TY  - JOUR
AU  - Filipović, Nenad R.
AU  - Bjelogrlic, Snežana
AU  - Pelliccia, Sveva
AU  - Jovanović, Vesna B.
AU  - Kojic, Milan
AU  - Sencanski, Milan
AU  - La Regina, Giuseppe
AU  - Silvestri, Romano
AU  - Muller, Christian D.
AU  - Todorović, Tamara R.
PY  - 2020
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1295
AB  - Triapine, the most studied alpha-N-heterocyclic thiosemicarbazone, revealed potent activity against advanced leukemia, but was ineffective against a variety of solid tumors. Moreover, methemoglobinemia, which is a side effect of triapine administration, may limits all clinical application. To enhance anticancer activity and reduce side effects, we applied an isosteric replacement of sulfur to selenium atom was performed by synthesis and characterization of selenium triapine analog, 3-aminopyridine-2-carboxaldehyde selenosemicarbazone (selenotriapine). Compared to triapine, selenotriapine revealed superior pro-apoptotic activity with activation of intrinsic apoptotic pathway in both human monocytic leukemia (THP-1) and mammary adenocarcinoma (MCF-7) cell lines. For MCF-7 2-D cultures, selenotriapine induced notable increase in mitochondrial superoxide radical generation and dissipation of mitochondrial transmembrane potential. A significant delay in growth of MCF-7 spheroids (3-D culture) was accompanied by phenotypic stem cell reprogramming (Oct-4 expression). Additionally, selenotriapine demonstrated a very low toxicity profile as compared to triapine, confirmed over alleviated extent of methemoglobin formation and higher IC50 value in brine shrimp cytotoxicity assay.
PB  - Elsevier, Amsterdam
T2  - Arabian Journal of Chemistry
T1  - Selenotriapine - An isostere of the most studied thiosemicarbazone with pronounced pro-apoptotic activity, low toxicity and ability to challenge phenotype reprogramming of 3-D mammary adenocarcinoma tumors
EP  - 1489
IS  - 1
SP  - 1466
VL  - 13
DO  - 10.1016/j.arabjc.2017.11.017
ER  - 

@article{
author = "Filipović, Nenad R. and Bjelogrlic, Snežana and Pelliccia, Sveva and Jovanović, Vesna B. and Kojic, Milan and Sencanski, Milan and La Regina, Giuseppe and Silvestri, Romano and Muller, Christian D. and Todorović, Tamara R.",
year = "2020",
abstract = "Triapine, the most studied alpha-N-heterocyclic thiosemicarbazone, revealed potent activity against advanced leukemia, but was ineffective against a variety of solid tumors. Moreover, methemoglobinemia, which is a side effect of triapine administration, may limits all clinical application. To enhance anticancer activity and reduce side effects, we applied an isosteric replacement of sulfur to selenium atom was performed by synthesis and characterization of selenium triapine analog, 3-aminopyridine-2-carboxaldehyde selenosemicarbazone (selenotriapine). Compared to triapine, selenotriapine revealed superior pro-apoptotic activity with activation of intrinsic apoptotic pathway in both human monocytic leukemia (THP-1) and mammary adenocarcinoma (MCF-7) cell lines. For MCF-7 2-D cultures, selenotriapine induced notable increase in mitochondrial superoxide radical generation and dissipation of mitochondrial transmembrane potential. A significant delay in growth of MCF-7 spheroids (3-D culture) was accompanied by phenotypic stem cell reprogramming (Oct-4 expression). Additionally, selenotriapine demonstrated a very low toxicity profile as compared to triapine, confirmed over alleviated extent of methemoglobin formation and higher IC50 value in brine shrimp cytotoxicity assay.",
publisher = "Elsevier, Amsterdam",
journal = "Arabian Journal of Chemistry",
title = "Selenotriapine - An isostere of the most studied thiosemicarbazone with pronounced pro-apoptotic activity, low toxicity and ability to challenge phenotype reprogramming of 3-D mammary adenocarcinoma tumors",
pages = "1489-1466",
number = "1",
volume = "13",
doi = "10.1016/j.arabjc.2017.11.017"
}

Filipović, N. R., Bjelogrlic, S., Pelliccia, S., Jovanović, V. B., Kojic, M., Sencanski, M., La Regina, G., Silvestri, R., Muller, C. D.,& Todorović, T. R.. (2020). Selenotriapine - An isostere of the most studied thiosemicarbazone with pronounced pro-apoptotic activity, low toxicity and ability to challenge phenotype reprogramming of 3-D mammary adenocarcinoma tumors. in Arabian Journal of Chemistry
Elsevier, Amsterdam., 13(1), 1466-1489.
https://doi.org/10.1016/j.arabjc.2017.11.017

Filipović NR, Bjelogrlic S, Pelliccia S, Jovanović VB, Kojic M, Sencanski M, La Regina G, Silvestri R, Muller CD, Todorović TR. Selenotriapine - An isostere of the most studied thiosemicarbazone with pronounced pro-apoptotic activity, low toxicity and ability to challenge phenotype reprogramming of 3-D mammary adenocarcinoma tumors. in Arabian Journal of Chemistry. 2020;13(1):1466-1489.
doi:10.1016/j.arabjc.2017.11.017 .

