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Xenobiotica
the fate of foreign compounds in biological systems
Volume 29, 1999 - Issue 4
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Research Article

Molecular modelling of CYP2B6, the human CYP2B isoform, by homology with the substrate-bound CYP102 crystal structure: evaluation of CYP2B6 substrate characteristics, the cytochrome b5 binding site and comparisons with CYP2B1 and CYP2B4

D. F. V. LEWIS Molecular Toxicology Group, School of Biological Sciences, University of Surrey, Guildford GU2 5XH, UK
,
B. G. LAKE Molecular Toxicology Group, School of Biological Sciences, University of Surrey, Guildford GU2 5XH, UK
,
M. DICKINS Molecular Toxicology Group, School of Biological Sciences, University of Surrey, Guildford GU2 5XH, UK
,
P. J. EDDERSHAW Molecular Toxicology Group, School of Biological Sciences, University of Surrey, Guildford GU2 5XH, UK
,
M. H. TARBIT Molecular Toxicology Group, School of Biological Sciences, University of Surrey, Guildford GU2 5XH, UK
&
P. S. GOLDFARB Molecular Toxicology Group, School of Biological Sciences, University of Surrey, Guildford GU2 5XH, UK
Pages 361-393 | Published online: 22 Sep 2008

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David FV Lewis, Yuko Ito & Brian G Lake. (2010) Quantitative structure-activity relationships (QSARs) for inhibitors and substrates of CYP2B enzymes: importance of compound lipophilicity in explanation of potency differences. Journal of Enzyme Inhibition and Medicinal Chemistry 25:5, pages 679-684.
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J.H. Ren, X.Q. Xiong, Y. Sha, M.C. Yan, B. Lin, J. Wang, Y.K. Jing, D.M. Zhao & M.S. Cheng. (2008) Structure prediction and R115866 binding study of human CYP26A1: homology modelling, fold recognition, molecular docking and MD simulations. Molecular Simulation 34:3, pages 337-346.
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Ram K. Sindhu, Ja-Ryung Koo, Kunal K. Sindhu, Ashkan Ehdaie, Farbod Farmand & Christian K. Roberts. (2006) Differential regulation of hepatic cytochrome P450 monooxygenases in streptozotocin-induced diabetic rats. Free Radical Research 40:9, pages 921-928.
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Guohua Qin & Ziqiang Meng$suffix/text()$suffix/text(). (2006) Effect of Sulfur Dioxide Inhalation on CYP2B1/2 and CYP2E1 in Rat Liver and Lung. Inhalation Toxicology 18:8, pages 581-588.
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Slobodan Rendic. (2002) Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metabolism Reviews 34:1-2, pages 83-448.
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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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DAVID F. V. LEWIS. (1999) FRONTIER ORBITALS IN CHEMICAL AND BIOLOGICAL ACTIVITY: QUANTITATIVE RELATIONSHIPS AND MECHANISTIC IMPLICATIONS*. Drug Metabolism Reviews 31:3, pages 755-816.
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SEAN EKINS & STEVEN A. WRIGHTON. (1999) THE ROLE OF CYP2B6 IN HUMAN XENOBIOTIC METABOLISM*. Drug Metabolism Reviews 31:3, pages 719-754.
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Articles from other publishers (40)

Ethan D. Angle & Philip M. Cox. (2023) Multidisciplinary Insights into the Structure–Function Relationship of the CYP2B6 Active Site. Drug Metabolism and Disposition 51:3, pages 369-384.
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Usman Ali Ashfaq, Farah Shahid & Samman Munir. 2022. Biochemistry of Drug Metabolizing Enzymes. Biochemistry of Drug Metabolizing Enzymes 29 72 .
Pan-Fen Wang, Alicia Neiner & Evan D. Kharasch. (2019) Efavirenz Metabolism: Influence of Polymorphic CYP2B6 Variants and Stereochemistry. Drug Metabolism and Disposition 47:10, pages 1195-1205.
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Pan-Fen Wang, Alicia Neiner, Thomas R. Lane, Kimberley M. Zorn, Sean Ekins & Evan D. Kharasch. (2018) Halogen Substitution Influences Ketamine Metabolism by Cytochrome P450 2B6: In Vitro and Computational Approaches. Molecular Pharmaceutics 16:2, pages 898-906.
