In situ spectroeletrochemistry and cytotoxic activities of natural ubiquinone analogues

被引:26
|
作者
Ma, Wei [1 ,2 ]
Zhou, Hao [1 ,2 ]
Ying, Yi-Lun [1 ,2 ]
Li, Da-Wei [1 ,2 ]
Chen, Guo-Rong [1 ,2 ]
Long, Yi-Tao [1 ,2 ]
Chen, Hong-Yuan [3 ]
机构
[1] E China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Shanghai 200237, Peoples R China
[2] E China Univ Sci & Technol, Dept Chem, Shanghai 200237, Peoples R China
[3] Nanjing Univ, Dept Chem, Nanjing 210093, Peoples R China
关键词
Ubiquinone/coenzyme Q; Electrochemistry; ESR; In situ spectroelectrochemistry; Cytotoxicity; ELECTRON-TRANSFER; PROTON-TRANSFER; COENZYME Q(10); QUINONES; ELECTROCHEMISTRY; DERIVATIVES; INHIBITORS; MOLECULES; RADICALS; BEHAVIOR;
D O I
10.1016/j.tet.2011.06.026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:5990 / 6000
页数:11
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