The ubiquitous roles of cytochrome P450 proteins:
Saved in:
| Format: | Book |
|---|---|
| Language: | English |
| Published: |
Chichester [u.a.]
Wiley
2007
|
| Series: | Metal ions in life sciences
3 |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XXVI, 652 S. Ill., graph. Darst. |
| ISBN: | 9780470016725 |
Staff View
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| adam_text | Contents
HISTORICAL DEVELOPMENT AND PERSPECTIVES
OF THE SERIES v
PREFACE TO VOLUME 3 vii
CONTRIBUTORS TO VOLUME 3 xvii
TITLES OF VOLUMES 1 44 IN THE
METAL IONS IN BIOLOGICAL SYSTEMS SERIES xxi
CONTENTS OF VOLUMES IN THE
METAL IONS IN LIFE SCIENCES SERIES xxiii
1 DIVERSITIES AND SIMILARITIES IN P450 SYSTEMS:
AN INTRODUCTION 1
Mary A. Schuler and Stephen G. Sligar
1. Oxygenases: Mediators of Biochemical Diversity 2
2. P450 Superfamily: Diversity at the Sequence Level 3
3. Diversity of P450 Structures: Folds and Conformations for
Functions 5
4. Diversity in P450 Mechanisms 6
5. Diversity in Regulation Across the Superfamily 13
6. Diversity in the Evolution of Common Metabolic Functions 16
7. Summary and Outlook 18
Acknowledgments 19
Abbreviations 19
References 19
2 STRUCTURAL AND FUNCTIONAL MIMICS
OF CYTOCHROMES P450 27
Wolf D. Woggon
1. Introduction 27
2. Iron Porphyrins Carrying a Thiolate or Modified Thiolate Ligand 31
x CONTENTS
3. Structurally Remote P450 Mimics 40
4. Concluding Remarks 52
Acknowledgments 52
Abbreviations 53
References 53
3 STRUCTURES OF P450 PROTEINS AND THEIR
MOLECULAR PHYLOGENY 57
Thomas L. Poulos and Yergalem T. Meharenna
1. Introduction 58
2. P450 Evolution 59
3. P450 Families and Subfamilies 60
4. P450 Structures 62
5. Variation in P450 Function and Fold 81
6. Archaeon P450s 86
7. Summary and Conclusions 90
Acknowledgments 91
Abbreviations 91
References 91
4 AQUATIC P450 SPECIES 97
Mark J. Snyder
1. Introduction. P450s Under the Surface 98
2. Diversity of Aquatic Species 100
3. P450 Activities in Aquatic Invertebrates 101
4. Aquatic P450 Gene Families Identified 108
5. How Can We Use Information About P450s in Aquatic Species? 116
6. Conclusions and Outlook 120
Acknowledgments 121
Abbreviations 121
References 122
5 THE ELECTROCHEMISTRY OF CYTOCHROME P450 127
Alan M. Bond, Barry D. Fleming, and Lisandra L. Martin
1. Introduction 127
2. Redox Titration (Potentiometric Equilibrium) Measurements 131
3. Voltammetric (Dynamic) Measurements 139
4. Conclusions 150
Acknowledgments 151
Abbreviations 151
References 152
CONTENTS xi
6 P450 ELECTRON TRANSFER REACTIONS 157
Andrew K. Udit, Stephen M. Contakes, and Harry B. Gray
1. Introduction 158
2. Catalytic Cycles 158
3. Electron Tunneling Wires 171
4. Concluding Remarks 180
Acknowledgments 181
Abbreviations 181
References 181
7 LEAKAGE IN CYTOCHROME P450 REACTIONS
IN RELATION TO PROTEIN STRUCTURAL
PROPERTIES 187
Christiane Jung
1. Introduction 188
2. Protein Structural Parameters 191
3. The Reaction Cycle of Cytochrome P450 195
4. Protein Structural Parameters and Extent of Competitive
Reactions 222
5. Concluding Remarks 225
Acknowledgments 226
Abbreviations 226
References 227
8 CYTOCHROMES P450 STRUCTURAL BASIS
