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Oxidative Stress Biomarkers and Antioxidant Protocols PDF

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Oxidative Stress Biomarkers and Antioxidant Protocols M E T H O D S I N M O L E C U L A R B I O L O G YTM John M.Walker, Series Editor 215.Cytokines and Colony Stimulating Factors:Methods and 184.Biostatistical Methods, edited by Stephen W. Looney, 2002 Protocols,edited byDieter Körholz and Wieland Kiess, 2003 183.Green Fluorescent Protein: Applications and Protocols, edited 214.Superantigen Protocols, edited by Teresa Krakauer, 2003 byBarry W. Hicks, 2002 213.Capillary Electrophoresis of Carbohydrates, edited by 182.In Vitro Mutagenesis Protocols, 2nd ed., edited by Jeff Pierre Thibault and Susumu Honda, 2003 Braman, 2002 212.Single Nucleotide Polymorphisms: Methods and Protocols, 181.Genomic Imprinting: Methods and Protocols, edited by edited by Piu-Yan Kwok, 2003 Andrew Ward, 2002 211.Protein Sequencing Protocols, 2nd ed., edited by Bryan John 180.Transgenesis Techniques, 2nd ed.: Principles and Protocols, Smith, 2003 edited by Alan R. Clarke, 2002 210.MHC Protocols, edited by Stephen H. Powis and Robert W. 179.Gene Probes: Principles and Protocols, edited by Marilena of Vaughan, 2003 Aquino de Muro and Ralph Rapley, 2002 209.Transgenic Mouse Methods and Protocols, edited by Marten 178.Antibody Phage Display: Methods and Protocols, edited by Hofker and Jan van Deursen, 2002 Philippa M. O’Brien and Robert Aitken, 2001 208.Peptide Nucleic Acids: Methods and Protocols, edited by 177.Two-Hybrid Systems: Methods and Protocols, edited by Paul Peter E. Nielsen, 2002 N. MacDonald, 2001 207.RecombinantAntibodies for Cancer Therapy: Methods and 176.Steroid Receptor Methods: Protocols and Assays, edited by Protocols.edited by Martin Welschof and Jürgen Krauss, 2002 Benjamin A. Lieberman, 2001 206.Endothelin Protocols, edited by Janet J. Maguire and Anthony 175.Genomics Protocols, edited by Michael P. Starkey and Ramnath P. Davenport, 2002 Elaswarapu, 2001 205.E. coli Gene Expression Protocols, edited by Peter E. 174.Epstein-Barr Virus Protocols, edited by Joanna B. Wilson and Vaillancourt, 2002 Gerhard H. W. May, 2001 204.Molecular Cytogenetics: Protocols and Applications, edited 173.Calcium-Binding Protein Protocols, Volume 2: Methods and byYao-Shan Fan, 2002 Techniques,edited by Hans J. Vogel, 2001 203.In Situ Detection of DNA Damage: Methods and Protocols, 172.Calcium-Binding Protein Protocols, Volume 1: Reviews and edited by Vladimir V. Didenko, 2002 Case Histories, edited by Hans J. Vogel, 2001 202.Thyroid Hormone Receptors: Methods and Protocols, edited 171.Proteoglycan Protocols, edited by Renato V. Iozzo, 2001 by Aria Baniahmad, 2002 170.DNA Arrays: Methods and Protocols, edited by Jang B. 201.Combinatorial Library Methods and Protocols, edited by Rampal, 2001 Lisa B. English, 2002 169.Neurotrophin Protocols, edited by Robert A. Rush, 2001 200.DNA Methylation Protocols, edited by Ken I. Mills and Bernie 168.Protein Structure, Stability, and Folding, edited by Kenneth H, Ramsahoye, 2002 P. Murphy, 2001 199.Liposome Methods and Protocols, edited by Subhash C. Basu 167.DNA Sequencing Protocols, Second Edition, edited by Colin and Manju Basu, 2002 A. Graham and Alison J. M. Hill, 2001 198.Neural Stem Cells: Methods and Protocols, edited by Tanja 166. Immunotoxin Methods and Protocols, edited by Walter A. Hall, 2001 Zigova, Juan R. Sanchez-Ramos, and Paul R. Sanberg, 2002 165.SV40 Protocols, edited by Leda Raptis, 2001 197.Mitochondrial DNA: Methods and Protocols, edited by William 164.Kinesin Protocols, edited by Isabelle Vernos, 2001 C. Copeland, 2002 163.Capillary Electrophoresis of Nucleic Acids, Volume 2: 196.Ultrastructural and Molecular Biology Protocols:edited by Practical Applications of Capillary Electrophoresis, edited by Donald Armstrong, 2002 Keith R. Mitchelson and Jing Cheng, 2001 195.Quantitative Trait Loci: Methods and Protocols,edited by 162.Capillary Electrophoresis of Nucleic Acids, Volume 1: Nicola J. Camp and Angela Cox, 2002 Introduction to the Capillary Electrophoresis of Nucleic Acids, 194.Posttranslational Modifications of Proteins: Tools for Functional edited by Keith R. Mitchelson and Jing Cheng, 2001 Proteomics,edited by Christoph Kannicht, 2002 161.Cytoskeleton Methods and Protocols, edited by Ray H. Gavin, 2001 193.RT-PCR Protocols, edited by Joseph O’Connell, 2002 160.Nuclease Methods and Protocols, edited by Catherine H. 192.PCR Cloning Protocols, 2nd ed., edited by Bing-Yuan Chen Schein, 2001 and Harry W. Janes, 2002 159.Amino Acid Analysis Protocols, edited by Catherine Cooper, 191.Telomeres and Telomerase:Methods and