Cytochrome P450

Paul R. Ortiz de MontellanoEditor

Cytochrome P450

Structure, Mechanism, and Biochemistry4th edition

ISBN 978-3-319-12107-9 ISBN 978-3-319-12108-6 (eBook)DOI 10.1007/978-3-319-12108-6

Library of Congress Control Number: 2014956772

Springer Cham Heidelberg New York Dordrecht London© Springer International Publishing Switzerland 2015This 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.

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Springer is part of Springer Science+Business Media (www.springer.com)

EditorPaul R. Ortiz de MontellanoUniversity of California, San Francisco,San FranciscoCaliforniaUSA

v

Contents

Part I Volume 1����������������������������������������������������������������������������������� 1

1 Structures of Cytochrome P450 Enzymes ������������������������������������ 3Thomas L� Poulos and Eric F� Johnson

2 Electron Transfer Partners of Cytochrome P450 ������������������������� 33Lucy Waskell and Jung-Ja P� Kim

3 Activation of Molecular Oxygen in Cytochromes P450 ��������������� 69Ilia G� Denisov and Stephen G� Sligar

4 Substrate Oxidation by Cytochrome P450 Enzymes �������������������� 111Paul R� Ortiz de Montellano

5 Inhibition of Cytochrome P450 Enzymes ������������������������������������� 177Maria Almira Correia and Paul� F� Hollenberg

6 Microbial Cytochromes P450 ��������������������������������������������������������� 261Kirsty J� McLean, David Leys and Andrew W� Munro

7 P450s in Plants, Insects, and Their Fungal Pathogens ���������������� 409Mary A� Schuler

8 P450 Biotechnology ������������������������������������������������������������������������� 451Marco Girhard, Patrick J� Bakkes, Osama Mahmoud and Vlada B� Urlacher

Part II Volume 2 ��������������������������������������������������������������������������������� 521

9 Human Cytochrome P450 Enzymes ���������������������������������������������� 523F� Peter Guengerich

10 Nuclear Receptor-Mediated Regulation of Cytochrome P450 Genes ����������������������������������������������������������������� 787Saki Gotoh, Marumi Ohno, Kouichi Yoshinari, Masahiko Negishi and Kaname Kawajiri

vi Contents

11 Hormonal Regulation of Liver Cytochrome P450 Enzymes ������� 813David J� Waxman and Thomas K� H� Chang

12 P450 Enzymes in Steroid Processing ��������������������������������������������� 851Richard J� Auchus and Walter L� Miller

13 P450 Enzymes in Lipid Oxidation ������������������������������������������������� 881Matthew L� Edin, Jennifer Cheng, Artiom Gruzdev, Samantha L� Hoopes and Darryl C� Zeldin

Index ������������������������������������������������������������������������������������������������������� 907

vii

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 cur-rently 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 B�B� Brodie Award in Drug Metabolism from the American Society of Phar-macology and Experimental Therapeutics, the R�T� 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�

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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 Pharmacol-ogy, 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 Düs-seldorf, Düsseldorf, Germany

Saki Gotoh Pharmacogenetics Section, Laboratory of Reproductive and Developmental Toxicology, National Institute of Environmental Health Sci-ences, 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

x Contributors

Kaname Kawajiri Research Institute for Clinical Oncology, Saitama Can-cer Center, Ina-machi, Saitama, Japan

J.-J. Kim Department of Biochemistry, Medical College of Wisconsin, Mil-waukee, WI, USA

David Leys Faculty of Life Sciences, Manchester Institute of Biotechnol-ogy, 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 Bio-technology, 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 Bio-technology, 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 Sci-ences, 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, Univer-sity 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 Phar-maceutical 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