Comparative tumor initiating activities of cyclopentano and methyl derivatives of 5-methylchrysene and chrysene.

Abstract

Previous studies showed that 5,6-dimethylchrysene (5,6-diMeC) and 5,7-diMec were significantly less tumorigenic than 5-methylchrysene (5-MeC). These results were unexpected based on the known mechanism of metabolic activation of 5-MeC and indicated the presence of critical steric requirements for tumorigenicity at the 6 and 7 positions of 5-MeC. In this study, the structure activity relationships were further extended by comparing the tumor-initiating activities on mouse skin of 5-MeC, 6,7-cyclopentano-5-MeC, 5,6-diMeC, 6,7-diMeC, 5,7-diMeC, chrysene and 6,7-cyclopentanochrysene. 5-MeC was the most tumorigenic compound, with activity significantly higher than all other compounds tested. Among the other compounds. Only 5,6-diMeC was significantly tumorigenic. The results demonstrate that substitution of methyl or methylene groups at the 6 or 7 positions of 5-MeC leads to a significant reduction of tumor initiating activity.

• Authors: S Amin, S S Hecht, P Di Raddo, R G Harvey
• Journal: Cancer letters (Cancer Lett) Vol. 51 Issue 1 Pg. 17-20 (May 15 1990) ISSN: 0304-3835 [Print] Ireland
• PMID: 2337893 (Publication Type: Comparative Study, Journal Article, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Carcinogens
• Chrysenes
• Phenanthrenes
• 6,7-cyclopentano-5-methylchrysene
• 5,6-dimethylchrysene
• 6,7-cyclopentanochrysene
• chrysene,2-diol-3,4-epoxide-1
• 5-methylchrysene

Topics

• Animals
• Biotransformation
• Carcinogens
• Chemical Phenomena
• Chemistry
• Chrysenes (metabolism, toxicity)
• Female
• Mice
• Phenanthrenes (toxicity)
• Skin Neoplasms (chemically induced)
• Structure-Activity Relationship