Protocols, edited Nicole Packer, and Keith Williams, 2001 byJohn A. Double and Michael J. Thompson, 2002 158.Gene Knockoout Protocols, edited by Martin J. Tymms and 190.High Throughput Screening: Methods and Protocols, edited Ismail Kola, 2001 byWilliam P. Janzen, 2002 157.Mycotoxin Protocols, edited by Mary W. Trucksess and Albert 189.GTPase Protocols: The RAS Superfamily, edited by Edward E. Pohland, 2001 J. Manser and Thomas Leung, 2002 156.Antigen Processing and Presentation Protocols, edited by 188.Epithelial Cell Culture Protocols, edited by Clare Wise, 2002 Joyce C. Solheim, 2001 187.PCR Mutation Detection Protocols, edited by Bimal D. M. 155.Adipose Tissue Protocols, edited by Gérard Ailhaud, 2000 Theophilus and Ralph Rapley, 2002 154.Connexin Methods and Protocols, edited by Roberto Bruzzone 186.Oxidative Stress Biomarkers and Antioxidant Protocols, and Christian Giaume, 2001 edited by Donald Armstrong, 2002 153.Neuropeptide Y Protocols, edited by Ambikaipakan 185.Embryonic Stem Cells: Methods and Protocols, edited by Balasubramaniam, 2000 Kursad Turksen, 2002 M E T H O D S I N M O L E C U L A R B I O L O G YTM Oxidative Stress Biomarkers and Antioxidant Protocols Edited by Donald Armstrong University of Florida, Gainesville, FL Humana Press Totowa, New Jersey © 2002 Humana Press Inc. 999 Riverview Drive, Suite 208 Totowa, New Jersey 07512 www.humanapress.com All rights reserved. No part of this book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise without written permission from the Publisher. Methods in Molecular Biology™ is a trademark of The Humana Press Inc. The content and opinions expressed in this book are the sole work of the authors and editors, who have warranted due diligence in the creation and issuance of their work. The publisher, editors, and authors are not responsible for errors or omissions or for any consequences arising from the information or opinions presented in this book and make no warranty, express or implied, with respect to its contents. This publication is printed on acid-free paper. ∞ ANSI Z39.48-1984 (American Standards Institute) Permanence of Paper for Printed Library Materials. Cover illustration: The false color image on the cover was provided by Professor Susumu Terakawa and illustrates glucose-induced superoxide production in the islet of Langerhans from rat pancreas maintained in culture. Superoxide was monitored in the dark by MCLA-dependent chemiluminescence as described in Chapter 24 of the companion volume to this book, titled “Ultrastructural and Molecular Biology Protocols,” Vol. 196 of the Methods in Molecular Biology™ Series. Production Editor: Kim Hoather-Potter. Cover design by Patricia F. Cleary. For additional copies, pricing for bulk purchases, and/or information about other Humana titles, contact Humana at the above address or at any of the following numbers: Tel: 973-256-1699; Fax: 973-256-8341; E-mail: [email protected], or visit our Website at www.humanapress.com Photocopy Authorization Policy: Authorization to photocopy items for internal or personal use, or the internal or personal use of specific clients, is granted by Humana Press Inc., provided that the base fee of US $10.00 per copy, plus US $00.25 per page, is paid directly to the Copyright Clearance Center at 222 Rosewood Drive, Danvers, MA 01923. For those organizations that have been granted a photocopy license from the CCC, a separate system of payment has been arranged and is acceptable to Humana Press Inc. The fee code for users of the Transactional Reporting Service is: [0-89603-850-5/02 $10.00 + $00.25]. Printed in the United States of America. 10 9 8 7 6 5 4 3 2 1 Library of Congress Cataloging in Publication Data available. Preface The first protocols book, Free Radical and Antioxidant Protocols (1) was published in late 1998. Sections were divided into three parts, covering selected biochemical techniques for measuring oxidative stress, antioxidant (AOX) activity, and combined applications. In choosing the 40 methods to be included in that book, I realized there were considerably more of equal value than that which we could have presented in a single volume. To produce a comprehensive resource, this book and a third are being compiled to expand coverage of the field. A summary of papers (2) published on this important subject emphasizes the continuing rapid growth in oxidative stress investigations relating to our understanding of biochemical reactions, their relevance to pathophysiological mechanisms, how disease may arise, and how therapeutic intervention may be achieved(3). Although there is some overlap between the categories, the analy- sis shown below illustrates where current