Identification of Mutagenic Metabolites Formed by C-Hydroxylation and Nitroreduction of 5-Nitroacenaphthene in Rat Liver

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Abstract

The metabolism of the mutagen and carcinogen, 5-nitroa-cenaphthene, by the 9000 Χ g supernatant from the livers of Aroclor-pretreated rats was studied. The major primary metabolites were 1 -hydroxy-5-nitroacenaphthene and 2-hydroxy-5-nitroacenaphthene. These metabolites were oxidized to 1-oxo-5-nitroacenaphthene and 2-oxo-6-nitroacenaphthene, hydrox-ylated to cis-1,2-dihydroxy-5-nitroacenaphthene and trans-1,2-dihydroxy-5-nitroacenaphthene, and reduced to 1-hy-droxy-5-aminoacenaphthene and 2-hydroxy-5-aminoace-naphthene. Reduction of 1- and 2-oxo-5-nitroacenaphthene to 1-oxo- and 2-oxo-5-aminoacenaphthene was also observed. When incubations were carried out in a N2-enriched atmosphere (10% O2 in N2), the major metabolites were 1-hydroxy-and 2-hydroxy-5-nitroacenaphthene and 2-oxo-5-aminoace-naphthene. Selected metabolites were tested for mutagenicity toward Salmonella typhimurium TA 98. The most mutagenic of the metabolites tested, in the presence or absence of rat liver 9000 Χ g supernatant, were 1-hydroxy-5-nitroacenaphthene and 1 -oxo-5-nitroacenaphthene. These results indicate that the 9000 Χ g • supernatant from the livers of Aroclor-pretreated rats is capable of catalyzing both the oxidation and reduction of 5-nitroacenaphthene and that the reduced derivatives of 1 -hydroxy- or 2-hydroxy- or 1 -oxo- or 2-oxo-5-nitroace-naphthene are proximate mutagens.

Original languageEnglish (US)
Pages (from-to)1243-1248
Number of pages6
JournalCancer Research
Volume42
Issue number4
StatePublished - Apr 1 1982

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