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Brooks T. McPhail, Catherine A. White, Brian S. Cummings, Srinivasa Muralidhara, Jewell T. Wilson & James V. Bruckner. (2016) The immature rat as a potential model for chemical risks to children: Ontogeny of selected hepatic P450s. Chemico-Biological Interactions 256, pages 167-177.
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Jiaojiao Cao, Liwei Zheng, Lin Ji, Dan Lu, Ying Peng & Jiang Zheng. (2015) Mechanism-based inactivation of cytochrome P450 2B6 by isoimperatorin. Chemico-Biological Interactions 226, pages 23-29.
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F. Peter Guengerich. 2015. Cytochrome P450. Cytochrome P450 523 785 .
Miia Turpeinen & Ulrich M. Zanger. (2012) Cytochrome P450 2B6: function, genetics, and clinical relevance. Drug Metabolism and Drug Interactions 27:4.
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Dumrongsak Pekthong, Coraline Desbans, Hélène Martin & Lysiane Richert. (2012) Bupropion Hydroxylation as a Selective Marker of Rat CYP2B1 Catalytic Activity. Drug Metabolism and Disposition 40:1, pages 32-38.
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Martha C. Rosales-Hernández, Jessica E. Mendieta-Wejebe, José G. Trujillo-Ferrara & José Correa-Basurto. (2010) Homology modeling and molecular dynamics of CYP1A1 and CYP2B1 to explore the metabolism of aryl derivatives by docking and experimental assays. European Journal of Medicinal Chemistry 45:11, pages 4845-4855.
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Max K. Leong, Yen-Ming Chen & Tzu-Hsien Chen. (2009) Prediction of human cytochrome P450 2B6-substrate interactions using hierarchical support vector regression approach. Journal of Computational Chemistry 30:12, pages 1899-1909.
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Larry J. Jolivette & Sean Ekins. 2007. 131 176 .
Monica I. Jushchyshyn, Jan L. Wahlstrom, Paul F. Hollenberg & Larry C. Wienkers. (2006) Mechanism of Inactivation of Human Cytochrome P450 2B6 by Phencyclidine. Drug Metabolism and Disposition 34:9, pages 1523-1529.
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Peter Hlavica. (2006) Functional interaction of nitrogenous organic bases with cytochrome P450: A critical assessment and update of substrate features and predicted key active-site elements steering the access, binding, and orientation of amines. Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics 1764:4, pages 645-670.
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David F.V. Lewis, Brian G. Lake, Yuko Ito & Pavel Anzenbacher. (2006) QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS (QSARs) WITHIN CYTOCHROMES P450 2B (CYP2B) SUBFAMILY ENZYMES: THE IMPORTANCE OF LIPOPHILICITY FOR BINDING AND METABOLISM. Drug Metabolism and Drug Interactions 21:3-4.
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Daniel Desaulniers, Gerard M. Cooke, Karen Leingartner, Korian Soumano, Jonathan Cole, Jack Yang, Michael Wade & Algis Yagminas. (2016) Effects of Postnatal Exposure to a Mixture of Polychlorinated Biphenyls, p , p ′-dichlorodiphenyltrichloroethane, and p - p ′-dichlorodiphenyldichloroethene in Prepubertal and Adult Female Sprague-Dawley Rats . International Journal of Toxicology 24:2, pages 111-127.
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Carol A. Kemp, Jean-Didier Maréchal & Michael J. Sutcliffe. (2005) Progress in cytochrome P450 active site modeling. Archives of Biochemistry and Biophysics 433:2, pages 361-368.
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F. Peter Guengerich. 2005. Cytochrome P450. Cytochrome P450 377 530 .
Thomas Lang, Kathrin Klein, Tanja Richter, Arne Zibat, Reinhold Kerb, Michel Eichelbaum, Matthias Schwab & Ulrich M. Zanger. (2004) Multiple Novel Nonsynonymous CYP2B6 Gene Polymorphisms in Caucasians: Demonstration of Phenotypic Null Alleles . Journal of Pharmacology and Experimental Therapeutics 311:1, pages 34-43.
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P. Hlavica, J. Schulze & D.F.V. Lewis. (2003) Functional interaction of cytochrome P450 with its redox partners: a critical assessment and update of the topology of predicted contact regions. Journal of Inorganic Biochemistry 96:2-3, pages 279-297.
