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The Ubiquitous Roles of Cytochrome P450 Proteins: Metal Ions in Life Sciences, Volume 3

Astrid Sigel (Editor), Helmut Sigel (Co-Editor), Roland K. O. Sigel (Co-Editor)
ISBN: 978-0-470-01672-5
678 pages
April 2007
The Ubiquitous Roles of Cytochrome P450 Proteins: Metal Ions in Life Sciences, Volume 3 (0470016728) cover image
Helmut Sigel, Astrid Sigel and Roland K.O. Sigel, in close cooperation with John Wiley & Sons launch a new Series “Metal Ions in Life Sciences”.

There exists a whole range of books on Cytochromes P450, but none with the focus of this volume. This new volume in the Series concentrates on current hot topics in the area and tries to work out the underlying common developments.

As a result the reader will find a systematic account of new results in this exciting research area. The table of contents gives an idea on the wide span of chapters, starting with overviews and the presentation of specific systems, and ending with chapters on carbon-carbon bond cleavage by P450 sytems, drug metabolism as catalyzed by P450 systems, decomposition of xenobiotics by P450 enzymes and design and engineering of new P450 systems.

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HISTORICAL DEVELOPMENT AND PERSPECTIVES OF THE SERIES.

PREFACE TO VOLUME 3.

CONTRIBUTORS TO VOLUME 3.

TITLES OF VOLUMES 1–44 IN THE METAL IONS IN BIOLOGICAL SYSTEMS SERIES.

CONTENTS OF VOLUMES IN THE METAL IONS IN LIFE SCIENCES SERIES.

1 DIVERSITIES AND SIMILARITIES IN P450 SYSTEMS: AN INTRODUCTION (Mary A. Schuler and Stephen G. Sligar).

1. Oxygenases: Mediators of Biochemical Diversity.

2. P450 Superfamily: Diversity at the Sequence Level.

3. Diversity of P450 Structures: Folds and Conformations for Functions.

4. Diversity in P450 Mechanisms.

5. Diversity in Regulation Across the Superfamily.

6. Diversity in the Evolution of Common Metabolic Functions.

7. Summary and Outlook.

Acknowledgments.

Abbreviations.

References.

2 STRUCTURAL AND FUNCTIONAL MIMICS OF CYTOCHROMES P450 (Wolf-D. Woggon).

1. Introduction.

2. Iron Porphyrins Carrying a Thiolate or Modified Thiolate Ligand.

3. Structurally Remote P450 Mimics.

4. Concluding Remarks.

Acknowledgments.

Abbreviations.

References.

3 STRUCTURES OF P450 PROTEINS AND THEIR MOLECULAR PHYLOGENY (Thomas L. Poulos and Yergalem T. Meharenna).

1. Introduction.

2. P450 Evolution.

3. P450 Families and Subfamilies.

4. P450 Structures.

5. Variation in P450 Function and Fold.

6. Archaeon P450s.

7. Summary and Conclusions.

Acknowledgments.

Abbreviations.

References.

4 AQUATIC P450 SPECIES (Mark J. Snyder).

1. Introduction. 'P450s Under the Surface.'

2. Diversity of Aquatic Species.

3. P450 Activities in Aquatic Invertebrates.

4. Aquatic P450 Gene Families Identified.

5. How Can We Use Information About P450s in Aquatic Species?

6. Conclusions and Outlook.

Acknowledgments.

Abbreviations.

References.

5 THE ELECTROCHEMISTRY OF CYTOCHROME P450 (Alan M. Bond, Barry D. Fleming, and Lisandra L. Martin).

1. Introduction.

2. Redox Titration (Potentiometric Equilibrium) Measurements.

3. Voltammetric (Dynamic) Measurements.

4. Conclusions.

Acknowledgments.

Abbreviations.

References.

6 P450 ELECTRON TRANSFER REACTIONS (Andrew K. Udit, Stephen M. Contakes, and Harry B. Gray).

1. Introduction.

2. Catalytic Cycles.

3. Electron Tunneling Wires.

4. Concluding Remarks.

Acknowledgments.

Abbreviations.

References.

