pevec, A., Turel, I., Milenković, M., Čobeljić, B., Sladić, D., Krstić, N. M.,& Anđelković, K. K.. (2015). Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard’s T reagent. in J. Coord. Chem.
Taylor and Francis., 68(16), 2858-2870.
https://doi.org/10.1080/00958972.2015.1055260

Milenković M, Pevec A, Turel I, Milenković M, Čobeljić B, Sladić D, Krstić NM, Anđelković KK. Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard’s T reagent. in J. Coord. Chem.. 2015;68(16):2858-2870.
doi:10.1080/00958972.2015.1055260 .

Milenković, Milica, Pevec, Andrej, Turel, Iztok, Milenković, Marina, Čobeljić, Božidar, Sladić, Dušan, Krstić, Natalija M., Anđelković, Katarina K., "Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard’s T reagent" in J. Coord. Chem., 68, no. 16 (2015):2858-2870,
https://doi.org/10.1080/00958972.2015.1055260 . .

TY  - DATA
AU  - Milenković, Milica R.
AU  - Pevec, Andrej
AU  - Turel, Iztok
AU  - Milenković, Marina
AU  - Čobeljić, Božidar
AU  - Sladić, Dušan
AU  - Krstić, Natalija M.
AU  - Anđelković, Katarina K.
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3447
PB  - Taylor & Francis Ltd, Abingdon
T2  - Journal of Coordination Chemistry
T1  - Supplementary data for article: Milenković, M. R.; Pevec, A.; Turel, I.; Milenković, M.; Čobeljić, B.; Sladić, D.; Krstic, N.; Anđelković, K. K. Synthesis, Crystal Structures, and Antimicrobial Activity of Square-Planar Chloride and Isocyanate Ni(II) Complexes with the Condensation Product of 2-(Diphenylphosphino)Benzaldehyde and Girard’s T Reagent. Journal of Coordination Chemistry 2015, 68 (16), 2858–2870. https://doi.org/10.1080/00958972.2015.1055260
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3447
ER  - 

@misc{
author = "Milenković, Milica R. and Pevec, Andrej and Turel, Iztok and Milenković, Marina and Čobeljić, Božidar and Sladić, Dušan and Krstić, Natalija M. and Anđelković, Katarina K.",
year = "2015",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Journal of Coordination Chemistry",
title = "Supplementary data for article: Milenković, M. R.; Pevec, A.; Turel, I.; Milenković, M.; Čobeljić, B.; Sladić, D.; Krstic, N.; Anđelković, K. K. Synthesis, Crystal Structures, and Antimicrobial Activity of Square-Planar Chloride and Isocyanate Ni(II) Complexes with the Condensation Product of 2-(Diphenylphosphino)Benzaldehyde and Girard’s T Reagent. Journal of Coordination Chemistry 2015, 68 (16), 2858–2870. https://doi.org/10.1080/00958972.2015.1055260",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3447"
}

Milenković, M. R., Pevec, A., Turel, I., Milenković, M., Čobeljić, B., Sladić, D., Krstić, N. M.,& Anđelković, K. K.. (2015). Supplementary data for article: Milenković, M. R.; Pevec, A.; Turel, I.; Milenković, M.; Čobeljić, B.; Sladić, D.; Krstic, N.; Anđelković, K. K. Synthesis, Crystal Structures, and Antimicrobial Activity of Square-Planar Chloride and Isocyanate Ni(II) Complexes with the Condensation Product of 2-(Diphenylphosphino)Benzaldehyde and Girard’s T Reagent. Journal of Coordination Chemistry 2015, 68 (16), 2858–2870. https://doi.org/10.1080/00958972.2015.1055260. in Journal of Coordination Chemistry
Taylor & Francis Ltd, Abingdon..
https://hdl.handle.net/21.15107/rcub_cherry_3447

Milenković MR, Pevec A, Turel I, Milenković M, Čobeljić B, Sladić D, Krstić NM, Anđelković KK. Supplementary data for article: Milenković, M. R.; Pevec, A.; Turel, I.; Milenković, M.; Čobeljić, B.; Sladić, D.; Krstic, N.; Anđelković, K. K. Synthesis, Crystal Structures, and Antimicrobial Activity of Square-Planar Chloride and Isocyanate Ni(II) Complexes with the Condensation Product of 2-(Diphenylphosphino)Benzaldehyde and Girard’s T Reagent. Journal of Coordination Chemistry 2015, 68 (16), 2858–2870. https://doi.org/10.1080/00958972.2015.1055260. in Journal of Coordination Chemistry. 2015;.
https://hdl.handle.net/21.15107/rcub_cherry_3447 .

