TY  - JOUR
AU  - Jakovljević, Katarina
AU  - Joksović, Milan D.
AU  - Matić, Ivana Z.
AU  - Petrović, Nina
AU  - Stanojković, Tatjana P.
AU  - Sladić, Dušan M.
AU  - Vujčić, Miroslava T.
AU  - Janović, Barbara S.
AU  - Joksović, Ljubinka G.
AU  - Trifunović, Snežana
AU  - Marković, Violeta
PY  - 2018
UR  - http://xlink.rsc.org/?DOI=C8MD00316E
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7928
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.
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 Joksović, Milan D. and Matić, Ivana Z. and Petrović, Nina and Stanojković, Tatjana P. and Sladić, Dušan M. and Vujčić, Miroslava T. and Janović, Barbara S. and Joksović, Ljubinka G. and Trifunović, Snežana and Marković, 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.",
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., Joksović, M. D., Matić, I. Z., Petrović, N., Stanojković, T. P., Sladić, D. M., Vujčić, M. T., Janović, B. S., Joksović, L. G., Trifunović, S.,& Marković, V.. (2018). Novel 1,3,4-thiadiazole–chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in MedChemComm, 9(10), 1679-1697.
https://doi.org/10.1039/C8MD00316E

Jakovljević K, Joksović MD, Matić IZ, Petrović N, Stanojković TP, Sladić DM, Vujčić MT, Janović BS, Joksović LG, Trifunović S, Marković 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, Joksović, Milan D., Matić, Ivana Z., Petrović, Nina, Stanojković, Tatjana P., Sladić, Dušan M., Vujčić, Miroslava T., Janović, Barbara S., Joksović, Ljubinka G., Trifunović, Snežana, Marković, 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  - Stanojković, Tatjana P.
AU  - Marković, Violeta
AU  - Matić, Ivana Z.
AU  - Mladenović, Milan P.
AU  - Petrović, Nina
AU  - Krivokuća, Ana M.
AU  - Petković, Miloš R.
AU  - Joksović, Milan D.
PY  - 2018
UR  - https://linkinghub.elsevier.com/retrieve/pii/S0960894X18305493
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7815
AB  - A series of 23 novel anthraquinone-chalcone hybrids containing amide function was synthesized and structurally characterized. Sixteen compounds exerted strong cytotoxic activities against K562, Jurkat and HL-60 leukemia cell lines and significantly lower cytotoxic effects against normal MRC-5 cells, indicating very high selectivity in their anticancer action. The compounds 6g, 6u and 6v activate apoptosis in K562 cells through the extrinsic and intrinsic apoptotic pathway. The compound 6e triggered apoptosis in K562 cells only through the extrinsic apoptotic pathway. Treatment of K562 cells with each of these four compounds caused decrease in the expression levels of MMP2, MMP9, and VEGF, suggesting their anti-invasive, antimetastatic and antiangiogenic properties. The compounds 6g and 6v downregulated expression levels of miR-155 in K562 cells, while compounds 6e and 6u upregulated miR-155 levels in treated cells, in comparison with control cells. The structure-based 3-D QSAR models for 6f, 6e, 6i and 6l describe pro-apoptotic activity against caspase-3. © 2018 Elsevier Ltd
T2  - Bioorganic and Medicinal Chemistry Letters
T1  - Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents
VL  - 28
IS  - 15
SP  - 2593
EP  - 2598
DO  - 10.1016/j.bmcl.2018.06.048
ER  - 