FOR BINDING AND CATALYSIS 235
Konstanze von Konig and lime Schlichting
1. Introduction 236
2. Ligand Binding: Substrate Recognition and Access to the
Distal Pocket 237
3. Architecture of the Active Site of CYP101 239
4. The Distal Acid Alcohol Pair 242
5. Experimental Characterization of Reaction Intermediates.
Radiolysis as a Tool to Study Redox Reactions 250
6. Crystal Structures of Oxy Ferrous Complexes 253
7. Mechanism: Summary, Conclusions, Speculations 258
Acknowledgments 260
Abbreviations 260
References 261
xii CONTENTS
9 BEYOND HEME THIOLATE INTERACTIONS: ROLES
OF THE SECONDARY COORDINATION SPHERE
IN CYTOCHROME P450 SYSTEMS 267
Yi Lu and Thomas D. Pfister
1. Overview of Cytochrome P450 Active Site Structure 268
2. Secondary Coordination Sphere on the Proximal Side 269
3. Secondary Coordination Sphere on the Distal Side 275
4. Summary and Outlook 280
Acknowledgments 281
Abbreviations 281
References 281
10 INTERACTIONS OF CYTOCHROME P450 WITH
NITRIC OXIDE AND RELATED LIGANDS 285
Andrew W. Munro, Kirsty J. McLean, and Hazel M. Girvan
1. Introduction. Interactions of Ligands and Substrates with P450
Enzymes: General Features 286
2. Nitric Oxide and Its Interactions with P450S 289
3. Interactions of Imidazoles and Substituted Imidazoles with
P450S 300
4. Other Ligands and Inhibitors of P450 Function 305
5. Conclusions and Future Prospects 310
Acknowledgments 310
Abbreviations 311
References 311
11 CYTOCHROME P450 CATALYZED
HYDROXYLATIONS AND EPOXIDATIONS 319
Roshan Perera, Shengxi Jin, Masanori Sono, and John H. Dawson
1. Introduction 320
2. The Cytochrome P450 Enzymes 322
3. Three Dimensional Structures of the Active Sites of
Cytochrome P450 Enzymes 327
4. Role of the Cys Ligand: the Proximal Thiolate Push and
Distal Proton Delivery 333
5. Multiple Mechanisms of P450 Catalysis 337
6. Multiple Oxidants in P450 Catalysis 343
7. Two States Theory 347
8. Influence of Substrate on the Spectral Properties and
Reactivity of P450 Intermediates 348
9. Formation and Reactivity of Transient P450 Oxygen
Intermediates 351
CONTENTS Xjji
10. Summary and Future Prospective 352
Acknowledgments 353
Abbreviations 353
References 354
12 CYTOCHROME P450 AND STEROID HORMONE
BIOSYNTHESIS 361
Rita Bernhardt and Michael R. Waterman
1. Introduction 362
2. Steroidogenic P450s 363
3. Steroid Hormone Biosynthesis in the Adrenal Cortex 374
4. Steroid Hormone Biosynthesis in the Gonads 379
5. Extraadrenal and Extragonadal Steroidogenesis 382
6. Outlook for the Future 385
Acknowledgments 386
Abbreviations 387
References 387
13 CARBON CARBON BOND CLEAVAGE BY P450
SYSTEMS 397
James J. De Voss and Max J. Cryle
1. Introduction 398
2. Cleavage Between Oxygenated Carbons 398
3. Cleavage Alpha to Oxygenated Carbons 408
4. Cleavage Alpha to Carbon Bearing Nitrogen 422
5. Carbon Carbon Bond Cleavage Involving Peroxides 423
6. General Conclusions 429
Acknowledgments 430
Abbreviations 430
References 430
14 DESIGN AND ENGINEERING OF CYTOCHROME
P450 SYSTEMS 437
Stephen G. Bell, Nicola Hoskins,
Christopher J. C. Whitehouse, and Luet L. Wong
1. Introduction 438
2. Engineering Bacterial Cytochrome P450 Systems 444
