Metabolism of 1- and 3-Fluorobenzo[a]pyrene by Cytochrome p450 and Horseradish Peroxidase
| Autor: | N. V. S. RamaKrishna, Eleanor G. Rogan, Prabhakar D. Devanesan, Patrick P.J. Mulder, Ercole L. Cavalieri |
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| Rok vydání: | 1994 |
| Předmět: | |
| Zdroj: | Polycyclic Aromatic Compounds. 7:129-136 |
| ISSN: | 1563-5333 1040-6638 |
| Popis: | Benzo[a]pyrene (BP) is a good model for elucidating the mechanism of oxygen transfer for substrates that are considered good electron donors. Fluoro substitution of BP represents a suitable probe for studying mechanisms of oxygen transfer in the metabolic formation of BP quinones and BP phenols. By using this strategy with 6-fluoroBP (6-FBP), we have previously demonstrated that the BP quinones are formed metabolically via an initial one-electron oxidation of BP catalyzed by cytochrome P450. Now we have synthesized 1-FBP and 3-FBP with the purpose of elucidating the mechanism of phenol formation. If formation of 3-hydroxyBP (3-OHBP) (major metabolite of BP) and 1-OHBP (minor metabolite of BP) occurs via an initial electron transfer from BP to cytochrome P450, when we use 3-FBP and 1-FBP as substrates, one of the metabolites formed should be BP-3,6-dione and BP-1,6-dione, respectively, with displacement of fluorine. Metabolism of 1-FBP and 3-FBP by rat liver microsomes and by horseradish peroxidas... |
| Databáze: | OpenAIRE |
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