Tumor-initiating activity, mutagenicity, and metabolism of methylated anthracenes.
Specific methylated derivatives of anthracene are mutagenic in S. typhimurium and have tumor-initiating activity on mouse skin. In this study, the mutagenic activities of 1-, 2-, and 9-methylanthracene, 2,9- and 9,10-dimethylanthracene, 2,9,-10-trimethylanthracene, 2,3,9,10-tetramethylanthracene, and the photo-oxide of 9,10-dimethylanthracene were determined in S. typhimurium TA98 and TA100. The relative tumor-initiating activities of these compounds were also evaluated. These bioassays indicate that increased mutagenic potency and tumor-initiating activity are associated with the presence of a methyl substituent at both the 9- and 10- position of anthracene. Metabolism studies suggest that the biological activity of specific methylated anthracenes may be related to the formation of a simple epoxide adjacent to a peri-methyl substituent.
D000873:Anthracenes / Q000378:metabolism / Q000633:toxicity*; D001711:Biotransformation; D002273:Carcinogens; D002851:Chromatography, High Pressure Liquid; D008745:Methylation; D009152:Mutagenicity Tests; D009153:Mutagens; D009374:Neoplasms, Experimental / Q000139:chemically induced*; D012486:Salmonella typhimurium; D012878:Skin Neoplasms / Q000139:chemically induced; D013057:Spectrum Analysis; D013329:Structure-Activity Relationship
D000873:Anthracenes; D002273:Carcinogens; D009153:Mutagens