TY  - JOUR
AU  - Pantelic, Nebojsa
AU  - Zmejkovski, Bojana
AU  - Kolundzija, Branka
AU  - Crnogorac, Marija Dordic
AU  - Vujic, Jelena M.
AU  - Dojčinović, Biljana
AU  - Trifunovic, Srecko R.
AU  - Stanojković, Tatjana
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2248
AB  - Four novel gold(III) complexes of general formulae [AuCl2{(S,S)-R(2)eddl}]PF6 (R(2)eddl = O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoate, R= n-Pr, n-Bu, n-Pe, i-Bu; 1-4, respectively), were synthesized and characterized by elemental analysis, UV/Vis, IR, and NMR spectroscopy, as well as high resolution mass spectrometry. Density functional theory calculations pointed out that (R,R)-N,N'-configuration diastereoisomers were energetically the most favorable. Duo to high cytotoxic activity complex 3 was chosen for stability study in DMSO, no decomposition occurs within 24 h, and for the reaction with ascorbic acid in which was reduced immediately. Additionally, 3 interacts with bovine serum albumin (BSA) as proven by UV/Vis spectroscopy. In vitro antitumor activity was determined against human cervix adenocarcinoma (HeLa), human myelogenous leukemia (K562), and human melanoma (Fem-x) cancer cell lines, as well as against non-cancerous human embryonic lung fibroblast cells MRC-5. The highest activity was observed against K562 cells (IC50: 5.04-6.51 mu M). Selectivity indices showed that these complexes are less toxic than cisplatin. 3 had a similar viability kinetics on HeLa cells as cisplatin. Drug accumulation studies in HeLa cells showed that the total gold uptake increased much faster than that of cisplatin pointing out that 3 more efficiently enters the cells than cisplatin. Furthermore, morphological and cell cycle analysis reveal that gold(III) complexes induced apoptosis in time- and dose-dependent manner.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands
VL  - 172
SP  - 55
EP  - 66
DO  - 10.1016/j.jinorgbio.2017.04.001
ER  - 

@article{
author = "Pantelic, Nebojsa and Zmejkovski, Bojana and Kolundzija, Branka and Crnogorac, Marija Dordic and Vujic, Jelena M. and Dojčinović, Biljana and Trifunovic, Srecko R. and Stanojković, Tatjana and Sabo, Tibor and Kaluđerović, Goran N.",
year = "2017",
abstract = "Four novel gold(III) complexes of general formulae [AuCl2{(S,S)-R(2)eddl}]PF6 (R(2)eddl = O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoate, R= n-Pr, n-Bu, n-Pe, i-Bu; 1-4, respectively), were synthesized and characterized by elemental analysis, UV/Vis, IR, and NMR spectroscopy, as well as high resolution mass spectrometry. Density functional theory calculations pointed out that (R,R)-N,N'-configuration diastereoisomers were energetically the most favorable. Duo to high cytotoxic activity complex 3 was chosen for stability study in DMSO, no decomposition occurs within 24 h, and for the reaction with ascorbic acid in which was reduced immediately. Additionally, 3 interacts with bovine serum albumin (BSA) as proven by UV/Vis spectroscopy. In vitro antitumor activity was determined against human cervix adenocarcinoma (HeLa), human myelogenous leukemia (K562), and human melanoma (Fem-x) cancer cell lines, as well as against non-cancerous human embryonic lung fibroblast cells MRC-5. The highest activity was observed against K562 cells (IC50: 5.04-6.51 mu M). Selectivity indices showed that these complexes are less toxic than cisplatin. 3 had a similar viability kinetics on HeLa cells as cisplatin. Drug accumulation studies in HeLa cells showed that the total gold uptake increased much faster than that of cisplatin pointing out that 3 more efficiently enters the cells than cisplatin. Furthermore, morphological and cell cycle analysis reveal that gold(III) complexes induced apoptosis in time- and dose-dependent manner.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands",
volume = "172",
pages = "55-66",
doi = "10.1016/j.jinorgbio.2017.04.001"
}

Pantelic, N., Zmejkovski, B., Kolundzija, B., Crnogorac, M. D., Vujic, J. M., Dojčinović, B., Trifunovic, S. R., Stanojković, T., Sabo, T.,& Kaluđerović, G. N.. (2017). In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 172, 55-66.
https://doi.org/10.1016/j.jinorgbio.2017.04.001

Pantelic N, Zmejkovski B, Kolundzija B, Crnogorac MD, Vujic JM, Dojčinović B, Trifunovic SR, Stanojković T, Sabo T, Kaluđerović GN. In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands. in Journal of Inorganic Biochemistry. 2017;172:55-66.
doi:10.1016/j.jinorgbio.2017.04.001 .

Pantelic, Nebojsa, Zmejkovski, Bojana, Kolundzija, Branka, Crnogorac, Marija Dordic, Vujic, Jelena M., Dojčinović, Biljana, Trifunovic, Srecko R., Stanojković, Tatjana, Sabo, Tibor, Kaluđerović, Goran N., "In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands" in Journal of Inorganic Biochemistry, 172 (2017):55-66,
https://doi.org/10.1016/j.jinorgbio.2017.04.001 . .

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  - 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 . .