TY  - JOUR
AU  - Jakovljević, Katarina
AU  - Joksovic, Milan D.
AU  - Matić, Ivana Z.
AU  - Petrovic, Nina
AU  - Stanojković, Tatjana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksovic, Ljubinka
AU  - Trifunović, Snežana
AU  - Markovic, Violeta
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2379
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3136
AB  - Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.
PB  - Royal Soc Chemistry, Cambridge
T2  - Medchemcomm
T1  - Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies
VL  - 9
IS  - 10
SP  - 1679
EP  - 1697
DO  - 10.1039/c8md00316e
ER  - 

@article{
author = "Jakovljević, Katarina and Joksovic, Milan D. and Matić, Ivana Z. and Petrovic, Nina and Stanojković, Tatjana and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksovic, Ljubinka and Trifunović, Snežana and Markovic, Violeta",
year = "2018",
abstract = "Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Medchemcomm",
title = "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies",
volume = "9",
number = "10",
pages = "1679-1697",
doi = "10.1039/c8md00316e"
}

Jakovljević, K., Joksovic, M. D., Matić, I. Z., Petrovic, N., Stanojković, T., Sladić, D., Vujčić, M., Janović, B., Joksovic, L., Trifunović, S.,& Markovic, V.. (2018). Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in Medchemcomm
Royal Soc Chemistry, Cambridge., 9(10), 1679-1697.
https://doi.org/10.1039/c8md00316e

Jakovljević K, Joksovic MD, Matić IZ, Petrovic N, Stanojković T, Sladić D, Vujčić M, Janović B, Joksovic L, Trifunović S, Markovic V. Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in Medchemcomm. 2018;9(10):1679-1697.
doi:10.1039/c8md00316e .

Jakovljević, Katarina, Joksovic, Milan D., Matić, Ivana Z., Petrovic, Nina, Stanojković, Tatjana, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksovic, Ljubinka, Trifunović, Snežana, Markovic, Violeta, "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies" in Medchemcomm, 9, no. 10 (2018):1679-1697,
https://doi.org/10.1039/c8md00316e . .

TY  - DATA
AU  - Jakovljević, Katarina
AU  - Joksovic, Milan D.
AU  - Matić, Ivana Z.
AU  - Petrovic, Nina
AU  - Stanojković, Tatjana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksovic, Ljubinka
AU  - Trifunović, Snežana
AU  - Markovic, Violeta
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4534
AB  - Copies of 1H and 13C NMR spectra for 5a-m
PB  - Royal Society of Chemistry, Cambridge
T2  - Medchemcomm
T1  - Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4534
ER  - 

@misc{
author = "Jakovljević, Katarina and Joksovic, Milan D. and Matić, Ivana Z. and Petrovic, Nina and Stanojković, Tatjana and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksovic, Ljubinka and Trifunović, Snežana and Markovic, Violeta",
year = "2018",
abstract = "Copies of 1H and 13C NMR spectra for 5a-m",
publisher = "Royal Society of Chemistry, Cambridge",
journal = "Medchemcomm",
title = "Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4534"
}

Jakovljević, K., Joksovic, M. D., Matić, I. Z., Petrovic, N., Stanojković, T., Sladić, D., Vujčić, M., Janović, B., Joksovic, L., Trifunović, S.,& Markovic, V.. (2018). Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies". in Medchemcomm
Royal Society of Chemistry, Cambridge..
https://hdl.handle.net/21.15107/rcub_cer_4534

Jakovljević K, Joksovic MD, Matić IZ, Petrovic N, Stanojković T, Sladić D, Vujčić M, Janović B, Joksovic L, Trifunović S, Markovic V. Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies". in Medchemcomm. 2018;.
https://hdl.handle.net/21.15107/rcub_cer_4534 .

Jakovljević, Katarina, Joksovic, Milan D., Matić, Ivana Z., Petrovic, Nina, Stanojković, Tatjana, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksovic, Ljubinka, Trifunović, Snežana, Markovic, Violeta, "Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies"" in Medchemcomm (2018),
https://hdl.handle.net/21.15107/rcub_cer_4534 .