Milenković, Milica R., Pevec, Andrej, Turel, Iztok, Milenković, Marina, Čobeljić, Božidar, Sladić, Dušan, Krstić, Natalija M., Anđelković, Katarina K., "Supplementary data for article: Milenković, M. R.; Pevec, A.; Turel, I.; Milenković, M.; Čobeljić, B.; Sladić, D.; Krstic, N.; Anđelković, K. K. Synthesis, Crystal Structures, and Antimicrobial Activity of Square-Planar Chloride and Isocyanate Ni(II) Complexes with the Condensation Product of 2-(Diphenylphosphino)Benzaldehyde and Girard’s T Reagent. Journal of Coordination Chemistry 2015, 68 (16), 2858–2870. https://doi.org/10.1080/00958972.2015.1055260" in Journal of Coordination Chemistry (2015),
https://hdl.handle.net/21.15107/rcub_cherry_3447 .

TY  - JOUR
AU  - Milenković, Milica R.
AU  - Pevec, Andrej
AU  - Turel, Iztok
AU  - Milenković, Marina
AU  - Čobeljić, Božidar
AU  - Sladić, Dušan
AU  - Krstić, Natalija M.
AU  - Anđelković, Katarina K.
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1759
AB  - Square-planar isocyanate and chloride Ni(II) complexes with tridentate PNO condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent have been synthesized and their crystal structures were determined. These Ni(II) complexes with different monodentate ligands, chloride, cyanate, and thiocyanate were tested for their antimicrobial activities against pathogenic microorganisms. The ligand and Ni(II) complexes were active not only against laboratory control strains of bacteria and yeast, but also on clinical isolates of Escherichia coli and Pseudomonas aeruginosa strains resistant to most of the clinically used antibiotics.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Journal of Coordination Chemistry
T1  - Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent
VL  - 68
IS  - 16
SP  - 2858
EP  - 2870
DO  - 10.1080/00958972.2015.1055260
ER  - 

@article{
author = "Milenković, Milica R. and Pevec, Andrej and Turel, Iztok and Milenković, Marina and Čobeljić, Božidar and Sladić, Dušan and Krstić, Natalija M. and Anđelković, Katarina K.",
year = "2015",
abstract = "Square-planar isocyanate and chloride Ni(II) complexes with tridentate PNO condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent have been synthesized and their crystal structures were determined. These Ni(II) complexes with different monodentate ligands, chloride, cyanate, and thiocyanate were tested for their antimicrobial activities against pathogenic microorganisms. The ligand and Ni(II) complexes were active not only against laboratory control strains of bacteria and yeast, but also on clinical isolates of Escherichia coli and Pseudomonas aeruginosa strains resistant to most of the clinically used antibiotics.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Journal of Coordination Chemistry",
title = "Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent",
volume = "68",
number = "16",
pages = "2858-2870",
doi = "10.1080/00958972.2015.1055260"
}

Milenković, M. R., Pevec, A., Turel, I., Milenković, M., Čobeljić, B., Sladić, D., Krstić, N. M.,& Anđelković, K. K.. (2015). Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent. in Journal of Coordination Chemistry
Taylor & Francis Ltd, Abingdon., 68(16), 2858-2870.
https://doi.org/10.1080/00958972.2015.1055260

Milenković MR, Pevec A, Turel I, Milenković M, Čobeljić B, Sladić D, Krstić NM, Anđelković KK. Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent. in Journal of Coordination Chemistry. 2015;68(16):2858-2870.
doi:10.1080/00958972.2015.1055260 .

Milenković, Milica R., Pevec, Andrej, Turel, Iztok, Milenković, Marina, Čobeljić, Božidar, Sladić, Dušan, Krstić, Natalija M., Anđelković, Katarina K., "Synthesis, crystal structures, and antimicrobial activity of square-planar chloride and isocyanate Ni(II) complexes with the condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent" in Journal of Coordination Chemistry, 68, no. 16 (2015):2858-2870,
https://doi.org/10.1080/00958972.2015.1055260 . .

