Solution study under physiological conditions and cytotoxic activity of the gold(III) complexes with L-histidine-containing peptides
Proton NMR spectroscopy and cyclic voltammetry have been applied to study the stability of three gold(III) complexes with L-histidine-containing peptides, [Au(Gly-L-His-N,N’,N’’)Cl]NO3.1.25H2O (Au1), [Au(L-Ala-L-His-N,N’,N’’)Cl]NO3.2.5H2O (Au2) and [Au(Gly-Gly-L-His-N,N’,N’’,N’’’)]Cl.H2O...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Serbian Chemical Society
2013-01-01
|
| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.doiserbia.nb.rs/img/doi/0352-5139/2013/0352-51391300105G.pdf |
| _version_ | 1818640719699509248 |
|---|---|
| author | Glišić Biljana Đ. Stanić Zorka D. Rajković Snežana Kojić Vesna Bogdanović Gordana Đuran Miloš I. |
| author_facet | Glišić Biljana Đ. Stanić Zorka D. Rajković Snežana Kojić Vesna Bogdanović Gordana Đuran Miloš I. |
| author_sort | Glišić Biljana Đ. |
| collection | DOAJ |
| description | Proton NMR spectroscopy and cyclic voltammetry have been applied to study the
stability of three gold(III) complexes with L-histidine-containing peptides,
[Au(Gly-L-His-N,N’,N’’)Cl]NO3.1.25H2O (Au1),
[Au(L-Ala-L-His-N,N’,N’’)Cl]NO3.2.5H2O (Au2) and
[Au(Gly-Gly-L-His-N,N’,N’’,N’’’)]Cl.H2O (Au3) under physiologically relevant
conditions. It was found that tridentate coordination of Gly-L-His and
L-Ala-L-His dipeptides, as well as tetradentate coordination of Gly-Gly-L-His
tripeptide in Au1, Au2 and Au3 complexes, respectively, stabilized +3
oxidation state of gold and prevented its reduction to Au(I) and Au(0). No
release of the coordinated peptides from Au(III) was observed under these
experimental conditions. Considering remarkable stability of Au1, Au2 and Au3
complexes, their cytotoxic activity was evaluated by MTT
(3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay toward
five human tumor cell lines, MCF-7 (human breast adenocarcinoma), HT-29
(human colon adenocarcinoma), HeLa (human cervix carcinoma), HL-60 (human
promyelocytic leukemia), Raji (human Burkitt’s lymphoma) and one human normal
cell line MRC-5 (human fetal lung fibroblasts). While the cytotoxic activity
of Au1, Au2 and Au3 against investigated human malignant cell lines was
strongly cell line dependent, none of these complexes was cytotoxic against
normal MRC-5 cell line. This study can contribute to the future development
of gold(III)-peptide complexes as potential antitumor agents. |
| first_indexed | 2024-12-16T23:15:45Z |
| format | Article |
| id | doaj.art-76805a34458f4f79ba2f3cb4856b42f5 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-12-16T23:15:45Z |
| publishDate | 2013-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-76805a34458f4f79ba2f3cb4856b42f52022-12-21T22:12:19ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212013-01-0178121911192410.2298/JSC130920105G0352-51391300105GSolution study under physiological conditions and cytotoxic activity of the gold(III) complexes with L-histidine-containing peptidesGlišić Biljana Đ.0Stanić Zorka D.1Rajković Snežana2Kojić Vesna3Bogdanović Gordana4Đuran Miloš I.5Faculty of Science, Department of Chemistry, KragujevacFaculty of Science, Department of Chemistry, KragujevacFaculty of Science, Department of Chemistry, KragujevacOncology Institute of Vojvodina, Sremska KamenicaOncology Institute of Vojvodina, Sremska KamenicaFaculty of Science, Department of Chemistry, KragujevacProton NMR spectroscopy and cyclic voltammetry have been applied to study the stability of three gold(III) complexes with L-histidine-containing peptides, [Au(Gly-L-His-N,N’,N’’)Cl]NO3.1.25H2O (Au1), [Au(L-Ala-L-His-N,N’,N’’)Cl]NO3.2.5H2O (Au2) and [Au(Gly-Gly-L-His-N,N’,N’’,N’’’)]Cl.H2O (Au3) under physiologically relevant conditions. It was found that tridentate coordination of Gly-L-His and L-Ala-L-His dipeptides, as well as tetradentate coordination of Gly-Gly-L-His tripeptide in Au1, Au2 and Au3 complexes, respectively, stabilized +3 oxidation state of gold and prevented its reduction to Au(I) and Au(0). No release of the coordinated peptides from Au(III) was observed under these experimental conditions. Considering remarkable stability of Au1, Au2 and Au3 complexes, their cytotoxic activity was evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay toward five human tumor cell lines, MCF-7 (human breast adenocarcinoma), HT-29 (human colon adenocarcinoma), HeLa (human cervix carcinoma), HL-60 (human promyelocytic leukemia), Raji (human Burkitt’s lymphoma) and one human normal cell line MRC-5 (human fetal lung fibroblasts). While the cytotoxic activity of Au1, Au2 and Au3 against investigated human malignant cell lines was strongly cell line dependent, none of these complexes was cytotoxic against normal MRC-5 cell line. This study can contribute to the future development of gold(III)-peptide complexes as potential antitumor agents.http://www.doiserbia.nb.rs/img/doi/0352-5139/2013/0352-51391300105G.pdfgold(III) complexesL-histidine-containing peptides1H NMR spectroscopycyclic voltammetrycytotoxic activity |
| spellingShingle | Glišić Biljana Đ. Stanić Zorka D. Rajković Snežana Kojić Vesna Bogdanović Gordana Đuran Miloš I. Solution study under physiological conditions and cytotoxic activity of the gold(III) complexes with L-histidine-containing peptides Journal of the Serbian Chemical Society gold(III) complexes L-histidine-containing peptides 1H NMR spectroscopy cyclic voltammetry cytotoxic activity |
| title | Solution study under physiological conditions and cytotoxic activity of the gold(III) complexes with L-histidine-containing peptides |
| title_full | Solution study under physiological conditions and cytotoxic activity of the gold(III) complexes with L-histidine-containing peptides |
| title_fullStr | Solution study under physiological conditions and cytotoxic activity of the gold(III) complexes with L-histidine-containing peptides |
| title_full_unstemmed | Solution study under physiological conditions and cytotoxic activity of the gold(III) complexes with L-histidine-containing peptides |
| title_short | Solution study under physiological conditions and cytotoxic activity of the gold(III) complexes with L-histidine-containing peptides |
| title_sort | solution study under physiological conditions and cytotoxic activity of the gold iii complexes with l histidine containing peptides |
| topic | gold(III) complexes L-histidine-containing peptides 1H NMR spectroscopy cyclic voltammetry cytotoxic activity |
| url | http://www.doiserbia.nb.rs/img/doi/0352-5139/2013/0352-51391300105G.pdf |
| work_keys_str_mv | AT glisicbiljanađ solutionstudyunderphysiologicalconditionsandcytotoxicactivityofthegoldiiicomplexeswithlhistidinecontainingpeptides AT staniczorkad solutionstudyunderphysiologicalconditionsandcytotoxicactivityofthegoldiiicomplexeswithlhistidinecontainingpeptides AT rajkovicsnezana solutionstudyunderphysiologicalconditionsandcytotoxicactivityofthegoldiiicomplexeswithlhistidinecontainingpeptides AT kojicvesna solutionstudyunderphysiologicalconditionsandcytotoxicactivityofthegoldiiicomplexeswithlhistidinecontainingpeptides AT bogdanovicgordana solutionstudyunderphysiologicalconditionsandcytotoxicactivityofthegoldiiicomplexeswithlhistidinecontainingpeptides AT đuranmilosi solutionstudyunderphysiologicalconditionsandcytotoxicactivityofthegoldiiicomplexeswithlhistidinecontainingpeptides |