3. Engineering Mammalian Cytochrome P450 Enzymes 462
4. Engineering Plant P450 Enzymes 467
5. Conclusions and Outlook 468
Abbreviations 469
References 469
Xiv CONTENTS
15 CHEMICAL DEFENSE AND EXPLOITATION.
BIOTRANSFORMATION OF XENOBIOTICS
BY CYTOCHROME P450 ENZYMES 477
Elizabeth M. J. Gillam and Dominic J. B. Hunter
1. Introduction. Chemical Defense 478
2. P450 Systems Involved in Chemical Defense 481
3. Common Themes 529
4. Industrial Applications of P450 Systems for Xenobiotic
Decomposition 530
5. Conclusions and Future Prospects 534
Acknowledgments 535
Abbreviations 535
References 537
16 DRUG METABOLISM AS CATALYZED BY HUMAN
CYTOCHROME P450 SYSTEMS 561
F. Peter Guengerich
1. Introduction 562
2. Importance of P450 Enzymes in Drug Metabolism 563
3. Approaches to Predicting P450 Activity in Humans 565
4. P450s Involved in Drug Metabolism 570
5. Examples of Major Issues Involving Drug Metabolism by
P450 576
6. Summary 582
Acknowledgments 583
Abbreviations 583
References 584
17 CYTOCHROME P450 ENZYMES: OBSERVATIONS
FROM THE CLINIC 591
Peggy L. Carver
1. Introduction 592
2. Drug Interactions 593
3. Drug Metabolism by Cytochrome P450 Enzymes 594
4. Alterations in P450 Enzymes 596
5. Active Transport of Drugs 603
6. Enzyme Transporter Cooperativity 603
7. Use of Probes to Quantitate CYP Activity in Humans 604
8. Prodrugs 604
9. The Effect of Intravenous Versus Oral Administration on
Drug Interactions 605
10. Additional Factors Affecting Drug Interactions 606
11. Herbal and Dietary Effects on CYP 608
CONTENTS xv
12. Interactions with Commonly Used Medications 610
13. Beneficial Effects of Drug Interactions 611
14. FDA Regulations Regarding CYP450 Mediated Drug
Interactions 612
15. Clinical Significance of Drug Interactions 613
16. Summary 614
Acknowledgment 615
Abbreviations 615
References 615
SUBJECT INDEX 619
|
| adam_txt |
Contents
HISTORICAL DEVELOPMENT AND PERSPECTIVES
OF THE SERIES v
PREFACE TO VOLUME 3 vii
CONTRIBUTORS TO VOLUME 3 xvii
TITLES OF VOLUMES 1 44 IN THE
METAL IONS IN BIOLOGICAL SYSTEMS SERIES xxi
CONTENTS OF VOLUMES IN THE
METAL IONS IN LIFE SCIENCES SERIES xxiii
1 DIVERSITIES AND SIMILARITIES IN P450 SYSTEMS:
AN INTRODUCTION 1
Mary A. Schuler and Stephen G. Sligar
1. Oxygenases: Mediators of Biochemical Diversity 2
2. P450 Superfamily: Diversity at the Sequence Level 3
3. Diversity of P450 Structures: Folds and Conformations for
Functions 5
4. Diversity in P450 Mechanisms 6
5. Diversity in Regulation Across the Superfamily 13
6. Diversity in the Evolution of Common Metabolic Functions 16
7. Summary and Outlook 18
Acknowledgments 19
Abbreviations 19
References 19
2 STRUCTURAL AND FUNCTIONAL MIMICS
OF CYTOCHROMES P450 27
Wolf D. Woggon
1. Introduction 27
2. Iron Porphyrins Carrying a Thiolate or Modified Thiolate Ligand 31
x CONTENTS
3. Structurally Remote P450 Mimics 40
4. Concluding Remarks 52
Acknowledgments 52
Abbreviations 53
References 53
3 STRUCTURES OF P450 PROTEINS AND THEIR
MOLECULAR PHYLOGENY 57
Thomas L. Poulos and Yergalem T. Meharenna
1. Introduction 58
2. P450 Evolution 59
3. P450 Families and Subfamilies 60
4. P450 Structures 62