Filipović, Nenad R., Bjelogrlic, Snežana, Pelliccia, Sveva, Jovanović, Vesna B., Kojic, Milan, Sencanski, Milan, La Regina, Giuseppe, Silvestri, Romano, Muller, Christian D., Todorović, Tamara R., "Selenotriapine - An isostere of the most studied thiosemicarbazone with pronounced pro-apoptotic activity, low toxicity and ability to challenge phenotype reprogramming of 3-D mammary adenocarcinoma tumors" in Arabian Journal of Chemistry, 13, no. 1 (2020):1466-1489,
https://doi.org/10.1016/j.arabjc.2017.11.017 . .

TY  - JOUR
AU  - Kolarević, Stoimir
AU  - Milovanović, Dragana
AU  - Kracun-Kolarević, Margareta
AU  - Kostić-Vuković, Jovana
AU  - Sunjog, Karolina
AU  - Martinović, Rajko
AU  - Đorđević Aleksić, Jelena
AU  - Novaković, Irena
AU  - Sladic, Dusan
AU  - Vukovic-Gacic, Branka
PY  - 2019
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1274
AB  - In this study, mutagenic and genotoxic potential of anti-tumor compounds avarol, avarone, and its derivatives 3 '-methoxyavarone, 4 '-(methylamino)avarone and 3 '-(methylamino)avarone was evaluated and compared to cytostatics commonly used in chemotherapy (5-fluorouracil, etoposid, and cisplatin). Mutagenic potential of selected hydroquinone and quinones was assessed in prokaryotic model by the SOS/umuC assay in Salmonella typhimurium TA1535/pSK1002. Genotoxic potential was also assessed in eukaryotic models using comet assay in human fetal lung cell line (MRC-5), human adenocarcinoma epithelial cell line (A549), and in human peripheral blood cells (HPBC). The results indicated that avarol and avarone do not exert mutagenic/genotoxic potential. Among the studied avarone derivatives, mutagenic potential was detected by SOS/umuC test for 3 '-(methylamino)avarone, but only after metabolic activation. The results of comet assay indicated that 3 '-methoxyavarone and 3 '-(methylamino)avarone have a significant impact on the level of DNA damage in the MRC-5 cell line. Genotoxic potential was not observed in A549 cells or HPBC probably due to a different uptake rate for the compounds and lower in metabolism rate within these cells.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Drug and Chemical Toxicology
T1  - Evaluation of genotoxic potential of avarol, avarone, and its methoxy and methylamino derivatives in prokaryotic and eukaryotic test models
EP  - 139
IS  - 2
SP  - 130
VL  - 42
DO  - 10.1080/01480545.2017.1413108
ER  - 

@article{
author = "Kolarević, Stoimir and Milovanović, Dragana and Kracun-Kolarević, Margareta and Kostić-Vuković, Jovana and Sunjog, Karolina and Martinović, Rajko and Đorđević Aleksić, Jelena and Novaković, Irena and Sladic, Dusan and Vukovic-Gacic, Branka",
year = "2019",
abstract = "In this study, mutagenic and genotoxic potential of anti-tumor compounds avarol, avarone, and its derivatives 3 '-methoxyavarone, 4 '-(methylamino)avarone and 3 '-(methylamino)avarone was evaluated and compared to cytostatics commonly used in chemotherapy (5-fluorouracil, etoposid, and cisplatin). Mutagenic potential of selected hydroquinone and quinones was assessed in prokaryotic model by the SOS/umuC assay in Salmonella typhimurium TA1535/pSK1002. Genotoxic potential was also assessed in eukaryotic models using comet assay in human fetal lung cell line (MRC-5), human adenocarcinoma epithelial cell line (A549), and in human peripheral blood cells (HPBC). The results indicated that avarol and avarone do not exert mutagenic/genotoxic potential. Among the studied avarone derivatives, mutagenic potential was detected by SOS/umuC test for 3 '-(methylamino)avarone, but only after metabolic activation. The results of comet assay indicated that 3 '-methoxyavarone and 3 '-(methylamino)avarone have a significant impact on the level of DNA damage in the MRC-5 cell line. Genotoxic potential was not observed in A549 cells or HPBC probably due to a different uptake rate for the compounds and lower in metabolism rate within these cells.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Drug and Chemical Toxicology",
title = "Evaluation of genotoxic potential of avarol, avarone, and its methoxy and methylamino derivatives in prokaryotic and eukaryotic test models",
pages = "139-130",
number = "2",
volume = "42",
doi = "10.1080/01480545.2017.1413108"
}

Kolarević, S., Milovanović, D., Kracun-Kolarević, M., Kostić-Vuković, J., Sunjog, K., Martinović, R., Đorđević Aleksić, J., Novaković, I., Sladic, D.,& Vukovic-Gacic, B.. (2019). Evaluation of genotoxic potential of avarol, avarone, and its methoxy and methylamino derivatives in prokaryotic and eukaryotic test models. in Drug and Chemical Toxicology
Taylor & Francis Ltd, Abingdon., 42(2), 130-139.
https://doi.org/10.1080/01480545.2017.1413108

Kolarević S, Milovanović D, Kracun-Kolarević M, Kostić-Vuković J, Sunjog K, Martinović R, Đorđević Aleksić J, Novaković I, Sladic D, Vukovic-Gacic B. Evaluation of genotoxic potential of avarol, avarone, and its methoxy and methylamino derivatives in prokaryotic and eukaryotic test models. in Drug and Chemical Toxicology. 2019;42(2):130-139.
doi:10.1080/01480545.2017.1413108 .