TY  - JOUR
AU  - Jakovljević, Katarina
AU  - Joksovic, Milan D.
AU  - Matić, Ivana Z.
AU  - Petrovic, Nina
AU  - Stanojković, Tatjana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksovic, Ljubinka
AU  - Trifunović, Snežana
AU  - Markovic, Violeta
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2379
AB  - Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.
PB  - Royal Soc Chemistry, Cambridge
T2  - Medchemcomm
T1  - Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies
VL  - 9
IS  - 10
SP  - 1679
EP  - 1697
DO  - 10.1039/c8md00316e
ER  - 

@article{
author = "Jakovljević, Katarina and Joksovic, Milan D. and Matić, Ivana Z. and Petrovic, Nina and Stanojković, Tatjana and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksovic, Ljubinka and Trifunović, Snežana and Markovic, Violeta",
year = "2018",
abstract = "Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Medchemcomm",
title = "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies",
volume = "9",
number = "10",
pages = "1679-1697",
doi = "10.1039/c8md00316e"
}

Jakovljević, K., Joksovic, M. D., Matić, I. Z., Petrovic, N., Stanojković, T., Sladić, D., Vujčić, M., Janović, B., Joksovic, L., Trifunović, S.,& Markovic, V.. (2018). Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in Medchemcomm
Royal Soc Chemistry, Cambridge., 9(10), 1679-1697.
https://doi.org/10.1039/c8md00316e

Jakovljević K, Joksovic MD, Matić IZ, Petrovic N, Stanojković T, Sladić D, Vujčić M, Janović B, Joksovic L, Trifunović S, Markovic V. Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in Medchemcomm. 2018;9(10):1679-1697.
doi:10.1039/c8md00316e .

Jakovljević, Katarina, Joksovic, Milan D., Matić, Ivana Z., Petrovic, Nina, Stanojković, Tatjana, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksovic, Ljubinka, Trifunović, Snežana, Markovic, Violeta, "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies" in Medchemcomm, 9, no. 10 (2018):1679-1697,
https://doi.org/10.1039/c8md00316e . .

TY  - JOUR
AU  - Leovac, Vukadin
AU  - Rodić, Marko V.
AU  - Jovanović, Ljiljana S.
AU  - Joksovic, Milan D.
AU  - Stanojković, Tatjana
AU  - Vujčić, Miroslava
AU  - Sladić, Dušan
AU  - Markovic, Violeta
AU  - Vojinovic-Jesic, Ljiljana S
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1735
AB  - Five pentacoordinate copper(II) complexes with 2-acetylpyridine or di(2-pyridyl) ketone 1-adamantoyl hydrazone ligands (Adpy and Addpy, respectively) of the formulae [CuCl2(Adpy)] (1), [Cu-2(-Cl)(2)(Adpy-H)(2)] (2), [Cu(NCS)(2)(Adpy)] (3), [Cu-2(-Cl)(2)(Addpy-H)(2)] (4), and [Cu-2(NCS)(2)(-Addpy-H)(2)] (5) were synthesized and characterized by spectral, electrochemical, and X-ray structural analysis. Flow cytometry and morphological analysis confirmed that the copper(II) complexes 2 and 5 induced accumulation of a sub-G1 phase population, and fluorescence microscopy indicated the presence of large cells in apoptosis. The interaction of the copper(II) complexes with calf thymus DNA (CT-DNA) was monitored by changes in their UV/Vis spectra. The observed intrinsic binding constants for 2 and 5 (K-b = 1.77x10(6) and 3.58x10(6) M-1, respectively) together with ethidium displacement fluorescence experiments indicate intercalative binding. Complexes 2 and 5 showed nuclease activity against pUC19 plasmid DNA.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Inorganic Chemistry
T1  - Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System
IS  - 5
SP  - 882
EP  - 895
DO  - 10.1002/ejic.201403050
ER  - 

