PMID: 2116904Jun 26, 1990Paper

Sequence preferences of covalent DNA binding by anti-(+)- and anti-(-)-benzo[a]pyrene diol epoxides

Biochemistry
R L Rill, G A Marsch

Abstract

The sequence preferences of formation of piperidine-labile adducts of guanine by individual (+)- and (-)-isomers of trans-7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene [anti-(+)- and anti-(-)-BPDE] were examined by techniques analogous to chemical DNA sequencing. Data were obtained on over 1200 bases with anti-(-)-BPDE and 1000 bases with anti-(+)-BPDE. Guanines on average yielded more labile adducts than other bases, and the reactivities of guanines with both anti-(+)- and anti-(-)-BPDE isomers were found to be distinctly nonrandom with respect to DNA sequence. The most and least reactive guanines, defined in terms of the upper and lower 10 percentiles of reactivity, differed on average by a factor of 17. This range of guanine reactivities was correlated with distinct sequence preferences, which differed in part for the two isomers. The strongest determinant for preferred reaction of anti-(-)-BPDE to form a labile adduct at a guanine was the presence of a 3'-flanking guanine, but a thymine 5'-flanking a guanine also generally enhanced reactivity. The triplets containing central guanines most preferred by anti-(-)-BPDE were AGG, CGG, and TG(G greater than T greater than C,A). anti-(+)-BPDE also formed labile ...Continue Reading

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Citations

Aug 1, 1992·Journal of Biomolecular Structure & Dynamics·M A MallamaciS A Winkle
Apr 7, 2000·Carcinogenesis·B S ShaneK R Tindall
Jan 1, 1994·Drug Metabolism Reviews·C A BiggerA Dipple
Oct 13, 2007·Mutation Research·Dhrubajyoti ChakravartiEleanor G Rogan
Sep 17, 2008·Rapid Communications in Mass Spectrometry : RCM·Emilien L JaminLaurent Debrauwer
Nov 22, 2005·Mutation Research·Dhrubajyoti ChakravartiErcole L Cavalieri

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