Kolarević, Stoimir, Milovanović, Dragana, Kracun-Kolarević, Margareta, Kostić-Vuković, Jovana, Sunjog, Karolina, Martinović, Rajko, Đorđević Aleksić, Jelena, Novaković, Irena, Sladic, Dusan, Vukovic-Gacic, Branka, "Evaluation of genotoxic potential of avarol, avarone, and its methoxy and methylamino derivatives in prokaryotic and eukaryotic test models" in Drug and Chemical Toxicology, 42, no. 2 (2019):130-139,
https://doi.org/10.1080/01480545.2017.1413108 . .

TY  - JOUR
AU  - Filipović, Nenad R.
AU  - Elshaflu, Hana
AU  - Grubisic, Sonja
AU  - Jovanović, Ljiljana S.
AU  - Rodic, Marko
AU  - Novaković, Irena
AU  - Malešević, Aleksandar
AU  - Đorđević, Ivana S.
AU  - Li, Haidong
AU  - Sojic, Neso
AU  - Marinković, Aleksandar
AU  - Todorović, Tamara R.
PY  - 2017
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1036
AB  - The first Co(III) complexes with (1,3-selenazol-2-yl)hydrazones as an unexplored class of ligands were prepared and characterized by NMR spectroscopy and X-ray diffraction analysis. The novel ligands act as NNN tridentate chelators forming octahedral Co(III) complexes. The impact of structural changes on ligands' periphery as well as that of isosteric replacement of sulphur with selenium on the electrochemical and electronic absorption features of complexes are explored. To support the experimental data, density functional theory (DFT) calculations were also conducted. Theoretical NMR chemical shifts, the relative energies and natural bond orbital (NBO) analysis are calculated within the DFT approach, while the singlet excited state energies and HOMO-LUMO energy gap were calculated with time-dependent density functional theory (TD-DFT). The electrophilic f(-) and nucleophilic f(+) Fukui functions are well adapted to find the electrophile and nucleophile centres in the molecules. Both (1,3-selenazol-2-yl)- and (1,3-thiazol-2-yl) hydrazone Co(III) complexes showed potent antimicrobial and antioxidant activity. A significant difference among them was a smaller cytotoxicity of selenium compounds.
PB  - Royal Soc Chemistry, Cambridge
T2  - Dalton Transactions
T1  - Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues
EP  - 2924
IS  - 9
SP  - 2910
VL  - 46
DO  - 10.1039/c6dt04785h
ER  - 

@article{
author = "Filipović, Nenad R. and Elshaflu, Hana and Grubisic, Sonja and Jovanović, Ljiljana S. and Rodic, Marko and Novaković, Irena and Malešević, Aleksandar and Đorđević, Ivana S. and Li, Haidong and Sojic, Neso and Marinković, Aleksandar and Todorović, Tamara R.",
year = "2017",
abstract = "The first Co(III) complexes with (1,3-selenazol-2-yl)hydrazones as an unexplored class of ligands were prepared and characterized by NMR spectroscopy and X-ray diffraction analysis. The novel ligands act as NNN tridentate chelators forming octahedral Co(III) complexes. The impact of structural changes on ligands' periphery as well as that of isosteric replacement of sulphur with selenium on the electrochemical and electronic absorption features of complexes are explored. To support the experimental data, density functional theory (DFT) calculations were also conducted. Theoretical NMR chemical shifts, the relative energies and natural bond orbital (NBO) analysis are calculated within the DFT approach, while the singlet excited state energies and HOMO-LUMO energy gap were calculated with time-dependent density functional theory (TD-DFT). The electrophilic f(-) and nucleophilic f(+) Fukui functions are well adapted to find the electrophile and nucleophile centres in the molecules. Both (1,3-selenazol-2-yl)- and (1,3-thiazol-2-yl) hydrazone Co(III) complexes showed potent antimicrobial and antioxidant activity. A significant difference among them was a smaller cytotoxicity of selenium compounds.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Dalton Transactions",
title = "Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues",
pages = "2924-2910",
number = "9",
volume = "46",
doi = "10.1039/c6dt04785h"
}

Filipović, N. R., Elshaflu, H., Grubisic, S., Jovanović, L. S., Rodic, M., Novaković, I., Malešević, A., Đorđević, I. S., Li, H., Sojic, N., Marinković, A.,& Todorović, T. R.. (2017). Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues. in Dalton Transactions
Royal Soc Chemistry, Cambridge., 46(9), 2910-2924.
https://doi.org/10.1039/c6dt04785h

Filipović NR, Elshaflu H, Grubisic S, Jovanović LS, Rodic M, Novaković I, Malešević A, Đorđević IS, Li H, Sojic N, Marinković A, Todorović TR. Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues. in Dalton Transactions. 2017;46(9):2910-2924.
doi:10.1039/c6dt04785h .

