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
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. Dens...
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doaj-062e19610e4c481986cfc6d044c9ea6e2020-11-24T23:47:49ZengMDPI AGMetals2075-47012016-09-016922610.3390/met6090226met6090226Synthesis, Characterization, and Cytotoxicity of a Novel Gold(III) Complex with O,O′-Diethyl Ester of Ethylenediamine-N,N′-Di-2-(4-Methyl)Pentanoic AcidNebojša Pantelić0Bojana B. Zmejkovski1Dragana D. Marković2Jelena M. Vujić3Tatjana P. Stanojković4Tibor J. Sabo5Goran N. Kaluđerović6Department of Chemistry and Biochemistry, Faculty of Agriculture, University of Belgrade, Nemanjina 6, Belgrade-Zemun 11080, SerbiaDepartment of Chemistry, Institute of Chemistry, Tehnology and Metallurgy, University of Belgrade, Studenski Trg 14, Belgrade 11000, SerbiaInstitute of Oncology and Radiology, Belgrade 11000, SerbiaFaculty of Agronomy, University of Kragujevac, Cara Dušana 34, Čačak, Serbia 32000Institute of Oncology and Radiology, Belgrade 11000, SerbiaFaculty of Chemistry, University of Belgrade, Studentski Trg 12-16, Belgrade 11001, SerbiaDepartment of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, Halle (Saale) 06120, GermanyA 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.http://www.mdpi.com/2075-4701/6/9/226gold(III) complexR2edda-type ligandDFTcytotoxicity |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Nebojša Pantelić Bojana B. Zmejkovski Dragana D. Marković Jelena M. Vujić Tatjana P. Stanojković Tibor J. Sabo Goran N. Kaluđerović |
| spellingShingle |
Nebojša Pantelić Bojana B. Zmejkovski Dragana D. Marković Jelena M. Vujić Tatjana P. Stanojković Tibor J. Sabo Goran N. Kaluđerović 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 gold(III) complex R2edda-type ligand DFT cytotoxicity |
| author_facet |
Nebojša Pantelić Bojana B. Zmejkovski Dragana D. Marković Jelena M. Vujić Tatjana P. Stanojković Tibor J. Sabo Goran N. Kaluđerović |
| author_sort |
Nebojša Pantelić |
| title |
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 |
| title_short |
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 |
| title_full |
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 |
| title_fullStr |
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 |
| title_full_unstemmed |
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 |
| title_sort |
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 |
| publisher |
MDPI AG |
| series |
Metals |
| issn |
2075-4701 |
| publishDate |
2016-09-01 |
| description |
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. |
| topic |
gold(III) complex R2edda-type ligand DFT cytotoxicity |
| url |
http://www.mdpi.com/2075-4701/6/9/226 |
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