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Research Article

The P450 Catalytic Cycle and Oxygenation Mechanism

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Pages 739-786 | Published online: 22 Sep 2008

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Read on this site (6)

David FV Lewis & Yuko Ito. (2010) Human CYPs involved in drug metabolism: structures, substrates and binding affinities. Expert Opinion on Drug Metabolism & Toxicology 6:6, pages 661-674.
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Jose M Jimenez-Lopez & Arthur I Cederbaum. (2005) CYP2E1-dependent oxidative stress and toxicity: role in ethanol-induced liver injury. Expert Opinion on Drug Metabolism & Toxicology 1:4, pages 671-685.
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David F. V. Lewis, Sandeep Modi & Maurice Dickins. (2002) Structure–activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metabolism Reviews 34:1-2, pages 69-82.
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David F. V. Lewis. (2002) Molecular modeling of human cytochrome P450–substrate interactions. Drug Metabolism Reviews 34:1-2, pages 55-67.
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Yurong Song, Chenxi Li, Guangzhi Liu, Rui Liu, Youwen Chen, Wen Li, Zhiwen Cao, Baosheng Zhao, Cheng Lu & Yuanyan Liu. (2021) Drug-Metabolizing Cytochrome P450 Enzymes Have Multifarious Influences on Treatment Outcomes. Clinical Pharmacokinetics 60:5, pages 585-601.
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Ajay Pradhan, Ceyhun Bereketoglu, Léa Martin, Justine Duhagon & Per-Erik Olsson. (2020) The food preservative ethoxyquin impairs zebrafish development, behavior and alters gene expression profile. Food and Chemical Toxicology 135, pages 110926.
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L. E. Khmelevtsova, I. S. Sazykin, M. A. Sazykina & E. Yu. Seliverstova. (2017) Prokaryotic cytochromes P450 (Review). Applied Biochemistry and Microbiology 53:4, pages 401-409.
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M. Tarocchi & A. Galli. 2017. Liver Pathophysiology. Liver Pathophysiology 279 287 .
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Andrew M. Smith. 2015. Functional Metallosupramolecular Materials. Functional Metallosupramolecular Materials 1 31 .
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Debdip Mukhopadhyay & Ansuman Chattopadhyay. (2014) Induction of Oxidative Stress and Related Transcriptional Effects of Sodium Fluoride in Female Zebrafish Liver. Bulletin of Environmental Contamination and Toxicology 93:1, pages 64-70.
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Arthur I. Cederbaum. (2012) Alcohol Metabolism. Clinics in Liver Disease 16:4, pages 667-685.
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Eugene G. Hrycay & Stelvio M. Bandiera. (2012) The monooxygenase, peroxidase, and peroxygenase properties of cytochrome P450. Archives of Biochemistry and Biophysics 522:2, pages 71-89.
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Manik C. Ghosh & Arun K. Ray. (2011) Regulation of cytochrome P4501A by protein kinase C: the role of heat shock protein70. Journal of Cell Communication and Signaling 6:1, pages 37-44.
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Ian Lai, Yingtao Chai, Don Simmons, Gregor Luthe, Mitchell C. Coleman, Douglas Spitz, Wanda M. Haschek, Gabriele Ludewig & Larry W. Robertson. (2010) Acute toxicity of 3,3′,4,4′,5-pentachlorobiphenyl (PCB 126) in male Sprague–Dawley rats: Effects on hepatic oxidative stress, glutathione and metals status. Environment International 36:8, pages 918-923.
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Adelina M. Voutchkova, Thomas G. Osimitz & Paul T. Anastas. (2010) Toward a Comprehensive Molecular Design Framework for Reduced Hazard. Chemical Reviews 110:10, pages 5845-5882.
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Yoshie Hirano & Takaharu Mizutani. (2003) Study of inhibition of CYP2A6 by some drugs derived from quinoline. Journal of Pharmacy and Pharmacology 55:12, pages 1667-1672.
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Julie A. Reisz, Erika Bechtold & S. Bruce King. (2010) Oxidative heme protein-mediated nitroxyl (HNO) generation. Dalton Transactions 39:22, pages 5203.
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Peter H. Bui & Oliver Hankinson. (2009) Functional Characterization of Human Cytochrome P450 2S1 Using a Synthetic Gene-Expressed Protein in Escherichia coli . Molecular Pharmacology 76:5, pages 1031-1043.
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Arthur I. Cederbaum, Yongke Lu & Defeng Wu. (2009) Role of oxidative stress in alcohol-induced liver injury. Archives of Toxicology 83:6, pages 519-548.
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Yongke Lu & Arthur I. Cederbaum. (2008) CYP2E1 and oxidative liver injury by alcohol. Free Radical Biology and Medicine 44:5, pages 723-738.
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Arthur I. Cederbaum. 2008. Advances in Bioactivation Research. Advances in Bioactivation Research 1 36 .
Daniel Collado, Ezequiel Perez-Inestrosa, Rafael Suau & Juan T. Lopez Navarrete. (2006) Regioselective hydroxylation of phenols by simultaneous photochemical generation of phenol cation-radical and hydroxyl radical. Tetrahedron 62:12, pages 2927-2935.
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David F.V. Lewis, Yuko Ito & Peter S. Goldfarb. (2005) Cytochrome P450 structures and their substrate interactions. Drug Development Research 66:1, pages 19-24.
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Hiroyuki Yasui, Seiko Hayashi & Hiromu Sakurai. (2005) Possible Involvement of Singlet Oxygen Species as Multiple Oxidants in P450 Catalytic Reactions. Drug Metabolism and Pharmacokinetics 20:1, pages 1-13.