Filipović, Nenad R., Elshaflu, Hana, Grubisic, Sonja, Jovanović, Ljiljana S., Rodic, Marko, Novaković, Irena, Malešević, Aleksandar, Đorđević, Ivana S., Li, Haidong, Sojic, Neso, Marinković, Aleksandar, Todorović, Tamara R., "Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues" in Dalton Transactions, 46, no. 9 (2017):2910-2924,
https://doi.org/10.1039/c6dt04785h . .

TY  - JOUR
AU  - Todorović, Tamara
AU  - Vukašinović, Jelena
AU  - Portalone, Gustavo
AU  - suleiman, sherif
AU  - Gligorijević, Nevenka
AU  - Bjelogrlic, Snezana K.
AU  - Jovanovic, Katarina
AU  - Radulović, Sinisa S
AU  - Andjelkovic, Katarina
AU  - Cassar, Analisse
AU  - Filipović, Nenad
AU  - Schembri-WIsmayer, Pierre
PY  - 2017
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/2027
AB  - Cobaltcomplexeswithsemi-andthiosemicarbazonesof8-quinolinecarboxaldehydehavebeensynthesizedandcharacterizedbyX-raydiffractionanalysis.Thesenovelcomplexesandapreviouslysynthesized cobaltcomplexwithaselenium-basedselenosemicarbazoneligandshowedmyeloiddifferentiationactivity onalltransretinoicacidresistantHL-60acutemyeloidleukaemiacells.Theyalsoshowedvaryinglevelsof cytotoxicityonfivehumantumorcelllines:cervixcarcinomacells(HeLa),lungadenocarcinomacells (A549),colorectaladenocarcinomacells(LS-174),breastcarcinomacells(MDA-MB-361),andchronicmyeloidleukaemia(K562)aswellasonenormalhumancellline:fetallungfibroblastcells(MRC-5).Leukaemia differentiationwasmoststronglyinducedbyametal-freeoxygenligandandtheseleniumligand,whilst thelatterandthecobaltIJII)complexwithanoxygenligandshowedthestrongestdose-dependentcytotoxic activity.Infouroutoffiveinvestigatedtumorcelllines,itwasofthesameorderofmagnitudeascisplatin. Thesebestcompounds,however,hadlowertoxicityonnon-transformedMRC-5cellsthancisplatin.
PB  - RSC Publishing
T2  - MedChemComm
T1  - (Chalcogen)semicarbazones and their cobalt complexes differentiate HL-60 myeloid leukaemia cells and are cytotoxic towards tumor cell lines
EP  - 111
IS  - 1
SP  - 103
VL  - 8
DO  - https://doi.org/10.1039/c6md00501b
ER  - 

@article{
author = "Todorović, Tamara and Vukašinović, Jelena and Portalone, Gustavo and suleiman, sherif and Gligorijević, Nevenka and Bjelogrlic, Snezana K. and Jovanovic, Katarina and Radulović, Sinisa S and Andjelkovic, Katarina and Cassar, Analisse and Filipović, Nenad and Schembri-WIsmayer, Pierre",
year = "2017",
abstract = "Cobaltcomplexeswithsemi-andthiosemicarbazonesof8-quinolinecarboxaldehydehavebeensynthesizedandcharacterizedbyX-raydiffractionanalysis.Thesenovelcomplexesandapreviouslysynthesized cobaltcomplexwithaselenium-basedselenosemicarbazoneligandshowedmyeloiddifferentiationactivity onalltransretinoicacidresistantHL-60acutemyeloidleukaemiacells.Theyalsoshowedvaryinglevelsof cytotoxicityonfivehumantumorcelllines:cervixcarcinomacells(HeLa),lungadenocarcinomacells (A549),colorectaladenocarcinomacells(LS-174),breastcarcinomacells(MDA-MB-361),andchronicmyeloidleukaemia(K562)aswellasonenormalhumancellline:fetallungfibroblastcells(MRC-5).Leukaemia differentiationwasmoststronglyinducedbyametal-freeoxygenligandandtheseleniumligand,whilst thelatterandthecobaltIJII)complexwithanoxygenligandshowedthestrongestdose-dependentcytotoxic activity.Infouroutoffiveinvestigatedtumorcelllines,itwasofthesameorderofmagnitudeascisplatin. Thesebestcompounds,however,hadlowertoxicityonnon-transformedMRC-5cellsthancisplatin.",
publisher = "RSC Publishing",
journal = "MedChemComm",
title = "(Chalcogen)semicarbazones and their cobalt complexes differentiate HL-60 myeloid leukaemia cells and are cytotoxic towards tumor cell lines",
pages = "111-103",
number = "1",
volume = "8",
doi = "https://doi.org/10.1039/c6md00501b"
}

