Oxygen Radicals in Biology and Medicine

1094 Pages·1988·4.78 MB·English

by  Michael G. Simic

OXYGEN RADICALS
IN
BIOLOGY MEDICINE
AND
BASIC LIFE SCIENCES
Alexander Hollaender, Founding Editor
Recent volumes in the series:
Volume 36 ANEUPLOIDY: Etiology and Mechanisms
Edited by Vicki L. Deliarco, Peter E. Voytek, and
Alexander Holiaender
Volume 37 GENETIC ENGINEERING OF ANIMALS: An Agricultural Perspective
Edited by J. Warren Evans and Alexander Hollaender
Volume 38 MECHANISMS OF DNA DAMAGE AND REPAIR: Implications
for Carcinogenesis and Risk Assessment
Edited by Michael G. Simic, Lawrence Grossman, and
Arthur C. Upton
Volume 39 ANTIMUTAGENESIS AND ANTICARCINOGENESIS MECHANISMS
Edited by Delbert M. Shankel, Philip E. Hartman, Tsuneo Kada,
and Alexander Holiaender
Volume 40 EXTRACHROMOSOMAL ELEMENTS IN LOWER EUKARYOTES
Edited by Reed B. Wickner, Alan Hinnebusch, Alan M. Lambowitz,
I. C. Gunsalus, and Alexander Hollaender
Volume 41 TAILORING GENES FOR CROP IMPROVEMENT:
An Agricultural Perspective
Edited by George Bruening, John Harada, Tsune Kosuge,
and Alexander Holiaender
Volume 42 EVOLUTION OF LONGEVITY IN ANIMALS: A Comparative Approach
Edited by Avril D. Woodhead and Keith H. Thompson
Volume 43 PHENOTYPIC VARIATION IN POPULATIONS: Relevance to Risk Assessment
Edited by Avril D. Woodhead, Michael A Bender, and Robin C. Leonard
Volume 44 GENETIC MANIPULATION OF WOODY PLANTS
Edited by James W. Hanover and Daniel E. Keathley
Volume 45 ENVIRONMENTAL BIOTECHNOLOGY: Reducing Risks from Environmental
Chemicals through Biotechnology
Edited by Gilbert S. Omenn
Volume 46 BIOTECHNOLOGY AND THE HUMAN GENOME: Innovations and Impact
Edited by Avril D. Woodhead and Benjamin J. Barnhart
Volume 47 PLANT TRANSPOSABLE ELEMENTS
Edited by Oliver Nelson
Volume 48 HUMAN ACHONDROPLASIA: A Multidisciplinary Approach
Edited by Benedetto Nicoletti, Steven E. Kopits,
Elio Ascani, and Victor A. McKusick
Volume 49 OXYGEN RADICALS IN BIOLOGY AND MEDICINE
Edited by Michael G. Simic, Karen A. Taylor,
John F. Ward, and Clemens von Sonntag
A Continuation Order Plan is available for this series. A continuation order will bring delivery of
each new volume immediately upon publication. Volumes are billed only upon actual shipment.
For further information please contact the publisher.
OXYGEN RADICALS
IN
BIOLOGY MEDICINE
AND
Edited by
Michael G. Simic
National Bureau of Standards
Gaithersburg, Maryland
Karen A. Taylor
In(ernational Life Sciences Institute
Washington, D.C.
John F. Ward
University of California, San Diego
La Jolla, California
and
Clemens von Sonntag
Max-Planck-Institut fiJr Strahlenchemie
Mjjlheim a.d. Ruhr, Federal Republic of Germany
Assistant Editor
Janet N. Hauber
PLENUM PRESS • NEW YORK AND LONDON
Library of Congress Cataloging in Publication Data
International Congress on Oxygen Radicals (4th: 1987: University of California
at San Diego)
Oxygen radicals in biology and medicine.
(Basic life sciences; v. 49)
"Proceedings of the Fourth International Congress on Oxygen Radicals,
held June 27-July 3,1987, at the University of California at San Diego, La Jolla,
California"-T.p. verso
Includes bibliographies and index.
1. Active oxygen-Physiological effect-Congresses. 2. Pathology,
Molecular-Congresses. 3. Free radical reactions-Congresses. 4. Oxidation,
Physiological-Congresses. I. Simic, Michael G. II. Title. III. Series. [DNLM: 1.