5. Variation in P450 Function and Fold 81
6. Archaeon P450s 86
7. Summary and Conclusions 90
Acknowledgments 91
Abbreviations 91
References 91
4 AQUATIC P450 SPECIES 97
Mark J. Snyder
1. Introduction. 'P450s Under the Surface' 98
2. Diversity of Aquatic Species 100
3. P450 Activities in Aquatic Invertebrates 101
4. Aquatic P450 Gene Families Identified 108
5. How Can We Use Information About P450s in Aquatic Species? 116
6. Conclusions and Outlook 120
Acknowledgments 121
Abbreviations 121
References 122
5 THE ELECTROCHEMISTRY OF CYTOCHROME P450 127
Alan M. Bond, Barry D. Fleming, and Lisandra L. Martin
1. Introduction 127
2. Redox Titration (Potentiometric Equilibrium) Measurements 131
3. Voltammetric (Dynamic) Measurements 139
4. Conclusions 150
Acknowledgments 151
Abbreviations 151
References 152
CONTENTS xi
6 P450 ELECTRON TRANSFER REACTIONS 157
Andrew K. Udit, Stephen M. Contakes, and Harry B. Gray
1. Introduction 158
2. Catalytic Cycles 158
3. Electron Tunneling Wires 171
4. Concluding Remarks 180
Acknowledgments 181
Abbreviations 181
References 181
7 LEAKAGE IN CYTOCHROME P450 REACTIONS
IN RELATION TO PROTEIN STRUCTURAL
PROPERTIES 187
Christiane Jung
1. Introduction 188
2. Protein Structural Parameters 191
3. The Reaction Cycle of Cytochrome P450 195
4. Protein Structural Parameters and Extent of Competitive
Reactions 222
5. Concluding Remarks 225
Acknowledgments 226
Abbreviations 226
References 227
8 CYTOCHROMES P450 STRUCTURAL BASIS
FOR BINDING AND CATALYSIS 235
Konstanze von Konig and lime Schlichting
1. Introduction 236
2. Ligand Binding: Substrate Recognition and Access to the
Distal Pocket 237
3. Architecture of the Active Site of CYP101 239
4. The Distal Acid Alcohol Pair 242
5. Experimental Characterization of Reaction Intermediates.
Radiolysis as a Tool to Study Redox Reactions 250
6. Crystal Structures of Oxy Ferrous Complexes 253
7. Mechanism: Summary, Conclusions, Speculations 258
Acknowledgments 260
Abbreviations 260
References 261
xii CONTENTS
9 BEYOND HEME THIOLATE INTERACTIONS: ROLES
OF THE SECONDARY COORDINATION SPHERE
IN CYTOCHROME P450 SYSTEMS 267
Yi Lu and Thomas D. Pfister
1. Overview of Cytochrome P450 Active Site Structure 268
2. Secondary Coordination Sphere on the Proximal Side 269
3. Secondary Coordination Sphere on the Distal Side 275
4. Summary and Outlook 280
Acknowledgments 281
Abbreviations 281
References 281
10 INTERACTIONS OF CYTOCHROME P450 WITH
NITRIC OXIDE AND RELATED LIGANDS 285
Andrew W. Munro, Kirsty J. McLean, and Hazel M. Girvan
1. Introduction. Interactions of Ligands and Substrates with P450
Enzymes: General Features 286
2. Nitric Oxide and Its Interactions with P450S 289
3. Interactions of Imidazoles and Substituted Imidazoles with
P450S 300
4. Other Ligands and Inhibitors of P450 Function 305
5. Conclusions and Future Prospects 310
Acknowledgments 310
Abbreviations 311
References 311
11 CYTOCHROME P450 CATALYZED
HYDROXYLATIONS AND EPOXIDATIONS 319
Roshan Perera, Shengxi Jin, Masanori Sono, and John H. Dawson
1. Introduction 320
2. The Cytochrome P450 Enzymes 322
3. Three Dimensional Structures of the Active Sites of
