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Chemical Compound Review:

NHAP N-pyren-1-ylhydroxylamine

Synonyms: AC1L3GBN, AC1Q7DJW, AR-1K7245, LS-185642, n-hydroxypyren-1-amine, ...

Thornton-Manning, J.R. et al., Howard, P.C. et al., Herreno-Saenz, D. et al., Fu, P.P. et al.

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High impact information on NHAP

The activated metabolite, N-hydroxy-2-aminopyrene, was prepared and reacted with calf thymus DNA [1].
DNA adduct analysis by 32P-postlabeling revealed that 1-NP treatment using the anaerobic procedure produced CHO-cell adducts by the reduction of 1-NP to N-hydroxy-1-aminopyrene, while aerobic incubations resulted in adducts produced by other metabolic pathways, probably involving ring-oxidation [2].
The suspected metabolites, N-acetyl-1-aminopyrene, 1-nitrosopyrene, N-hydroxy-1-aminopyrene, and 3-, 6-, and 8-hydroxy-1-nitropyrene were synthesized, but these derivatives were not detected in culture extracts from rat intestinal contents incubated anaerobically with 1-nitropyrene [3].

Associations of NHAP with other chemical compounds

Early studies on DNA adduct characterization for 1-nitropyrene identified N-(deoxyguanosin-8-yl)-1-aminopyrene as the major product from the modification of calf thymus DNA with N-hydroxy-1-aminopyrene, the activated metabolite from nitroreduction of 1-nitropyrene [4].

References

Formation of C8-modified deoxyguanosine and C8-modified deoxyadenosine as major DNA adducts from 2-nitropyrene metabolism mediated by rat and mouse liver microsomes and cytosols. Fu, P.P., Miller, D.W., Von Tungeln, L.S., Bryant, M.S., Lay, J.O., Huang, K., Jones, L., Evans, F.E. Carcinogenesis (1991) [Pubmed]
S9-mediated metabolism of 1-nitropyrene to a mutagen in Chinese hamster ovary cells by ring-oxidation under aerobic conditions and by nitroreduction under anaerobic conditions. Thornton-Manning, J.R., Smith, B.A., Beland, F.A., Heflich, R.H. Carcinogenesis (1991) [Pubmed]
Reduction of the carcinogen 1-nitropyrene to 1-aminopyrene by rat intestinal bacteria. Howard, P.C., Beland, F.A., Cerniglia, C.E. Carcinogenesis (1983) [Pubmed]
Identification of two N2-deoxyguanosinyl DNA adducts upon nitroreduction of the environmental mutagen 1-nitropyrene. Herreno-Saenz, D., Evans, F.E., Beland, F.A., Fu, P.P. Chem. Res. Toxicol. (1995) [Pubmed]

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