A reactive hydroxymethyl sulfate ester formed regioselectively from the carcinogen, 7,12-dihydroxymethylbenz[alpha]anthracene, by rat liver sulfotransferase.
The carcinogen, 7,12-dihydroxymethylbenz[alpha]anthracene (DHBA), was regioselectively conjugated in the presence of 3'-phosphoadenosine 5'-phosphosulfate by male rat liver cytosolic sulfotransferase to DHBA 7-sulfate. The sulfate ester was highly reactive and showed a potent, intrinsic mutagenicity toward Salmonella typhimurium TA 98.
D000818:Animals; D001551:Benz(a)Anthracenes / Q000378:metabolism* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D003600:Cytosol / Q000201:enzymology; D006207:Half-Life; D008099:Liver / Q000201:enzymology*; D008297:Male; D009152:Mutagenicity Tests; D010724:Phosphoadenosine Phosphosulfate / Q000494:pharmacology; D051381:Rats; D011919:Rats, Inbred Strains; D012486:Salmonella typhimurium; D013466:Sulfurtransferases / Q000378:metabolism*
D001551:Benz(a)Anthracenes; C046810:7,12-dihydroxymethylbenz(a)anthracene; D010724:Phosphoadenosine Phosphosulfate; C046811:7,12-dihydroxymethylbenz(a)anthracene 7-sulfate; D013466:Sulfurtransferases