title: 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.
abstract: 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.
mesh_terms: 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
chemical_list: D001580:Benzopyrenes; D004269:DNA, Bacterial; D004279:DNA, Viral; D004852:Epoxy Compounds; D011089:Polydeoxyribonucleotides; D004247:DNA; D003851:Deoxyribonucleases; D004720:Endonucleases
references.citation: Nature. 1964 May 23;202:781-4
references.pmid: 14187619
references.citation: Proc Natl Acad Sci U S A. 1976 Oct;73(10):3381-5
references.pmid: 1068451
references.citation: Proc Natl Acad Sci U S A. 1977 May;74(5):1865-9
references.pmid: 325558
references.citation: Proc Natl Acad Sci U S A. 1977 Jan;74(1):106-10
references.pmid: 319453
references.citation: Science. 1977 Aug 12;197(4304):671-4
references.pmid: 877583
references.citation: Science. 1976 Aug 13;193(4253):592-5
references.pmid: 959820
references.citation: Proc Natl Acad Sci U S A. 1974 Jun;71(6):2260-4
references.pmid: 4601821
references.citation: Biochemistry. 1972 Mar 28;11(7):1242-50
references.pmid: 4335136
references.citation: J Mol Biol. 1967 Apr 14;25(1):23-30
references.pmid: 4291871
references.citation: Proc Natl Acad Sci U S A. 1976 Aug;73(8):2594-8
references.pmid: 1066669
references.citation: Nature. 1974 Nov 22;252(5481):326-8
references.pmid: 4473724
references.citation: Cancer Res. 1973 Oct;33(10):2378-85
references.pmid: 4795390
references.citation: Eur J Biochem. 1973 Feb 15;33(1):192-200
references.pmid: 4691350
references.citation: Cancer Res. 1976 Jun;36(6):2059-64
references.pmid: 817799
references.citation: Chem Biol Interact. 1976 Jun;13(3-4):349-52
references.pmid: 773563
references.citation: Proc Natl Acad Sci U S A. 1976 Feb;73(2):607-11
references.pmid: 1061161
references.citation: Chem Biol Interact. 1976 Jun;13(3-4):343-8
references.pmid: 1269050
references.citation: J Am Chem Soc. 1975 Nov 12;97(23):6881-3
references.pmid: 1184887
references.citation: FEBS Lett. 1975 Oct 1;57(3):250-3
references.pmid: 1181196