Effects of 6-nitro substitution on 5-methylchrysene tumorigenicity, mutagenicity and metabolism.

Abstract

6-Nitro-5-methylchrysene was prepared by nitration of 5-methylchrysene and the mutagenic and tumorigenic activities of the two compounds were compared. Whereas 5-methylchrysene was a strong tumor initiator on mouse skin, no tumors were observed in the mice treated with 6-nitro-5-methylchrysene. In Salmonella typhimurium TA100, both compounds were mutagenic in the presence, but not in the absence, of rat liver 9000 g supernatant. The major metabolite of 6-nitro-5-methylchrysene in rat liver in vitro was trans-1,2-dihydro-1,2-dihydroxy-6-nitro-5-methylchrysene. In view of the ready conversion of 6-nitro-5-methylchrysene to a 1,2-dihydrodiol, its apparent lack of tumorigenicity in mouse skin was intriguing.

• Authors: K el-Bayoumy, S Amin, S S Hecht
• Journal: Carcinogenesis (Carcinogenesis) Vol. 7 Issue 4 Pg. 673-6 (Apr 1986) ISSN: 0143-3334 [Print] England
• PMID: 3509952 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S., Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Chrysenes
• Phenanthrenes
• 6-nitro-5-methylchrysene
• 5-methylchrysene

Topics

• Animals
• Chromatography, High Pressure Liquid
• Chrysenes (toxicity)
• Liver (metabolism)
• Magnetic Resonance Spectroscopy
• Mass Spectrometry
• Mice
• Mutagenicity Tests
• Phenanthrenes (toxicity)
• Rats
• Rats, Inbred F344
• Skin Neoplasms (chemically induced)
• Structure-Activity Relationship