Characterization of DNA adducts formed by the four configurationally isomeric 5,6-dimethylchrysene 1,2-dihydrodiol 3,4-epoxides

Jan Szeliga, Bruce D. Hilton, Gwendolyn N. Chmurny, Jacek Krzeminski, Shantu Amin, Anthony Dipple

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

The DNA adducts formed from the racemic syn and anti dihydrodiol epoxides of 5,6-dimethylchrysene were characterized through various spectroscopic methods. Substantial reaction with the amino groups of both deoxyadenosine and deoxyguanosine residues were detected with both the syn and anti derivatives. The chemical shifts and coupling constants for the cis and trans opened adducts from the syn dihydrodiol epoxide were distinctly different, whereas far the anti dihydrodiol epoxide these properties were fairly similar for cis and trans adducts. In the latter case, assignment of trans and cis configurations was less obvious, and the finding that trans adducts have always predominated over cis adducts for all dihydrodiol epoxides studied to date was helpful in making these assignments. The preferential formation of cis adducts in DNA by the syn dihydrodiol epoxide is more like the chemistry of the dihydrodiol epoxide of benzo[c]phenanthrene than of benzo[g]chrysene, although both of these, like 5,6-dimethylchrysene, are non-planar compounds.

Original languageEnglish (US)
Pages (from-to)378-385
Number of pages8
JournalChemical Research in Toxicology
Volume10
Issue number4
DOIs
StatePublished - Apr 1 1997

All Science Journal Classification (ASJC) codes

  • Toxicology

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