ArticleArchives of biochemistry and biophysics2011
Molecular probes of the mechanism of cytochrome P450. Oxygen traps a substrate radical intermediate.
Article in Archives of biochemistry and biophysics, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 45 citations in OpenAlex.
- High-Valent Late Transition Metal-Oxo Complexes: Breaking Boundaries at the Oxo Wall and Beyond.Chemical reviews · 2026Review
- Influence of Cage Effects in Directing the Outcome of C-X Bond Forming Reactions.ACS organic & inorganic Au · 2024Review
- Current state and future perspectives of cytochrome P450 enzymes for C-H and C=C oxygenation.Synthetic and systems biotechnology · 2022Article
- Oxygen Activation and Radical Transformations in Heme Proteins and Metalloporphyrins.Chemical reviews · 2018Review
- The Enigmatic P450 Decarboxylase OleT Is Capable of, but Evolved To Frustrate, Oxygen Rebound Chemistry.Biochemistry · 2017Article
- Divergent mechanisms of iron-containing enzymes for hydrocarbon biosynthesis.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2017Review
- Beyond ferryl-mediated hydroxylation: 40 years of the rebound mechanism and C-H activation.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2017Review
- O-H Activation by an Unexpected Ferryl Intermediate during Catalysis by 2-Hydroxyethylphosphonate Dioxygenase.Journal of the American Chemical Society · 2017Article
- OBiochemistry · 2016Article
- Rapid kinetic methods to dissect steroidogenic cytochrome P450 reaction mechanisms.The Journal of steroid biochemistry and molecular biology · 2016Review
- Protective effects of acerola juice on genotoxicity induced by iron in vivo.Genetics and molecular biology · 2016Article
- A comprehensive test set of epoxidation rate constants for iron(iv)-oxo porphyrin cation radical complexes.Chemical science · 2015Article
- Differences and comparisons of the properties and reactivities of iron(III)-hydroperoxo complexes with saturated coordination sphere.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Human recombinant cytochrome P450 enzymes display distinct hydrogen peroxide generating activities during substrate independent NADPH oxidase reactions.Toxicological sciences : an official journal of the Society of Toxicology · 2014Article
- Unusual cytochrome p450 enzymes and reactions.The Journal of biological chemistry · 2013Review
- Article
- Substrate specificity and reaction mechanism of purified alkane hydroxylase from the hydrocarbonoclastic bacterium Alcanivorax borkumensis (AbAlkB).Journal of inorganic biochemistry · 2013Article
- Article
- Parallel and competitive pathways for substrate desaturation, hydroxylation, and radical rearrangement by the non-heme diiron hydroxylase AlkB.Journal of the American Chemical Society · 2012Article
- NADPH-cytochrome P450 oxidoreductase: prototypic member of the diflavin reductase family.Archives of biochemistry and biophysics · 2012Review
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
The diagnostic substrate tetramethylcyclopropane (TMCP) has been reexamined as a substrate with three drug- and xenobiotic-metabolizing cytochrome P450 enzymes, human CYP2E1, CYP3A4 and rat CYP2B1. The major hydroxylation product in all cases was the unrearranged primary alcohol along with smaller amounts of a rearranged tertiary alcohol. Significantly, another ring-opened product, diacetone alcohol, was also observed. With CYP2E1 this product accounted for 20% of the total turnover. Diacetone alcohol also was detected as a product from TMCP with a biomimetic model catalyst, FeTMPyP, but not with a ruthenium porphyrin catalyst. Lifetimes of the intermediate radicals were determined from the ratios of rearranged and unrearranged products to be 120, 13 and 1ps for CYP2E1, CYP3A4 and CYP2B1, respectively, corresponding to rebound rates of 0.9×10(10)s(-1), 7.2×10(10)s(-1) and 1.0×10(12)s(-1). For the model iron porphyrin, FeTMPyP, a radical lifetime of 81ps and a rebound rate of 1.2×10(10)s(-1) were determined. These apparent radical lifetimes are consistent with earlier reports with a variety of CYP enzymes and radical clock substrates, however, the large amounts of diacetone alcohol with CYP2E1 and the iron porphyrin suggest that for these systems a considerable amount of the intermediate carbon radical is trapped by molecular oxygen. These results add to the view that cage escape of the intermediate carbon radical in [Fe(IV)-OH ()R] can compete with cage collapse to form a C-O bond. The results could be significant with regard to our understanding of iron-catalyzed C-H hydroxylation, the observation of P450-dependent peroxidation and the development of oxidative stress, especially for CYP2E1.
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