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Quinones and Quinone Enzymes Part A

8th May 2007

Quinones and Quinone Enzymes Part A

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Developments in genomics and proteomics rapidly generated focus on new -omics, particularly metabolomics and phenomics. Quinones, hydroquinones, semiquinones, and their metabolites are naturally-occurring compounds that serve as wonderful examples for this new paradigm of interdigitating -omics; in addition to a role as substrates and products in metabolism, quinone compounds are intermediates in many pathways of gene regulation, enzyme protein induction, feedback control, and waste product elimination. Quinones play a pivotal role in energy metabolism (Peter Mitchell’s protonmotive ‘‘Q cycle’’), many other key processes, and even in chemotherapy, where redox cycling drugs are utilized.

The present volume of Methods in Enzymology on quinones and quinone enzymes serves to bring together current methods and concepts on this topic. It focuses on the role in the so-called Phase II of drug metabolism (xenobiotics), but includes aspects on Phase I (CYP, cytochromes P-450) and Phase III (transport systems) as well. This volume of Methods in Enzymology (Part A) focuses on quinones and quinone enzymes in terms of coenzyme Q (detection and quinone reductases), plasma membrane quinone reductases, and the role of quinones in cellular signaling and modulation of gene expression, whereas Part B addresses mitochondrial ubiquinone and reductases, anticancer quinones, and the role of quinone reductases in chemoprevention and nutrition, as well as the role of quinones in age-related diseases. Phase II Enzymes, Part C, will focus on glutathione, glutathione S-transferases, and other conjugation enzymes.

There are human polymorphisms in these enzymes relating to variations in cancer risk, and enzymes targeted by quinones are being investigated. Modern methods in assaying quinone reactions and, indeed, various quinones themselves, are also included in this volume.The enzyme, NAD(P)H: quinone oxidoreductase, is the subject of a major section in this volume. This enzyme, discovered in 1958 in Stockholm by Lars Ernster and named DT-Diaphorase by him, has multiple roles, some of which were only recently discovered.

Ubiquinone (Coenzyme Q10) as a major naturally-occurring quinone became a highlight of scientific interest following its discovery in 1957, and was discovered to have an established role in mitochondrial electron transport by Frederick Crane. Fundamental contributions were made by Karl Folkers on its supplemental use for health benefits in disease prevention and by Andre?s O. M. Stoppani, a pioneer of Argentinian biochemistry, in utilizing quinones for the treatment of Chagas disease. Authors: Helmut Sies and Lester Packer