TY  - JOUR
AU  - Krstić, Natalija M.
AU  - Matić, Ivana Z.
AU  - Juranić, Zorica D.
AU  - Novaković, Irena T.
AU  - Sladić, Dušan
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1843
AB  - The in vitro cytotoxic activity of previously synthesized steroid dimers with different spacer group (sulfide, trithiolane ring or phosphorotrithioate) and the substituent at C-17 position was tested for their possible effects against following human tumor cell lines: cervical adenocarcinoma (HeLa), chronic myelogenous leukemia (K562) and two human breast cancer cell lines (MDA-MB-361 and MDA-MB-453). These compounds, applied at micromolar concentrations, exhibited cytotoxic activity of different intensity (compared with cisplatin as a control), modality and selectivity in these malignant cell lines. The best activity against all four cell cancer lines was exhibited by dimer-sulfides. All screened compounds exerted concentration-dependent cytotoxic activity against leukemia K562 cells. The compounds which exerted the most pronounced cytotoxic action exhibited notably higher cytotoxic activities against K562, HeLa and MDA-MB-453 cells in comparison to resting and PHA-stimulated PBMC, pointing to a significant selectivity in their antitumor actions. Examination of the mechanisms of cytotoxicity on leukemia K562 cells revealed pro-apoptotic action of each of the investigated compounds applied at concentrations 2IC(50). The most prominent pro-apoptotic action was exhibited by dimer-sulfide of cholest-4-en-3-one. Furthermore, almost all of the tested compounds at IC50 concentrations induced G1 phase cell cycle arrest in K562 cells. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, and toxicity to brine shrimp Artemia sauna, were evaluated. There was no antibacterial activity. The best antifungal activity was exhibited against Saccharomyces cerevisiae by dimers linked with trithiolane ring, indicating a selective activity of investigated compounds. (C) 2014 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Journal of Steroid Biochemistry and Molecular Biology
T1  - Steroid dimers-In vitro cytotoxic and antimicrobial activities
VL  - 143
SP  - 365
EP  - 375
DO  - 10.1016/j.jsbmb.2014.06.005
ER  - 

@article{
author = "Krstić, Natalija M. and Matić, Ivana Z. and Juranić, Zorica D. and Novaković, Irena T. and Sladić, Dušan",
year = "2014",
abstract = "The in vitro cytotoxic activity of previously synthesized steroid dimers with different spacer group (sulfide, trithiolane ring or phosphorotrithioate) and the substituent at C-17 position was tested for their possible effects against following human tumor cell lines: cervical adenocarcinoma (HeLa), chronic myelogenous leukemia (K562) and two human breast cancer cell lines (MDA-MB-361 and MDA-MB-453). These compounds, applied at micromolar concentrations, exhibited cytotoxic activity of different intensity (compared with cisplatin as a control), modality and selectivity in these malignant cell lines. The best activity against all four cell cancer lines was exhibited by dimer-sulfides. All screened compounds exerted concentration-dependent cytotoxic activity against leukemia K562 cells. The compounds which exerted the most pronounced cytotoxic action exhibited notably higher cytotoxic activities against K562, HeLa and MDA-MB-453 cells in comparison to resting and PHA-stimulated PBMC, pointing to a significant selectivity in their antitumor actions. Examination of the mechanisms of cytotoxicity on leukemia K562 cells revealed pro-apoptotic action of each of the investigated compounds applied at concentrations 2IC(50). The most prominent pro-apoptotic action was exhibited by dimer-sulfide of cholest-4-en-3-one. Furthermore, almost all of the tested compounds at IC50 concentrations induced G1 phase cell cycle arrest in K562 cells. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, and toxicity to brine shrimp Artemia sauna, were evaluated. There was no antibacterial activity. The best antifungal activity was exhibited against Saccharomyces cerevisiae by dimers linked with trithiolane ring, indicating a selective activity of investigated compounds. (C) 2014 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Journal of Steroid Biochemistry and Molecular Biology",
title = "Steroid dimers-In vitro cytotoxic and antimicrobial activities",
volume = "143",
pages = "365-375",
doi = "10.1016/j.jsbmb.2014.06.005"
}

