oxygen radicals3a978-1-4684-5568-7%2f1.pdfgeneration of free radicals and peroxy products in...
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OXYGEN RADICALS IN
BIOLOGY AND MEDICINE
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 AND MEDICINE
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:
viii
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.
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 (KlausDieter 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
Donald T. Sawyer
Electron Spin Resonance Investigations of Oxygen-Centered Free Radicals in Biological Systems . . . . . . . . .
Ronald P. Mason and Kim M. Morehouse
Superoxide Chemistry in Non-Aqueous Media Aryeh A. Frimer
Peroxy Radicals and Singlet Oxygen (10Z) from the Addition of Superoxide Ion (Oz~) to CC1 4 , CF3 CC1 3 , PhCC1 3 , N-BuBr and
11
21
29
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 . J. C. Scaiano
Radical-Induced Degradation of Organic Halogen and Sulfur Compounds in Oxygenated Aqueous Solutions ...
Klaus-Dieter Asmus, Manohar Lal, Jorg Monig, and Christian Schoneich
59
67
xi
Thiyl Free Radical Metabolites of Thiol Drugs and Glutathione 75 Kathryn T. Knecht, Carolyn Mottley, and Ronald P. Mason
Oxidation of Quinones by H2 02 : Formation of Epoxy- and Hydroxyquinone Adducts and Electronically Excited States .. 81
Anders Brunmark and Enrique Cadenas
From Nitric Oxide to Desferal: Iron in Oxidative Injury
Robin L. Willson
Nitrogen Free Radicals and 87
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 Steven D. Aust
The Generation of Ferryl or Hydroxyl Radicals during Interaction of Hemeproteins with Hydrogen Peroxide
Joseph Kanner, Stella Harel, and Avior Menahem Salan
The Production of Hydroxyl and Semiquinone Free Radicals during
137
145
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. .
K. M. Schaich and D. C. Borg 153
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
Quantitative Determination of Fatty Acid Hydroperoxides in vivo. . . . . . . . . .. . ...
Hartmut Frank, Manfred Wiegand, and Dietmar Thiel
Detection of Lipid Peroxidation Products in Lipids and Tissues by Gas Chromatography-Mass Spectrometry.
F. J. G. M. van Kuijk, D. W. Thomas, R. J. Stephens, and E. A. Dratz
Direct Chemical Ionization Mass Spectrometry of Underivatized Arachidonic Acid Metabolites: Application to Leukotriene Biosynthesis . . . . . . .
Josef Gut, Gene C. Jamieson, and James R. Trudell
Chemiluminescence - High Performance Liquid Chromatography of Phosphatidylcholine Hydroperoxide in Human Blood Plasma.
Teruo Miyazawa, Keiichi Yasuda, Kenshiro Fujimoto, and Takashi Kaneda
Method for Tracing Oxygen-18 in vivo: Application to Ozone Dosimetry in Animals . .
Mourad Aissa and Gary E. Hatch
Malondialdehyde Derivatives in Urine. H. H. Draper and M. Hadley
Electron Spin Resonance of the Semiquinone of the Antitumor Antibiotic Streptonigrin and Its Metal Complexes .
Helena S. Soedjak, Barney L. Bales, and Joseph Hajdu
CHEMILUMINESCENCE
The Detection of Singlet Oxygen in Biochemical Systems Using 1268 nm Chemiluminescence .............. .
Jeffrey R. Kanofsky
Phagocyte Dioxygenation Reactions Yielding Chemiluminescence: The Maximum Multiplicity and Spin Conservation Rules Relative to Oxygen Reactivity ............ .
Robert C. Allen
Bryostatin Stimulation of Human Neutrophil Luminol and DBA (Lucigenin) Chemiluminescence .......... .
J. T. Warren, A. H. Esa, G. R. Pettit, and W. S. May
Luciferase Reverse Micellar Bioluminescence: Kinetics and Emission Spectra . . . . . . . . . .
Ambler Thompson, W. H. Biggley, and Howard H. Seliger
Platelet Chemiluminiscence Induced by Linoleic and Arachidonic Acids ............ .
T. Metsa-Ketela, A. Montfoort, and T. Kunnas
Low Level Chemiluminescence from Isolated Rat Hepatocytes, Intact Lung and Intestine in situ. . . . . . .
