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Quinones and Quinone Enzymes, Part B - 1st Edition - ISBN: 9780121827861, 9780080497204

Quinones and Quinone Enzymes, Part B, Volume 382

1st Edition

Serial Volume Editors: Helmut Sies Lester Packer
Hardcover ISBN: 9780121827861
eBook ISBN: 9780080497204
Imprint: Academic Press
Published Date: 20th February 2004
Page Count: 572
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Table of Contents

    <li>Dedication</li> <li>Contributors to Volume 382</li> <li>Preface</li> <li>Methods In Enzymology</li> <li>Section I: Mitochondrial Ubiquinone and Reductases<ul><li>1: Mitochondrial Quinone Reductases: Complex I<ul><li>Publisher Summary</li><li>Introduction</li><li>Assay of Redox Activities of Complex I</li><li>Other Activities of Complex I</li><li>Production of Superoxide Radical</li></ul></li><li>2: Q-Cycle Bypass Reactions at the Q<sub>o</sub> Site of the Cytochrome bc<sub>1</sub> (and Related) Complexes<ul><li>Publisher Summary</li><li>The Q-Cycle and Its Bypass Reactions</li><li>Estimating the Concentrations of cyt bc<sub>1</sub> and b<sub>6</sub>f Complexes</li><li>Probing the Involvement of ISP Domain Movements in Restricting Bypass Reactions</li><li>Acknowledgements</li></ul></li><li>3: Targeting Coenzyme Q Derivatives to Mitochondria<ul><li>Publisher Summary</li><li>Introduction</li><li>Synthesis and Handling of Mitochondria-Targeted Coenzyme Q Derivatives</li><li>Modifying and Measuring Coenzyme Q Redox State</li><li>Experiments with Mitochondria-Targeted Coenzyme Q Derivatives</li><li>Location of Targeted Coenzyme Q Derivatives Within Mitochondria</li><li>Conclusion</li><li>Acknowledgements</li></ul></li><li>4: The Mitochondrial Interplay of Ubiquinol and Nitric Oxide in Endotoxemia<ul><li>Publisher Summary</li><li>Introduction</li><li>Experimental Model: Endotoxemic Animals and Sample Preparation</li><li>Sources of NO in Endotoxemia: iNOS Expression and Activity</li><li>The Role of Ubiquinol in Endotoxemia</li><li>The Endotoxemic Mitochondrial Damage</li><li>Acknowledgements</li></ul></li><li>5: Mitochondrial Respiratory Chain Dysfunction Caused by Coenzyme Q Deficiency<ul><li>Publisher Summary</li><li>Introduction</li><li>Respiratory Chain and Ubiquinone</li><li>Cellular Consequences of CoQ<sub>10</sub> Depletion</li><li>Clinical Presentation of Coenzyme Q<sub>10</sub> Depletion</li><li>Detecting CoQ<sub>10</sub> Deficiency</li><li>Supplementation Therapy</li><li>Conclusion</li></ul></li><li>6: Coenzyme Q Cytoprotective Mechanisms<ul><li>Publisher Summary</li><li>Introduction</li><li>Cytoprotective Activities of CoQ: Antioxidant Activity</li><li>Diversity of Antioxidant/Pro-Oxidant Capacity Between Different CoQ Analogs</li><li>Cytoprotective Activities of CoQ: Protection Against Reductive Stress Caused by Complex I Inhibition in Isolated Rat Hepatocytes</li><li>Cytoprotective Activities of CoQ: Re-establishing Mitochondrial Function in Complex I Inhibited Isolated Rat Hepatocytes</li><li>Diversity of Mitochondrial Function Between Different CoQ Analogs</li><li>Materials and Methods</li><li>Discussion</li><li>Role of CoQ and Analogs in the Modulation of Mitochondrial Permeability Transition: Possible Link Between Mitochondrial Permeability Transition and CoQ<sub>1</sub>-Mediated Cytoprotection</li><li>Conclusions</li><li>Acknowledgements</li></ul></li><li>7: Dietary Coenzyme Q<sub>10</sub> and Mitochondrial Status<ul><li>Publisher Summary</li><li>Introduction</li><li>Absorption, Tissue Distribution, and Metabolism of Coenzyme Q<sub>10</sub></li><li>Effect of Dietary Coenzyme Q<sub>10</sub> on Levels of Coenzyme Q<sub>10</sub> in Tissues and Mitochondria</li><li>Dietary Vitamin E and Coenzyme Q<sub>10</sub> Uptake and Retention</li><li>Measurement of Mitochondrial Levels of Coenzyme Q<sub>10</sub></li><li>Implications of the Effect of Dietary Coenzyme Q<sub>10</sub> and Vitamin E on Mitochondrial Coenzyme Q<sub>10</sub></li></ul></li></ul></li> <li>Section II: Anticancer Quinones and Quinone Oxidoreductases<ul><li>8: NAD(P)H:Quinone