In vitro anticancer activity of gold(III) complexes with some esters of (S,S)-ethylenediamine-N,N '-di-2-propanoic acid
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2015
Authors
Pantelić, Nebojša Đ.Stanojković, Tatjana
Zmejkovski, Bojana
Sabo, Tibor
Kaluđerović, Goran N.
Article (Published version)
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Five novel gold(III) complexes of general formulas [AuCl2{(S,S)-R(2)eddip}]PF6, ((S,S)-eddip = (S,S)-ethylenediamine-N,N'-di-2-propanoate, R = n-Bu, n-Pe, i-Bu, i-Am, cPe; 1-5, respectively) were synthesized and characterized by UV/Vis, IR and NMR spectroscopy and mass spectrometry. DFT calculations indicated that (R,R)-N,N'-configuration diastereoisomers were the most stable for 1-5. 3 is stable in DMSO for at least 24 h, but immediate hydrolysis in PBS occurs. 3 is readily reduced with ascorbic acid and forms adducts with bovine serum albumin (BSA). In vitro anticancer activity of the gold(III) complexes against human cervix adenocarcinoma HeLa, human myelogenous leukemia K562, human melanoma Fem-x tumor cell lines, as well as against non-cancerous human embryonic lung fibroblast cell line MRC5 was determined using MIT assay. Complex 4 showed highest activity and selectivity (IC50(Femx) = 1.3 +/- 0.2; IC50(MRC-5)/IC50(Fem-x) = 72.5 +/- 12.4), 4 times more active and 28 times more sel...ective than cisplatin. Complexes induced apoptotic mode of death in a time-dependent manner in HeLa cells.
Keywords:
Gold(III) complexes / R(2)edda-type ligands / DFT / Apoptosis / Cell cycle / cytotoxicitySource:
European Journal of Medicinal Chemistry, 2015, 90, 766-774Publisher:
- Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
Funding / projects:
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-MESTD-Basic Research (BR or ON)-172035)
- Biological response modifiers in physiological and pathological conditions (RS-MESTD-Basic Research (BR or ON)-175011)
DOI: 10.1016/j.ejmech.2014.12.019
ISSN: 0223-5234
PubMed: 25528331
WoS: 000348951900060
Scopus: 2-s2.0-84918804131
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IHTMTY - JOUR AU - Pantelić, Nebojša Đ. AU - Stanojković, Tatjana AU - Zmejkovski, Bojana AU - Sabo, Tibor AU - Kaluđerović, Goran N. PY - 2015 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1803 AB - Five novel gold(III) complexes of general formulas [AuCl2{(S,S)-R(2)eddip}]PF6, ((S,S)-eddip = (S,S)-ethylenediamine-N,N'-di-2-propanoate, R = n-Bu, n-Pe, i-Bu, i-Am, cPe; 1-5, respectively) were synthesized and characterized by UV/Vis, IR and NMR spectroscopy and mass spectrometry. DFT calculations indicated that (R,R)-N,N'-configuration diastereoisomers were the most stable for 1-5. 3 is stable in DMSO for at least 24 h, but immediate hydrolysis in PBS occurs. 3 is readily reduced with ascorbic acid and forms adducts with bovine serum albumin (BSA). In vitro anticancer activity of the gold(III) complexes against human cervix adenocarcinoma HeLa, human myelogenous leukemia K562, human melanoma Fem-x tumor cell lines, as well as against non-cancerous human embryonic lung fibroblast cell line MRC5 was determined using MIT assay. Complex 4 showed highest activity and selectivity (IC50(Femx) = 1.3 +/- 0.2; IC50(MRC-5)/IC50(Fem-x) = 72.5 +/- 12.4), 4 times more active and 28 times more selective than cisplatin. Complexes induced apoptotic mode of death in a time-dependent manner in HeLa cells. PB - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux T2 - European Journal of Medicinal Chemistry T1 - In vitro anticancer activity of gold(III) complexes with some esters of (S,S)-ethylenediamine-N,N '-di-2-propanoic acid VL - 90 SP - 766 EP - 774 DO - 10.1016/j.ejmech.2014.12.019 ER -
@article{ author = "Pantelić, Nebojša Đ. and Stanojković, Tatjana and Zmejkovski, Bojana and Sabo, Tibor and Kaluđerović, Goran N.", year = "2015", abstract = "Five novel gold(III) complexes of general formulas [AuCl2{(S,S)-R(2)eddip}]PF6, ((S,S)-eddip = (S,S)-ethylenediamine-N,N'-di-2-propanoate, R = n-Bu, n-Pe, i-Bu, i-Am, cPe; 1-5, respectively) were synthesized and characterized by UV/Vis, IR and NMR spectroscopy and mass spectrometry. DFT calculations indicated that (R,R)-N,N'-configuration diastereoisomers were the most stable for 1-5. 3 is stable in DMSO for at least 24 h, but immediate hydrolysis in PBS occurs. 3 is readily reduced with ascorbic acid and forms adducts with bovine serum albumin (BSA). In vitro anticancer activity of the gold(III) complexes against human cervix adenocarcinoma HeLa, human myelogenous leukemia K562, human melanoma Fem-x tumor cell lines, as well as against non-cancerous human embryonic lung fibroblast cell line MRC5 was determined using MIT assay. Complex 4 showed highest activity and selectivity (IC50(Femx) = 1.3 +/- 0.2; IC50(MRC-5)/IC50(Fem-x) = 72.5 +/- 12.4), 4 times more active and 28 times more selective than cisplatin. Complexes induced apoptotic mode of death in a time-dependent manner in HeLa cells.", publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux", journal = "European Journal of Medicinal Chemistry", title = "In vitro anticancer activity of gold(III) complexes with some esters of (S,S)-ethylenediamine-N,N '-di-2-propanoic acid", volume = "90", pages = "766-774", doi = "10.1016/j.ejmech.2014.12.019" }
Pantelić, N. Đ., Stanojković, T., Zmejkovski, B., Sabo, T.,& Kaluđerović, G. N.. (2015). In vitro anticancer activity of gold(III) complexes with some esters of (S,S)-ethylenediamine-N,N '-di-2-propanoic acid. in European Journal of Medicinal Chemistry Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux., 90, 766-774. https://doi.org/10.1016/j.ejmech.2014.12.019
Pantelić NĐ, Stanojković T, Zmejkovski B, Sabo T, Kaluđerović GN. In vitro anticancer activity of gold(III) complexes with some esters of (S,S)-ethylenediamine-N,N '-di-2-propanoic acid. in European Journal of Medicinal Chemistry. 2015;90:766-774. doi:10.1016/j.ejmech.2014.12.019 .
Pantelić, Nebojša Đ., Stanojković, Tatjana, Zmejkovski, Bojana, Sabo, Tibor, Kaluđerović, Goran N., "In vitro anticancer activity of gold(III) complexes with some esters of (S,S)-ethylenediamine-N,N '-di-2-propanoic acid" in European Journal of Medicinal Chemistry, 90 (2015):766-774, https://doi.org/10.1016/j.ejmech.2014.12.019 . .