US EPA

625870 

Journal Article 

Identification of mutagenic metabolites formed by C-hydroxylation and nitroreduction of 5-nitroacenaphthene in rat liver 

El-Bayoumy, K; Hecht, SS 

1982 

Yes 

Cancer Research
ISSN: 0008-5472
EISSN: 1538-7445 

HEEP/82/13248 

42 

4 

1243-1248 

English 

7060001 

http://cancerres.aacrjournals.org/cgi/reprint/42/4/1243.pdf
Exit
 

The metabolism of the mutagen and carcinogen, 5-nitroacenaphthene, by the 9000 x 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-5-nitroacenaphthene, hydroxylated to cis-1,2-dihydroxy-5-nitroacenaphthene and trans-1,2-dihydroxy-5-nitroacenaphthene, and reduced to 1-hydroxy-5-aminoacenaphthene and 2-hydroxy-5-aminoacenaphthene. 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-aminoacenaphthene. 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 x g supernatant, were 1-hydroxy-5-nitroacenaphthene and 1-oxo-5-nitroacenaphthene. These results indicate that the 9000 x 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-nitroacenaphthene are proximate mutagens.