Table of Contents

  • Editors-In-Chief (Page ii)
  • Contributors to Volume 378 (pp.xi-xiv )
  • Preface (pp.xv-xvi)
  • Methods In Enzymology (pp.xvii-xxxviii )
  1. Investigation of Regulatory Mechanisms in Coenzyme Q Metabolism (pp3-17)
    Jacob Grunler and Gustav Dallner
  2. Methods for Characterizing TPQ-Containing Proteins (pp17-31)
    Jennifer L. DuBois and Judith P. Klinman
  3. Aldo-Keto Reductases and Formation of Polycyclic Aromatic Hydrocarbon o-Quinones (pp31-67)
    Trevor M. Penning
  4. Redox Cycling of -Lapachone and Structural Analogues in Microsomal andCytosol Liver Preparations (pp67-87)
    Silvia Ferna?ndez Villamil , Andre?s O. M. Stoppani and Marta Dubin
  5. Quinone Chemistry and Melanogenesis (pp88-109)
    Edward J. Land , Christopher A. Ramsden and Patrick A. Riley
  6. Quinoids Formed from Estrogens and Antiestrogens (pp110-123)
    Judy L. Bolton , Linning Yu and Gregory R. J. Thatcher
  7. Ubiquinone and Plastoquinone Metabolism in Plants (pp124-131)
    Ewa Swiezewska
  8. Extramitochondrial Reduction of Ubiquinone by Flavoenzymes (pp131-138)
    Mikael Bjornstedt , Tomas Nordman and Jerker M. Olsson
  9. Tissue Bioavailability and Detection of Coenzyme Q (pp138-145)
    Igor Rebrin , Sergey Kamzalov and Rajindar S. Sohal
  10. Coenzyme Q and Vitamin E Interactions (pp146-151)
    Rajindar S. Sohal
  11. Preparation of Tritium-Labeled 3-Methyl-3-buten-1[3H]-yl Diphosphate (3H-Isopentenyl Diphosphate) (pp152-156)
    Tadeusz Chojnacki
  12. High-Performance Liquid Chromatography–EC Assay of Mitochondrial Coenzyme Q9, Coenzyme Q9H2, Coenzyme Q10, Coenzyme Q10H2, and Vitamin E with a Simplified On-Line Solid-Phase Extraction (pp156-162)
    Maurizio Battino , Luciana Leone and Stefano Bompadre
  13. Simultaneous Determination of Coenzyme Q10, Cholesterol, and Major Cholesterylesters in Human Blood Plasma (pp162-169)
    Craig A. Gay and Roland Stocker
  14. Assay of Coenzyme Q10 in Plasma by a Single Dilution Step (pp170-176)
    Gian Paolo Littarru , Fabrizio Mosca , Daniele Fattorini , Stefano Bompadre and Maurizio Battino
  15. Quinone Oxidoreductases of the Plasma Membrane (pp179-199)
    D. James Morre
  16. Regulation of Ceramide Signaling by Plasma Membrane Coenzyme Q Reductases (pp200-206)
    Placido Navas and Jose Manuel Villalba
  17. Stabilization of Extracellular Ascorbate Mediated by Coenzyme Q Transmembrane Electron Transport (pp207-217)
    Antonio Arroyo , Juan C. Rodriguez-Aguilera , Carlos Santos-Ocana , Jose Manuel Villalba and Placido Navas
  18. Regulation of Antioxidant Response Element–Dependent Induction of Detoxifying Enzyme Synthesis (pp221-238)
    Anil K. Jaiswal
  19. Antioxidant Responsive Element Activation by Quinones: Antioxidant Responsive Element Target Genes, Role of PI3 Kinase in Activation (pp238-258)
    Jiang Li , Jong-Min Lee , Delinda A. Johnson and Jeffrey A. Johnson
  20. Signaling Effects of Menadione: From Tyrosine Phosphatase Inactivation to Connexin Phosphorylation (pp258-272)
    Kotb Abdelmohsen , Pauline Patak , Claudia von Montfort , Ira Melchheier , Helmut Sies and Lars-Oliver Klotz
  21. Unique Function of the Nrf2–Keap1 Pathway in the Inducible Expression of Antioxidant and Detoxifying Enzymes (pp273-286)
    Akira Kobayashi , Tsutomu Ohta and Masayuki Yamamoto
  22. Role of Protein Phosphorylation in the Regulation of NF-E2–Related Factor 2 Activity (pp286-301)
    Philip J. Sherratt , H. -C. Huang , Truyen Nguyen and Cecil B. Pickett
  23. Analysis of Transcription Factor Remodeling in Phase II Gene Expression with Curcumin (pp302-318)
    Dale A. Dickinson , Karen E. Iles , Amanda F. Wigley and Henry Jay Forman
  24. Quinones and Glutathione Metabolism (pp319-340)
    Nobuo Watanabe , Dale A. Dickinson , Rui-Ming Liu and Henry Jay Forman
  25. Doxorubicin Cardiotoxicity and the Control of Iron Metabolism: Quinone-Dependent and Independent Mechanisms (pp340-361)
    Giorgio Minotti , Stefania Recalcati , Pierantonio Menna , Emanuela Salvatorelli , Gianfranca Corna and Gaetano Cairo
  26. Oxidant-Induced Iron Signaling in Doxorubicin-Mediated Apoptosis (pp362-382)
    Srigiridhar Kotamraju , Shasi V. Kalivendi , Eugene Konorev , Christopher R. Chitambar , Joy Joseph and B. Kalyanaraman
  • Author Index (pp383-409 )
  • Subject Index (pp411-421)

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