Chemical oxidation of nitrated polycyclic aromatic hydrocarbons: Hydroxylation with superoxide anion radical
- National Institute of Health Sciences, Tokyo (Japan)
Nitrated polycyclic aromatic hydrocarbon (nitroPAH) is a potent mutagen which is reductively and/or oxidatively metabolized. Biological oxidation of nitroPAH, such as hydroxylation and epoxidation, is known, but chemical oxidation has been reported in only a few papers. NitroPAH is barely oxidized by various chemical oxidants because of the electron deficient property of the aromatic ring with the nitro substituent. Nucleophilic reactivity of superoxide anion radical is known, and thus the oxidation of nitroPAH with the chemically generated superoxide anion radical was carried out in this study. When 1-nitropyrene was reacted with KO{sub 2}/18-crown-6 in dimethylformamide, 5-,6-,8j-, and 9-hydroxy-1-nitropyrenes and 1-hydroxypyrene were obtained in preparative yields. Three isomeric dinitropyrenes, 3-nitrofluoranthene, 6-nitrobenzo[a]pyrene, and 6j-nitrochrysene, were oxidized to hydrozy derivatives, some of which correspond to the oxidative metabolite of nitroPAH. The oxidation of dinitropyrenes with trifluoroperacetic acid gave K-region oxidized products. 38 refs., 4 tabs.
- Sponsoring Organization:
- USDOE
- OSTI ID:
- 86710
- Journal Information:
- Chemical Research in Toxicology, Vol. 8, Issue 1; Other Information: PBD: Jan-Feb 1995
- Country of Publication:
- United States
- Language:
- English
Similar Records
Effect of nitro-substitution of environmental polycyclic aromatic hydrocarbons on activities of hepatic phase II enzymes in rats
Comparative lung tumorigenicity of parent and mononitro-polynuclear aromatic hydrocarbons in the BLU:Ha newborn mouse assay