Microsome-mediated reactions of phenols of polycyclic hydrocarbons with DNA.
Phenolic metabolites of 7 polycyclic hydrocarbons were incubated with rat-liver microsomal fractions in the presence of DNA. Hydrocarbon-nucleoside adducts with chromatographic properties similar to those of diol-epoxide-deoxyribonucleoside adducts, were detected in hydrolysates of DNA that had been incubated with phenols of benzo[a]pyrene, benz[a]anthracene and chrysene. Adducts were not detected when phenols of phenanthrene, pyrene, dibenz[a,c]anthracene or dibenz[a,h]anthracene were further metabolised. The possible contribution of phenolic metabolites to the carcinogenic activity and DNA binding of polycyclic hydrocarbons is discussed.
D000818:Animals; D001551:Benz(a)Anthracenes / Q000378:metabolism; D001564:Benzo(a)pyrene; D001580:Benzopyrenes / Q000378:metabolism; D001711:Biotransformation; D002845:Chromatography; D002911:Chrysenes / Q000378:metabolism; D004247:DNA / Q000302:isolation & purification / Q000378:metabolism*; D066298:In Vitro Techniques; D008297:Male; D008748:Methylcholanthrene; D008862:Microsomes, Liver / Q000378:metabolism*; D010636:Phenols / Q000378:metabolism*; D011083:Polycyclic Compounds / Q000378:metabolism*; D051381:Rats; D011919:Rats, Inbred Strains
D001551:Benz(a)Anthracenes; D001580:Benzopyrenes; D002911:Chrysenes; D010636:Phenols; D011083:Polycyclic Compounds; D001564:Benzo(a)pyrene; D008748:Methylcholanthrene; D004247:DNA; C030935:benz(a)anthracene