@article{
author = "Leovac, Vukadin and Rodić, Marko V. and Jovanović, Ljiljana S. and Joksovic, Milan D. and Stanojković, Tatjana and Vujčić, Miroslava and Sladić, Dušan and Markovic, Violeta and Vojinovic-Jesic, Ljiljana S",
year = "2015",
abstract = "Five pentacoordinate copper(II) complexes with 2-acetylpyridine or di(2-pyridyl) ketone 1-adamantoyl hydrazone ligands (Adpy and Addpy, respectively) of the formulae [CuCl2(Adpy)] (1), [Cu-2(-Cl)(2)(Adpy-H)(2)] (2), [Cu(NCS)(2)(Adpy)] (3), [Cu-2(-Cl)(2)(Addpy-H)(2)] (4), and [Cu-2(NCS)(2)(-Addpy-H)(2)] (5) were synthesized and characterized by spectral, electrochemical, and X-ray structural analysis. Flow cytometry and morphological analysis confirmed that the copper(II) complexes 2 and 5 induced accumulation of a sub-G1 phase population, and fluorescence microscopy indicated the presence of large cells in apoptosis. The interaction of the copper(II) complexes with calf thymus DNA (CT-DNA) was monitored by changes in their UV/Vis spectra. The observed intrinsic binding constants for 2 and 5 (K-b = 1.77x10(6) and 3.58x10(6) M-1, respectively) together with ethidium displacement fluorescence experiments indicate intercalative binding. Complexes 2 and 5 showed nuclease activity against pUC19 plasmid DNA.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Inorganic Chemistry",
title = "Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System",
number = "5",
pages = "882-895",
doi = "10.1002/ejic.201403050"
}

Leovac, V., Rodić, M. V., Jovanović, L. S., Joksovic, M. D., Stanojković, T., Vujčić, M., Sladić, D., Markovic, V.,& Vojinovic-Jesic, L. S.. (2015). Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System. in European Journal of Inorganic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(5), 882-895.
https://doi.org/10.1002/ejic.201403050

Leovac V, Rodić MV, Jovanović LS, Joksovic MD, Stanojković T, Vujčić M, Sladić D, Markovic V, Vojinovic-Jesic LS. Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System. in European Journal of Inorganic Chemistry. 2015;(5):882-895.
doi:10.1002/ejic.201403050 .

Leovac, Vukadin, Rodić, Marko V., Jovanović, Ljiljana S., Joksovic, Milan D., Stanojković, Tatjana, Vujčić, Miroslava, Sladić, Dušan, Markovic, Violeta, Vojinovic-Jesic, Ljiljana S, "Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System" in European Journal of Inorganic Chemistry, no. 5 (2015):882-895,
https://doi.org/10.1002/ejic.201403050 . .

TY  - JOUR
AU  - Markovic, Violeta
AU  - Debeljak, Nevena
AU  - Stanojković, Tatjana
AU  - Kolundzija, Branka
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Tanic, Nikola
AU  - Perovic, Milka
AU  - Tesic, Vesna
AU  - Antic, Jadranka
AU  - Joksovic, Milan D.
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1745
AB  - Novel anthraquinone based chalcone compounds were synthesized starting from 1-acetylanthraquinone in a Claisen-Schmidt reaction and evaluated for their anticancer potential against three human cancer cell lines. Compounds 4a, 4b and 4j showed promising activity in inhibition of HeLa cells with IC50 values ranging from 2.36 to 2.73 mu M and low cytotoxicity against healthy MRC-5 cell lines. The effects that compounds produces on the cell cycle were investigated by flow cytometry. It was found that 4a, 4b and 4j cause the accumulation of cells in the S and G2/M phases in a dose-dependent manner and induce caspase-dependent apoptosis. All of three compounds exhibit calf thymus DNA-binding activity. The determined binding constants by absorption titrations (2.65 x 10(3) M-1, 1.36 x 10(3) M(-1)and 2.51 x 10(3) M-1 of 4a/CT-DNA, 4b/CT-DNA and 4j/CT-DNA, respectively) together with fluorescence displacement analysis designate 4a, 4b and 4j as strong minor groove binders, but no cleavage of plasmid DNA was observed.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies
VL  - 89
SP  - 401
EP  - 410
DO  - 10.1016/j.ejmech.2014.10.055
ER  - 