Todorović, T., Vukašinović, J., Portalone, G., suleiman, s., Gligorijević, N., Bjelogrlic, S. K., Jovanovic, K., Radulović, S. S., Andjelkovic, K., Cassar, A., Filipović, N.,& Schembri-WIsmayer, P.. (2017). (Chalcogen)semicarbazones and their cobalt complexes differentiate HL-60 myeloid leukaemia cells and are cytotoxic towards tumor cell lines. in MedChemComm
RSC Publishing., 8(1), 103-111.
https://doi.org/https://doi.org/10.1039/c6md00501b

Todorović T, Vukašinović J, Portalone G, suleiman S, Gligorijević N, Bjelogrlic SK, Jovanovic K, Radulović SS, Andjelkovic K, Cassar A, Filipović N, Schembri-WIsmayer P. (Chalcogen)semicarbazones and their cobalt complexes differentiate HL-60 myeloid leukaemia cells and are cytotoxic towards tumor cell lines. in MedChemComm. 2017;8(1):103-111.
doi:https://doi.org/10.1039/c6md00501b .

Todorović, Tamara, Vukašinović, Jelena, Portalone, Gustavo, suleiman, sherif, Gligorijević, Nevenka, Bjelogrlic, Snezana K., Jovanovic, Katarina, Radulović, Sinisa S, Andjelkovic, Katarina, Cassar, Analisse, Filipović, Nenad, Schembri-WIsmayer, Pierre, "(Chalcogen)semicarbazones and their cobalt complexes differentiate HL-60 myeloid leukaemia cells and are cytotoxic towards tumor cell lines" in MedChemComm, 8, no. 1 (2017):103-111,
https://doi.org/https://doi.org/10.1039/c6md00501b . .

TY  - JOUR
AU  - Đorđević, Ivana S.
AU  - Mitrović, Jelena
AU  - Todorović, Tamara R.
AU  - Filipović, Nenad R.
AU  - Rodic, Marko
AU  - Lolic, Aleksandar
AU  - Portalone, Gustavo
AU  - Zlatović, Mario
AU  - Grubisic, Sonja
PY  - 2017
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1032
AB  - Cobalt(III) complexes derived from thio-and selenosemicarbazone ligands have been studied to elucidate the nature and consequences of S to Se substitution on their possible biological activity. Solid state structures of cobalt(III) complexes with bis-tridentate coordinated 2-quinolinecarboxaldehyde thio-and selenosemicarbazone were determined by single crystal X-ray diffraction analysis. The complexes were also characterized by spectroscopic methods and cyclic voltammetry. Electronic properties of the complexes were studied using DFT and TD-DFT methods. Finally, evident in vitro antioxidant activity of the complexes was demonstrated.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study
EP  - 839
IS  - 7-8
SP  - 825
VL  - 82
DO  - 10.2298/JSC170412062D
ER  - 

@article{
author = "Đorđević, Ivana S. and Mitrović, Jelena and Todorović, Tamara R. and Filipović, Nenad R. and Rodic, Marko and Lolic, Aleksandar and Portalone, Gustavo and Zlatović, Mario and Grubisic, Sonja",
year = "2017",
abstract = "Cobalt(III) complexes derived from thio-and selenosemicarbazone ligands have been studied to elucidate the nature and consequences of S to Se substitution on their possible biological activity. Solid state structures of cobalt(III) complexes with bis-tridentate coordinated 2-quinolinecarboxaldehyde thio-and selenosemicarbazone were determined by single crystal X-ray diffraction analysis. The complexes were also characterized by spectroscopic methods and cyclic voltammetry. Electronic properties of the complexes were studied using DFT and TD-DFT methods. Finally, evident in vitro antioxidant activity of the complexes was demonstrated.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study",
pages = "839-825",
number = "7-8",
volume = "82",
doi = "10.2298/JSC170412062D"
}

Đorđević, I. S., Mitrović, J., Todorović, T. R., Filipović, N. R., Rodic, M., Lolic, A., Portalone, G., Zlatović, M.,& Grubisic, S.. (2017). Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 82(7-8), 825-839.
https://doi.org/10.2298/JSC170412062D

Đorđević IS, Mitrović J, Todorović TR, Filipović NR, Rodic M, Lolic A, Portalone G, Zlatović M, Grubisic S. Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study. in Journal of the Serbian Chemical Society. 2017;82(7-8):825-839.
doi:10.2298/JSC170412062D .

Đorđević, Ivana S., Mitrović, Jelena, Todorović, Tamara R., Filipović, Nenad R., Rodic, Marko, Lolic, Aleksandar, Portalone, Gustavo, Zlatović, Mario, Grubisic, Sonja, "Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study" in Journal of the Serbian Chemical Society, 82, no. 7-8 (2017):825-839,
https://doi.org/10.2298/JSC170412062D . .

