Paul R. Ortiz de Montellano Editor. Cytochrome P450. Structure, Mechanism, and Biochemistry. 4th edition

Transcription

1 Cytochrome P450

2 Paul R. Ortiz de Montellano Editor Cytochrome P450 Structure, Mechanism, and Biochemistry 4th edition

3 Editor Paul R. Ortiz de Montellano University of California, San Francisco, San Francisco California USA ISBN DOI / ISBN (ebook) Library of Congress Control Number: Springer Cham Heidelberg New York Dordrecht London Springer International Publishing Switzerland 2015 This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. The publisher, the authors and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained herein or for any errors or omissions that may have been made. Printed on acid-free paper Springer is part of Springer Science+Business Media (

4 Contents Part I Volume Structures of Cytochrome P450 Enzymes 3 Thomas L. Poulos and Eric F. Johnson 2 Electron Transfer Partners of Cytochrome P Lucy Waskell and Jung-Ja P. Kim 3 Activation of Molecular Oxygen in Cytochromes P Ilia G. Denisov and Stephen G. Sligar 4 Substrate Oxidation by Cytochrome P450 Enzymes 111 Paul R. Ortiz de Montellano 5 Inhibition of Cytochrome P450 Enzymes 177 Maria Almira Correia and Paul. F. Hollenberg 6 Microbial Cytochromes P Kirsty J. McLean, David Leys and Andrew W. Munro 7 P450s in Plants, Insects, and Their Fungal Pathogens 409 Mary A. Schuler 8 P450 Biotechnology 451 Marco Girhard, Patrick J. Bakkes, Osama Mahmoud and Vlada B. Urlacher Part II Volume Human Cytochrome P450 Enzymes 523 F. Peter Guengerich 10 Nuclear Receptor-Mediated Regulation of Cytochrome P450 Genes 787 Saki Gotoh, Marumi Ohno, Kouichi Yoshinari, Masahiko Negishi and Kaname Kawajiri v

5 vi Contents 11 Hormonal Regulation of Liver Cytochrome P450 Enzymes 813 David J Waxman and Thomas K H Chang 12 P450 Enzymes in Steroid Processing 851 Richard J Auchus and Walter L Miller 13 P450 Enzymes in Lipid Oxidation 881 Matthew L Edin, Jennifer Cheng, Artiom Gruzdev, Samantha L Hoopes and Darryl C Zeldin Index 907

6 About the Editor Paul R. Ortiz de Montellano received his PhD in bioorganic chemistry from Harvard University, Cambridge, MA After postdoctoral work as a North Atlantic Treaty Organization Fellow in Zürich, Switzerland, and a stint with Syntex in Mexico City and Palo Alto, California, he joined the faculty of the University of California in San Francisco, where he is currently Professor, Vice-chair of the Department of Pharmaceutical Chemistry, and Associate Dean for Research of the School of Pharmacy His research interests center on the structure, mechanism, inhibition, and biochemistry of hemoproteins, including the cytochrome P450 enzymes He has received the BB Brodie Award in Drug Metabolism from the American Society of Pharmacology and Experimental Therapeutics, the RT Williams Distinguished Scientific Achievement Award from the International Society for the Study of Xenobiotics, and the Ernest H Volwiler Research Achievement Award from the American Association of Colleges of Pharmacy vii

7 Contributors Richard J. Auchus Division of Metabolism, Endocrinology, and Diabetes, Department of Internal Medicine, University of Michigan Medical Center, Ann Arbor, MI, USA Patrick J. Bakkes Institute of Biochemistry, Heinrich Heine University Düsseldorf, Düsseldorf, Germany Thomas K. H. Chang Faculty of Pharmaceutical Sciences, The University of British Columbia, Vancouver, BC, Canada Jennifer Cheng Division of Intramural Research, National Institute of Environmental Health Sciences, Research Triangle Park, NC, USA Maria Almira Correia Department of Cellular and Molecular Pharmacology, University of California, San Francisco, CA, USA Ilia G. Denisov Department of Biochemistry, The School of Molecular and Cellular Biology, University of Illinois, Urbana, IL, USA Matthew L. Edin Division of Intramural Research, National Institute of Environmental Health Sciences, Research Triangle Park, NC, USA Marco Girhard Institute of Biochemistry, Heinrich Heine University Düsseldorf, Düsseldorf, Germany Saki Gotoh Pharmacogenetics Section, Laboratory of Reproductive and Developmental Toxicology, National Institute of Environmental Health Sciences, National Institutes of Health, Research Triangle Park, NC, USA Artiom Gruzdev Division of Intramural Research, National Institute of Environmental Health Sciences, Research Triangle Park, NC, USA F. Peter Guengerich Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine, Nashville, TN, USA Paul. F. Hollenberg Department of Pharmacology, University of Michigan, Ann Arbor, MI, USA Samantha L. Hoopes Division of Intramural Research, National Institute of Environmental Health Sciences, Research Triangle Park, NC, USA Eric F. Johnson Department of Molecular and Experimental Medicine, The Scripps Research Institute, La Jolla, CA, USA ix

8 x Contributors Kaname Kawajiri Research Institute for Clinical Oncology, Saitama Cancer Center, Ina-machi, Saitama, Japan J.-J. Kim Department of Biochemistry, Medical College of Wisconsin, Milwaukee, WI, USA David Leys Faculty of Life Sciences, Manchester Institute of Biotechnology, The University of Manchester, Manchester, UK Osama Mahmoud Institute of Biochemistry, Heinrich Heine University Düsseldorf, Düsseldorf, Germany Kirsty J. McLean Faculty of Life Sciences, Manchester Institute of Biotechnology, The University of Manchester, Manchester, UK Walter L. Miller Division of Endocrinology, Department of Pediatrics, University of California, San Francisco, CA, USA Andrew W. Munro Faculty of Life Sciences, Manchester Institute of Biotechnology, The University of Manchester, Manchester, UK Masahiko Negishi Pharmacogenetics Section, Laboratory of Reproductive and Developmental Toxicology, National Institute of Environmental Health Sciences, National Institutes of Health, Research Triangle Park, NC, USA Marumi Ohno Pharmacogenetics Section, Laboratory of Reproductive and Developmental Toxicology, National Institute of Environmental Health Sciences, National Institutes of Health, Research Triangle Park, NC, USA Paul R. Ortiz de Montellano Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA Thomas L. Poulos Departments of Molecular Biology and Biochemistry, Pharmaceutical Sciences, and Chemistry, University of California, Irvine, CA, USA Mary A. Schuler Department of Cell and Developmental Biology, University of Illinois, Urbana, IL, USA Stephen G. Sligar Department of Biochemistry, The School of Molecular and Cellular Biology, University of Illinois, Urbana, IL, USA Vlada B. Urlacher Institute of Biochemistry, Heinrich Heine University Düsseldorf, Düsseldorf, Germany Lucy Waskell University of Michigan Medical School and VA Medical Center, Ann Arbor, MI, USA David J. Waxman Division of Cell and Molecular Biology, Department of Biology, Boston University, Boston, MA, USA Kouichi Yoshinari Department of Molecular Toxicology, School of Pharmaceutical Sciences, University of Shizuoka, Suruga-ku, Shizuoka, Japan Darryl C. Zeldin Division of Intramural Research, National Institute of Environmental Health Sciences, Research Triangle Park, NC, USA