@article{
author = "Markovic, Violeta and Debeljak, Nevena and Stanojković, Tatjana and Kolundzija, Branka and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Tanic, Nikola and Perovic, Milka and Tesic, Vesna and Antic, Jadranka and Joksovic, Milan D.",
year = "2015",
abstract = "Novel anthraquinone based chalcone compounds were synthesized starting from 1-acetylanthraquinone in a Claisen-Schmidt reaction and evaluated for their anticancer potential against three human cancer cell lines. Compounds 4a, 4b and 4j showed promising activity in inhibition of HeLa cells with IC50 values ranging from 2.36 to 2.73 mu M and low cytotoxicity against healthy MRC-5 cell lines. The effects that compounds produces on the cell cycle were investigated by flow cytometry. It was found that 4a, 4b and 4j cause the accumulation of cells in the S and G2/M phases in a dose-dependent manner and induce caspase-dependent apoptosis. All of three compounds exhibit calf thymus DNA-binding activity. The determined binding constants by absorption titrations (2.65 x 10(3) M-1, 1.36 x 10(3) M(-1)and 2.51 x 10(3) M-1 of 4a/CT-DNA, 4b/CT-DNA and 4j/CT-DNA, respectively) together with fluorescence displacement analysis designate 4a, 4b and 4j as strong minor groove binders, but no cleavage of plasmid DNA was observed.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies",
volume = "89",
pages = "401-410",
doi = "10.1016/j.ejmech.2014.10.055"
}

Markovic, V., Debeljak, N., Stanojković, T., Kolundzija, B., Sladić, D., Vujčić, M., Janović, B., Tanic, N., Perovic, M., Tesic, V., Antic, J.,& Joksovic, M. D.. (2015). Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 89, 401-410.
https://doi.org/10.1016/j.ejmech.2014.10.055

Markovic V, Debeljak N, Stanojković T, Kolundzija B, Sladić D, Vujčić M, Janović B, Tanic N, Perovic M, Tesic V, Antic J, Joksovic MD. Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies. in European Journal of Medicinal Chemistry. 2015;89:401-410.
doi:10.1016/j.ejmech.2014.10.055 .

Markovic, Violeta, Debeljak, Nevena, Stanojković, Tatjana, Kolundzija, Branka, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Tanic, Nikola, Perovic, Milka, Tesic, Vesna, Antic, Jadranka, Joksovic, Milan D., "Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies" in European Journal of Medicinal Chemistry, 89 (2015):401-410,
https://doi.org/10.1016/j.ejmech.2014.10.055 . .

TY  - JOUR
AU  - Kolundzija, Branka
AU  - Markovic, Violeta
AU  - Stanojković, Tatjana
AU  - Joksovic, Ljubinka
AU  - Matić, Ivana Z.
AU  - Todorović, Nina
AU  - Nikolić, Marijana
AU  - Joksovic, Milan D.
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1523
AB  - A new class of imine derivatives of hybrid chalcone analogues containing anthraquinone scaffold was synthesized and evaluated for their in vitro cytotoxic activity against HeLa, LS174, and A549 cancer cells. The compound 5n with furan ring linked to imino group showed potent activity against all target cells with IC50 values ranging from 1.76 to 6.11 mu M. A mode of action study suggested that compounds induced changes typical for apoptosis in HeLa cells. The most active compounds inhibited tubulogenesis and 5h was found to exhibit a strong anti-angiogenic effect.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Bioorganic and Medicinal Chemistry Letters
T1  - Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity
VL  - 24
IS  - 1
SP  - 65
EP  - 71
DO  - 10.1016/j.bmcl.2013.11.075
ER  - 