Krstić, N. M., Matić, I. Z., Juranić, Z. D., Novaković, I. T.,& Sladić, D.. (2014). Steroid dimers-In vitro cytotoxic and antimicrobial activities. in Journal of Steroid Biochemistry and Molecular Biology
Pergamon-Elsevier Science Ltd, Oxford., 143, 365-375.
https://doi.org/10.1016/j.jsbmb.2014.06.005

Krstić NM, Matić IZ, Juranić ZD, Novaković IT, Sladić D. Steroid dimers-In vitro cytotoxic and antimicrobial activities. in Journal of Steroid Biochemistry and Molecular Biology. 2014;143:365-375.
doi:10.1016/j.jsbmb.2014.06.005 .

Krstić, Natalija M., Matić, Ivana Z., Juranić, Zorica D., Novaković, Irena T., Sladić, Dušan, "Steroid dimers-In vitro cytotoxic and antimicrobial activities" in Journal of Steroid Biochemistry and Molecular Biology, 143 (2014):365-375,
https://doi.org/10.1016/j.jsbmb.2014.06.005 . .

TY  - JOUR
AU  - Milenković, Milica R.
AU  - Cantoni, Giulia
AU  - Bacchi, Alessia
AU  - Spasojević, Vojislav
AU  - Milenković, Marina
AU  - Sladić, Dušan
AU  - Krstić, Natalija M.
AU  - Anđelković, Katarina K.
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1838
AB  - Complexes of Pd(II) and Fe(III) with the condensation derivative of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate were synthesized, characterized, and their antimicrobial activity was evaluated. The structures of the Pd(II) and Fe(III) complexes in solid state were determined by IR, elemental analysis and X-ray analysis. The structure of Pd(II) complex in solution was determined by NMR spectroscopy. Results of magnetic measurements for Fe(III) complex were reported. In both complexes the ligand is coordinated as tridentate via the phosphorus, the imine nitrogen and the carbonyl oxygen atoms. Results of antimicrobial activity investigation indicate that the activity of the ligand is enhanced upon complexation, and that the MIC values of the iron complex to some bacterial strains are not much higher than those of cefotaxime. (C) 2014 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Polyhedron
T1  - Synthesis, characterization and antimicrobial activity of Pd(II) and Fe(III) complexes with ethyl (2E)-2-[2-(diphenylphosphino)benzylidene]hydrazinecarboxylate
VL  - 80
SP  - 47
EP  - 52
DO  - 10.1016/j.poly.2014.01.022
ER  - 

@article{
author = "Milenković, Milica R. and Cantoni, Giulia and Bacchi, Alessia and Spasojević, Vojislav and Milenković, Marina and Sladić, Dušan and Krstić, Natalija M. and Anđelković, Katarina K.",
year = "2014",
abstract = "Complexes of Pd(II) and Fe(III) with the condensation derivative of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate were synthesized, characterized, and their antimicrobial activity was evaluated. The structures of the Pd(II) and Fe(III) complexes in solid state were determined by IR, elemental analysis and X-ray analysis. The structure of Pd(II) complex in solution was determined by NMR spectroscopy. Results of magnetic measurements for Fe(III) complex were reported. In both complexes the ligand is coordinated as tridentate via the phosphorus, the imine nitrogen and the carbonyl oxygen atoms. Results of antimicrobial activity investigation indicate that the activity of the ligand is enhanced upon complexation, and that the MIC values of the iron complex to some bacterial strains are not much higher than those of cefotaxime. (C) 2014 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Polyhedron",
title = "Synthesis, characterization and antimicrobial activity of Pd(II) and Fe(III) complexes with ethyl (2E)-2-[2-(diphenylphosphino)benzylidene]hydrazinecarboxylate",
volume = "80",
pages = "47-52",
doi = "10.1016/j.poly.2014.01.022"
}

Milenković, M. R., Cantoni, G., Bacchi, A., Spasojević, V., Milenković, M., Sladić, D., Krstić, N. M.,& Anđelković, K. K.. (2014). Synthesis, characterization and antimicrobial activity of Pd(II) and Fe(III) complexes with ethyl (2E)-2-[2-(diphenylphosphino)benzylidene]hydrazinecarboxylate. in Polyhedron
Pergamon-Elsevier Science Ltd, Oxford., 80, 47-52.
https://doi.org/10.1016/j.poly.2014.01.022

Milenković MR, Cantoni G, Bacchi A, Spasojević V, Milenković M, Sladić D, Krstić NM, Anđelković KK. Synthesis, characterization and antimicrobial activity of Pd(II) and Fe(III) complexes with ethyl (2E)-2-[2-(diphenylphosphino)benzylidene]hydrazinecarboxylate. in Polyhedron. 2014;80:47-52.
doi:10.1016/j.poly.2014.01.022 .