@article{
author = "Stanojković, Tatjana P. and Marković, Violeta and Matić, Ivana Z. and Mladenović, Milan P. and Petrović, Nina and Krivokuća, Ana M. and Petković, Miloš R. and Joksović, Milan D.",
year = "2018",
abstract = "A series of 23 novel anthraquinone-chalcone hybrids containing amide function was synthesized and structurally characterized. Sixteen compounds exerted strong cytotoxic activities against K562, Jurkat and HL-60 leukemia cell lines and significantly lower cytotoxic effects against normal MRC-5 cells, indicating very high selectivity in their anticancer action. The compounds 6g, 6u and 6v activate apoptosis in K562 cells through the extrinsic and intrinsic apoptotic pathway. The compound 6e triggered apoptosis in K562 cells only through the extrinsic apoptotic pathway. Treatment of K562 cells with each of these four compounds caused decrease in the expression levels of MMP2, MMP9, and VEGF, suggesting their anti-invasive, antimetastatic and antiangiogenic properties. The compounds 6g and 6v downregulated expression levels of miR-155 in K562 cells, while compounds 6e and 6u upregulated miR-155 levels in treated cells, in comparison with control cells. The structure-based 3-D QSAR models for 6f, 6e, 6i and 6l describe pro-apoptotic activity against caspase-3. © 2018 Elsevier Ltd",
journal = "Bioorganic and Medicinal Chemistry Letters",
title = "Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents",
volume = "28",
number = "15",
pages = "2593-2598",
doi = "10.1016/j.bmcl.2018.06.048"
}

Stanojković, T. P., Marković, V., Matić, I. Z., Mladenović, M. P., Petrović, N., Krivokuća, A. M., Petković, M. R.,& Joksović, M. D.. (2018). Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents. in Bioorganic and Medicinal Chemistry Letters, 28(15), 2593-2598.
https://doi.org/10.1016/j.bmcl.2018.06.048

Stanojković TP, Marković V, Matić IZ, Mladenović MP, Petrović N, Krivokuća AM, Petković MR, Joksović MD. Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents. in Bioorganic and Medicinal Chemistry Letters. 2018;28(15):2593-2598.
doi:10.1016/j.bmcl.2018.06.048 .

Stanojković, Tatjana P., Marković, Violeta, Matić, Ivana Z., Mladenović, Milan P., Petrović, Nina, Krivokuća, Ana M., Petković, Miloš R., Joksović, Milan D., "Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents" in Bioorganic and Medicinal Chemistry Letters, 28, no. 15 (2018):2593-2598,
https://doi.org/10.1016/j.bmcl.2018.06.048 . .

TY  - JOUR
AU  - Rodić, Marko V.
AU  - Leovac, Vukadin M.
AU  - Jovanović, Ljiljana S.
AU  - Spasojević, Vojislav
AU  - Joksović, Milan D.
AU  - Stanojković, Tatjana P.
AU  - Matić, Ivana Z.
AU  - Vojinović-Ješić, Ljiljana S.
AU  - Marković, Violeta
PY  - 2016
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1053
AB  - Three novel copper complexes with tridentate N2O ligand di(2-pyridil) ketone 1-adamantoyl hydrazone (Addpy) of the formula [(Cu2Cu2I)-Cu-II(Addpy)(2)Br-2(mu-Br-4)] (1), catena-poly[CuCl(mu-Addpy)(mu-Cl)CuCl2](n) (2) and [Cu(Addpy)(NCS)(2)] (3) were synthesized. Complexes are characterized by X-ray crystallography, spectral (UV-Vis, FTIR), electrochemical (CV) analyses, and magnetochemical measurements. Investigation of anticancer potential of Cu(II) complexes, mode of cell death, apoptosis, and inhibition of angiogenesis were performed. All tested malignant cell lines (HeLa, LS174, A549, K562, and MDA-MB-231) showed high sensitivity to the examined Cu(II) complexes. It has been shown that the complexes induce apoptosis in the caspase 3-dependent manner, whereas the anti-angiogenic effects of 1, 2, and 3 have been confirmed in EA.hy926 cells using a tube formation assay. (C) 2016 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis, characterization, cytotoxicity and antiangiogenic activity of copper(II) complexes with 1-adamantoyl hydrazone bearing pyridine rings
VL  - 115
SP  - 75
EP  - 81
DO  - 10.1016/j.ejmech.2016.03.003
ER  - 