TY  - JOUR
AU  - Filipović, Nenad R.
AU  - Bjelogrlic, Snežana
AU  - Todorović, Tamara R.
AU  - Blagojević, Vladimir A.
AU  - Muller, Christian D.
AU  - Marinković, Aleksandar
AU  - Vujcic, Miroslava
AU  - Janović, Barbara
AU  - Malešević, Aleksandar
AU  - Begović, Nebojša
AU  - Sencanski, Milan
AU  - Minic, Dragica
PY  - 2016
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/972
AB  - A new Ni(II) complex, [Ni(L)(H2O)] (1), with diethyl 3,3'-(2,2'-(1,1'-(pyridine-2,6-diyl) bis(ethan-1-yl-1-ylidene)) bis(hydrazin-1-yl-2-ylidene)) bis(3-oxopropanoate) ligand (H2L) was synthesized as a potential chemotherapeutic agent. Polidentate ligand was coordinated to Ni(II) NNN-tridentately, in dianionic form, while monodentate water coordination completed square-planar geometry around metal. Structure in the solution was determined by NMR spectroscopy and the same coordination mode was observed in the solid state using IR spectroscopy and further verified by DFT calculations and electrochemical studies. Thermal stability of 1 was determined in both air and nitrogen atmosphere. Anticancer activity of 1 was investigated on acute monocytic leukemia (THP-1) and pancreatic adenocarcinoma (AsPC-1) cell lines. On THP-1 cells 1 induced powerful apoptotic response (ED50 = 10 +/- 3 mu M), which was revealed to be only partially caspase-dependent, with activation of caspase-8 as the dominant course. This suggested that experimentally validated covalent binding of 1 to DNA is not the only mechanism responsible for programmed cell death. This was supported with experiments on AsPC-1 cells. Although treatment of those cells with 1 resulted in poor apoptotic response, cell cycle changes showed concentration-dependent shifts indicating a dual mechanism of activity. This study also reviews the results of preliminary biological screening, which demonstrates that 1 displays a unique pattern of anticancer activity with at least two mechanisms involved.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Ni(II) complex with bishydrazone ligand: synthesis, characterization, DNA binding studies and pro-apoptotic and pro-differentiation induction in human cancerous cell lines
EP  - 108740
IS  - 110
SP  - 108726
VL  - 6
DO  - 10.1039/c6ra24604d
ER  - 

@article{
author = "Filipović, Nenad R. and Bjelogrlic, Snežana and Todorović, Tamara R. and Blagojević, Vladimir A. and Muller, Christian D. and Marinković, Aleksandar and Vujcic, Miroslava and Janović, Barbara and Malešević, Aleksandar and Begović, Nebojša and Sencanski, Milan and Minic, Dragica",
year = "2016",
abstract = "A new Ni(II) complex, [Ni(L)(H2O)] (1), with diethyl 3,3'-(2,2'-(1,1'-(pyridine-2,6-diyl) bis(ethan-1-yl-1-ylidene)) bis(hydrazin-1-yl-2-ylidene)) bis(3-oxopropanoate) ligand (H2L) was synthesized as a potential chemotherapeutic agent. Polidentate ligand was coordinated to Ni(II) NNN-tridentately, in dianionic form, while monodentate water coordination completed square-planar geometry around metal. Structure in the solution was determined by NMR spectroscopy and the same coordination mode was observed in the solid state using IR spectroscopy and further verified by DFT calculations and electrochemical studies. Thermal stability of 1 was determined in both air and nitrogen atmosphere. Anticancer activity of 1 was investigated on acute monocytic leukemia (THP-1) and pancreatic adenocarcinoma (AsPC-1) cell lines. On THP-1 cells 1 induced powerful apoptotic response (ED50 = 10 +/- 3 mu M), which was revealed to be only partially caspase-dependent, with activation of caspase-8 as the dominant course. This suggested that experimentally validated covalent binding of 1 to DNA is not the only mechanism responsible for programmed cell death. This was supported with experiments on AsPC-1 cells. Although treatment of those cells with 1 resulted in poor apoptotic response, cell cycle changes showed concentration-dependent shifts indicating a dual mechanism of activity. This study also reviews the results of preliminary biological screening, which demonstrates that 1 displays a unique pattern of anticancer activity with at least two mechanisms involved.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Ni(II) complex with bishydrazone ligand: synthesis, characterization, DNA binding studies and pro-apoptotic and pro-differentiation induction in human cancerous cell lines",
pages = "108740-108726",
number = "110",
volume = "6",
doi = "10.1039/c6ra24604d"
}

Filipović, N. R., Bjelogrlic, S., Todorović, T. R., Blagojević, V. A., Muller, C. D., Marinković, A., Vujcic, M., Janović, B., Malešević, A., Begović, N., Sencanski, M.,& Minic, D.. (2016). Ni(II) complex with bishydrazone ligand: synthesis, characterization, DNA binding studies and pro-apoptotic and pro-differentiation induction in human cancerous cell lines. in RSC Advances
Royal Soc Chemistry, Cambridge., 6(110), 108726-108740.
https://doi.org/10.1039/c6ra24604d

Filipović NR, Bjelogrlic S, Todorović TR, Blagojević VA, Muller CD, Marinković A, Vujcic M, Janović B, Malešević A, Begović N, Sencanski M, Minic D. Ni(II) complex with bishydrazone ligand: synthesis, characterization, DNA binding studies and pro-apoptotic and pro-differentiation induction in human cancerous cell lines. in RSC Advances. 2016;6(110):108726-108740.
doi:10.1039/c6ra24604d .