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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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Kerri A Schoedel & Rachel F Tyndale. (2003) Induction of nicotine-metabolizing CYP2B1 by ethanol and ethanol-metabolizing CYP2E1 by nicotine: summary and implications. Biochimica et Biophysica Acta (BBA) - General Subjects 1619:3, pages 283-290.
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Monica I. Jushchyshyn, Ute M. Kent & Paul F. Hollenberg. (2003) The Mechanism-Based Inactivation of Human Cytochrome P450 2B6 by Phencyclidine. Drug Metabolism and Disposition 31:1, pages 46-52.
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Anna Gorokhov, Masahiko Negishi, Eric F. Johnson, Lars C. Pedersen, Lalith Perera, Tom A. Darden & Lee G. Pedersen. (2003) Explicit Water Near the Catalytic I Helix Thr in the Predicted Solution Structure of CYP2A4. Biophysical Journal 84:1, pages 57-68.
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David F.V. Lewis. (2002) Modelling human cytochromes P450 involved in drug metabolism from the CYP2C5 crystallographic template. Journal of Inorganic Biochemistry 91:4, pages 502-514.
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Stewart B Kirton, Carol A Baxter & Michael J Sutcliffe. (2002) Comparative modelling of cytochromes P450. Advanced Drug Delivery Reviews 54:3, pages 385-406.
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Marcel J. de Groot & Sean Ekins. (2002) Pharmacophore modeling of cytochromes P450. Advanced Drug Delivery Reviews 54:3, pages 367-383.
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D.F.V. Lewis, B.G. Lake, M. Dickins & P.S. Goldfarb. (2002) Molecular Modelling of CYP2B6 Based on Homology with the CYP2C5 Crystal Structure: Analysis of Enzyme-Substrate Interactions. Drug Metabolism and Drug Interactions 19:2.
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Qinmi Wang & James R. Halpert. (2002) Combined Three-Dimensional Quantitative Structure-Activity Relationship Analysis of Cytochrome P450 2B6 Substrates and Protein Homology Modeling. Drug Metabolism and Disposition 30:1, pages 86-95.
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D. F. V. Lewis. 2002. Pharmacokinetic Challenges in Drug Discovery. Pharmacokinetic Challenges in Drug Discovery 235 248 .
Kerri A. Schoedel, Edward M. Sellers & Rachel F. Tyndale. (2001) Induction of CYP2B1/2 and nicotine metabolism by ethanol in rat liver but not rat brain22Abbreviations: CYP, cytochrome P450; C8 xanthate, potassium octylxanthate; NCO, nicotine C-oxidation; NDMA, N-nitrosodimethylamine; NMA, N-nitroso-N-methylaniline; NNK, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone; and SSC, saline-sodium citrate buffer.. Biochemical Pharmacology 62:8, pages 1025-1036.
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Emily E. Scott, Margit Spatzenegger & James R. Halpert. (2001) A Truncation of 2B Subfamily Cytochromes P450 Yields Increased Expression Levels, Increased Solubility, and Decreased Aggregation While Retaining Function. Archives of Biochemistry and Biophysics 395:1, pages 57-68.
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Peter Hlavica & David F. V. Lewis. (2008) Allosteric phenomena in cytochrome P450‐catalyzed monooxygenations. European Journal of Biochemistry 268:18, pages 4817-4832.
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Thomas N. Thompson. (2001) Optimization of metabolic stability as a goal of modern drug design. Medicinal Research Reviews 21:5, pages 412-449.
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David Lewis. 2001. Guide to Cytochromes P450. Guide to Cytochromes P450 164 210 .
D.F.V. Lewis, S. Modi & M. Dickins. (2001) Quantitative Structure-Activity Relationships (QSARs) Within Substrates of Human Cytochromes P450 Involved in Drug Metabolism. Drug Metabolism and Drug Interactions 18:3-4.
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Matthew D. Wessel & Scot Mente. 2001. 257 266 .
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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Kelly A. Regal, Michael L. Schrag, Ute M. Kent, Larry C. Wienkers & Paul F. Hollenberg. (2000) Mechanism-Based Inactivation of Cytochrome P450 2B1 by 7-Ethynylcoumarin:  Verification of Apo-P450 Adduction by Electrospray Ion Trap Mass Spectrometry. Chemical Research in Toxicology 13:4, pages 262-270.
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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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