7 LEAKAGE IN CYTOCHROME P450 REACTIONS IN RELATION TO PROTEIN STRUCTURAL PROPERTIES (Christiane Jung).

1. Introduction.

2. Protein Structural Parameters.

3. The Reaction Cycle of Cytochrome P450.

4. Protein Structural Parameters and Extent of Competitive Reactions.

5. Concluding Remarks.

Acknowledgments.

Abbreviations.

References.

8 CYTOCHROMES P450 – STRUCTURAL BASIS FOR BINDING AND CATALYSIS (Konstanze von König and Ilme Schlichting).

1. Introduction.

2. Ligand Binding: Substrate Recognition and Access to the Distal Pocket.

3. Architecture of the Active Site of CYP101.

4. The Distal Acid-Alcohol Pair.

5. Experimental Characterization of Reaction Intermediates. Radiolysis as a Tool to Study Redox Reactions.

6. Crystal Structures of Oxy-Ferrous Complexes.

7. Mechanism: Summary, Conclusions, Speculations.

Acknowledgments.

Abbreviations.

References.

9 BEYOND HEME-THIOLATE INTERACTIONS: ROLES OF THE SECONDARY COORDINATION SPHERE IN CYTOCHROME P450 SYSTEMS (Yi Lu and Thomas D. Pfister).

1. Overview of Cytochrome P450 Active Site Structure.

2. Secondary Coordination Sphere on the Proximal Side.

3. Secondary Coordination Sphere on the Distal Side.

4. Summary and Outlook.

Acknowledgments.

Abbreviations.

References.

10 INTERACTIONS OF CYTOCHROME P450 WITH NITRIC OXIDE AND RELATED LIGANDS (Andrew W. Munro, Kirsty J. McLean, and Hazel M. Girvan).

1. Introduction. Interactions of Ligands and Substrates with P450 Enzymes: General Features.

2. Nitric Oxide and Its Interactions with P450S.

3. Interactions of Imidazoles and Substituted Imidazoles with P450S.

4. Other Ligands and Inhibitors of P450 Function.

5. Conclusions and Future Prospects.

Acknowledgments.

Abbreviations.

References.

11 CYTOCHROME P450-CATALYZED HYDROXYLATIONS AND EPOXIDATIONS (Roshan Perera, Shengxi Jin, Masanori Sono, and John H. Dawson).

1. Introduction.

2. The Cytochrome P450 Enzymes.

3. Three-Dimensional Structures of the Active Sites of Cytochrome P450 Enzymes.

4. Role of the Cys Ligand: the Proximal Thiolate 'Push' and Distal Proton-Delivery.

5. Multiple Mechanisms of P450 Catalysis.

6. Multiple Oxidants in P450 Catalysis.

7. Two States Theory.

8. Influence of Substrate on the Spectral Properties and Reactivity of P450 Intermediates.

9. Formation and Reactivity of Transient P450 Oxygen Intermediates.

10. Summary and Future Prospective.

Acknowledgments.

Abbreviations.

References.

12 CYTOCHROME P450 AND STEROID HORMONE BIOSYNTHESIS (Rita Bernhardt and Michael R. Waterman).

1. Introduction.

2. Steroidogenic P450s.

3. Steroid Hormone Biosynthesis in the Adrenal Cortex.

4. Steroid Hormone Biosynthesis in the Gonads.

5. Extraadrenal and Extragonadal Steroidogenesis.

6. Outlook for the Future.

Acknowledgments.

Abbreviations.

References.

13 CARBON-CARBON BOND CLEAVAGE BY P450 SYSTEMS (James J. De Voss and Max J. Cryle).

1. Introduction.

2. Cleavage Between Oxygenated Carbons.

3. Cleavage Alpha to Oxygenated Carbons.

4. Cleavage Alpha to Carbon Bearing Nitrogen.

5. Carbon-Carbon Bond Cleavage Involving Peroxides.

6. General Conclusions.

Acknowledgments.

Abbreviations.

References.

14 DESIGN AND ENGINEERING OF CYTOCHROME P450 SYSTEMS (Stephen G. Bell, Nicola Hoskins, Christopher J. C. Whitehouse, and Luet L. Wong).

1. Introduction.

2. Engineering Bacterial Cytochrome P450 Systems.

3. Engineering Mammalian Cytochrome P450 Enzymes.

4. Engineering Plant P450 Enzymes.

5. Conclusions and Outlook.

Abbreviations.

