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  • Title: Effects of 6-nitro substitution on 5-methylchrysene tumorigenicity, mutagenicity and metabolism.
    Author: el-Bayoumy K, Amin S, Hecht SS.
    Journal: Carcinogenesis; 1986 Apr; 7(4):673-6. PubMed ID: 3509952.
    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.
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