Milenković, Milica R., Cantoni, Giulia, Bacchi, Alessia, Spasojević, Vojislav, Milenković, Marina, Sladić, Dušan, Krstić, Natalija M., Anđelković, Katarina K., "Synthesis, characterization and antimicrobial activity of Pd(II) and Fe(III) complexes with ethyl (2E)-2-[2-(diphenylphosphino)benzylidene]hydrazinecarboxylate" in Polyhedron, 80 (2014):47-52,
https://doi.org/10.1016/j.poly.2014.01.022 . .

TY  - DATA
AU  - Krstić, Natalija M.
AU  - Pavlović, Vladimir D.
AU  - Novaković, Irena T.
AU  - Matić, Ivana Z.
AU  - Sladić, Dušan
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3537
PB  - Springer, Dordrecht
T2  - Molecular Diversity
T1  - Supplementary data for article: Krstić, N. M.; Pavlović, V. D.; Novaković, I. T.; Matić, I. Z.; Sladić, D. Synthesis, Characterization and Biological Evaluation of Some Novel P-Heterocyclic Androst-4-Ene Derivatives. Molecular Diversity 2013, 17 (3), 547–561. https://doi.org/10.1007/s11030-013-9455-9
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3537
ER  - 

@misc{
author = "Krstić, Natalija M. and Pavlović, Vladimir D. and Novaković, Irena T. and Matić, Ivana Z. and Sladić, Dušan",
year = "2013",
publisher = "Springer, Dordrecht",
journal = "Molecular Diversity",
title = "Supplementary data for article: Krstić, N. M.; Pavlović, V. D.; Novaković, I. T.; Matić, I. Z.; Sladić, D. Synthesis, Characterization and Biological Evaluation of Some Novel P-Heterocyclic Androst-4-Ene Derivatives. Molecular Diversity 2013, 17 (3), 547–561. https://doi.org/10.1007/s11030-013-9455-9",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3537"
}

Krstić, N. M., Pavlović, V. D., Novaković, I. T., Matić, I. Z.,& Sladić, D.. (2013). Supplementary data for article: Krstić, N. M.; Pavlović, V. D.; Novaković, I. T.; Matić, I. Z.; Sladić, D. Synthesis, Characterization and Biological Evaluation of Some Novel P-Heterocyclic Androst-4-Ene Derivatives. Molecular Diversity 2013, 17 (3), 547–561. https://doi.org/10.1007/s11030-013-9455-9. in Molecular Diversity
Springer, Dordrecht..
https://hdl.handle.net/21.15107/rcub_cherry_3537

Krstić NM, Pavlović VD, Novaković IT, Matić IZ, Sladić D. Supplementary data for article: Krstić, N. M.; Pavlović, V. D.; Novaković, I. T.; Matić, I. Z.; Sladić, D. Synthesis, Characterization and Biological Evaluation of Some Novel P-Heterocyclic Androst-4-Ene Derivatives. Molecular Diversity 2013, 17 (3), 547–561. https://doi.org/10.1007/s11030-013-9455-9. in Molecular Diversity. 2013;.
https://hdl.handle.net/21.15107/rcub_cherry_3537 .

Krstić, Natalija M., Pavlović, Vladimir D., Novaković, Irena T., Matić, Ivana Z., Sladić, Dušan, "Supplementary data for article: Krstić, N. M.; Pavlović, V. D.; Novaković, I. T.; Matić, I. Z.; Sladić, D. Synthesis, Characterization and Biological Evaluation of Some Novel P-Heterocyclic Androst-4-Ene Derivatives. Molecular Diversity 2013, 17 (3), 547–561. https://doi.org/10.1007/s11030-013-9455-9" in Molecular Diversity (2013),
https://hdl.handle.net/21.15107/rcub_cherry_3537 .

