Characterization of DNA Adducts Formed by the Four Configurationally Isomeric 5,6-Dimethylchrysene 1,2-Dihydrodiol 3,4-Epoxides

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• 作者：Jan Szeliga ; Bruce D. Hilton ; Gwendolyn N. Chmurny ; Jacek Krzeminski ; Shantu Amin ; and Anthony Dipple
• 刊名：Chemical Research in Toxicology
• 出版年：1997
• 出版时间：April 1997
• 年：1997
• 卷：10
• 期：4
• 页码：378 - 385
• 全文大小：161K
• 年卷期：v.10,no.4(April 1997)
• ISSN：1520-5010

文摘

The DNA adducts formed from the racemic syn andanti dihydrodiol epoxides of 5,6-dimethylchrysene were characterized through various spectroscopicmethods. Substantialreaction with the amino groups of both deoxyadenosine anddeoxyguanosine residues weredetected with both the syn and anti derivatives.The chemical shifts and coupling constantsfor the cis and trans opened adducts from thesyn dihydrodiol epoxide were distinctlydifferent,whereas for the anti dihydrodiol epoxide these propertieswere fairly similar for cis andtransadducts. In the latter case, assignment of trans andcis configurations was less obvious, andthe finding that trans adducts have always predominated overcis adducts for all dihydrodiolepoxides studied to date was helpful in making these assignments.The preferential formationof cis adducts in DNA by the syn dihydrodiolepoxide is more like the chemistry of thedihydrodiol epoxide of benzo[c]phenanthrene thanof benzo[g]chrysene, although both ofthese,like 5,6-dimethylchrysene, are non-planar compounds.