Cytochrome P450 Enzymes 327
4. Role of the Cys Ligand: the Proximal Thiolate 'Push' and
Distal Proton Delivery 333
5. Multiple Mechanisms of P450 Catalysis 337
6. Multiple Oxidants in P450 Catalysis 343
7. Two States Theory 347
8. Influence of Substrate on the Spectral Properties and
Reactivity of P450 Intermediates 348
9. Formation and Reactivity of Transient P450 Oxygen
Intermediates 351
CONTENTS Xjji
10. Summary and Future Prospective 352
Acknowledgments 353
Abbreviations 353
References 354
12 CYTOCHROME P450 AND STEROID HORMONE
BIOSYNTHESIS 361
Rita Bernhardt and Michael R. Waterman
1. Introduction 362
2. Steroidogenic P450s 363
3. Steroid Hormone Biosynthesis in the Adrenal Cortex 374
4. Steroid Hormone Biosynthesis in the Gonads 379
5. Extraadrenal and Extragonadal Steroidogenesis 382
6. Outlook for the Future 385
Acknowledgments 386
Abbreviations 387
References 387
13 CARBON CARBON BOND CLEAVAGE BY P450
SYSTEMS 397
James J. De Voss and Max J. Cryle
1. Introduction 398
2. Cleavage Between Oxygenated Carbons 398
3. Cleavage Alpha to Oxygenated Carbons 408
4. Cleavage Alpha to Carbon Bearing Nitrogen 422
5. Carbon Carbon Bond Cleavage Involving Peroxides 423
6. General Conclusions 429
Acknowledgments 430
Abbreviations 430
References 430
14 DESIGN AND ENGINEERING OF CYTOCHROME
P450 SYSTEMS 437
Stephen G. Bell, Nicola Hoskins,
Christopher J. C. Whitehouse, and Luet L. Wong
1. Introduction 438
2. Engineering Bacterial Cytochrome P450 Systems 444
3. Engineering Mammalian Cytochrome P450 Enzymes 462
4. Engineering Plant P450 Enzymes 467
5. Conclusions and Outlook 468
Abbreviations 469
References 469
Xiv CONTENTS
15 CHEMICAL DEFENSE AND EXPLOITATION.
BIOTRANSFORMATION OF XENOBIOTICS
BY CYTOCHROME P450 ENZYMES 477
Elizabeth M. J. Gillam and Dominic J. B. Hunter
1. Introduction. Chemical Defense 478
2. P450 Systems Involved in Chemical Defense 481
3. Common Themes 529
4. Industrial Applications of P450 Systems for Xenobiotic
Decomposition 530
5. Conclusions and Future Prospects 534
Acknowledgments 535
Abbreviations 535
References 537
16 DRUG METABOLISM AS CATALYZED BY HUMAN
CYTOCHROME P450 SYSTEMS 561
F. Peter Guengerich
1. Introduction 562
2. Importance of P450 Enzymes in Drug Metabolism 563
3. Approaches to Predicting P450 Activity in Humans 565
4. P450s Involved in Drug Metabolism 570
5. Examples of Major Issues Involving Drug Metabolism by
P450 576
6. Summary 582
Acknowledgments 583
Abbreviations 583
References 584
17 CYTOCHROME P450 ENZYMES: OBSERVATIONS
FROM THE CLINIC 591
Peggy L. Carver
1. Introduction 592
2. Drug Interactions 593
3. Drug Metabolism by Cytochrome P450 Enzymes 594
4. Alterations in P450 Enzymes 596
5. Active Transport of Drugs 603
6. Enzyme Transporter Cooperativity 603
7. Use of Probes to Quantitate CYP Activity in Humans 604
8. Prodrugs 604
9. The Effect of Intravenous Versus Oral Administration on
Drug Interactions 605
10. Additional Factors Affecting Drug Interactions 606
11. Herbal and Dietary Effects on CYP 608
CONTENTS xv
12. Interactions with Commonly Used Medications 610
13. Beneficial Effects of Drug Interactions 611