Free Radicals-congresses. 2. Oxygen-congresses. W3 BA255 v. 49 I QV
312161051987]
QP535.0114731987 574.19/214 88-25494
Proceedings of the Fourth International Congress on
Oxygen Radicals, held June 27-July 3, 1987,
at the University of California at San Diego,
La Jolla, California
ISBN-13 978-1-4684-5570-0 e-ISBN-13: 978-1-4684-5568-7
001: 10.1007/978-1-4684-5568-7
© 1988 Plenum Press, New York
Softcover reprint of the hardcover 15t edition 1988
A Division of Plenum Publishing Corporation
233 Spring Street, New York, N.Y. 10013
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
OXYGEN RADICALS IN BIOLOGY AND MEDICINE
is dedicated to the memory of
Dr. Alexander Hollaender
(1898-1986)
Honorary Chairman of the
Fourth International Congress on Oxygen Radicals
PREFACE
This book is based on the papers presented at the "Fourth
International Congress on Oxygen Radicals (4-ICOR)," held June 27 -
July 3, 1987, at the University of California, La Jolla. The chapters
deal with the phenomena associated with highly reactive oxygen species
(hydroxy, peroxy, alkoxy, aroxy, and superoxide radicals, as well as
singlet oxygen) and their peroxidation products (hydrogen peroxide,
hydroperoxides, peroxides, and epoxides) as they relate to the fields of
chemistry, food technology, nutrition, biology, pharmacology, and
medicine. The kinetics, energetics, and mechanistic aspects of the
reactions of these species and the interrelationship of oxygen radicals
(or any other free radicals) and peroxidized products have been
emphasized. Special attention is focused on the mechanisms of the
generation of free radicals and peroxy products in biosystems and on the
adverse effects of these radicals and products in humans. The topics
span the continuum from the simple chemistry of model systems to the
complex considerations of clinical medicine.
The book also explores the mechanisms of agents that protect
against free radicals and peroxy products in vitro and in vivo. These
agents include antioxidants used in materials, food antioxidants,
physiological antioxidants, and antioxienzymes (SOD, glutathione
peroxidase, and catalases). The use of these inhibitors to prevent
damage to organs being prepared for transplantation, thereby maintaining
the quality of transplanted organs and/or extending their "shelf-life,"
also is examined.
The recognition of free radical processes and a better
understanding of their mechanisms forecasts a revolution in the life
sciences and in medicine. It is hoped that this book not only will
inform readers but also will inspire them to continue expanding our
ability to deal with these elusive transient species in vivo by
providing the intellectual stimuli for imaginative research and originaJ
ideas for the development of preventive medicine.
Michael G. Simic
4-ICOR Chairman
vii
SPONSORS
The sponsorship, financial assistance, and encouragement of the
following organizations is gratefully acknowledged:
Sponsors
National Bureau of Standards
National Heart, Lung, and Blood institute
International Life Sciences Institute
National Cancer Institute
American Industrial Health Council
Institute for Research on Aging
Oxygen Society
Benefactors
Grunenthal GMBH
Major Contributors
Burroughs Wellcome Company
Henkel Corporation
The Upjohn Company
Shell Oil Company
Contributors
Johnson & Johnson
The Council for Tobacco Research
Pharmacia-Chiron Partnership
Glaxo, Inc.
Bristol-Meyers Company
Alcon Laboratories
Sandoz Pharmaceutical Company
Nabisco Brands, Inc.
E.I. duPont de Nemours & Company
Pfizer, Inc.
Hoffmann-La Roche, Inc.
Calreco, Inc.
Eastman Kodak Co.
viii
ACKNOWLEDGMENTS
The editors wish to thank the many individuals whose contributions
and assistance made possible the 4th International Congress on Oxygen
Radicals (4-ICOR) and publication of the proceedings in this book.
For their help in planning and implementing the 4-ICOR program, we
acknowledge the organizing committee (Steven D. Aust, Benon H.J.
Bielski, Christopher S. Foote, Norman I. Krinsky, Chris E. Kuyatt,
William E.M. Lands, Etsuo Niki, and Helmut Sies), chairmen of the
previous ICOR meetings (Ajit Singh, E. Lawrence Powers, Michael A.J.
Rodgers, and Wolf Bors), and chairmen of scientific sessions (Klaus
Dieter Asmus, William A. Pryor, Lester Packer, Britton Chance, Helmut
Sies, Irwin Fridovich, Irving H. Goldberg, Gregory B. Bulkley, Peter A.
Ward, E. Lawrence Powers, John W. Finley, Clemens von Sonntag, Robin L.
Willson, Etsuo Niki, Edward A. Dratz, Erik van Kuijk, John F. Ward,
Daniel M. Ziegler, Michael A. Trush, J. Edwin Seegmiller, Denham Harman,
Hermann Esterbauer, Sampath Parthasarathy, Bernard M. Babior, Joe M.
McCord, Earl R. Stadtman, Kelvin J.A. Davies, Ambler Thompson, Stefan L.
Marklund, John E. Biaglow, Michael A.J. Rodgers, Alex Sevanian, Steven
Aust, Thomas L. Robertson, and William B. Weglicki).
We are exceptionally grateful to Ernest Ambler, Director of NBS,
and Raymond G. Kammer, Deputy Director of NBS, for their farsighted
support of interdisciplinary research and the 4-ICOR meeting.
The support and encouragement of Claude Lenfant, Director of the
National Heart, Lung, and Blood Institute, Leopold Flohe, Director of
Research and Development, Gr~nethal GMBH, and Donald E. Stevenson,
Director of Toxicology, Health, Safety and Environment, Shell Oil
Company, are deeply appreciated.