Julio F. Turrens, Cecilia Giulivi, Claudia Pinus, Emilio Roldan, Carla Lavagno, and Alberto Boveris
175
179
185
191
195
199
203
211
219
223
229
233
239
xiii
Prevention by Propionylcarnitine of NADPH and tert-Butyl Hydroperoxide-Dependent Chemiluminescence in Heart Microsomes . . . . . . . . . . . . . . . . .
M. L. Schinetti, D. Rossini, and A. Bertelli
Chemiluminescence from Vitamin E-Deficient Erythrocyte Induced by Xanthine Oxidase Reaction . . . . .
Hiroshi Yasuda, Masayuki Miki, Yoshito Takenaka, Hiroshi Tarnai, and Makoto Mino
Membranes
Monitoring the Interactions of Environmental Agents by CellDependent Chemiluminescence: Studies with Polycyclic Aromatic Hydrocarbons ........ .
Lorraine E. Twerdok and Michael A. Trush
Gel State Chemiluminescence: An Artificial Electron Transport System . .. .......... .
Johnathan L. Kiel, David M. Simmons, and David N. Erwin
FREE RADICALS AND OXYGEN SPECIES INLIPIDS
Hydroperoxidation of Unsaturated Fatty Esters . . . . . . . Edwin N. Frankel
Lipid Peroxidation and Retinal Phototoxic Degeneration. Robert J. Stephens, Dalbir S. Negi, Sarah M. Short, Frederik J. G. M. van Kuijk, Edward A. Dratz, and David W. Thomas
Production and Metabolism of Cytotoxic Phospholipids Generated
243
249
255
261
265
283
during Incubation of Liposomes with Oxyhemoglobin. 291 Keizo Inoue, Hiroyuki Itabe, and Ichiro Kudo
Lipid Peroxidation Dependent on Oxygen and Catalytic Free Iron Ions in situ Storage Muscle Foods. . . . . . 301
Stella Harel, Joseph Shagalovich, Bella Hazan, and Joseph Kanner
A Unique Role of Histidine in Fe-Catalyzed Lipid Oxidation by Fish Sarcoplasmic Reticulum. . . . . . . . . . . . . .
Marilyn C. Erickson and Herbert O. Hultin
Cholesterol Epoxidations by Defined Oxygen Species. Leland L. Smith and Krzysztof Jaworski
Thermal Decomposition of Methyl Linoleate and Methyl Linolenate
307
313
Hydroperoxides Analyzed by Capillary Gas Chromatography. 319 Edwin N. Frankel, Edward Selke, and William E. Neff
Effect of Dietary Lipid Peroxides on Lymphoid Tissues Motoko Oarada, Teruo Miyazawa, Kenshiro Fujimoto, Takashi Kaneda, Emiko Ito, and Kiyoshi Terao
xiv
327
FREE RADICALS AND OXYGEN SPECIES IN PROTEINS
Implication of Protein Oxidation in Protein Turnover, Aging, and Oxygen Toxicity. . . . 331
E. R. Stadtman, C. N. Oliver, R. L. Levine, L. Fucci, and A. J. Rivett
Role of Oxidative Modification in the Lability of Ceruloplasmin 341 Paul G. Winyard, Robert C. Hider, Joseph Lunec, Alex F. Drake, and David R. Blake
The Oxidative Modification of Lens Proteins 347 Donita Garland, Paul Russell, and J. Samuel Zigler, Jr.
Degradation of the Proteoglycans of Human Articular Cartilage by Reactive Oxygen Metabolites . . . . . . 353
Clive R. Roberts, John S. Mort, and Peter J. Roughley
Free Radical Denaturation of Immunoglobulin G Is due to Amino Acid Oxidation: Implications for Rheumatoid Arthritis 357
H. R. Griffiths, J. Lunec, D. R. Blake, and R. L. Willson
A Study of ROS Induced Denaturation of IgG3 Using Monoclonal Antibodies; Implications for Inflammatory Joint Disease. 361
H. R. Griffiths, J. Lunec, R. Jefferis, D. R. Blake, and R. L. Willson
Oxy Radical-Initiated Protein S-Thiolation and Enzymic Dethiolation
James A. Thomas and Eun-Mi Park
FREE RADICALS AND OXYGEN SPECIES IN LIPOPROTEINS
Modification of Human Low Density Lipoprotein by Lipid Peroxidation . . . . . . . . . . . . . .