14. FDA Regulations Regarding CYP450 Mediated Drug
Interactions 612
15. Clinical Significance of Drug Interactions 613
16. Summary 614
Acknowledgment 615
Abbreviations 615
References 615
SUBJECT INDEX 619 |
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| id | DE-604.BV022514757 |
| illustrated | Illustrated |
| index_date | 2024-07-02T18:00:49Z |
| indexdate | 2024-07-09T20:59:16Z |
| institution | BVB |
| isbn | 9780470016725 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-015721578 |
| oclc_num | 72868166 |
| open_access_boolean | |
| owner | DE-703 DE-19 DE-BY-UBM DE-83 DE-11 DE-91G DE-BY-TUM |
| owner_facet | DE-703 DE-19 DE-BY-UBM DE-83 DE-11 DE-91G DE-BY-TUM |
| physical | XXVI, 652 S. Ill., graph. Darst. |
| publishDate | 2007 |
| publishDateSearch | 2007 |
| publishDateSort | 2007 |
| publisher | Wiley |
| record_format | marc |
| series | Metal ions in life sciences |
| series2 | Metal ions in life sciences |
| spelling | The ubiquitous roles of cytochrome P450 proteins ed. by Astrid Sigel ... Chichester [u.a.] Wiley 2007 XXVI, 652 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Metal ions in life sciences 3 Cytochrom P-450 - Biochemie - Aufsatzsammlung swd Camphor 5-Monooxygenase Cytochrome P-450 Cytochrom P-450 (DE-588)4148705-9 gnd rswk-swf Biochemie (DE-588)4006777-4 gnd rswk-swf Cytochrom P-450 (DE-588)4148705-9 s Biochemie (DE-588)4006777-4 s DE-604 Sigel, Astrid Sonstige (DE-588)103367866X oth Metal ions in life sciences 3 (DE-604)BV022275400 3 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015721578&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | The ubiquitous roles of cytochrome P450 proteins Metal ions in life sciences Cytochrom P-450 - Biochemie - Aufsatzsammlung swd Camphor 5-Monooxygenase Cytochrome P-450 Cytochrom P-450 (DE-588)4148705-9 gnd Biochemie (DE-588)4006777-4 gnd |
| subject_GND | (DE-588)4148705-9 (DE-588)4006777-4 |
| title | The ubiquitous roles of cytochrome P450 proteins |
| title_auth | The ubiquitous roles of cytochrome P450 proteins |
| title_exact_search | The ubiquitous roles of cytochrome P450 proteins |
| title_exact_search_txtP | The ubiquitous roles of cytochrome P450 proteins |
| title_full | The ubiquitous roles of cytochrome P450 proteins ed. by Astrid Sigel ... |
| title_fullStr | The ubiquitous roles of cytochrome P450 proteins ed. by Astrid Sigel ... |
| title_full_unstemmed | The ubiquitous roles of cytochrome P450 proteins ed. by Astrid Sigel ... |
| title_short | The ubiquitous roles of cytochrome P450 proteins |
| title_sort | the ubiquitous roles of cytochrome p450 proteins |
| topic | Cytochrom P-450 - Biochemie - Aufsatzsammlung swd Camphor 5-Monooxygenase Cytochrome P-450 Cytochrom P-450 (DE-588)4148705-9 gnd Biochemie (DE-588)4006777-4 gnd |
| topic_facet | Cytochrom P-450 - Biochemie - Aufsatzsammlung Camphor 5-Monooxygenase Cytochrome P-450 Cytochrom P-450 Biochemie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015721578&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV022275400 |
| work_keys_str_mv | AT sigelastrid theubiquitousrolesofcytochromep450proteins |