Identification of the DNA adduct formed by metabolism of 1,8-dinitropyrene in Salmonella typhimurium
The incubation of (3H)1,8-dinitropyrene with Salmonella typhimurium TA98NR followed by isolation of the DNA from these cells, hydrolysis of the DNA to nucleosides, butanol extraction of the hydrolysate and purification by reversed-phase liquid chromatography afforded a single product. Calf thymus DNA, after treatment with N-hydroxyl-1-amino-8-nitro-pyrene, was hydrolyzed, extracted and purified in a similar fashion to give a single compound which was shown to be the deoxyguanosine derivative 1-N-(2'-deoxyguanosin-8-yl)-amino-8-nitropyrene by a combination of proton n.m.r. and u.v.-vis. spectroscopy and fast atom bombardment mass spectrometry. The DNA adducts formed in vivo and in vitro exhibited identical chromatographic and chemical behavior. Under acidic or basic conditions in the vivo and in vitro adducts were converted to identical products. Reduction of the adduct gave a new, highly fluorescent product that had a fluorescence emission spectrum identical to that of 1,8-diaminopyrene.
- Research Organization:
- McMaster Univ., Hamilton, Ontario, Canada
- OSTI ID:
- 5842880
- Journal Information:
- Carcinogenesis; (United States), Journal Name: Carcinogenesis; (United States) Vol. 1; ISSN CRNGD
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ADDUCTS
AROMATICS
BACTERIA
CONDENSED AROMATICS
DNA ADDUCTS
FLUORESCENCE
HYDROCARBONS
LABELLED COMPOUNDS
LUMINESCENCE
MAGNETIC RESONANCE
METABOLISM
MICROORGANISMS
NITRO COMPOUNDS
NUCLEAR MAGNETIC RESONANCE
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PYRENE
RESONANCE
SALMONELLA
SALMONELLA TYPHIMURIUM
TRITIUM COMPOUNDS