TY  - JOUR
AU  - Krstić, Natalija M.
AU  - Pavlović, Vladimir D.
AU  - Novaković, Irena T.
AU  - Matić, Ivana Z.
AU  - Sladić, Dušan
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1376
AB  - The reactions of 21-hydroxyprogesterone with Lawesson's reagent in toluene or gave four P-heterocyclic androst-4-ene derivatives (two tautomeric pairs): 4-(3-thioxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2- sulfide (2), 4-(3-thioxoandrost-4-en-17-ylidene)-1,3,2-oxathiaphospholane-2-sulfide (3), 4-(3-oxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2-sulfide (4), and 4-(3-oxoandrost-4-en-17-ylidene)-1,3,2- oxathiaphospholane-2-sulfide (5). The structures of all novel 17-substituted steroids were elucidated from their analytic and spectral data (HRMS, IR, 1D NMR and 2D NMR-HSQC, HMBC, NOESY, COSY). The detailed NMR analysis for all compounds revealed the presence of two pairs of signals in approx. 8:2 ratio indicating the existence of two diastereoisomers (a and b) with different configurations at the phosphorus atom. A parallel analysis of heteronuclear 2D - spectra (HSQC and HMBC) and homonuclear 2D spectra (NOESY and COSY) enabled complete and assignments of each isomer and provided evidence for the preferred configuration on phosphorus atom. Cytotoxic activity in vitro was tested against four tumor cell lines (human cervix carcinoma HeLa cells, chronic myelogenous leukemia K-562 and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compounds 3a,b and 4a,b showed a poor activity against HeLa and MDA-MB-453 cell lines, while against MDA-MB-361 cell line, all tested compounds exerted very weak cytotoxic effect. All compounds exerted moderate activity against K562 cells. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, and toxicity to brine shrimp Artemia salina were evaluated. All tested compounds showed strong antifungal activity.
PB  - Springer, Dordrecht
T2  - Molecular Diversity
T1  - Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives
VL  - 17
IS  - 3
SP  - 547
EP  - 561
DO  - 10.1007/s11030-013-9455-9
ER  - 

@article{
author = "Krstić, Natalija M. and Pavlović, Vladimir D. and Novaković, Irena T. and Matić, Ivana Z. and Sladić, Dušan",
year = "2013",
abstract = "The reactions of 21-hydroxyprogesterone with Lawesson's reagent in toluene or gave four P-heterocyclic androst-4-ene derivatives (two tautomeric pairs): 4-(3-thioxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2- sulfide (2), 4-(3-thioxoandrost-4-en-17-ylidene)-1,3,2-oxathiaphospholane-2-sulfide (3), 4-(3-oxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2-sulfide (4), and 4-(3-oxoandrost-4-en-17-ylidene)-1,3,2- oxathiaphospholane-2-sulfide (5). The structures of all novel 17-substituted steroids were elucidated from their analytic and spectral data (HRMS, IR, 1D NMR and 2D NMR-HSQC, HMBC, NOESY, COSY). The detailed NMR analysis for all compounds revealed the presence of two pairs of signals in approx. 8:2 ratio indicating the existence of two diastereoisomers (a and b) with different configurations at the phosphorus atom. A parallel analysis of heteronuclear 2D - spectra (HSQC and HMBC) and homonuclear 2D spectra (NOESY and COSY) enabled complete and assignments of each isomer and provided evidence for the preferred configuration on phosphorus atom. Cytotoxic activity in vitro was tested against four tumor cell lines (human cervix carcinoma HeLa cells, chronic myelogenous leukemia K-562 and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compounds 3a,b and 4a,b showed a poor activity against HeLa and MDA-MB-453 cell lines, while against MDA-MB-361 cell line, all tested compounds exerted very weak cytotoxic effect. All compounds exerted moderate activity against K562 cells. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, and toxicity to brine shrimp Artemia salina were evaluated. All tested compounds showed strong antifungal activity.",
publisher = "Springer, Dordrecht",
journal = "Molecular Diversity",
title = "Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives",
volume = "17",
number = "3",
pages = "547-561",
doi = "10.1007/s11030-013-9455-9"
}

Krstić, N. M., Pavlović, V. D., Novaković, I. T., Matić, I. Z.,& Sladić, D.. (2013). Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives. in Molecular Diversity
Springer, Dordrecht., 17(3), 547-561.
https://doi.org/10.1007/s11030-013-9455-9

Krstić NM, Pavlović VD, Novaković IT, Matić IZ, Sladić D. Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives. in Molecular Diversity. 2013;17(3):547-561.
doi:10.1007/s11030-013-9455-9 .