Filipović, Nenad R., Bjelogrlic, Snežana, Todorović, Tamara R., Blagojević, Vladimir A., Muller, Christian D., Marinković, Aleksandar, Vujcic, Miroslava, Janović, Barbara, Malešević, Aleksandar, Begović, Nebojša, Sencanski, Milan, Minic, Dragica, "Ni(II) complex with bishydrazone ligand: synthesis, characterization, DNA binding studies and pro-apoptotic and pro-differentiation induction in human cancerous cell lines" in RSC Advances, 6, no. 110 (2016):108726-108740,
https://doi.org/10.1039/c6ra24604d . .

TY  - JOUR
AU  - Todorović, Tamara R.
AU  - Grubisic, Sonja
AU  - Pregelj, Matej
AU  - Jagodic, Marko
AU  - Misirlic-Dencic, Sonja
AU  - Dulović, Marija
AU  - Marković, Ivanka
AU  - Klisuric, Olivera
AU  - Malešević, Aleksandar
AU  - Mitic, Dragana
AU  - Anđelković, Katarina
AU  - Filipović, Nenad
PY  - 2015
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/920
AB  - Copper(II) complexes with the condensation derivative of methyl hydrazinoacetate and 2-acetylpyridine were synthesized. The X-ray crystal structures for both complexes revealed that they are polymerized isomers. A common feature of both complexes is the bidentate coordination of the ligand by one hydrazone and one pyridine nitrogen atom. In the monomeric complex, the copper(II) center is tetracoordinate, whereas dimerization through chlorido bridges results in a pentacoordinate arrangement about the metal ions in the dimer. The electronic and magnetic properties of both complexes are discussed on the basis of their X-ray structures, electron paramagnetic resonance (EPR) spectroscopy studies, and superconducting quantum interference device (SQUID) magnetization measurements combined with DFT calculations. Magnetostructural comparisons with structurally similar copper(II) complexes are also provided, and a possible correlation has been established. The antitumor activities of the Cu-II complexes were investigated against six different cancer cell lines, and the results suggest that the antiglioma action of the dimeric species is based on oxidative-stress-mediated phosphatidylserine externalization and caspase activation, which indicate apoptosis.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Inorganic Chemistry
T1  - Structural, Magnetic, DFT, and Biological Studies of Mononuclear and Dinuclear Cu-II Complexes with Bidentate N-Heteroaromatic Schiff Base Ligands
EP  - 3931
IS  - 23
SP  - 3921
DO  - 10.1002/ejic.201500349
ER  - 

@article{
author = "Todorović, Tamara R. and Grubisic, Sonja and Pregelj, Matej and Jagodic, Marko and Misirlic-Dencic, Sonja and Dulović, Marija and Marković, Ivanka and Klisuric, Olivera and Malešević, Aleksandar and Mitic, Dragana and Anđelković, Katarina and Filipović, Nenad",
year = "2015",
abstract = "Copper(II) complexes with the condensation derivative of methyl hydrazinoacetate and 2-acetylpyridine were synthesized. The X-ray crystal structures for both complexes revealed that they are polymerized isomers. A common feature of both complexes is the bidentate coordination of the ligand by one hydrazone and one pyridine nitrogen atom. In the monomeric complex, the copper(II) center is tetracoordinate, whereas dimerization through chlorido bridges results in a pentacoordinate arrangement about the metal ions in the dimer. The electronic and magnetic properties of both complexes are discussed on the basis of their X-ray structures, electron paramagnetic resonance (EPR) spectroscopy studies, and superconducting quantum interference device (SQUID) magnetization measurements combined with DFT calculations. Magnetostructural comparisons with structurally similar copper(II) complexes are also provided, and a possible correlation has been established. The antitumor activities of the Cu-II complexes were investigated against six different cancer cell lines, and the results suggest that the antiglioma action of the dimeric species is based on oxidative-stress-mediated phosphatidylserine externalization and caspase activation, which indicate apoptosis.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Inorganic Chemistry",
title = "Structural, Magnetic, DFT, and Biological Studies of Mononuclear and Dinuclear Cu-II Complexes with Bidentate N-Heteroaromatic Schiff Base Ligands",
pages = "3931-3921",
number = "23",
doi = "10.1002/ejic.201500349"
}

Todorović, T. R., Grubisic, S., Pregelj, M., Jagodic, M., Misirlic-Dencic, S., Dulović, M., Marković, I., Klisuric, O., Malešević, A., Mitic, D., Anđelković, K.,& Filipović, N.. (2015). Structural, Magnetic, DFT, and Biological Studies of Mononuclear and Dinuclear Cu-II Complexes with Bidentate N-Heteroaromatic Schiff Base Ligands. in European Journal of Inorganic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(23), 3921-3931.
https://doi.org/10.1002/ejic.201500349

Todorović TR, Grubisic S, Pregelj M, Jagodic M, Misirlic-Dencic S, Dulović M, Marković I, Klisuric O, Malešević A, Mitic D, Anđelković K, Filipović N. Structural, Magnetic, DFT, and Biological Studies of Mononuclear and Dinuclear Cu-II Complexes with Bidentate N-Heteroaromatic Schiff Base Ligands. in European Journal of Inorganic Chemistry. 2015;(23):3921-3931.
doi:10.1002/ejic.201500349 .