Oxidoreductase 1 (NQO1, DT-Diaphorase), Functions and Pharmacogenetics<ul><li>Publisher Summary</li><li>Introduction</li><li>Possible Functions of NQO1</li><li>Polymorphisms in NQO1</li><li>Acknowledgements</li></ul></li><li>9: Structure and Mechanism of NAD[P]H:Quinone Acceptor Oxidoreductases (NQO)<ul><li>Publisher Summary</li><li>Introduction</li><li>Primary Structure Analysis</li><li>Structure Description</li><li>Mechanism</li><li>Structure-Based Mutagenesis</li><li>Species Differences</li><li>Crystallography Studies of Complexes of hNQO1 with Chemotherapeutic Compounds</li><li>Computer Modeling of Other Complexes of NQO1</li><li>Acknowledgements</li></ul></li><li>10: Diaziridinylbenzoquinones<ul><li>Publisher Summary</li><li>Introduction</li><li>History</li><li>Mechanisms</li><li>The Future</li></ul></li><li>11: Quinone Reductase&#x2013;Mediated Nitro-Reduction: Clinical Applications<ul><li>Publisher Summary</li><li>Introduction</li><li>Prodrugs Activated by Nitro-Reduction in Cancer Therapy</li><li>NAD(P)H Quinone Oxidoreductase 2 (NQO2)</li><li>Conclusions</li></ul></li><li>12: Bioactivation and Resistance to Mitomycin C<ul><li>Publisher Summary</li><li>Introduction</li><li>MC as a Prototypic Bioreductive Agent</li><li>Mechanism of the Reductive Activation of MC</li><li>MC Bioreduction</li><li>MC Resistance</li><li>MC Resistance Protein A (MCRA)</li><li>MCRA as a Selection Marker</li><li>Mammalian MCRA Functional Homolog</li><li>Reversal of MC Resistance</li><li>Rapid Screening for DTD Activity by Using a Microtiter Assay</li><li>Search for Oxygen-Sensitive Resistance Mechanisms</li><li>Methodology for the Indirect Determination of MC Activation</li></ul></li><li>13: NAD(P)H:Quinone Oxidoreductase 1 Expression, Hydrogen Peroxide Levels, and Growth Phase in HeLa Cells<ul><li>Publisher Summary</li><li>Introduction</li><li>Methods</li><li>Conclusions</li><li>Acknowledgements</li></ul></li><li>14: The &#x201C;Prochaska&#x201D; Microtiter Plate Bioassay for Inducers of NQO1<ul><li>Publisher Summary</li><li>Introduction</li><li>Prochaska Bioassay Protocol</li><li>Novel Findings Made with The Prochaska Bioassay</li><li>Versatility and Limitations of The Prochaska Bioassay</li><li>Acknowledgements</li></ul></li><li>15: Structure-Activity Relationships in Two-Electron Reduction of Quinones<ul><li>Publisher Summary</li><li>Introduction</li><li>Single-Electron Reduction of Quinones by Flavoenzymes</li><li>Two-Electron Reduction of Quinones by Flavoenzymes</li><li>Conclusions</li><li>Acknowledgements</li></ul></li><li>16: p53-Dependent Apoptosis and NAD(P)H:Quinone Oxidoreductase 1<ul><li>Publisher Summary</li><li>Introduction</li><li>Principle of p53-Dependent Apoptosis Assays</li><li>Cells and Reagents</li><li>Methods</li></ul></li><li>17: The Role of Endogenous Catechol Quinones in the Initiation of Cancer and Neurodegenerative Diseases<ul><li>Publisher Summary</li><li>Evolution of Fundamental Concepts And Principles of Chemical Carcinogenesis</li><li>Catechol Quinones as Mutagens Initiating Cancer And Other Diseases</li><li>Unifying Mechanism of Initiation of Cancer by Endogenous and Synthetic Estrogens</li><li>Unifying Mechanism of Initiation of Cancer and Other Diseases by Catechol Quinones</li><li>Conclusions</li><li>Acknowledgements</li></ul></li><li>18: Induction of NQO1 in Cancer Cells<ul><li>Publisher Summary</li><li>Introduction</li><li>Structure and Activity of NQO1</li><li>Expression and Induction of NQO1</li><li>Selective Induction of NQO1 in Cancer Cells to Enhance Antitumor Activity</li><li>Future Perspectives</li><li>Acknowledgements</li></ul></li></ul></li> <li>Section III: Quinone Reductases: Chemoprevention and Nutrition<ul><li>19: Role of Nicotinamide Quinone Oxidoreductase 1 (NQO1) in Protection against Toxicity of Electrophiles and Reactive Oxygen Intermediates<ul><li>Publisher Summary</li><li>Introduction</li><li>Elucidation of the Physiological Functions of NQO1</li><li>Evidence That NQO1 Protects Against Electrophile Toxicity, Oxidative Stress, and Neoplasia</li><li>Conclusions</li></ul></li><li>20: Activation and Detoxification of Naphthoquinones by NAD(P)H: Quinone Oxidoreductase<ul><li>Publisher Summary</li><li>Rates of Naphthoquinone Reduction by QR and Rates of Naphthohydroquinone Autoxidation</li><li>Inhibition of Hydroquinone Autoxidation by QR</li><li>Redox Cycling of Naphthoquinones in the Presence of QR</li><li>Mechanism of Naphthohydroquinone Autoxidation</li><li>Two Classes of Naphthoquinone</li><li>Cytotoxicity of Naphthoquinones In Vitro</li><li>Toxicity of Naphthoquinones In Vivo</li><li>Conclusion</li></ul></li><li>21: Induction of Quinone Reductase as a Primary Screen for Natural Product Anticarcinogens<ul><li>Publisher Summary</li><li>Introduction</li><li>Role of Phase II Enzymes in Cancer</li><li>Quinone Reductase Induction and Cancer Chemoprevention</li><li>In Vitro Quinone Reductase Assay</li><li>Screening of Medicinal Plants</li><li>Quinone Reductase Inducers Present in Edible Plants</li><li>Phytochemicals Inducing Quinone Reductase</li><li>Conclusions</li><li>Acknowledgements</li></ul></li><li>22: Chemoprevention by 1,2-Dithiole-3-Thiones Through Induction of NQO1 and Other Phase 2 Enzymes<ul><li>Publisher Summary</li><li>Introduction</li><li>Induction of NQO1 by Chemopreventive Dithiolethiones and a Role of NRF2 in the Induction of NQO1 in Mice</li><li>Microarray Analysis of Dithiolethione-Inducible Genes in Mouse Liver and Effect of nrf2 Genotype</li><li>NQO1 Levels and Cytotoxicity Against Quinone Compound Menadione in Murine Embryonic Fibroblasts (MEF)</li></ul></li><li>23: Chemical Structures of Inducers of Nicotinamide Quinone Oxidoreductase 1 (NQO1)<ul><li>Publisher Summary</li><li>Introduction</li><li>Identification of the Chemical Signals for Monofunctional Phase 2 Gene Induction</li><li>Nine Chemical Classes of Inducers</li><li>Implications of the Chemical Structures of Inducers for their Mechanism of Action</li></ul></li><li>24: Induction of Phase II Enzymes by Aliphatic Sulfides Derived from Garlic and Onions: An Overview<ul><li>Publisher Summary</li><li>Introduction</li><li>Materials and Assay Methods</li><li>Phase II Enzyme Induction by Allium-Derived Sulfides</li><li>Relevance of Animal Studies to the Human Situation</li><li>Toxicity of Sulfides and Relationship to Mechanism of Enzyme Induction</li><li>Conclusions</li></ul></li><li>25: Upregulation of Quinone Reductase by Glucosinolate Hydrolysis Products From Dietary Broccoli<ul><li>Publisher Summary</li><li>Introduction</li><li>Crucifers, Cancer Prevention and Quinone Reductase</li><li>Sulforaphane</li><li>Sulforaphane Nitrile</li><li>Synergistic Effects of Glucosinolate Metabolites</li><li>Variability in the Effect of Dietary Cruciferous Vegetables on Induction of QR</li><li>Genotype Variation in Glucosinolate Content of Cruciferous Vegetables</li><li>Environmental Effects on Glucosinolate Content of Crucifers</li><li>Microbial Conversion</li><li>Effects of Processing on Quinone Reductase-Inducing Activity</li><li>Effects of Vegetable Tissue Matrix on Bioavailabilityof Sulforaphane</li></ul></li></ul></li> <li>Section IV: Quinones and Age-Related Diseases<ul><li>26: Therapeutic Effects of Coenzyme Q<sub>10</sub> in Neurodegenerative Diseases<ul><li>Publisher Summary</li><li>Introduction</li><li>Effects in the Central Nervous System</li><li>Pharmacokinetics of Orally Administered CoQ<sub>10</sub></li><li>The Antioxidant Properties and Effects of CoQ<sub>10</sub> Supplementation in Animals</li><li>Neuroprotective Effects in Animal Models of Neurodegeneration</li><li>The Effects of CoQ<sub>10</sub> Supplementation in Patients With Neurodegenerative Diseases</li><li>Conclusions</li></ul></li><li>27: Neuroprotective Actions of Coenzyme Q<sub>10</sub> in Parkinson's Disease<ul><li>Publisher Summary</li><li>Introduction</li><li>Materials and Methods</li><li>Observations and Results</li><li>Discussion</li><li>Repairing the Brain in Parkinson's Disease and Providing Neuroprotection</li><li>Summary and Conclusions</li><li>Acknowledgements</li></ul></li></ul></li> <li>Author Index</li> <li>Subject Index</li>


