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Metals 2016, 6(9), 226; doi:10.3390/met6090226

Synthesis, Characterization, and Cytotoxicity of a Novel Gold(III) Complex with O,O′-Diethyl Ester of Ethylenediamine-N,N′-Di-2-(4-Methyl)Pentanoic Acid

1
Department of Chemistry and Biochemistry, Faculty of Agriculture, University of Belgrade, Nemanjina 6, Belgrade-Zemun 11080, Serbia
2
Department of Chemistry, Institute of Chemistry, Tehnology and Metallurgy, University of Belgrade, Studenski Trg 14, Belgrade 11000, Serbia
3
Institute of Oncology and Radiology, Belgrade 11000, Serbia
4
Faculty of Agronomy, University of Kragujevac, Cara Dušana 34, Čačak, Serbia 32000
5
Faculty of Chemistry, University of Belgrade, Studentski Trg 12-16, Belgrade 11001, Serbia
6
Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, Halle (Saale) 06120, Germany
*
Author to whom correspondence should be addressed.
Academic Editor: Grasso Giuseppe
Received: 16 June 2016 / Revised: 12 September 2016 / Accepted: 14 September 2016 / Published: 20 September 2016
(This article belongs to the Special Issue Metallomics)
View Full-Text   |   Download PDF [1383 KB, uploaded 20 September 2016]   |  

Abstract

A novel gold(III) complex, [AuCl2{(S,S)-Et2eddl}]PF6, ((S,S)-Et2eddl = O,O′-diethyl ester of ethylenediamine-N,N′-di-2-(4-methyl)pentanoic acid) was synthesized and characterized by IR, 1D (1H and 13C), and 2D (H,H-COSY and H,H-NOESY) NMR spectroscopy, mass spectrometry, and elemental analysis. Density functional theory calculations confirmed that (R,R)-N,N′ diastereoisomer was energetically the most stable isomer. In vitro antitumor action of ligand precursor [(S,S)-H2Et2eddl]Cl2 and corresponding gold(III) complex was determined against tumor cell lines: human adenocarcinoma (HeLa), human colon carcinoma (LS174), human breast cancer (MCF7), non-small cell lung carcinoma cell line (A549), and non-cancerous cell line human embryonic lung fibroblast (MRC-5) using microculture tetrazolium test (MTT) assay. The results indicate that both ligand precursor and gold(III) complex have showed very good to moderate cytotoxic activity against all tested malignant cell lines. The highest activity was expressed by [AuCl2{(S,S)-Et2eddl}]PF6 against the LS174 cells, with IC50 value of 7.4 ± 1.2 µM. View Full-Text
Keywords: gold(III) complex; R2edda-type ligand; DFT; cytotoxicity gold(III) complex; R2edda-type ligand; DFT; cytotoxicity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Pantelić, N.; Zmejkovski, B.B.; Marković, D.D.; Vujić, J.M.; Stanojković, T.P.; Sabo, T.J.; Kaluđerović, G.N. Synthesis, Characterization, and Cytotoxicity of a Novel Gold(III) Complex with O,O′-Diethyl Ester of Ethylenediamine-N,N′-Di-2-(4-Methyl)Pentanoic Acid. Metals 2016, 6, 226.

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