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Peter Hlavica. (2004) Models and mechanisms of O‐O bond activation by cytochrome P450. European Journal of Biochemistry 271:22, pages 4335-4360.
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Shahriar Haji-Momenian, Jayson M Rieger, Timothy L Macdonald & Milton L Brown. (2003) Comparative molecular field analysis and QSAR on substrates binding to cytochrome P450 2D6. Bioorganic & Medicinal Chemistry 11:24, pages 5545-5554.
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Ulrik Jurva, Håkan V. Wikström, Lars Weidolf & Andries P. Bruins. (2003) Comparison between electrochemistry/mass spectrometry and cytochrome P450 catalyzed oxidation reactions. Rapid Communications in Mass Spectrometry 17:8, pages 800-810.
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David F. V. Lewis. (2003) Quantitative structure–activity relationships (QSARs) within the cytochrome P450 system: QSARs describing substrate binding, inhibition and induction of P450s. InflammoPharmacology 11:1, pages 43-73.
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W. Nam. 2003. Comprehensive Coordination Chemistry II. Comprehensive Coordination Chemistry II 281 307 .
David F?V Lewis. (2002) Oxidative stress: the role of cytochromes P450 in oxygen activation. Journal of Chemical Technology & Biotechnology 77:10, pages 1095-1100.
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Hossein Hamzeiy, Nasser Vahdati-Mashhadian, Helen J. Edwards & Peter S. Goldfarb. (2002) Mutation analysis of the human CYP3A4 gene 5′ regulatory region: population screening using non-radioactive SSCP. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis 500:1-2, pages 103-110.
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Hiroyuki Yasui, Kazuko Deo, Yuko Ogura, Hiromi Yoshida, Toshifumi Shiraga, Akira Kagayama & Hiromu Sakurai. (2002) Evidence for Singlet Oxygen Involvement in Rat and Human Cytochrome P450-dependent Substrate Oxidations. Drug Metabolism and Pharmacokinetics 17:5, pages 416-426.
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Yoshie Hirano, Mayumi Uehara, Ken-ichi Saeki, Taka-aki Kato, Kazuhiko Takahashi & Takaharu Mizutani. (2002) The Influence of Quinolines on Coumarin 7-Hydroxylation in Bovine Liver Microsomes and Human CYP2A6.. Journal of Health Science 48:2, pages 118-125.
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D.F.V Lewis & M Dickins. (2002) Factors influencing rates and clearance in P450-mediated reactions: QSARs for substrates of the xenobiotic-metabolizing hepatic microsomal P450s. Toxicology 170:1-2, pages 45-53.
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D. F. V. Lewis. 2002. Pharmacokinetic Challenges in Drug Discovery. Pharmacokinetic Challenges in Drug Discovery 235 248 .
Damián A. Scherlis, Marcelo A. Martí, Pablo Ordejón & Darío A. Estrin. (2002) Environment effects on chemical reactivity of heme proteins. International Journal of Quantum Chemistry 90:4-5, pages 1505-1514.
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David Lewis. 2001. Guide to Cytochromes P450. Guide to Cytochromes P450 164 210 .
Robert Barouki & Yannick Morel. (2001) Repression of cytochrome P450 1A1 gene expression by oxidative stress: mechanisms and biological implications. Biochemical Pharmacology 61:5, pages 511-516.
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David F.V. Lewis & Peter Hlavica. (2000) Interactions between redox partners in various cytochrome P450 systems: functional and structural aspects. Biochimica et Biophysica Acta (BBA) - Bioenergetics 1460:2-3, pages 353-374.
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P. J. Korytko, R. J. Maclntyre & J. G. Scott. (2001) Expression and activity of a house‐fly cytochrome P450, CYP6D1, in Drosophila melanogaster . Insect Molecular Biology 9:5, pages 441-449.
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Frank A.E. Kruyt & Hagop Youssoufian. (2000) Do Fanconi anemia genes control cell response to cross-linking agents by modulating cytochrome P-450 reductase activity?. Drug Resistance Updates 3:4, pages 211-215.
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David F.V. Lewis. (2000) On the recognition of mammalian microsomal cytochrome P450 substrates and their characteristics. Biochemical Pharmacology 60:3, pages 293-306.
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Damián A. Scherlis, Cora B. Cymeryng & Darío A. Estrin. (2000) Nitric Oxide Binding to Ferric Cytochrome P450:  A Computational Study. Inorganic Chemistry 39:11, pages 2352-2359.
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André Rico. (2000) Pollutions et pratiques agricoles. Deux concepts : dose journalière admissible et chimiodéfense. Comptes Rendus de l'Académie des Sciences - Series III - Sciences de la Vie 323:5, pages 435-440.
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David F.V. Lewis. (2000) Structural characteristics of human P450s involved in drug metabolism: QSARs and lipophilicity profiles. Toxicology 144:1-3, pages 197-203.
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Slobodan Rendic, Eckhard Nolteernsting & Wilhelm Schänzer. (1999) Metabolism of anabolic steroids by recombinant human cytochrome P450 enzymes. Journal of Chromatography B: Biomedical Sciences and Applications 735:1, pages 73-83.
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David F.V. Lewis. (1999) Homology modelling of human cytochromes P450 involved in xenobiotic metabolism and rationalization of substrate selectivity. Experimental and Toxicologic Pathology 51:4-5, pages 369-374.
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D.F.V. Lewis, P.J. Eddershaw, M. Dickins, M.H. Tarbit & P.S. Goldfarb. (1998) Structural determinants of cytochrome P450 substrate specificity, binding affinity and catalytic rate. Chemico-Biological Interactions 115:3, pages 175-199.
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