Krstić, Natalija M., Pavlović, Vladimir D., Novaković, Irena T., Matić, Ivana Z., Sladić, Dušan, "Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives" in Molecular Diversity, 17, no. 3 (2013):547-561,
https://doi.org/10.1007/s11030-013-9455-9 . .

TY  - JOUR
AU  - Krstić, Natalija M.
AU  - Bjelaković, Mira S.
AU  - Pavlović, Vladimir D.
AU  - Robeyns, Koen
AU  - Juranić, Zorica D.
AU  - Matić, Ivana Z.
AU  - Novaković, Irena T.
AU  - Sladić, Dušan
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1282
AB  - The reactions of 17 alpha-hydroxyprogesterone with Lawesson's reagent (LR) in toluene, CH2Cl2 and/or CCl4 gave, depending on the duration of the reaction, two diastereoisomeric androst-4-en-17-spiro-1,3,2-oxathiaphospholane-2-sulfide pairs 2a,b and 3a,b in approximately 7:3 ratio, differing in configuration at the phosphorus atom. A parallel analysis of heteronuclear 2D H-1-C-13 spectra (HSQC and HMBC) and homo-nuclear 2D spectra (NOESY) enabled complete H-1 and C-13 assignments of each isomer. Also, analysis of NOESY correlations provided evidence for the preferred conformation. X-ray analysis of 3a confirmed the structure and absolute configuration on phosphorus. A pathway for the formation of 1,3,2-oxathiaphospholane ring was proposed. Cytotoxic activity in vitro was tested against three tumor cell lines (human cervix carcinoma HeLa cells and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compound 3a and mixture 3a,b showed a moderate activity against HeLa and MDA-MB-453 cell lines while against MDA-MB-361 cell line all tested compounds exerted very weak cytotoxic effect. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, toxicity to brine shrimp Artemia sauna, were evaluated. All tested compounds showed strong antifungal activity. (C) 2012 Elsevier Inc. All rights reserved.
PB  - Elsevier Science Inc, New York
T2  - Steroids
T1  - New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities
VL  - 77
IS  - 5
SP  - 558
EP  - 565
DO  - 10.1016/j.steroids.2012.01.021
ER  - 

@article{
author = "Krstić, Natalija M. and Bjelaković, Mira S. and Pavlović, Vladimir D. and Robeyns, Koen and Juranić, Zorica D. and Matić, Ivana Z. and Novaković, Irena T. and Sladić, Dušan",
year = "2012",
abstract = "The reactions of 17 alpha-hydroxyprogesterone with Lawesson's reagent (LR) in toluene, CH2Cl2 and/or CCl4 gave, depending on the duration of the reaction, two diastereoisomeric androst-4-en-17-spiro-1,3,2-oxathiaphospholane-2-sulfide pairs 2a,b and 3a,b in approximately 7:3 ratio, differing in configuration at the phosphorus atom. A parallel analysis of heteronuclear 2D H-1-C-13 spectra (HSQC and HMBC) and homo-nuclear 2D spectra (NOESY) enabled complete H-1 and C-13 assignments of each isomer. Also, analysis of NOESY correlations provided evidence for the preferred conformation. X-ray analysis of 3a confirmed the structure and absolute configuration on phosphorus. A pathway for the formation of 1,3,2-oxathiaphospholane ring was proposed. Cytotoxic activity in vitro was tested against three tumor cell lines (human cervix carcinoma HeLa cells and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compound 3a and mixture 3a,b showed a moderate activity against HeLa and MDA-MB-453 cell lines while against MDA-MB-361 cell line all tested compounds exerted very weak cytotoxic effect. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, toxicity to brine shrimp Artemia sauna, were evaluated. All tested compounds showed strong antifungal activity. (C) 2012 Elsevier Inc. All rights reserved.",
publisher = "Elsevier Science Inc, New York",
journal = "Steroids",
title = "New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities",
volume = "77",
number = "5",
pages = "558-565",
doi = "10.1016/j.steroids.2012.01.021"
}

Krstić, N. M., Bjelaković, M. S., Pavlović, V. D., Robeyns, K., Juranić, Z. D., Matić, I. Z., Novaković, I. T.,& Sladić, D.. (2012). New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities. in Steroids
Elsevier Science Inc, New York., 77(5), 558-565.
https://doi.org/10.1016/j.steroids.2012.01.021

Krstić NM, Bjelaković MS, Pavlović VD, Robeyns K, Juranić ZD, Matić IZ, Novaković IT, Sladić D. New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities. in Steroids. 2012;77(5):558-565.
doi:10.1016/j.steroids.2012.01.021 .

