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Chemical Compound Review:

CHEMBL167525 8-nitropyren-1-ol

Synonyms: CCRIS 3454, AG-E-22730, AC1L2XWE, CTK0H5068, AR-1H4828, ...

Cerniglia, C.E. et al., Ball, L.M. et al., Ball, L.M. et al., el-Bayoumy, K. et al., Kanoh, T. et al., et al.

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Disease relevance of CCRIS 3454

Consistent with the loss in mutagenic activity, the glucoside conjugates of 6- and 8-hydroxy-1-nitropyrene were nonmutagenic in the Salmonella reversion assay [1].

High impact information on CCRIS 3454

3-Hydroxy-1-nitropyrene bound extensively to DNA upon nitroreduction by rat liver cytosol or xanthine oxidase, while 6- and 8-hydroxy-1-nitropyrene bound only slightly [2].
Among the principal metabolite fractions identified were 3-hydroxy-1-nitropyrene and 8-hydroxy-1-nitropyrene (already known as hepatic in vitro metabolites of 1-nitropyrene) and the hitherto unreported metabolites 6-hydroxy-N-acetyl-1-aminopyrene and 8-hydroxy-N-acetyl-1-aminopyrene [3].
Cunninghamella elegans metabolized 1-nitropyrene to form glucoside conjugates of 6-hydroxy-1-nitropyrene and 8-hydroxy-1-nitropyrene [1].
High-performance liquid chromatography (HPLC) analyses revealed the formation of 1-nitropyrene-6-ol and also 1-nitropyrene-3-ol, 1-nitropyrene-8-ol, and trans-4,5-dihydroxy-4,5-diol-1-nitropyrene from 1-NP (10microM), catalyzed by P450 1B1 [4].
The mutagenic compounds 3-hydroxy-1-nitropyrene, 6-hydroxy-1-nitropyrene, 8-hydroxy-1-nitropyrene, and 1-hydroxypyrene were identified in the mutagenic fractions by mass spectrometry and UV-visible spectrophotometry with synthetic reference substances [5].

Biological context of CCRIS 3454

1-Nitropyrene was metabolized to 3-hydroxy-1-nitropyrene, 6- or 8-hydroxy-1-nitropyrene, 1-aminopyrene, N-acetyl-1-aminopyrene and other unidentified products (including some bound to protein) by an S9 preparation analogous to that used for exogenous metabolic activation in the Ames assay [6].

Analytical, diagnostic and therapeutic context of CCRIS 3454

The ethyl acetate soluble metabolites of 1-nitropyrene were identified as 1-aminopyrene, trans-4,5-dihydro-4,5-dihydroxy-1-nitropyrene, 1-nitropyren-3-ol, 1-nitropyren-6-ol, and 1-nitropyren-8-ol on the basis of cochromatography with synthetic standards in two different HPLC systems [7].

References

Fungal metabolism and detoxification of the nitropolycyclic aromatic hydrocarbon 1-nitropyrene. Cerniglia, C.E., Freeman, J.P., White, G.L., Heflich, R.H., Miller, D.W. Appl. Environ. Microbiol. (1985) [Pubmed]
Oxidative microsomal metabolism of 1-nitropyrene and DNA-binding of oxidized metabolites following nitroreduction. Djurić, Z., Fifer, E.K., Howard, P.C., Beland, F.A. Carcinogenesis (1986) [Pubmed]
Metabolism of 1-nitro[14C]pyrene in vivo in the rat and mutagenicity of urinary metabolites. Ball, L.M., Kohan, M.J., Inmon, J.P., Claxton, L.D., Lewtas, J. Carcinogenesis (1984) [Pubmed]
Metabolic activation of carcinogenic 1-nitropyrene by human cytochrome P450 1B1 in Salmonella typhimurium strain expressing an O-acetyltransferase in SOS/umu assay. Hatanaka, N., Yamazaki, H., Oda, Y., Guengerich, F.P., Nakajima, M., Yokoi, T. Mutat. Res. (2001) [Pubmed]
Detection of mutagenic compounds in the urine of mice administered pyrene during exposure to NO2. Kanoh, T., Fukuda, M., Mizoguchi, I., Kinouchi, T., Nishifuji, K., Ohnishi, Y. Jpn. J. Cancer Res. (1987) [Pubmed]
Mutagenicity of derivatives and metabolites of 1-nitropyrene: activation by rat liver S9 and bacterial enzymes. Ball, L.M., Kohan, M.J., Claxton, L.D., Lewtas, J. Mutat. Res. (1984) [Pubmed]
Metabolism and DNA binding of 1-nitropyrene and 1-nitrosopyrene in newborn mice. el-Bayoumy, K., Shiue, G.H., Hecht, S.S. Chem. Res. Toxicol. (1988) [Pubmed]

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