Comparative mutagenicity of nitrofluoranthenes in Salmonella typhimurium TA98, TA98NR, and TA98/1,8DNP6
| Autor: | B. S. Shane, G. L. Squadrito, D. F. Church, W. A. Pryor, D. G. MacPhee |
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| Rok vydání: | 1991 |
| Předmět: |
Fluoranthene
Steric effects Salmonella typhimurium Fluorenes biology Free Radicals Epidemiology Chemistry Mutagenicity Tests Health Toxicology and Mutagenesis Radical biology.organism_classification Enterobacteriaceae Orders of magnitude (mass) Ames test chemistry.chemical_compound Species Specificity Nitration Electrophile Electrochemistry Organic chemistry Oxidation-Reduction Genetics (clinical) Mutagens |
| Zdroj: | Environmental and molecular mutagenesis. 17(2) |
| ISSN: | 0893-6692 |
| Popis: | 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. Thus, 3-NF is a more potent mutagen than 2-NF and 1,3-DNF is more potent than 1,2-DNF, an isomer with one near coplanar nitro group and one nitro group substantially out of plane with the fluoranthene skeleton, when tested against Salmonella typhimurium TA98, TA98NR, and TA98/1,8-DNP6. In addition, the activation of these dinitro-PAH to mutagens does not depend on the "classical nitroreductase" and/or O-acetylase, suggesting that they are activated via different pathways. 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. |
| Databáze: | OpenAIRE |
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