Special thanks are extended to Professors Etsuo Niki and Toshikazu
Yoshikawa for their crucial support in the organization of the program
and the preparation of this book.
The technical and management assistance of Janet N. Hauber, Kathy
C. Stang, Sara R. Torrence, Lene Hartman, Cassandra Beck, Terry W.
Shuggars, Gloria G. Wiersma, Eva M. Wood, and Christopher Soares is
greatly appreciated.
The press coordination of Michael Baum was invaluable in
publicizing oxygen radicals and their impact on biology and medicine.
M.G.S.
K.A.T.
J.F.W.
C.v.S.
CONTENTS
INTRODUCTION
Introduction to Peroxidation and Antioxidation Mechanisms . .
Michael G. Simic and Karen A. Taylor
KINETICS AND MECHANISMS
The Redox Thermodynamics for Dioxygen Species (Oz, 0z~' HOO·,
HOOH, and HOO-) and Monooxygen Species (0, O~, ·OH,
and -OH) in Water and Aprotic Solvents 11
Donald T. Sawyer
Electron Spin Resonance Investigations of Oxygen-Centered Free
Radicals in Biological Systems . . . . . . . . . 21
Ronald P. Mason and Kim M. Morehouse
Superoxide Chemistry in Non-Aqueous Media 29
Aryeh A. Frimer
Peroxy Radicals and Singlet Oxygen (10Z) from the Addition of
Superoxide Ion (Oz~) to CC14 , CF3CC13 , PhCC13 , N-BuBr and
N-BuCl in Acetonitrile . . . . . 39
Shigenobu Matsumoto, Hiroshi Sugimoto, and Donald T. Sawyer
The Uniqueness Both of Superoxide Toxicity and of the Protective
Role of Superoxide Dismutase. ..... 43
Gidon Czapski and Sara Goldstein
Peroxyl Radicals in Aqueous Media . . 47
C. von Sonntag
Aspects of the HO; Elimination Reaction from Organic Peroxyl
Radicals: Some Recent Examples. 55
S. Das, O. J. Mieden, X.-M. Pan, M. Repas, M. N. Schuchmann,
H.-P. Schuchmann, C. von Sonntag, and H. Zegota
Kinetic Studies of Alkoxyl Radicals . 59
J. C. Scaiano
Radical-Induced Degradation of Organic Halogen and Sulfur
Compounds in Oxygenated Aqueous Solutions ... 67
Klaus-Dieter Asmus, Manohar Lal, Jorg Monig, and
Christian Schoneich
xi
Thiyl Free Radical Metabolites of Thiol Drugs and Glutathione 75
Kathryn T. Knecht, Carolyn Mottley, and Ronald P. Mason
Oxidation of Quinones by H202 : Formation of Epoxy- and
Hydroxyquinone Adducts and Electronically Excited States .. 81
Anders Brunmark and Enrique Cadenas
From Nitric Oxide to Desferal: Nitrogen Free Radicals and
Iron in Oxidative Injury 87
Robin L. Willson
Singlet Oxygen: Current Mechanistic Aspects of Photo-Oxidation . . 101
A. A. Gorman
Homolysis of Substituted Anisoles: Substituent Effects on
Phenoxy I Radical Stabilities . . .. .... 105
Stephen E. Stein and Mahendra M. Suryan
Redox Properties of Oxy and Antioxidant Radicals. 115
Slobodan V. Jovanovic and Michael G. Simic
GENERATION OF OXY RADICALS
The Role of Metals in Aqueous Superoxide Chemistry. 123
Benon H. J. Bielski
Fenton Chemistry Revisited: Amino Acid Oxidation . . . . . . . . . 131
E. R. Stadtman and B. S. Berlett
Iron Redox Reactions and Lipid Peroxidation 137
Steven D. Aust
The Generation of Ferryl or Hydroxyl Radicals during
Interaction of Hemeproteins with Hydrogen Peroxide 145
Joseph Kanner, Stella Harel, and Avior Menahem Salan
The Production of Hydroxyl and Semiquinone Free Radicals during
the Autoxidation of Redox Active Flavonoids. . . . . . . 149
William F. Hodnick, B. Kalyanaraman, Chris A. Pritsos, and
Ronald S. Pardini
Fenton Reactions in Lipid Phases: Iron Solubility, ·OH
Production, and Initiation of Lipid Oxidation. . 153
K. M. Schaich and D. C. Borg
The Role of Hemoglobin in Generating Oxyradicals. . . . . . . . 157
Joseph M. Rifkind, Lu Zhang, Jane M. Heim, and Abraham Levy
DETECTION AND MEASUREMENTS
Specific Detection of Lipid Hydroperoxides Using HPLC-EC Method 163
S. Matsushita, J. Terao, K. Yamada, and S. S. Shibata