In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid
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Zmejkovski, Bojana B.
Pantelić, Nebojša Đ.
Filipović, Lana
Aranđelović, Sandra

Radulović, Siniša

Sabo, Tibor

Kaluđerović, Goran N.

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Aims: Platinum(II) and platinum(IV) complexes [PtCln{(S,S)-(i-Am)(2)eddip}] (n = 2, 4: 1, 2, respectively; (S,S)-(i-Am)(2)eddip = O,O'-diisoamyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate) were synthesized and characterized by elemental analysis, IR, H-1 and C-13 NMR spectroscopy and mass spectrometry. Method: Quantum chemical calculations were used to predict formed isomers of 1 and 2. Furthermore, reduction of 2 with ascorbic acid was followed by time-dependant C-13 NMR spectroscopy in order to enable assignation of the formed isomers for complex 1. In vitro cytotoxic activity was determined for 1 and 2 on a panel of five human tumor cell lines derived from cervix adenocarcinoma (HeLa), alveolar basal adenocarcinoma (A549), breast adenocarcinoma (MDA-453), colorectal cancer (LS 174), erythromyeloblastoid leukemia (K562), as well as one non-malignant human lung fibroblast cell line (MRC-5), using MTT assay. Result: Both complexes exhibited high (2 against K562: IC50 = 5.4 mu M), more ...active than cisplatin, to moderate activity (1). Both complexes caused considerable decrease of cell number in K562 cells in G1, S and G2 phases, concordantly increasing subpopulation in sub-G1 fraction. Morphological analysis of K562 cell death induced by platinum(II/IV) complexes indicate apoptosis.
Keywords:
Platinum complexes / R(2)eddip ligands / DFT calculations / anticancer activity / apoptosis / cell cycleSource:
Anti-Cancer Agents in Medicinal Chemistry, 2017, 17, 8, 1136-1143Publisher:
- Bentham Science Publ Ltd, Sharjah
Funding / projects:
- Pharmacodynamic and pharmacogenomic research of new drugs in the treatment of solid tumors (RS-41026)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
DOI: 10.2174/1871520616666161207155634
ISSN: 1871-5206
PubMed: 27928952
WoS: 000407271800011
Scopus: 2-s2.0-85027877786
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Zmejkovski, Bojana B. AU - Pantelić, Nebojša Đ. AU - Filipović, Lana AU - Aranđelović, Sandra AU - Radulović, Siniša AU - Sabo, Tibor AU - Kaluđerović, Goran N. PY - 2017 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2501 AB - Aims: Platinum(II) and platinum(IV) complexes [PtCln{(S,S)-(i-Am)(2)eddip}] (n = 2, 4: 1, 2, respectively; (S,S)-(i-Am)(2)eddip = O,O'-diisoamyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate) were synthesized and characterized by elemental analysis, IR, H-1 and C-13 NMR spectroscopy and mass spectrometry. Method: Quantum chemical calculations were used to predict formed isomers of 1 and 2. Furthermore, reduction of 2 with ascorbic acid was followed by time-dependant C-13 NMR spectroscopy in order to enable assignation of the formed isomers for complex 1. In vitro cytotoxic activity was determined for 1 and 2 on a panel of five human tumor cell lines derived from cervix adenocarcinoma (HeLa), alveolar basal adenocarcinoma (A549), breast adenocarcinoma (MDA-453), colorectal cancer (LS 174), erythromyeloblastoid leukemia (K562), as well as one non-malignant human lung fibroblast cell line (MRC-5), using MTT assay. Result: Both complexes exhibited high (2 against K562: IC50 = 5.4 mu M), more active than cisplatin, to moderate activity (1). Both complexes caused considerable decrease of cell number in K562 cells in G1, S and G2 phases, concordantly increasing subpopulation in sub-G1 fraction. Morphological analysis of K562 cell death induced by platinum(II/IV) complexes indicate apoptosis. PB - Bentham Science Publ Ltd, Sharjah T2 - Anti-Cancer Agents in Medicinal Chemistry T1 - In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid VL - 17 IS - 8 SP - 1136 EP - 1143 DO - 10.2174/1871520616666161207155634 ER -
@article{ author = "Zmejkovski, Bojana B. and Pantelić, Nebojša Đ. and Filipović, Lana and Aranđelović, Sandra and Radulović, Siniša and Sabo, Tibor and Kaluđerović, Goran N.", year = "2017", abstract = "Aims: Platinum(II) and platinum(IV) complexes [PtCln{(S,S)-(i-Am)(2)eddip}] (n = 2, 4: 1, 2, respectively; (S,S)-(i-Am)(2)eddip = O,O'-diisoamyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate) were synthesized and characterized by elemental analysis, IR, H-1 and C-13 NMR spectroscopy and mass spectrometry. Method: Quantum chemical calculations were used to predict formed isomers of 1 and 2. Furthermore, reduction of 2 with ascorbic acid was followed by time-dependant C-13 NMR spectroscopy in order to enable assignation of the formed isomers for complex 1. In vitro cytotoxic activity was determined for 1 and 2 on a panel of five human tumor cell lines derived from cervix adenocarcinoma (HeLa), alveolar basal adenocarcinoma (A549), breast adenocarcinoma (MDA-453), colorectal cancer (LS 174), erythromyeloblastoid leukemia (K562), as well as one non-malignant human lung fibroblast cell line (MRC-5), using MTT assay. Result: Both complexes exhibited high (2 against K562: IC50 = 5.4 mu M), more active than cisplatin, to moderate activity (1). Both complexes caused considerable decrease of cell number in K562 cells in G1, S and G2 phases, concordantly increasing subpopulation in sub-G1 fraction. Morphological analysis of K562 cell death induced by platinum(II/IV) complexes indicate apoptosis.", publisher = "Bentham Science Publ Ltd, Sharjah", journal = "Anti-Cancer Agents in Medicinal Chemistry", title = "In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid", volume = "17", number = "8", pages = "1136-1143", doi = "10.2174/1871520616666161207155634" }
Zmejkovski, B. B., Pantelić, N. Đ., Filipović, L., Aranđelović, S., Radulović, S., Sabo, T.,& Kaluđerović, G. N.. (2017). In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid. in Anti-Cancer Agents in Medicinal Chemistry Bentham Science Publ Ltd, Sharjah., 17(8), 1136-1143. https://doi.org/10.2174/1871520616666161207155634
Zmejkovski BB, Pantelić NĐ, Filipović L, Aranđelović S, Radulović S, Sabo T, Kaluđerović GN. In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid. in Anti-Cancer Agents in Medicinal Chemistry. 2017;17(8):1136-1143. doi:10.2174/1871520616666161207155634 .
Zmejkovski, Bojana B., Pantelić, Nebojša Đ., Filipović, Lana, Aranđelović, Sandra, Radulović, Siniša, Sabo, Tibor, Kaluđerović, Goran N., "In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid" in Anti-Cancer Agents in Medicinal Chemistry, 17, no. 8 (2017):1136-1143, https://doi.org/10.2174/1871520616666161207155634 . .