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

• Published in: Carcinogenesis (New York) 1985-10, Vol.6 (10), p.1483-1488
• Main Authors: LaVoie, Edmond J., Coleman, Daniel T., Rice, Joseph E., Geddie, Nora G., Hoffmann, Dietrich
• Format: Article
• Language: English
• Subjects: Anthracenes - metabolism; Anthracenes - toxicity; Biological and medical sciences; Biotransformation; Carcinogens; Chemical mutagenesis; Chromatography, High Pressure Liquid; Medical sciences; Methylation; Mutagenicity Tests; Mutagens; Neoplasms, Experimental - chemically induced; Salmonella typhimurium; Skin Neoplasms - chemically induced; Spectrum Analysis; Structure-Activity Relationship; Toxicology
• ISSN: 0143-3334; 1460-2180
• DOI: 10.1093/carcin/6.10.1483

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.