Identification of two N{sup 2}-deoxyguanosinyl DNA adducts upon nitroreduction of the environmental mutagen 1-nitropyrene
Journal Article
·
· Chemical Research in Toxicology
- National Center for Toxicological Research, Jefferson, AR (United States); and others
1-Nitropyrene, the most abundant nitro-polycyclic aromatic hydrocarbon in the environment, is a known mammalian and bacterial mutagen and a tumorigen in animals. 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. In this paper, we report the identification of two N{sup 2}-deoxyguanosinyl adducts, in addition to N-(deoxyguanosin-8-yl)-1-aminopyrene, formed from the reaction of N-hydroxy-1-aminopyrene, prepared in situ, with calf thymus DNA. These DNA adducts were identified as 6-(deoxyguanosin-N{sup 2}-yl)-1-aminopyrene and 8-(deoxyguanosin-N{sup 2}-yl)-1-aminopyrene. The two N{sup 2}-deoxyguanosinyl adducts were also identified in an ascorbic acid-catalyzed activation of 1-nitropyrene and in the mammary gland of female Sprague-Dawley rats administered 1-nitropyrene. The DNA adducts were also formed when 1-nitropyrene was metabolized by xanthine oxidase in the presence of calf thymus DNA, and when 1-nitropyrene was activated by rat liver microsomes and cytosols, as well as from DNA isolated from Salmonella typhimurium suspension cultures incubated with 1-nitropyrene. 45 refs., 7 figs., 1 tab.
- Sponsoring Organization:
- USDOE
- OSTI ID:
- 105184
- Journal Information:
- Chemical Research in Toxicology, Journal Name: Chemical Research in Toxicology Journal Issue: 2 Vol. 8; ISSN CRTOEC; ISSN 0893-228X
- Country of Publication:
- United States
- Language:
- English
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