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List of Contributors xxi Preface to Second Edition xxix Preface First Edition xxxi 1 Chemistry of Reactive Species 1 Frederick A. Villamena
1.1 Redox Chemistry 1
1.2 Classification of Reactive Species 2
1.3 Reactive Oxygen Species 4
1.4 Reactive Nitrogen Species 15
1.5 Reactive Sulfur and Chlorine Species 18
1.6 Reactivity 23
1.7 Origins of Reactive Species 27
1.8 Methods of Detection 32 References 39 2 Lipid Peroxidation and Nitration 49 Sean S. Davies and Lilu Guo Overview 49
2.1 Peroxidation of PUFAs 49
2.2 Cyclic Endoperoxides and Their Products 52
2.3 Fragmented Products of Lipid Peroxidation 58
2.4 Epoxy Fatty Acids 62
2.5 Lipid Nitrosylation 62 Summary 65 References 65 3 Protein Posttranslational Modification 71 James L. Hougland Joseph Darling and Susan Flynn Overview 71
3.1 Oxidative Stress-Related PTMs: Oxidation Reactions 71
3.2 Amino Acid Modification by Oxidation-Produced Electrophiles 80
3.3 Detection of Oxidative-Stress Related PTMs 81
3.4 Role of PTMs in Cellular Redox Signaling 84 Summary 85 References 85 4 DNA Oxidation 93 Dessalegn B. Nemera Amy R. Jones and Edward J. Merino Overview 93
4.1 The Context of Cellular DNA Oxidation 93
4.2 Oxidation of Oligonucleotides 94
4.3 Examination of Specific Oxidative Lesions 96 Future Outlook of DNA Oxidative Lesions 103 References 103 5 Cellular Antioxidants and Phase 2 Proteins 113 Yunbo li
5.1 Definitions 113
5.2 Roles in Oxidative Stress 113
5.3 Molecular Regulation 117
5.4 Induction in Chemoprevention 119
5.5 Inactivation 119 References 121 6 Mitochondrial Dysfunction 129 Yeong-Renn Chen and Chwen-Lin Chen
6.1 Mitochondria and Submitochondrial Particles 129
6.2 Energy Transduction 131
6.3 Mitochondrial Stress 132
6.4 Superoxide Anion Radical Generation as Mediated by Î?PH Î?Ï? ETC and Disease Pathogenesis 133 References 143 7 NADPH Oxidases: Structure and Function 147 Mark T. Quinn Overview 147
7.1 Introduction 147
7.2 Phagocyte NADPH Oxidase Structure 147
7.3 Phagocyte ROS Production 152
7.4 Phagocyte NADPH Oxidase Function 155
7.5 Nonphagocyte NADPH Oxidase Structure 156
7.6 Nonphagocyte ROS Production 161
7.7 Functions of Nonphagocyte NADPH Oxidases 162 Summary 169 Acknowledgments 169 References 170 8 Cell Signaling and Transcription 189 Imran Rehmani Fange Liu and Aimin Liu Overview 189
8.1 Common Mechanisms of Redox Signaling 189
8.2 Redox and Oxygen-Sensitive Transcription Factors in Prokaryotes 191
8.3 Redox Signaling in Metazoans 195
8.4 Oxygen Sensing in Metazoans 200
8.5 Medical Significance of Redox and Oxygen-Sensing Pathways 204 Concluding Remarks 205 References 205 9 Oxidative Stress and Redox Signaling in Carcinogenesis 213 Rodrigo Franco Aracely Garcia-Garcia Thomas B. Kryston Alexandros G. Georgakilas Mihalis I. Panayiotidis and Aglaia Pappa Overview 213
9.1 Redox Environment and Cancer 213
9.2 Oxidative Modifications to Biomolecules and Carcinogenesis 217
9.3 Measurement of Oxidative DNA Damage in Human Cancer 223
9.4 Epigenetic Involvement in Oxidative Stress-Induced Carcinogenesis 223
9.5 Deregulation of Cell Death Pathways by Oxidative Stress in Cancer Progression 226 Conclusions and Perspective 230 Acknowledgments 231 References 231 10 Neurodegeneration from Drugs and Aging-Derived Free Radicals 247 Annmarie Ramkissoon Aaron M. Shapiro Margaret M. Loniewska and Peter G. Wells Overview 247
10.1 ROS Formation 247
10.2 Protection against ROS 273
10.3 Nrf2 Regulation of Protective Responses 279 Summary and Conclusions 291 Acknowledgments 291 References 291 11 Cardiac Ischemia and Reperfusion 321 Murugesan Velayutham and Jay L. Zweier Overview 321
11.1 Oxygen in the Heart 321
11.2 Sources of ROS during Ischemia and Reperfusion 322
11.3 Modulation of Substrates Metabolites and Cofactors during I-R 326
11.4 ROS-Mediated Cellular Communication during I-R 328
