2-Nitrofluoren-9-one: a unique mutagen formed in the photo-oxidation of 2-aminofluorene
Exposure of solutions of 2-aminofluorene (2-AF, dissolved in dimethylsulfoxide) to near ultraviolet light (u.v.a. wavelengths of 320-400 nm) results in the formation of a variety of photo-products, several of which are direct-acting mutagens in the Ames/Salmonella standard-plate assay. Previously published results from our laboratory have described the chemical identification and kinetics of formation of two of these photo-induced mutagens, 2-nitrosofluorene and 2-nitrofluorene. In this report we present recent data concerning the isolation and chemical identification of another mutagenic photoproduct of u.v.a.-irradiated 2-AF, 2-nitrofluoren-9-one (2-NO2F-9-one). Data are also presented concerning the kinetics of phototransformation of 2-aminofluoren-9-one, an early-appearing and predominant photoproduct in u.v.a.-irradiated solutions of 2-AF, into 2-NO2F-9-one. It is well established that N-oxidation is a critical step in the biotransformations (i.e. enzymatic metabolism) of primary aromatic amines into proximate mutagens/carcinogens. In addition to u.v.a.-mediated N-oxidation of aromatic amines, selective ring photo-oxidation can also occur, resulting in, for example, the production of a carbonyl group at the 9-position of the fluorene molecule. The formation of mutagenic 2-NO2F-9-one in the photochemical oxidation of 2-AF appears to be unique to this process.
- Research Organization:
- Los Alamos National Lab., NM
- OSTI ID:
- 5736779
- Journal Information:
- Carcinogenesis; (United States), Journal Name: Carcinogenesis; (United States) Vol. 3; ISSN CRNGD
- Country of Publication:
- United States
- Language:
- English
Similar Records
Frameshift mutagenicity of aromatic amines related to aminofluorene in a lacZ reversion assay in E. coli
Mutagenic activation of 2-aminofluorene by fluorescent light
Related Subjects
400500 -- Photochemistry
560302* -- Chemicals Metabolism & Toxicology-- Microorganisms-- (-1987)
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AROMATICS
CHEMICAL REACTIONS
CHEMISTRY
CONDENSED AROMATICS
DMSO
ELECTROMAGNETIC RADIATION
FLUORENE
HYDROCARBONS
MUTAGEN SCREENING
MUTAGENS
NITRO COMPOUNDS
NITROSO COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PHOTOCHEMICAL REACTIONS
PHOTOCHEMISTRY
RADIATIONS
SCREENING
SULFOXIDES
ULTRAVIOLET RADIATION