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, a...

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Bibliographic Details
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
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Summary: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.
ISSN:0143-3334
1460-2180
DOI:10.1093/carcin/6.10.1483