studies are concentrated and are almost evenly distributed between free radicals and AOX. Over the last 4 yr, there has been a 55% increase in the number of papers published in the area. Table 1 Recent Citations of Oxidative Stress Biomarkers 1997 1998 1999 2000 Free radical mechanisms 60 72 75 92 Free radicals in disease 78 88 109 111 AOX mechanisms 87 91 150 160 AOX in disease 94 122 155 204 Applications for treatment 0 2 5 8 TOTAL 319 375 494 575 Oxidative Stress Biomarkers and Antioxidant Protocols has added 33 more high-tech methods written by 73 authors from prestigious universities/institutes around the world, which together with our previous volume 108, provide a wide range of procedures for evaluating perturbations in cell function resulting from increased oxidative stress. Although primarily a reference for research, these two books also provide easy-to-follow directions that make them readily adapt- v vi Preface able for academic use as a laboratory manual for graduate students in the basic sciences. Of particular interest is the final chapter, which describes how the grouping of data from more than two biomarkers can be used to derive an appropriate statistical measure of change in the biological systems under study. The ability to more accurately interpret oxidative stress results in terms of either free radicals or AOX by using data from each to characterize laboratory or clinical observa- tions, greatly enhances the value of this specific biostatistical approach. I thank the Department of Small Animal Clinical Services, University of Florida College of Veterinary Medicine, and the Department of Clinical Labo- ratory Science, University at Buffalo for administrative support and facilities to produce this book. Professor John Walker, the Methods in Molecular Biology™ Series Editor, was helpful in the review process. Linda Rose and Chris Armstrong provided essential secretarial assistance and Aqeela Afzal compiled the litera- ture search data shown in Table 1. I am indebted to authors in this volume and colleagues who alerted me to other technologies that were ultimately included to broaden its scope. Donald Armstrong References 1. Armstrong, D. (ed.) (1998) Free Radical and Antioxidant Protocols, Methods in Molecular Biology, vol. 108. Humana Press Inc., Totowa, NJ. 2. Internet Grateful Med (2001). 3. Armstrong, D. (1994) Free Radicals in Diagnostic Medicine, Advances in Experi- mental Medicine and Biology, vol. 366. Plenum Press, NY. Contents Preface .............................................................................................................v Contributors..................................................................................................xi PART I. TECHNIQUES FOR FREE RADICAL DERIVED BIOMARKERS 1 Human Xanthine Oxidoreductase Determination by a Competitive ELISA Maria Giulia Battelli and Silvia Musiani.............................................. 3 2 Simultaneous Determination of Polyunsaturated Fatty Acids and Corresponding Monohydroperoxy and Monohydroxy Peroxidation Products by HPLC Richard W. Browne and Donald Armstrong..................................... 13 3 Determination of Products of Lipid Oxidation by Infrared Spectroscopy Douglas Borchman and Santosh Sinha............................................ 21 4 Detection of Docosahexaenoic Acid Hydroperoxides in Retina by Gas Chromatography/Mass Spectrometry Guey-Shuang Wu and Narsing A. Rao....................................................29 5 Detection of Lipid Hydroperoxide-Derived Protein Modification with Polyclonal Antibodies Yoji Kato and Toshihiko Osawa......................................................... 37 6 Techniques for Determining the Metabolic Pathways of Eicosanoids and for Evaluating the Rate-Controlling Enzymes Ninder Panesar, Yashwant G. Deshpande, and Donald L. Kaminski................................................................. 45 7 Mass Spectrometric Quantification of F -Isoprostanes as Indicators 2 of Oxidant Stress Jason D. Morrow and L. Jackson Roberts, II................................... 57 8 Formation of Apolipoprotein AI-AII Heterodimers by Oxidation of High-Density Lipoprotein Audric S. Moses and Gordon A. Francis.......................................... 67 9 Detection of Certain Peroxynitrite-Induced DNA Modifications Hiroshi Ohshima, László Virág, Jose Souza, Vladimir Yermilov, Brigitte Pignatelli, Mitsuharu Masuda, and Csaba Szabó.......... 77 10 Hydroxyl and 1-Hydroxyethyl Radical Detection by Spin Trapping and GC-MS José A. Castro and Gerardo D. Castro............................................. 