Naphthazarin derivatives(V): formation of glutathione conjugate and cytotoxic activity of 2-or 6-substituted 5,8-dimethoxy-1,4-napthoquinones in the presence of glutathinoe-S-transferase, in rat liver S-9 fraction and mouse liver perfusate

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Title
Naphthazarin derivatives(V): formation of glutathione conjugate and cytotoxic activity of 2-or 6-substituted 5,8-dimethoxy-1,4-napthoquinones in the presence of glutathinoe-S-transferase, in rat liver S-9 fraction and mouse liver perfusate
Author(s)
Xiang Guo Zheng; Jong Seong Kang; Hwan Mook Kim; Guang Zhu Jin; Byung Zun Ahn
Bibliographic Citation
Archives of Pharmacal Research, vol. 23, no. 1, pp. 22-25
Publication Year
2000
Abstract
Formation of glutathione (GSH) conjugates with 2- or 6-(1-hydroxymethyl)- and 2-(1-hydroxyethyl)-DMNQ derivatives (DMNQ, 5,8-dimethoxy-1,4-naphthoquone) was carried out in phosphate buffer (pH 7.4), in the presence of glutathione-S-transferase (GST), in rat liver S-9 fraction and by perfusion, and the rates of conjugates formation were compared and correlated to cytotoxicity. The GSH conjugates of 6-(1-hydroxyalky1)-DMNQ derivatives were formed faster than 2-(1-hydroxyalkyl)-DMNQ derivatives under all of the media, implying that steric hindrance was the cause of lowering the rate of conjugate formation of 2-substituted derivatives. For both isomers, addition of GST did not improve the reaction rate, compared with that in buffer, while the reaction in the S-9 fraction and the perfusate was accelerated to a great extent. The catalytic effect of the S-9 fraction and the perfusion on 2-isomers was greater than on 6-substituted ones, suggesting that S-9 fraction and the perfusate contain an effective system relaxing the steric hindrance of 2-(1-hydroxyalkyl)-DMNQ derivtives. Furthermore, a good correlation between the formation of the GSH conjugates and the cytotoxic activity of both naphthazarin isomers suggests that the steric hindrance is a cause of lowering the cytotoxicity of 2-isomers.
Keyword
naphthazarin derivativesformation of glutathione conjugatesglutathione-S-transferaserat liver S-9 fractionmouse liver perfusion
ISSN
0253-6269
Publisher
Pharmaceutical Soc Korea
Type
Article
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1. Journal Articles > Journal Articles
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