Krstić, Natalija M., Bjelaković, Mira S., Pavlović, Vladimir D., Robeyns, Koen, Juranić, Zorica D., Matić, Ivana Z., Novaković, Irena T., Sladić, Dušan, "New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities" in Steroids, 77, no. 5 (2012):558-565,
https://doi.org/10.1016/j.steroids.2012.01.021 . .

TY  - JOUR
AU  - Bjelaković, Mira S.
AU  - Krstić, Natalija M.
AU  - Milić, Dragana
AU  - Kop, Tatjana
AU  - Robeyns, Koen
AU  - Pavlović, Vladimir D.
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1329
AB  - The present study is concerned with the oxidative behaviour of unsaturated and epoxy 5-oxo-5,10-secosteroids in the presence of m-CPBA or TFAA-UHP as oxidants in order to investigate potential parameters controlling the chemoselectivity and regioselectivity. In the study we discovered a striking difference in the chemical behaviour of stereoisomeric compounds, (Z)- and (E)-3 beta-acetoxy-5,10-secocholest-1(10)-en-5-ones, as well as 1S,10R- and 1R,10R-epoxides. The secoketones were oxidized with exclusively C-6 migration and Baeyer-Villiger rearrangement product formation, whereas their stereoisomers provided the ring-contracted products, without lactone formation. The preferred conformation of expanded and contracted rings was established by NOESY correlations. The structures of two obtained lactones were also confirmed by X-ray analysis. The mechanistic and stereochemical aspects of these transformations are discussed. (C) 2012 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids
VL  - 68
IS  - 36
SP  - 7479
EP  - 7488
DO  - 10.1016/j.tet.2012.06.024
ER  - 

@article{
author = "Bjelaković, Mira S. and Krstić, Natalija M. and Milić, Dragana and Kop, Tatjana and Robeyns, Koen and Pavlović, Vladimir D.",
year = "2012",
abstract = "The present study is concerned with the oxidative behaviour of unsaturated and epoxy 5-oxo-5,10-secosteroids in the presence of m-CPBA or TFAA-UHP as oxidants in order to investigate potential parameters controlling the chemoselectivity and regioselectivity. In the study we discovered a striking difference in the chemical behaviour of stereoisomeric compounds, (Z)- and (E)-3 beta-acetoxy-5,10-secocholest-1(10)-en-5-ones, as well as 1S,10R- and 1R,10R-epoxides. The secoketones were oxidized with exclusively C-6 migration and Baeyer-Villiger rearrangement product formation, whereas their stereoisomers provided the ring-contracted products, without lactone formation. The preferred conformation of expanded and contracted rings was established by NOESY correlations. The structures of two obtained lactones were also confirmed by X-ray analysis. The mechanistic and stereochemical aspects of these transformations are discussed. (C) 2012 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids",
volume = "68",
number = "36",
pages = "7479-7488",
doi = "10.1016/j.tet.2012.06.024"
}

Bjelaković, M. S., Krstić, N. M., Milić, D., Kop, T., Robeyns, K.,& Pavlović, V. D.. (2012). Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids. in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 68(36), 7479-7488.
https://doi.org/10.1016/j.tet.2012.06.024

Bjelaković MS, Krstić NM, Milić D, Kop T, Robeyns K, Pavlović VD. Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids. in Tetrahedron. 2012;68(36):7479-7488.
doi:10.1016/j.tet.2012.06.024 .

Bjelaković, Mira S., Krstić, Natalija M., Milić, Dragana, Kop, Tatjana, Robeyns, Koen, Pavlović, Vladimir D., "Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids" in Tetrahedron, 68, no. 36 (2012):7479-7488,
https://doi.org/10.1016/j.tet.2012.06.024 . .