Tumor-initiating activity, mutagenicity, and metabolism of methylated anthracenes

Specific methylated derivatives of anthracene are mutagenicin S. typhimurium and have tumor-initiating activity on mouseskin. In this study, the mutagenic activities of 1-, 2-, and9-methylanthracene, 2,9- and 9,10-dimethylanthracene, 2,9, -10-trimethylanthracene,2,3,9,10-tetramethylanthracene, and the photo-oxide of 9,10-dimethylanthracenewere determined in S. typhimurium TA98 and TA100. The relativetumor-initiating activities of these compounds were also evaluated.These bioassays indicate that increased mutagenic potency andtumor-initiating activity are associated with the presence ofa methyl substituent at both the 9- and 10- position of anthracene.Metabolism studies suggest that the biological activity of specificmethylated anthracenes may be related to the formation of asimple epoxide adjacent to a peri-methyl substituent.