Inherent Stereospecificity in the Reaction of Aflatoxin B1 8,9-Epoxide with Deoxyguanosine and Efficiency of DNA Catalysis

被引：30

作者：

Brown, Kyle L. ^{[1
]}

Bren, Urban ^{[3
]}

Stone, Michael P. ^{[1
,2
]}

Guengerich, F. Peter ^{[1
,2
]}

机构：

[1] Vanderbilt Univ, Ctr Mol Toxicol, Nashville, TN 37232 USA

[2] Vanderbilt Univ, Dept Chem & Biochem, Nashville, TN 37232 USA

[3] Natl Inst Chem, SI-1001 Ljubljana, Slovenia

来源：

CHEMICAL RESEARCH IN TOXICOLOGY | 2009年 / 22卷 / 05期

关键词：

EPOXIDES; ADDUCTS; BINDING; EXO-8,9-EPOXIDE; INTERCALATION; SPECTROSCOPY; SUPPRESSION; HYDROLYSIS; WET;

D O I：

10.1021/tx900002g

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Kinetic analysis of guanine alkylation by aflatoxin B-1 exo-8,9-epoxide, the reactive form of the hepatocarcinogen aflatoxin B-1, shows the reaction to be >2000 times more efficient in DNA than in aqueous solution, that is, with free 2'-deoxyguanosine. Thermodynamic analysis reveals AFB(1) exo-8,9-epoxide intercalation as the predominant source of the observed DNA catalytic effect. However, the known exo > endo epoxide stereospecificity of the DNA alkylation is observed even with free deoxyguarrosine (ratio >20:1 determined by LC-MS and NMR measurements), as predicted by theoretical calculations [Bren, U., et at. (2007) Chem. Res. Toxciol. 20, 1134-1140].

引用

页码：913 / 917

页数：5

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