The molecular mechanisms involved in the cytotoxicity of alkannin derivatives.
In order to better understand the molecular aspects of the cytotoxic action mechanisms, the cytotoxicity of alkannin derivatives, 1-10, on five human tumor cell lines were examined and their standard redox potentials in aprotic medium were tested by means of cyclic voltammetry. It was suggested that the oxidative potential is closely related to the cytotoxicity. The more negative the oxidative potential of the hydroquinones, the higher cytotoxicity of these derivatives. The results of the compounds 5, 7, 9 and 10 with bad leaving groups, have higher cytotoxic action is not agreed with the bioreductive alkylation mechanism of quinones. It indicates that the molecular mechanism involving cytotoxicity of alkannin derivatives may favor the mechanism of production of reactive oxygen.
Wu
Hai-Qiang
HQ
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China.
Huang
Zhi-Shu
ZS
Bu
Xian-Zhang
XZ
Shen
Yu-Dong
YD
Zhang
Zhu-Lin
ZL
Xie
Bing-Fen
BF
Liu
Zong-Chao
ZC
Gu
Lian-Quan
LQ
Chan
Albert S C
AS
D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010084:Oxidation-Reduction; D010100:Oxygen / Q000378:metabolism; D013329:Structure-Activity Relationship
D009285:Naphthoquinones; C018204:alkannin; D010100:Oxygen