@article{
author = "Rodić, Marko V. and Leovac, Vukadin M. and Jovanović, Ljiljana S. and Spasojević, Vojislav and Joksović, Milan D. and Stanojković, Tatjana P. and Matić, Ivana Z. and Vojinović-Ješić, Ljiljana S. and Marković, Violeta",
year = "2016",
abstract = "Three novel copper complexes with tridentate N2O ligand di(2-pyridil) ketone 1-adamantoyl hydrazone (Addpy) of the formula [(Cu2Cu2I)-Cu-II(Addpy)(2)Br-2(mu-Br-4)] (1), catena-poly[CuCl(mu-Addpy)(mu-Cl)CuCl2](n) (2) and [Cu(Addpy)(NCS)(2)] (3) were synthesized. Complexes are characterized by X-ray crystallography, spectral (UV-Vis, FTIR), electrochemical (CV) analyses, and magnetochemical measurements. Investigation of anticancer potential of Cu(II) complexes, mode of cell death, apoptosis, and inhibition of angiogenesis were performed. All tested malignant cell lines (HeLa, LS174, A549, K562, and MDA-MB-231) showed high sensitivity to the examined Cu(II) complexes. It has been shown that the complexes induce apoptosis in the caspase 3-dependent manner, whereas the anti-angiogenic effects of 1, 2, and 3 have been confirmed in EA.hy926 cells using a tube formation assay. (C) 2016 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis, characterization, cytotoxicity and antiangiogenic activity of copper(II) complexes with 1-adamantoyl hydrazone bearing pyridine rings",
volume = "115",
pages = "75-81",
doi = "10.1016/j.ejmech.2016.03.003"
}

Rodić, M. V., Leovac, V. M., Jovanović, L. S., Spasojević, V., Joksović, M. D., Stanojković, T. P., Matić, I. Z., Vojinović-Ješić, L. S.,& Marković, V.. (2016). Synthesis, characterization, cytotoxicity and antiangiogenic activity of copper(II) complexes with 1-adamantoyl hydrazone bearing pyridine rings. in European Journal of Medicinal Chemistry
Elsevier., 115, 75-81.
https://doi.org/10.1016/j.ejmech.2016.03.003

Rodić MV, Leovac VM, Jovanović LS, Spasojević V, Joksović MD, Stanojković TP, Matić IZ, Vojinović-Ješić LS, Marković V. Synthesis, characterization, cytotoxicity and antiangiogenic activity of copper(II) complexes with 1-adamantoyl hydrazone bearing pyridine rings. in European Journal of Medicinal Chemistry. 2016;115:75-81.
doi:10.1016/j.ejmech.2016.03.003 .

Rodić, Marko V., Leovac, Vukadin M., Jovanović, Ljiljana S., Spasojević, Vojislav, Joksović, Milan D., Stanojković, Tatjana P., Matić, Ivana Z., Vojinović-Ješić, Ljiljana S., Marković, Violeta, "Synthesis, characterization, cytotoxicity and antiangiogenic activity of copper(II) complexes with 1-adamantoyl hydrazone bearing pyridine rings" in European Journal of Medicinal Chemistry, 115 (2016):75-81,
https://doi.org/10.1016/j.ejmech.2016.03.003 . .

TY  - JOUR
AU  - Leovac, Vukadin M.
AU  - Bogdanović, Goran A.
AU  - Jovanović, Ljiljana S.
AU  - Joksović, Ljubinka G.
AU  - Marković, Violeta
AU  - Joksović, Milan D.
AU  - Misirlić-Denčić, Sonja
AU  - Isaković, Anđelka
AU  - Markovic, Ivanka
AU  - Heinemann, Frank W.
AU  - Trifunović, Srećko R.
AU  - Dalovic, Ivica
PY  - 2011
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/4592
AB  - New polymeric copper(II) complexes with two tridentate ONS thiosemicarbazone ligands containing substituted pyrazolone moiety were synthesized and characterized by means of spectroscopic, electrochemical and crystallographic techniques. While both ligands exist as different tautomers in the solid state and DMSO-d(6) solution, Cu(II) ion coordinates the ligands from the same tautomeric form with square-pyramidal geometry around each Cu atom. In the crystal structures, the copper(II) complex cation forms polymeric chains {[Cu(L)Cl(+)]}(n) with a bridging chlorine atom. One of the complexes was found to have a significantly higher cytotoxic potential in comparison with cisplatin in inhibition of several cell lines (HL60, REH, C6, L929 and B16). The results obtained on the basis of flow cytometry indicated that apoptosis could be possible mechanism of cell death. (C) 2011 Elsevier Inc. All rights reserved.
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis, characterization and antitumor activity of polymeric copper(II) complexes with thiosemicarbazones of 3-methyl-5-oxo-1-phenyl-3-pyrazolin-4-carboxaldehyde and 5-oxo-3-phenyl-3-pyrazolin-4-carboxaldehyde
VL  - 105
IS  - 11
SP  - 1413
EP  - 1421
DO  - 10.1016/j.jinorgbio.2011.07.021
ER  - 

