Chromatographic and spectral investigations on the in vivo metabolites of 6-nitrobenzo[a]pyrene

Raha, Chitta R.; Williamson, Daniel; Thakran, Purnima; Cassada, David A.; Iversen, Patrick L.

doi:10.1016/s0021-9673(01)83587-1

Cited by 4 publications

(1 citation statement)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Oxidation of 1,3-, 1,6-, and 1,8-Dinitropyrenes (3, 4, 6-nitrochrysene and 6-nitrobenzo[o]pyrene were reacted with 02'~, the nucleophilic displacement of nitro groups by 02*~predominantly proceeded to give 6-hydroxychrysene and 6-hydroxybenzo[o]pyrene, respectively (21 and 22, 65% and 70% yield). 6-Hydroxybenzo[a]pyrene formation from 6-nitrobenzo[o]pyrene with rat lung preparations was reported by Raha et al (29). The oxidation of nitroPAH with K02-crown is thus shown as a useful means for the preparation of oxidative metabolites of nitroPAH.…”

Section: Resultsmentioning

confidence: 83%

Chemical Oxidation of Nitrated Polycyclic Aromatic Hydrocarbons: Hydroxylation with Superoxide Anion Radical

Fukuhara

Miyata²

1995

Chem. Res. Toxicol.

View full text Add to dashboard Cite

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 KO2/18-crown-6 in dimethylformamide, 5-, 6-, 8-, and 9-hydroxy-1-nitropyrenes and 1-hydroxypyrene were obtained in preparative yields. Three isomeric dinitropyrenes, 3-nitrofluoranthene, 6-nitrobenzo[a]pyrene, and 6-nitrochrysene, were oxidized to hydroxy derivatives, some of which correspond to the oxidative metabolite of nitroPAH. The oxidation of dinitropyrenes with trifluoroperacetic acid gave K-region oxidized products.

show abstract

Section: Resultsmentioning

confidence: 83%