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Quinones and Quinone Enzymes, Part B
1st Edition, Volume 382 - February 20, 2004
Editors: Helmut Sies, Lester Packer
Language: English
Hardback ISBN:9780121827861
9 7 8 - 0 - 1 2 - 1 8 2 7 8 6 - 1
eBook ISBN:9780080497204
9 7 8 - 0 - 0 8 - 0 4 9 7 2 0 - 4
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…Read more
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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.
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
Dedication
Contributors to Volume 382
Preface
Methods In Enzymology
Section I: Mitochondrial Ubiquinone and Reductases
1: Mitochondrial Quinone Reductases: Complex I
Publisher Summary
Introduction
Assay of Redox Activities of Complex I
Other Activities of Complex I
Production of Superoxide Radical
2: Q-Cycle Bypass Reactions at the Qo Site of the Cytochrome bc1 (and Related) Complexes
Publisher Summary
The Q-Cycle and Its Bypass Reactions
Estimating the Concentrations of cyt bc1 and b6f Complexes
Probing the Involvement of ISP Domain Movements in Restricting Bypass Reactions
Acknowledgements
3: Targeting Coenzyme Q Derivatives to Mitochondria
Publisher Summary
Introduction
Synthesis and Handling of Mitochondria-Targeted Coenzyme Q Derivatives
Modifying and Measuring Coenzyme Q Redox State
Experiments with Mitochondria-Targeted Coenzyme Q Derivatives
Location of Targeted Coenzyme Q Derivatives Within Mitochondria
Conclusion
Acknowledgements
4: The Mitochondrial Interplay of Ubiquinol and Nitric Oxide in Endotoxemia
Publisher Summary
Introduction
Experimental Model: Endotoxemic Animals and Sample Preparation
Sources of NO in Endotoxemia: iNOS Expression and Activity
The Role of Ubiquinol in Endotoxemia
The Endotoxemic Mitochondrial Damage
Acknowledgements
5: Mitochondrial Respiratory Chain Dysfunction Caused by Coenzyme Q Deficiency
Publisher Summary
Introduction
Respiratory Chain and Ubiquinone
Cellular Consequences of CoQ10 Depletion
Clinical Presentation of Coenzyme Q10 Depletion
Detecting CoQ10 Deficiency
Supplementation Therapy
Conclusion
6: Coenzyme Q Cytoprotective Mechanisms
Publisher Summary
Introduction
Cytoprotective Activities of CoQ: Antioxidant Activity
Diversity of Antioxidant/Pro-Oxidant Capacity Between Different CoQ Analogs
Cytoprotective Activities of CoQ: Protection Against Reductive Stress Caused by Complex I Inhibition in Isolated Rat Hepatocytes
Cytoprotective Activities of CoQ: Re-establishing Mitochondrial Function in Complex I Inhibited Isolated Rat Hepatocytes
Diversity of Mitochondrial Function Between Different CoQ Analogs
Materials and Methods
Discussion
Role of CoQ and Analogs in the Modulation of Mitochondrial Permeability Transition: Possible Link Between Mitochondrial Permeability Transition and CoQ1-Mediated Cytoprotection
Conclusions
Acknowledgements
7: Dietary Coenzyme Q10 and Mitochondrial Status
Publisher Summary
Introduction
Absorption, Tissue Distribution, and Metabolism of Coenzyme Q10
Effect of Dietary Coenzyme Q10 on Levels of Coenzyme Q10 in Tissues and Mitochondria
Dietary Vitamin E and Coenzyme Q10 Uptake and Retention
Measurement of Mitochondrial Levels of Coenzyme Q10
Implications of the Effect of Dietary Coenzyme Q10 and Vitamin E on Mitochondrial Coenzyme Q10
Section II: Anticancer Quinones and Quinone Oxidoreductases
8: NAD(P)H:Quinone Oxidoreductase 1 (NQO1, DT-Diaphorase), Functions and Pharmacogenetics
Publisher Summary
Introduction
Possible Functions of NQO1
Polymorphisms in NQO1
Acknowledgements
9: Structure and Mechanism of NAD[P]H:Quinone Acceptor Oxidoreductases (NQO)
Publisher Summary
Introduction
Primary Structure Analysis
Structure Description
Mechanism
Structure-Based Mutagenesis
Species Differences
Crystallography Studies of Complexes of hNQO1 with Chemotherapeutic Compounds
Prodrugs Activated by Nitro-Reduction in Cancer Therapy
NAD(P)H Quinone Oxidoreductase 2 (NQO2)
Conclusions
12: Bioactivation and Resistance to Mitomycin C
Publisher Summary
Introduction
MC as a Prototypic Bioreductive Agent
Mechanism of the Reductive Activation of MC
MC Bioreduction
MC Resistance
MC Resistance Protein A (MCRA)
MCRA as a Selection Marker
Mammalian MCRA Functional Homolog
Reversal of MC Resistance
Rapid Screening for DTD Activity by Using a Microtiter Assay
Search for Oxygen-Sensitive Resistance Mechanisms
Methodology for the Indirect Determination of MC Activation
13: NAD(P)H:Quinone Oxidoreductase 1 Expression, Hydrogen Peroxide Levels, and Growth Phase in HeLa Cells
Publisher Summary
Introduction
Methods
Conclusions
Acknowledgements
14: The “Prochaska” Microtiter Plate Bioassay for Inducers of NQO1
Publisher Summary
Introduction
Prochaska Bioassay Protocol
Novel Findings Made with The Prochaska Bioassay
Versatility and Limitations of The Prochaska Bioassay
Acknowledgements
15: Structure-Activity Relationships in Two-Electron Reduction of Quinones
Publisher Summary
Introduction
Single-Electron Reduction of Quinones by Flavoenzymes