@article{
author = "Leovac, Vukadin M. and Bogdanović, Goran A. and Jovanović, Ljiljana S. and Joksović, Ljubinka G. and Marković, Violeta and Joksović, Milan D. and Misirlić-Denčić, Sonja and Isaković, Anđelka and Markovic, Ivanka and Heinemann, Frank W. and Trifunović, Srećko R. and Dalovic, Ivica",
year = "2011",
abstract = "New polymeric copper(II) complexes with two tridentate ONS thiosemicarbazone ligands containing substituted pyrazolone moiety were synthesized and characterized by means of spectroscopic, electrochemical and crystallographic techniques. While both ligands exist as different tautomers in the solid state and DMSO-d(6) solution, Cu(II) ion coordinates the ligands from the same tautomeric form with square-pyramidal geometry around each Cu atom. In the crystal structures, the copper(II) complex cation forms polymeric chains {[Cu(L)Cl(+)]}(n) with a bridging chlorine atom. One of the complexes was found to have a significantly higher cytotoxic potential in comparison with cisplatin in inhibition of several cell lines (HL60, REH, C6, L929 and B16). The results obtained on the basis of flow cytometry indicated that apoptosis could be possible mechanism of cell death. (C) 2011 Elsevier Inc. All rights reserved.",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis, characterization and antitumor activity of polymeric copper(II) complexes with thiosemicarbazones of 3-methyl-5-oxo-1-phenyl-3-pyrazolin-4-carboxaldehyde and 5-oxo-3-phenyl-3-pyrazolin-4-carboxaldehyde",
volume = "105",
number = "11",
pages = "1413-1421",
doi = "10.1016/j.jinorgbio.2011.07.021"
}

Leovac, V. M., Bogdanović, G. A., Jovanović, L. S., Joksović, L. G., Marković, V., Joksović, M. D., Misirlić-Denčić, S., Isaković, A., Markovic, I., Heinemann, F. W., Trifunović, S. R.,& Dalovic, I.. (2011). Synthesis, characterization and antitumor activity of polymeric copper(II) complexes with thiosemicarbazones of 3-methyl-5-oxo-1-phenyl-3-pyrazolin-4-carboxaldehyde and 5-oxo-3-phenyl-3-pyrazolin-4-carboxaldehyde. in Journal of Inorganic Biochemistry, 105(11), 1413-1421.
https://doi.org/10.1016/j.jinorgbio.2011.07.021

Leovac VM, Bogdanović GA, Jovanović LS, Joksović LG, Marković V, Joksović MD, Misirlić-Denčić S, Isaković A, Markovic I, Heinemann FW, Trifunović SR, Dalovic I. Synthesis, characterization and antitumor activity of polymeric copper(II) complexes with thiosemicarbazones of 3-methyl-5-oxo-1-phenyl-3-pyrazolin-4-carboxaldehyde and 5-oxo-3-phenyl-3-pyrazolin-4-carboxaldehyde. in Journal of Inorganic Biochemistry. 2011;105(11):1413-1421.
doi:10.1016/j.jinorgbio.2011.07.021 .

Leovac, Vukadin M., Bogdanović, Goran A., Jovanović, Ljiljana S., Joksović, Ljubinka G., Marković, Violeta, Joksović, Milan D., Misirlić-Denčić, Sonja, Isaković, Anđelka, Markovic, Ivanka, Heinemann, Frank W., Trifunović, Srećko R., Dalovic, Ivica, "Synthesis, characterization and antitumor activity of polymeric copper(II) complexes with thiosemicarbazones of 3-methyl-5-oxo-1-phenyl-3-pyrazolin-4-carboxaldehyde and 5-oxo-3-phenyl-3-pyrazolin-4-carboxaldehyde" in Journal of Inorganic Biochemistry, 105, no. 11 (2011):1413-1421,
https://doi.org/10.1016/j.jinorgbio.2011.07.021 . .