Bioalkylation and biooxidation of anthracene, in vitro and in vivo.
Anthracene undergoes biomethylation in rat liver cytosol preparations in vitro and in rat subcutaneous tissue, in vivo. The in vitro reaction is dependent on cytosol preparations fortified by the addition of S-adenosyl-L-methionine. The products of the reaction are the meso-anthracenic or L-region derivatives 9-methylanthracene and 9,10-dimethylanthracene. The latter compound may be the simplest polynuclear aromatic hydrocarbon carcinogen known. These reactive methylated metabolites are readily oxidized in cytosol preparations and in subcutaneous tissue, in vivo, to hydroxymethyl and formyl derivatives. Oxidation takes place mainly on the methyl groups since ring oxidized products were not detected.
Myers
S R
SR
Department of Pharmacology, Albert B. Chandler Medical Center, University of Kentucky, Lexington.
Blake
J W
JW
Flesher
J W
JW
D000478:Alkylation; D000818:Animals; D000873:Anthracenes / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D003600:Cytosol / Q000378:metabolism; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism; D008297:Male; D010084:Oxidation-Reduction; D051381:Rats; D011919:Rats, Inbred Strains; D012436:S-Adenosylmethionine / Q000378:metabolism
D000873:Anthracenes; D012436:S-Adenosylmethionine; C034020:anthracene