期刊
TETRAHEDRON
卷 67, 期 33, 页码 5990-6000出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.06.026
关键词
Ubiquinone/coenzyme Q; Electrochemistry; ESR; In situ spectroelectrochemistry; Cytotoxicity
资金
- Key Lab of Analytical Chemistry for Life Science of Nanjing University
- Natural Science Foundation of China [91027035]
- Fundamental Research Funds for the Central Universities [WK1013002]
- Shanghai Institutions of Higher Learning
Quinones are a group of potent antineoplastic agents. Here we described effective and facile routes to synthesize a series of ubiquinone analogues (UQAs). These unique compounds have been investigated by electrochemistry and in situ UV-vis spectroelectrochemistry to explore their electron-transfer processes and radical properties in aprotic media. The structure-activities relationships of inhibiting cancer cell proliferation of UQAs were examined in murine melanoma B16F10 cells using a 72 h continuous exposure MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Our results revealed that UQAs had improved antiproliferative activity and displayed better inhibitory effects than natural ubiquinone 10. The cytotoxic activities of UQAs were correlated to the semiubiquinone radicals, which were confirmed by in situ electron spin resonance (ESR). In the cytotoxicity test, 6-vinylubiquinone 5 and 6-(4'-fluorophenyl) ubiquinone 7 that possess half maximal inhibitory concentration value (IC50) of 6.1 mu M and 6.2 mu M. This would make them as valuable candidates for future pharmacological studies. (C) 2011 Published by Elsevier Ltd.
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