89 vii viii Contents 11 Analysis of Aliphatic Amino Acid Alcohols in Oxidized Proteins Bénédicte Morin, Shanlin Fu, Hongjie Wang, Michael J. Davies, and Roger T. Dean........................................ 101 12 Rapid Determination of Glutamate Using HPLC Technology Aqeela Afzal, Mohammed Afzal, Andrew Jones, and Donald Armstrong................................................................. 111 13 A Rapid Method for the Quantification of GSH and GSSG in Biological Samples Mohammed Afzal, Aqeela Afzal, Andrew Jones, and Donald Armstrong................................................................. 117 14 Protein Carbonyl Measurement by ELISA I. Hendrikje Buss and Christine C. Winterbourn........................... 123 15 Nε-(carboxymethyl)lysine (CML) as a Biomarker of Oxidative Stress in Long-Lived Tissue Proteins J. Nikki Shaw, John W. Baynes, and Suzanne R. Thorpe............ 129 16 Measurement of S-Glutathionated Hemoglobin in Human Erythrocytes by Isoelectric Focusing Electrophoresis Haw-Wen Chen and Chong-Kuei Lii................................................ 139 17 Oxidation of Cellular DNA Measured with the Comet Assay Andrew R. Collins and Mária Dusˇ inská........................................... 147 18 Measurement of DNA Double-Strand Breaks with Giant DNA and High Molecular-Weight DNA Fragments by Pulsed-Field Gel Electrophoresis Yoshihiro Higuchi.............................................................................. 161 19 Evaluation of Antibodies Against Oxygen Free Radical-Modified DNA by ELISA Rashid Ali and Khurshid Alam......................................................... 171 P II. T A B ART ECHNIQUES FOR NTIOXIDANT IOMARKERS 20 Simultaneous Analysis of Multiple Redox-Active Metabolites from Biological Matrices Bruce S. Kristal, Karen Vigneau-Callahan, and Wayne R. Matson.................................................................... 185 21 Determination of Uric Acid in Urine by Fast-Scan Voltammetry (FSV) Using a Highly Activated Carbon Fiber Electrode Roberto Bravo, Dawn M. Stickle, and Anna Brajter-Toth............. 195 22 Measurement of α-Tocopherol Turnover in Plasma and in Lipoproteins Using Stable Isotopes and Gas Chromatography/Mass Spectrometry Elizabeth J. Parks.............................................................................. 209 Contents ix 23 Analysis of Tocotrienols in Different Sample Matrixes by HPLC Kalyana Sundram and Rosnah Md. Nor.......................................... 221 24 Measurement of β-Carotene15,15'-Dioxygenase Activity by Reverse-Phase HPLC Alexandrine During, Akihiko Nagao, and James Cecil Smith, Jr........................................................... 233 25 Ubiquinol/Ubiquinone Ratio as a Marker of Oxidative Stress Yorihiro Yamamoto and Satoshi Yamashita.................................. 241 26 Catechol- and Pyrogallol-Type Flavonoids: Analysis of Tea Catechins in Plasma Keizo Umegaki, Mituaki Sano, and Isao Tomita............................ 247 27 Pyruvate Dehydrogenase Complex as a Marker of Mitochondrial Metabolism: Inhibition by 4-Hydroxy-2-Nonenal Mulchand S. Patel and Lioubov G. Korotchkina........................... 255 28 Ceruloplasmin Detection by SDS-PAGE, Immunoblotting, and In Situ Oxidase Activity Leonard A. Levin................................................................................ 265 29 Metallothionein Determination by Isocratic HPLC with Fluorescence Derivatization Shinichi Miyairi and Akira Naganuma............................................. 273 30 Quantification of Oxidized Metallothionein by a Cd-Saturation Method Dominik Klein, Uma Arora, Shin Sato, and Karl H. Summer........ 285 31 Fractionation of Herbal Medicine for Identifying Antioxidant Activity Mohammed Afzal and Donald Armstrong...................................... 293 32 Designing Safer (Soft) Drugs by Avoiding the Formation of Toxic and Oxidative Metabolites Nicholas Bodor and Peter Buchwald.............................................. 301 33 Statistical Correction of the Area Under the ROC Curve in the Presence of Random Measurement Error and Applications to Biomarkers of Oxidative Stress Enrique F. Schisterman.................................................................... 313 Index ............................................................................................................ 319

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Oxidative stress has been linked to a variety of medical problems, including cardiovascular disease, cancer, arthritis, diabetes, and aging. Drawing on the growing volume of research into the impact of oxidative stress on pathophysiological mechanisms, Donald Armstrong updates and expands his highly
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