References.

15 CHEMICAL DEFENSE AND EXPLOITATION. BIOTRANSFORMATION OF XENOBIOTICS BY CYTOCHROME P450 ENZYMES (Elizabeth M. J. Gillam and Dominic J. B. Hunter).

1. Introduction. Chemical Defense.

2. P450 Systems Involved in Chemical Defense.

3. Common Themes.

4. Industrial Applications of P450 Systems for Xenobiotic Decomposition.

5. Conclusions and Future Prospects.

Acknowledgments.

Abbreviations.

References.

16 DRUG METABOLISM AS CATALYZED BY HUMAN CYTOCHROME P450 SYSTEMS (F. Peter Guengerich).

1. Introduction.

2. Importance of P450 Enzymes in Drug Metabolism.

3. Approaches to Predicting P450 Activity in Humans.

4. P450s Involved in Drug Metabolism.

5. Examples of Major Issues Involving Drug Metabolism by P450.

6. Summary.

Acknowledgments.

Abbreviations.

References.

17 CYTOCHROME P450 ENZYMES: OBSERVATIONS FROM THE CLINIC (Peggy L. Carver).

1. Introduction.

2. Drug Interactions.

3. Drug Metabolism by Cytochrome P450 Enzymes.

4. Alterations in P450 Enzymes.

5. Active Transport of Drugs.

6. Enzyme-Transporter Cooperativity.

7. Use of Probes to Quantitate CYP Activity in Humans.

8. Prodrugs.

9. The Effect of Intravenous Versus Oral Administration on Drug Interactions.

10. Additional Factors Affecting Drug Interactions.

11. Herbal and Dietary Effects on CYP.

12. Interactions with Commonly Used Medications.

13. Beneficial Effects of Drug Interactions.

14. FDA Regulations Regarding CYP450-Mediated Drug Interactions.

15. Clinical Significance of Drug Interactions.

16. Summary.

Acknowledgment.

Abbreviations.

References.

SUBJECT INDEX.

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Astrid Sigel has studied languages and was an editor of the Metal Ions in Biological Systems series (until Volume 44) and also of the Handbooks on Toxicity of Inorganic Compounds (1988), on Metals in Clinical and Analytical Chemistry (1994; both with H.G. Seiler), and on Metalloproteins (2001; with Ivano Bertini) (Dekker, New York).

Helmut Sigel is Emeritus Professor (2003) of Inorganic Chemistry at the University of Basel, Switzerland, and a previous editor of the MIBS series until Volume 44. He serves on various editorial and advisory boards, published over 300 articles on metal ion complexes of nucleotides, coenzymes, and other ligands of biological relevance, and lectured worldwide. He was named Protagonist in Chemistry (2002) by ICA (issue 339); among further honors are the P. Ray Award (Indian Chemical Society, of which he is also an Honorary Fellow), the Werner Award (Swiss Chemical Society), a Doctor of Science honoris causa degree (Kalyani University, India), appointments as Visiting Professor (e.g., Austria, China, UK) and Endowed Lectureships.

Roland K.O. Sigel is Assistant Professor (2003) of Inorganic Chemistry at the University of Zürich, Switzerland, endowed with a Förderungsprofessur of the Swiss National Science Foundation. He received his doctoral degree summa cum laude (1999) from the University of Dortmund, Germany, working with Bernhard Lippert; thereafter he spent nearly three years at Columbia University, New York, USA, in the group of Anna Marie Pyle (now Yale University); during the six years abroad he received several fellowships from various sources. His research focuses on the structural and catalytic role of metal ions in ribozymes, especially group II introns, and on related topics. He was also an editor of Volumes 43 and 44 of the MIBS series.

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"This collective volume is extremely rich, as rich as the chemistry of P450 enzymes. It shows the vast field, its many facts and unresolved issues. It will be highly interesting primarily to the P540 community, medicinal chemists, and biochemists." (Coordination Chemistry Reviews, February 2009)

"Cytochrome P450 aficionados will not want to be without either of these two books." (Journal of the American Chemical Society, December 26, 2007)

"This is a well produced and comprehensive effort." (Doody's Health Services)

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by Astrid Sigel, Helmut Sigel, Roland K. O. Sigel
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