Comparative mutagenicity of nitrofluoranthenes in Salmonella typhimurium TA98, TA98NR, and TA98/1,8DNP sub 6
- Louisiana State Univ. Baton Rouge (United States)
The nitration of fluoranthene, one of the most abundant polycyclic aromatic hydrocarbons (PAH) in diesel fuels, occurs in the laboratory under either electrophilic or free-radical conditions to give nitro-PAH. 3-Nitrofluoranthene (3-NF) is the major product under electrophilic ionic conditions while 2-nitrofluoranthene (2-NF) is the major product under free-radical nitration conditions. The free-radical nitration of fluoranthene also yields 1,2- and 1,3-dinitrofluoranthene (1,2-DNF and 1,3-DNF). Nitration on the 3-position of fluoranthene enhances the mutagenic potency more strongly than on the 2-position. Despite the fact that 3-NF and 1-phenyl-4-nitronaphthalene (1-P-4NN), a non-planar analog of 3-NF, have virtually identical reduction potentials, their mutagenic potencies differ by three orders of magnitude. This finding suggests that when nitro-PAH of varying steric requirements are compared, the reduction potential may not predict mutagenic potency as well as had been previously suggested.
- OSTI ID:
- 6097882
- Journal Information:
- Environmental and Molecular Mutagenesis; (United States), Journal Name: Environmental and Molecular Mutagenesis; (United States) Vol. 17:2; ISSN 0893-6692; ISSN EMMUE
- 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.
AROMATICS
BACTERIA
FLUORINATED AROMATIC HYDROCARBONS
HALOGENATED AROMATIC HYDROCARBONS
MICROORGANISMS
MUTAGEN SCREENING
MUTANTS
MUTATION FREQUENCY
NITRATION
NITRO COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
POLYCYCLIC NITRO COMPOUNDS
RADICALS
REVERTANTS
SALMONELLA
SALMONELLA TYPHIMURIUM
SCREENING