@article{
author = "Kolundzija, Branka and Markovic, Violeta and Stanojković, Tatjana and Joksovic, Ljubinka and Matić, Ivana Z. and Todorović, Nina and Nikolić, Marijana and Joksovic, Milan D.",
year = "2014",
abstract = "A new class of imine derivatives of hybrid chalcone analogues containing anthraquinone scaffold was synthesized and evaluated for their in vitro cytotoxic activity against HeLa, LS174, and A549 cancer cells. The compound 5n with furan ring linked to imino group showed potent activity against all target cells with IC50 values ranging from 1.76 to 6.11 mu M. A mode of action study suggested that compounds induced changes typical for apoptosis in HeLa cells. The most active compounds inhibited tubulogenesis and 5h was found to exhibit a strong anti-angiogenic effect.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Bioorganic and Medicinal Chemistry Letters",
title = "Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity",
volume = "24",
number = "1",
pages = "65-71",
doi = "10.1016/j.bmcl.2013.11.075"
}

Kolundzija, B., Markovic, V., Stanojković, T., Joksovic, L., Matić, I. Z., Todorović, N., Nikolić, M.,& Joksovic, M. D.. (2014). Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity. in Bioorganic and Medicinal Chemistry Letters
Oxford : Pergamon-Elsevier Science Ltd., 24(1), 65-71.
https://doi.org/10.1016/j.bmcl.2013.11.075

Kolundzija B, Markovic V, Stanojković T, Joksovic L, Matić IZ, Todorović N, Nikolić M, Joksovic MD. Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity. in Bioorganic and Medicinal Chemistry Letters. 2014;24(1):65-71.
doi:10.1016/j.bmcl.2013.11.075 .

Kolundzija, Branka, Markovic, Violeta, Stanojković, Tatjana, Joksovic, Ljubinka, Matić, Ivana Z., Todorović, Nina, Nikolić, Marijana, Joksovic, Milan D., "Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity" in Bioorganic and Medicinal Chemistry Letters, 24, no. 1 (2014):65-71,
https://doi.org/10.1016/j.bmcl.2013.11.075 . .

TY  - JOUR
AU  - Markovic, Violeta
AU  - Marković, Svetlana
AU  - Janicijevic, Ana
AU  - Rodić, Marko V.
AU  - Leovac, Vukadin
AU  - Todorović, Nina
AU  - Trifunović, Snežana
AU  - Joksovic, Milan D.
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1225
AB  - A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.
PB  - Springer/Plenum Publishers, New York
T2  - Structural Chemistry
T1  - Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate
VL  - 24
IS  - 6
SP  - 2127
EP  - 2136
DO  - 10.1007/s11224-013-0223-3
ER  - 

@article{
author = "Markovic, Violeta and Marković, Svetlana and Janicijevic, Ana and Rodić, Marko V. and Leovac, Vukadin and Todorović, Nina and Trifunović, Snežana and Joksovic, Milan D.",
year = "2013",
abstract = "A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.",
publisher = "Springer/Plenum Publishers, New York",
journal = "Structural Chemistry",
title = "Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate",
volume = "24",
number = "6",
pages = "2127-2136",
doi = "10.1007/s11224-013-0223-3"
}

Markovic, V., Marković, S., Janicijevic, A., Rodić, M. V., Leovac, V., Todorović, N., Trifunović, S.,& Joksovic, M. D.. (2013). Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate. in Structural Chemistry
Springer/Plenum Publishers, New York., 24(6), 2127-2136.
https://doi.org/10.1007/s11224-013-0223-3

Markovic V, Marković S, Janicijevic A, Rodić MV, Leovac V, Todorović N, Trifunović S, Joksovic MD. Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate. in Structural Chemistry. 2013;24(6):2127-2136.
doi:10.1007/s11224-013-0223-3 .

Markovic, Violeta, Marković, Svetlana, Janicijevic, Ana, Rodić, Marko V., Leovac, Vukadin, Todorović, Nina, Trifunović, Snežana, Joksovic, Milan D., "Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate" in Structural Chemistry, 24, no. 6 (2013):2127-2136,
https://doi.org/10.1007/s11224-013-0223-3 . .