Two-Electron Reduction of Quinones by Flavoenzymes
Conclusions
Acknowledgements
16: p53-Dependent Apoptosis and NAD(P)H:Quinone Oxidoreductase 1
Publisher Summary
Introduction
Principle of p53-Dependent Apoptosis Assays
Cells and Reagents
Methods
17: The Role of Endogenous Catechol Quinones in the Initiation of Cancer and Neurodegenerative Diseases
Publisher Summary
Evolution of Fundamental Concepts And Principles of Chemical Carcinogenesis
Catechol Quinones as Mutagens Initiating Cancer And Other Diseases
Unifying Mechanism of Initiation of Cancer by Endogenous and Synthetic Estrogens
Unifying Mechanism of Initiation of Cancer and Other Diseases by Catechol Quinones
Conclusions
Acknowledgements
18: Induction of NQO1 in Cancer Cells
Publisher Summary
Introduction
Structure and Activity of NQO1
Expression and Induction of NQO1
Selective Induction of NQO1 in Cancer Cells to Enhance Antitumor Activity
Future Perspectives
Acknowledgements
Section III: Quinone Reductases: Chemoprevention and Nutrition
19: Role of Nicotinamide Quinone Oxidoreductase 1 (NQO1) in Protection against Toxicity of Electrophiles and Reactive Oxygen Intermediates
Publisher Summary
Introduction
Elucidation of the Physiological Functions of NQO1
Evidence That NQO1 Protects Against Electrophile Toxicity, Oxidative Stress, and Neoplasia
Conclusions
20: Activation and Detoxification of Naphthoquinones by NAD(P)H: Quinone Oxidoreductase
Publisher Summary
Rates of Naphthoquinone Reduction by QR and Rates of Naphthohydroquinone Autoxidation
Inhibition of Hydroquinone Autoxidation by QR
Redox Cycling of Naphthoquinones in the Presence of QR
Mechanism of Naphthohydroquinone Autoxidation
Two Classes of Naphthoquinone
Cytotoxicity of Naphthoquinones In Vitro
Toxicity of Naphthoquinones In Vivo
Conclusion
21: Induction of Quinone Reductase as a Primary Screen for Natural Product Anticarcinogens
Publisher Summary
Introduction
Role of Phase II Enzymes in Cancer
Quinone Reductase Induction and Cancer Chemoprevention
In Vitro Quinone Reductase Assay
Screening of Medicinal Plants
Quinone Reductase Inducers Present in Edible Plants
Phytochemicals Inducing Quinone Reductase
Conclusions
Acknowledgements
22: Chemoprevention by 1,2-Dithiole-3-Thiones Through Induction of NQO1 and Other Phase 2 Enzymes
Publisher Summary
Introduction
Induction of NQO1 by Chemopreventive Dithiolethiones and a Role of NRF2 in the Induction of NQO1 in Mice
Microarray Analysis of Dithiolethione-Inducible Genes in Mouse Liver and Effect of nrf2 Genotype
NQO1 Levels and Cytotoxicity Against Quinone Compound Menadione in Murine Embryonic Fibroblasts (MEF)
23: Chemical Structures of Inducers of Nicotinamide Quinone Oxidoreductase 1 (NQO1)
Publisher Summary
Introduction
Identification of the Chemical Signals for Monofunctional Phase 2 Gene Induction
Nine Chemical Classes of Inducers
Implications of the Chemical Structures of Inducers for their Mechanism of Action
24: Induction of Phase II Enzymes by Aliphatic Sulfides Derived from Garlic and Onions: An Overview
Publisher Summary
Introduction
Materials and Assay Methods
Phase II Enzyme Induction by Allium-Derived Sulfides
Relevance of Animal Studies to the Human Situation
Toxicity of Sulfides and Relationship to Mechanism of Enzyme Induction
Conclusions
25: Upregulation of Quinone Reductase by Glucosinolate Hydrolysis Products From Dietary Broccoli
Publisher Summary
Introduction
Crucifers, Cancer Prevention and Quinone Reductase
Sulforaphane
Sulforaphane Nitrile
Synergistic Effects of Glucosinolate Metabolites
Variability in the Effect of Dietary Cruciferous Vegetables on Induction of QR
Genotype Variation in Glucosinolate Content of Cruciferous Vegetables
Environmental Effects on Glucosinolate Content of Crucifers
Microbial Conversion
Effects of Processing on Quinone Reductase-Inducing Activity
Effects of Vegetable Tissue Matrix on Bioavailabilityof Sulforaphane
Section IV: Quinones and Age-Related Diseases
26: Therapeutic Effects of Coenzyme Q10 in Neurodegenerative Diseases
Publisher Summary
Introduction
Effects in the Central Nervous System
Pharmacokinetics of Orally Administered CoQ10
The Antioxidant Properties and Effects of CoQ10 Supplementation in Animals
Neuroprotective Effects in Animal Models of Neurodegeneration
The Effects of CoQ10 Supplementation in Patients With Neurodegenerative Diseases
Conclusions
27: Neuroprotective Actions of Coenzyme Q10 in Parkinson's Disease
Publisher Summary
Introduction
Materials and Methods
Observations and Results
Discussion
Repairing the Brain in Parkinson's Disease and Providing Neuroprotection
Summary and Conclusions
Acknowledgements
Author Index
Subject Index
No. of pages: 572
Language: English
Edition: 1
Volume: 382
Published: February 20, 2004
Imprint: Academic Press
Hardback ISBN: 9780121827861
eBook ISBN: 9780080497204
HS
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
LP
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
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