Todorović, Tamara R., Grubisic, Sonja, Pregelj, Matej, Jagodic, Marko, Misirlic-Dencic, Sonja, Dulović, Marija, Marković, Ivanka, Klisuric, Olivera, Malešević, Aleksandar, Mitic, Dragana, Anđelković, Katarina, Filipović, Nenad, "Structural, Magnetic, DFT, and Biological Studies of Mononuclear and Dinuclear Cu-II Complexes with Bidentate N-Heteroaromatic Schiff Base Ligands" in European Journal of Inorganic Chemistry, no. 23 (2015):3921-3931,
https://doi.org/10.1002/ejic.201500349 . .

TY  - JOUR
AU  - Vujcic, Miroslava T
AU  - Tufegdžić, Srđan J.
AU  - Novaković, Irena T
AU  - Đikanović, Daniela
AU  - Gasic, Miroslav J
AU  - Sladic, Dusan
PY  - 2013
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/734
AB  - The interactions of avarone, a quinone from the marine sponge Dysideaavara, and the methylamino derivatives of avarone (2), 3'-(methylamino)avarone (3) and 4'-(methylamino)avarone (4) with calf thymus DNA (CT-DNA) were studied. Agarose gel electrophoreticanalysis showed that binding of the quinones quenched fluorescence of ethidium bromide (EB). The extent of fluorescence quenching of intercalator EB by competitive displacement from EB-CT-DNA system and of groove binder Hoechst 33258 (H) from H-CT-DNA system with the quinones was analyzed by fluorescence spectroscopy. The obtained results demonstrated that the quinones reduced binding of both the intercalator EB and the minor groove binder H, indicating possible degradation of DNA. The substituent on the quinone moiety determined the extent of DNA damaging effect of the quinone, which was the most extensive with 3'-(methylamino)avarone and the least extensive with its regioisomer 4'-(methylamino)avarone. The results were confirmed by the observed hyperchromic effects in UV-visible spectra measured after interactions of the derivatives with CT-DNA.
PB  - Elsevier, Amsterdam
T2  - International Journal of Biological Macromolecules
T1  - Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA
EP  - 410
SP  - 405
VL  - 62
DO  - 10.1016/j.ijbiomac.2013.09.013
ER  - 

@article{
author = "Vujcic, Miroslava T and Tufegdžić, Srđan J. and Novaković, Irena T and Đikanović, Daniela and Gasic, Miroslav J and Sladic, Dusan",
year = "2013",
abstract = "The interactions of avarone, a quinone from the marine sponge Dysideaavara, and the methylamino derivatives of avarone (2), 3'-(methylamino)avarone (3) and 4'-(methylamino)avarone (4) with calf thymus DNA (CT-DNA) were studied. Agarose gel electrophoreticanalysis showed that binding of the quinones quenched fluorescence of ethidium bromide (EB). The extent of fluorescence quenching of intercalator EB by competitive displacement from EB-CT-DNA system and of groove binder Hoechst 33258 (H) from H-CT-DNA system with the quinones was analyzed by fluorescence spectroscopy. The obtained results demonstrated that the quinones reduced binding of both the intercalator EB and the minor groove binder H, indicating possible degradation of DNA. The substituent on the quinone moiety determined the extent of DNA damaging effect of the quinone, which was the most extensive with 3'-(methylamino)avarone and the least extensive with its regioisomer 4'-(methylamino)avarone. The results were confirmed by the observed hyperchromic effects in UV-visible spectra measured after interactions of the derivatives with CT-DNA.",
publisher = "Elsevier, Amsterdam",
journal = "International Journal of Biological Macromolecules",
title = "Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA",
pages = "410-405",
volume = "62",
doi = "10.1016/j.ijbiomac.2013.09.013"
}

Vujcic, M. T., Tufegdžić, S. J., Novaković, I. T., Đikanović, D., Gasic, M. J.,& Sladic, D.. (2013). Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA. in International Journal of Biological Macromolecules
Elsevier, Amsterdam., 62, 405-410.
https://doi.org/10.1016/j.ijbiomac.2013.09.013

Vujcic MT, Tufegdžić SJ, Novaković IT, Đikanović D, Gasic MJ, Sladic D. Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA. in International Journal of Biological Macromolecules. 2013;62:405-410.
doi:10.1016/j.ijbiomac.2013.09.013 .

Vujcic, Miroslava T, Tufegdžić, Srđan J., Novaković, Irena T, Đikanović, Daniela, Gasic, Miroslav J, Sladic, Dusan, "Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA" in International Journal of Biological Macromolecules, 62 (2013):405-410,
https://doi.org/10.1016/j.ijbiomac.2013.09.013 . .