TY  - JOUR
AU  - Markovic, Violeta
AU  - Janicijevic, Ana
AU  - Stanojković, Tatjana
AU  - Kolundzija, Branka
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksovic, Ljubinka
AU  - Djurdjevic, Predrag T.
AU  - Todorović, Nina
AU  - Trifunović, Snežana
AU  - Joksovic, Milan D.
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1343
AB  - A series of novel anthraquinone thiosemicarbazone derivatives in a tautomerizable keto-imine form was synthesized and tested for their in vitro cytotoxic activity against human cancer cells (HeLa, MDA-MB-361, MDA-MB-453, K562, A549) and human normal MRC-5 cells. Several compounds efficiently inhibited cancer cell growth at micromolar concentrations, especially against K562 and HeLa cells. As determined by flow cytometric analysis, anthraquinone thiosemicarbazone caused significant increase in the number of sub-G1 phase of HeLa cells and apoptosis in a concentration-dependent manner. Also, inhibition of caspase-3, -8, and -9 with specific caspase inhibitors reduced the apoptosis mediated by the tested compounds in HeLa cells. All anthraquinone-thiosemicarbazones exhibit calf thymus DNA-binding activity, but no cleavage of plasmid DNA was observed.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group
VL  - 64
SP  - 228
EP  - 238
DO  - 10.1016/j.ejmech.2013.03.071
ER  - 

@article{
author = "Markovic, Violeta and Janicijevic, Ana and Stanojković, Tatjana and Kolundzija, Branka and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksovic, Ljubinka and Djurdjevic, Predrag T. and Todorović, Nina and Trifunović, Snežana and Joksovic, Milan D.",
year = "2013",
abstract = "A series of novel anthraquinone thiosemicarbazone derivatives in a tautomerizable keto-imine form was synthesized and tested for their in vitro cytotoxic activity against human cancer cells (HeLa, MDA-MB-361, MDA-MB-453, K562, A549) and human normal MRC-5 cells. Several compounds efficiently inhibited cancer cell growth at micromolar concentrations, especially against K562 and HeLa cells. As determined by flow cytometric analysis, anthraquinone thiosemicarbazone caused significant increase in the number of sub-G1 phase of HeLa cells and apoptosis in a concentration-dependent manner. Also, inhibition of caspase-3, -8, and -9 with specific caspase inhibitors reduced the apoptosis mediated by the tested compounds in HeLa cells. All anthraquinone-thiosemicarbazones exhibit calf thymus DNA-binding activity, but no cleavage of plasmid DNA was observed.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group",
volume = "64",
pages = "228-238",
doi = "10.1016/j.ejmech.2013.03.071"
}

Markovic, V., Janicijevic, A., Stanojković, T., Kolundzija, B., Sladić, D., Vujčić, M., Janović, B., Joksovic, L., Djurdjevic, P. T., Todorović, N., Trifunović, S.,& Joksovic, M. D.. (2013). Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 64, 228-238.
https://doi.org/10.1016/j.ejmech.2013.03.071

Markovic V, Janicijevic A, Stanojković T, Kolundzija B, Sladić D, Vujčić M, Janović B, Joksovic L, Djurdjevic PT, Todorović N, Trifunović S, Joksovic MD. Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group. in European Journal of Medicinal Chemistry. 2013;64:228-238.
doi:10.1016/j.ejmech.2013.03.071 .

Markovic, Violeta, Janicijevic, Ana, Stanojković, Tatjana, Kolundzija, Branka, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksovic, Ljubinka, Djurdjevic, Predrag T., Todorović, Nina, Trifunović, Snežana, Joksovic, Milan D., "Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group" in European Journal of Medicinal Chemistry, 64 (2013):228-238,
https://doi.org/10.1016/j.ejmech.2013.03.071 . .