11.5 ROS and Cell Death during Ischemia and Reperfusion 329
11.6 Potential Therapeutic Strategies 330 Summary and Conclusion 331 References 331 12 Atherosclerosis: Oxidation Hypothesis 339 Chandrakala Aluganti Narasimhulu Dmitry Litvinov Xueting Jiang Zhaohui Yang and Sampath Parthasarathy Overview 339
12.1 Lipid Peroxidation 339
12.2 Oxidation Hypothesis of Atherosclerosis 340
12.3 Animal Models of Atherosclerosis 341
12.4 Aldehyde Generation from Peroxidized Lipids 343 Summary 344 Acknowledgments 345 References 345 13 Cystic Fibrosis 355 Neal S. Gould and Brian J. Day Overview 355
13.1 Lung Disease Characteristics in CF 355
13.2 Role of CFTR in the Lung 358
13.3 Oxidative Stress in the CFTR-Deficient Lung 358
13.4 Antioxidant Therapies for CF 361 Summary 363 References 363 14 Cigarette Smoking and Air Pollution 369 Andrew J. Ghio and Urmila Kodavanti
14.1 Exposure to Cigarette Smoke 369
14.2 Air Pollution Particles 371
14.3 Ozone 374
14.4 Nitrogen and Sulfur Oxides 374
14.5 Interaction between PM and Oxidant Gases 375
14.6 Oxidative Stress and Mechanistic Pathways of Disease After Exposure to Air Pollutants 375 References 375 15 Oxidative Stress in Chronic Obstructive Pulmonary Disease 381 Peter J. Barnes
15.1 Introduction 381
15.2 Increased Oxidative Stress in COPD 382
15.3 Effects of Oxidative Stress in COPD 384
15.4 Strategies for Reducing Oxidative Stress 386
15.5 Conclusions 389 References 389 16 Oxidative Stress in the Eye 395 Annie K. Ryan Wade W. Rich Peter A. Jansen Megan M. Allyn Katelyn E. Swindle-Reilly and Matthew A. Reilly
16.1 Introduction 395
16.2 The Cornea 396
16.3 The Lens 400
16.4 The Vitreous Humor 403
16.5 The Retina and Optic Nerve 404
16.6 Therapeutic Approaches to ROS Elevation in the Eye 407
16.7 Conclusion 408 References 408 17 The Role of Oxidative Stress in Chronic Kidney Disease (CKD) 417 Ara Aboolian Jordan Younes Alejandra Romero Jay C. Jha Karin Jandeleit-Dahm and Jaroslawna Meister
17.1 Introduction 417
17.2 Sources of Oxidative Stress in CKD 419
17.3 Mechanisms by Which Oxidative Stress Contributes to CKD 421
17.4 Interplay Between Oxidative Stress and Senescence in CKD 423
17.5 Treatment Options for CKD 423 References 429 18 Biomarkers of Oxidative Stress in Neurodegenerative Diseases 437 Rukhsana Sultana Giovanna Cenini and D. Allan Butterfield Overview 437
18.1 Introduction 437
18.2 Biomarkers of Protein Oxidation/Nitration 439
18.3 Biomarkers of Lipid Peroxidation 441
18.4 Biomarkers of Carbohydrate Oxidation 444
18.5 Biomarkers of Nucleic Acid Oxidation 445 Acknowledgments 446 References 446 19 Cysteinylated Albumin as Oxidative Stress Biomarker and Therapeutic Target 455 Alessandra Altomare Giulio Vistoli Cristina Banfi and Giancarlo Aldini
19.1 Introduction 455
19.2 Cellular and Extracellular Thiols Distribution 455
19.3 HSA and CYS34 456
19.4 CYS34 Reactivity and Reactions 458
19.5 CYS34 Oxidized Forms in Physio-Pathological Conditions 460
19.6 Endogenous Regulation of Intracellular and Extracellular Thiol-Redox Homeostasis 462
19.7 Molecular and Therapeutic Strategies for Reversing Mercaptalbumin from the Oxidized Forms 462
19.8 Conclusion 464 References 465 20 Nitroalkene Fatty Acids: Formation Metabolism Reactivity and Signaling 469 Martina Steglich Martín Sosa Francisco J. Schopfer and Lucía Turell
20.1 Introduction 469
20.2 Diet and Fatty Acids 469
20.3 Nitroalkene Fatty Acids in Vivo Formation 470
20.4 Metabolism and Distribution 471
20.5 Reactivity of Nitroalkene Fatty Acids 472
20.6 Nitroalkylation as A Protein Post-Translational Modification 473
20.7 Nitrooleic Acid and Disease 475
20.8 Concluding Remarks 477 Abbreviations 477 References 478 21 Synthetic Antioxidants 483 Grégory Durand Overview 483
21.1 Endogenous Enzymatic System of Defense 483
21.2 Metal-Based Synthetic Antioxidants 484
21.3 Nonmetal-Based Antioxidants 488
21.4 Nitrones 495 References 504 Index 513