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  - 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  - 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 . .