TY  - JOUR
AU  - Marković, Svetlana
AU  - Markovic, Violeta
AU  - Joksovic, Milan D.
AU  - Todorović, Nina
AU  - Joksovic, Ljubinka
AU  - Divjakovic, Vladimir
AU  - Trifunović, Snežana
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1222
AB  - Reductive debromination of endo-(+)-3-bromocamphor with different primary amines followed by imine formation was investigated. This reaction requires simple experimental procedure without any organic solvent, metal or conventional reducing agent. A strong influence of amine polarity on the efficacy of debromination process was observed, and ethanolamine and ethylene diamine having sufficiently high boiling points can debrominate 3-bromocamphor giving corresponding camphanimines in good isolated yields. The mechanisms of debromination of 3-bromocamphor with ethanolamine and n-hexylamine were investigated at the B3LYP/6-311+G(d,p) level of theory. The radical mechanism was revealed, and it was shown that the reaction with more polar ethanolamine is energetically more favorable.
PB  - Soc Brasileira Quimica, Sao Paulo
T2  - Journal of the Brazilian Chemical Society
T1  - Debromination of endo-(+)-3-Bromocamphor with Primary Amines
VL  - 24
IS  - 7
SP  - 1099
DO  - 10.5935/0103-5053.20130144
ER  - 

@article{
author = "Marković, Svetlana and Markovic, Violeta and Joksovic, Milan D. and Todorović, Nina and Joksovic, Ljubinka and Divjakovic, Vladimir and Trifunović, Snežana",
year = "2013",
abstract = "Reductive debromination of endo-(+)-3-bromocamphor with different primary amines followed by imine formation was investigated. This reaction requires simple experimental procedure without any organic solvent, metal or conventional reducing agent. A strong influence of amine polarity on the efficacy of debromination process was observed, and ethanolamine and ethylene diamine having sufficiently high boiling points can debrominate 3-bromocamphor giving corresponding camphanimines in good isolated yields. The mechanisms of debromination of 3-bromocamphor with ethanolamine and n-hexylamine were investigated at the B3LYP/6-311+G(d,p) level of theory. The radical mechanism was revealed, and it was shown that the reaction with more polar ethanolamine is energetically more favorable.",
publisher = "Soc Brasileira Quimica, Sao Paulo",
journal = "Journal of the Brazilian Chemical Society",
title = "Debromination of endo-(+)-3-Bromocamphor with Primary Amines",
volume = "24",
number = "7",
pages = "1099",
doi = "10.5935/0103-5053.20130144"
}

Marković, S., Markovic, V., Joksovic, M. D., Todorović, N., Joksovic, L., Divjakovic, V.,& Trifunović, S.. (2013). Debromination of endo-(+)-3-Bromocamphor with Primary Amines. in Journal of the Brazilian Chemical Society
Soc Brasileira Quimica, Sao Paulo., 24(7), 1099.
https://doi.org/10.5935/0103-5053.20130144

Marković S, Markovic V, Joksovic MD, Todorović N, Joksovic L, Divjakovic V, Trifunović S. Debromination of endo-(+)-3-Bromocamphor with Primary Amines. in Journal of the Brazilian Chemical Society. 2013;24(7):1099.
doi:10.5935/0103-5053.20130144 .

Marković, Svetlana, Markovic, Violeta, Joksovic, Milan D., Todorović, Nina, Joksovic, Ljubinka, Divjakovic, Vladimir, Trifunović, Snežana, "Debromination of endo-(+)-3-Bromocamphor with Primary Amines" in Journal of the Brazilian Chemical Society, 24, no. 7 (2013):1099,
https://doi.org/10.5935/0103-5053.20130144 . .

