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© 1982 Oxford University Press

research-article

7, 12-Dimethylbenz[a]anthracene-deoxyribonucleoside adduct formation in vivo: evidence for the formation and binding of a monohydroxymethyl-DMBA metabolite to rat liver DNA

N.J. Joyce and F.B. Daniel 1

Health Effects Research Laboratory, U.S. Environmental Protection Agency 26 W. St. Clair Street, Cincinnati, OH 45268, USA.

1To whom correspondence should be addressed.

The polycyclic aromatic hydrocarbon, 7, 12-dimethyl benz[a]anthracene (DMBA) is a potent carcinogen to the female Sprague-Dawley rat, and when administered under conditions that have been shown to produce cancer, results in extensive formation of hydrocarbon-deoxyribonucleoside adducts. Sephadex LH-20 and reverse-phase h.p.l.c. and spectrofluorometric analysis of these adducts demonstrate that at least one adduct results from the binding of 7, 12-dimethylbenz[a]anthracene-1, 2, 3, 4-tetrahydro-3, 4-dihydroxy-1, 2-oxide. In these experiments, employing i.p. administration of the hydrocarbon, a second more polar adduct was observed. Evidence is presented that this adduct results from the formation of a monohydroxymethyl-methylbenz[a]anthracene-A-ring-diol-epoxide. While both of the monohydroxymethyl-DMBA metabolites have been shown to bind cellular DNA following their administration this is the first evidence of monohydroxymethyl-DMBA-deoxyribonucleoside adducts being formed after the administration of DMBA per se. The evidence suggests that this more polar adduct is a 7-hydroxymethyl-12-methylbenz[a]anthracenedeoxyribonucleoside adduct.


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