Modification of DNA by the benzo[a]pyrene metabolite diol-epoxide r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene.
The structural modification of double-stranded circular DNA of simian virus 40 and plasmid ColE1 by in vitro binding of r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene was studied. Stepwise hydrolysis with endonuclease S1 and DNase followed by DNA base analysis by thin-layer chromatography provided evidence that binding to adenine caused the local denaturation of DNA, whereas the more than 10-fold greater binding to guanine did not create such local denaturation. Of the  two synthetic double-stranded polymers, poly(dA-dT).poly(dA-dT) and poly(dG-dC).poly(dG-dC), bound to the diol-epoxide, only the former showed a marked hydrolysis after endonuclease S1 treatment, whereas binding occurred 24-fold more on the latter.
D001580:Benzopyrenes / Q000494:pharmacology*; D001665:Binding Sites; D055598:Chemical Phenomena; D002621:Chemistry; D004247:DNA; D004269:DNA, Bacterial; D004279:DNA, Viral; D003851:Deoxyribonucleases / Q000378:metabolism; D004720:Endonucleases / Q000378:metabolism; D004852:Epoxy Compounds; D008854:Microscopy, Electron; D010957:Plasmids; D011089:Polydeoxyribonucleotides
D001580:Benzopyrenes; D004269:DNA, Bacterial; D004279:DNA, Viral; D004852:Epoxy Compounds; D011089:Polydeoxyribonucleotides; D004247:DNA; D003851:Deoxyribonucleases; D004720:Endonucleases
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