TY  - JOUR
AU  - Markovic, Violeta
AU  - Erić, Slavica
AU  - Stanojković, Tatjana
AU  - Gligorijević, Nevenka
AU  - Arandelovic, Sandra
AU  - Todorović, Nina
AU  - Trifunović, Snežana
AU  - Manojlović, Nedeljko
AU  - Jelić, Ratomir
AU  - Joksovic, Milan D.
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/791
AB  - Twenty five 4-aminomethylidene derivatives obtained from 3-phenyl-2-pyrazolin-5-one and 1,3-diphenyl-2-pyrazolin-5-one were synthesized and tested for their antiproliferative activity against human breast cancer MDA-MB-361 and MDA-MB-453 cell lines. The compounds derived from 1,3-diphenyl-2-pyrazolin-5-one exhibited the most remarkable activity in the treatment of both cell lines. In vitro antiproliferative activities were accompanied by an important apoptotic fraction of both cell lines; also, compounds inhibited key endothelial cell functions implicated in invasion and angiogenesis. QSAR methods were performed in order to analyze the influence of structural features of the compounds investigated on the antiproliferative potential on MDA-MB-361 and MDA-MB-453 cancer cells. One-parameter heuristic analysis was performed and different whole molecule and fragmental descriptors were considered for rationalization of mechanism of interaction of these compounds with active place of hypothetical target included in tumorigenesis.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Bioorganic and Medicinal Chemistry Letters
T1  - Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones
VL  - 21
IS  - 15
SP  - 4416
EP  - 4421
DO  - 10.1016/j.bmcl.2011.06.025
ER  - 

@article{
author = "Markovic, Violeta and Erić, Slavica and Stanojković, Tatjana and Gligorijević, Nevenka and Arandelovic, Sandra and Todorović, Nina and Trifunović, Snežana and Manojlović, Nedeljko and Jelić, Ratomir and Joksovic, Milan D.",
year = "2011",
abstract = "Twenty five 4-aminomethylidene derivatives obtained from 3-phenyl-2-pyrazolin-5-one and 1,3-diphenyl-2-pyrazolin-5-one were synthesized and tested for their antiproliferative activity against human breast cancer MDA-MB-361 and MDA-MB-453 cell lines. The compounds derived from 1,3-diphenyl-2-pyrazolin-5-one exhibited the most remarkable activity in the treatment of both cell lines. In vitro antiproliferative activities were accompanied by an important apoptotic fraction of both cell lines; also, compounds inhibited key endothelial cell functions implicated in invasion and angiogenesis. QSAR methods were performed in order to analyze the influence of structural features of the compounds investigated on the antiproliferative potential on MDA-MB-361 and MDA-MB-453 cancer cells. One-parameter heuristic analysis was performed and different whole molecule and fragmental descriptors were considered for rationalization of mechanism of interaction of these compounds with active place of hypothetical target included in tumorigenesis.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Bioorganic and Medicinal Chemistry Letters",
title = "Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones",
volume = "21",
number = "15",
pages = "4416-4421",
doi = "10.1016/j.bmcl.2011.06.025"
}

Markovic, V., Erić, S., Stanojković, T., Gligorijević, N., Arandelovic, S., Todorović, N., Trifunović, S., Manojlović, N., Jelić, R.,& Joksovic, M. D.. (2011). Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones. in Bioorganic and Medicinal Chemistry Letters
Oxford : Pergamon-Elsevier Science Ltd., 21(15), 4416-4421.
https://doi.org/10.1016/j.bmcl.2011.06.025

Markovic V, Erić S, Stanojković T, Gligorijević N, Arandelovic S, Todorović N, Trifunović S, Manojlović N, Jelić R, Joksovic MD. Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones. in Bioorganic and Medicinal Chemistry Letters. 2011;21(15):4416-4421.
doi:10.1016/j.bmcl.2011.06.025 .

Markovic, Violeta, Erić, Slavica, Stanojković, Tatjana, Gligorijević, Nevenka, Arandelovic, Sandra, Todorović, Nina, Trifunović, Snežana, Manojlović, Nedeljko, Jelić, Ratomir, Joksovic, Milan D., "Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones" in Bioorganic and Medicinal Chemistry Letters, 21, no. 15 (2011):4416-4421,
https://doi.org/10.1016/j.bmcl.2011.06.025 . .