Quinones are members of a class of aromatic compounds with two oxygen atoms bonded to the ring as carbonyl groups. This volume covers more clinical aspects of quinines, such as anticancer properties, as well as their role in nutrition and in age-related diseases.

Key Features

  • Mitochondrial Ubiquinone and Reductases
  • Anticancer Quinones and Quinone Oxido-Reductases
  • Quininone Reductases: Chemoprevention, Nutrition
  • Quinones and Age-Related Diseases


Biochemists, cell biologists, molecular biologists, geneticists and biophysicists


No. of pages:
© Academic Press 2004
20th February 2004
Academic Press
Hardcover ISBN:
eBook ISBN:

Ratings and Reviews

About the Serial Volume Editors

Helmut Sies

Helmut Sies, MD, PhD (hon), studied medicine at the universities of Tübingen, Munich, and Paris. He was the professor and chair of the Institute for Biochemistry and Molecular Biology I at Heinrich-Heine-University Düsseldorf, Germany, where he is now professor emeritus. He is a member of the German National Academy of Sciences Leopoldina and was the president of the North Rhine-Westphalian Academy of Sciences and Arts. He was named ‘Redox Pioneer’; was the president of the Society for Free Radical Research International (SFRRI). Helmut Sies introduced the concept of “Oxidative Stress” in 1985, and was the first to reveal hydrogen peroxide as a normal constituent of aerobic cell metabolism. His research interests comprise redox biology, oxidants, antioxidants, micronutrients.

Affiliations and Expertise

Heinrich-Heine-University Düsseldorf, Germany

Lester Packer

Lester Packer

Lester Packer received a PhD in Microbiology and Biochemistry in 1956 from Yale University. In 1961, he joined the University of California at Berkeley serving as Professor of Cell and Molecular Biology until 2000, and then was appointed Adjunct Professor, Pharmacology and Pharmaceutical Sciences, School of Pharmacy at the University of Southern California.

Dr Packer received numerous distinctions including three honorary doctoral degrees, several distinguished Professor appointments. He was awarded Chevalier de l’Ordre National du Merite (Knight of the French National Order of Merit) and later promoted to the rank of Officier. He served as President of the Society for Free Radical Research International (SFRRI), founder and Honorary President of the Oxygen Club of California.

He has edited numerous books and published research; some of the most cited articles have become classics in the field of free radical biology:

Dr Packer is a member of many professional societies and editorial boards. His research elucidated - the Antioxidant Network concept. Exogenous lipoic acid was discovered to be one of the most potent natural antioxidants and placed as the ultimate reductant or in the pecking order of the “Antioxidant Network” regenerating vitamins C and E and stimulating glutathione synthesis, thereby improving the overall cellular antioxidant defense. The Antioxidant Network is a concept addressing the cell’s redox status. He established a world-wide network of research programs by supporting and co-organizing conferences on free radical research and redox biology in Asia, Europe, and America.

Affiliations and Expertise

Department of Molecular Pharmacology and Toxicology, School of Pharmaceutical Sciences, University of Southern California, USA