Evidence for a 2,3-epoxide as an intermediate in the microsomal metabolism of benzo[a]pyrene to 3-hydroxybenzo[a]pyrene
| Autor: | P.P. Fu, H.V. Gelboin, Ronald G. Harvey, Shen K. Yang, P.P. Roller |
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| Rok vydání: | 1977 |
| Předmět: |
Male
Stereochemistry Metabolite Biophysics Epoxide Biochemistry Mass Spectrometry chemistry.chemical_compound Ethers Cyclic Animals TCPO Benzopyrenes Molecular Biology Benzopyrene Hydroxylase Chromatography Cell Biology Deuterium Rats chemistry NIH shift Benzo(a)pyrene Isotope Labeling Benzopyrene Microsome Microsomes Liver Pyrene |
| Zdroj: | Biochemical and biophysical research communications. 77(4) |
| ISSN: | 0006-291X |
| Popis: | Summary A synthetic benzo[a]pyrene (BP) specifically labeled with deuterium at the 3-position was incubated with rat liver microsomes in the presence of NADPH and oxygen. Mass spectral analysis of the metabolites isolated by high pressure liquid chromatography indicated that the 3-hydroxybenzo[a]pyrene (3-OH-BP) and BP-3,6-quinone retained 29% and 15% of the deuterium label respectively, whereas the BP 4,5-, 7,8-, and 9,10- diols, 9-OH-BP, BP-1,6-quinone, and BP-6,12-quinone retained essentially all the deuterium label. The results indicate that at least 29% of the 3-OH-BP detected as metabolite is formed through a 2,3-epoxide intermediate which rearranges spontaneously via an NIH shift mechanism to 3-OH-BP. At least 15% of the BP-3,6-quinone detected as a metabolite is derived from the enzymatically formed 3-OH-BP. |
| Databáze: | OpenAIRE |
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