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
2016
Authors
Pantelic, NebojsaZmejkovski, Bojana
Markovic, Dragana D
Vujic, Jelena M
Stanojković, Tatjana
Sabo, Tibor
Kaluđerović, Goran N.
Article (Published version)
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A novel gold(III) complex, [AuCl2{(S,S)-Et(2)eddl}]PF6, ((S,S)-Et(2)eddl = O,O-diethyl ester of ethylenediamine-N,N-di-2-(4-methyl)pentanoic acid) was synthesized and characterized by IR, 1D (H-1 and C-13), 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)-H(2)Et(2)eddl]Cl-2 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)-Et(2)eddl}]PF6 against the LS174 cells, with IC50 value of 7.4 +/- 1.2 mu M.
Keywords:
gold(III) complex / R(2)edda-type ligand / DFT / cytotoxicitySource:
Metals, 2016, 6, 9Publisher:
- MDPI
Funding / projects:
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
- Synthesis, modeling, physicochemical and biological properties of organic compounds and related metal complexes (RS-172016)
- Biological response modifiers in physiological and pathological conditions (RS-175011)
DOI: 10.3390/met6090226
ISSN: 2075-4701
WoS: 000385527100033
Scopus: 2-s2.0-85006722238
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IHTMTY - JOUR AU - Pantelic, Nebojsa AU - Zmejkovski, Bojana AU - Markovic, Dragana D AU - Vujic, Jelena M AU - Stanojković, Tatjana AU - Sabo, Tibor AU - Kaluđerović, Goran N. PY - 2016 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1938 AB - A novel gold(III) complex, [AuCl2{(S,S)-Et(2)eddl}]PF6, ((S,S)-Et(2)eddl = O,O-diethyl ester of ethylenediamine-N,N-di-2-(4-methyl)pentanoic acid) was synthesized and characterized by IR, 1D (H-1 and C-13), 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)-H(2)Et(2)eddl]Cl-2 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)-Et(2)eddl}]PF6 against the LS174 cells, with IC50 value of 7.4 +/- 1.2 mu M. PB - MDPI T2 - Metals T1 - 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 VL - 6 IS - 9 DO - 10.3390/met6090226 ER -
@article{ author = "Pantelic, Nebojsa and Zmejkovski, Bojana and Markovic, Dragana D and Vujic, Jelena M and Stanojković, Tatjana and Sabo, Tibor and Kaluđerović, Goran N.", year = "2016", abstract = "A novel gold(III) complex, [AuCl2{(S,S)-Et(2)eddl}]PF6, ((S,S)-Et(2)eddl = O,O-diethyl ester of ethylenediamine-N,N-di-2-(4-methyl)pentanoic acid) was synthesized and characterized by IR, 1D (H-1 and C-13), 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)-H(2)Et(2)eddl]Cl-2 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)-Et(2)eddl}]PF6 against the LS174 cells, with IC50 value of 7.4 +/- 1.2 mu M.", publisher = "MDPI", journal = "Metals", 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", volume = "6", number = "9", doi = "10.3390/met6090226" }
Pantelic, N., Zmejkovski, B., Markovic, D. D., Vujic, J. M., Stanojković, T., Sabo, T.,& Kaluđerović, G. N.. (2016). 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. in Metals MDPI., 6(9). https://doi.org/10.3390/met6090226
Pantelic N, Zmejkovski B, Markovic DD, Vujic JM, Stanojković T, Sabo T, Kaluđerović GN. 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. in Metals. 2016;6(9). doi:10.3390/met6090226 .
Pantelic, Nebojsa, Zmejkovski, Bojana, Markovic, Dragana D, Vujic, Jelena M, Stanojković, Tatjana, Sabo, Tibor, Kaluđerović, Goran 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" in Metals, 6, no. 9 (2016), https://doi.org/10.3390/met6090226 . .