Hermann Esterbauer, Gunther Jurgens, and Oswald Quehenberger
Is Oxidized Low Density Lipoprotein Involved in the Recruitment and Retention of Monocyte/Macrophages in the Artery Wall
365
369
during the Initiation of Atherosclerosis? 375 Sampath Parthasarathy, Mark T. Quinn, and Daniel Steinberg
Copper and Copper-Nicotinic Acid Complexes Mediated Oxidation of High Density Lipoprotein . . . . . . 381
Mohamed El-Saadani, Hermann Esterbauer, Gunther Jurgens, Mohamed El-Sayed, Ahmed Nassar, Mohamed Goher, and Anton Holasek
Oxidation of Human Low Density Lipoprotein Initiated by Copper(II)Chloride . . . . . . . . 387
Oswald Quehenberger, Gunther Jurgens, Silvia Zadravec, and Hermann Esterbauer
Isolation and Partial Characterization of an Oxidized LDL in Humans. . _........ 391
Pietro Avogaro, Gabriele Bittolo Bon, and Giuseppe Cazzolato
xv
Coronary Disease: Spectroscopic Correlation of Structure and Size of Plasma Lipoproteins with Patient Clinical History. 397
B. Simic-Glavaski and J. J. Opplt
FREE RADICALS AND OXYGEN SPECIES IN DNA
The Effect of Oxygen on the OH Radical-Induced Strand Break Formation of DNA in vitro and in vivo .....
Dietrich Schulte-Frohlinde
Double Strand Breakage in DNA and Cellular Radiation Sensitivity:
403
Linear Energy Transfer and the Oxygen Effect . . . . . .. 419 J. T. Lett
Effect of ·OH Scavenging on the Yield of Radiation-Induced DNA Double-Strand Breaks in Isolated Nuclei. . . . . . 429
Edward A. Bump, Susan M. Pierce, Ceferino H. Obcemea, Lee Chin, and C. Norman Coleman
Sonochemistry of Nucleic Acid Constituents in Aqueous Solution. A Spin-Trapping Study. . . . . . . . . . 433
Takashi Kondo, C. Murali Krishna, and Peter Riesz
Gamma Radiolysis of RNA. An ESR and Spin-Trapping Study. Alasdair J. Carmichael, Carmen M. Arroyo, and Thomas L. Walden
Interactions of Oxygen and Sulfhydryls with Free Radicals in Irradiated Mammalian Cells . . . . . . . . . . . .
Kathryn D. Held
Oxygen Radicals, Lipid Peroxidation and DNA Damage in Mi tochondria . . . . . . . . .
Andrew M. Hruszkewycz and David S. Bergtold
Involvement of Reactive Oxygen Intermediates in the Mutagenicity of Tumor Promoters . . . . . . .. ...... .
Neal Wallis Biggart and Edwin C. Murphy, Jr.
Oxidative Damage to DNA in Adrenocortical Cells during Senescence in Culture
Kim H. Norris and Peter J. Hornsby
437
441
449
457
461
Substituted Phthalocyanines as Photodynamic Sensitizers . . . . 467 I. Rosenthal, E. Ben-Hur, S. Greenberg, A. Conception-Lam, D. M. Drew, and C. C. Leznoff
Effects of Singlet Oxygen on the Biological Activity of DNA and Its Involvement in Single Strand-Break Formation 473
Heribert Wefers, Paolo Di Mascio, Hong-Phuc Do-Thi, Dietrich Schulte-Frohlinde, and Helmut Sies
Determination of 8-Hydroxydeoxyguanosine in Human Urine: A Possible Assay for in vivo Oxidative DNA Damage. 479
Kenneth C. Cundy, Ron Kohen, and Bruce N. Ames
Urine Biomarkers for Oxidative DNA Damage . . . . . . . 483 D. S. Bergtold, M. G. Simic, H. Alessio, and R. G. Cutler
xvi
P-450
The Generation of Radicals during the Normal and Abnormal Functioning of Cytochromes P-450 . . . . . . .
David Dolphin
Radical Intermediates in the Catalytic Cycles of Cytochrome P-450 . . . . . . . . . . . . .
Alfin D. N. Vaz, Elizabeth S. Roberts, and Minor J. Coon
Cytochrome P-450 Model Systems: Alkene Oxidation. Teddy G. Traylor, Beth E. Dunlap, and Andrew R. Miksztal
Cytochrome P-448 Induction Restores the Propagation of ·Oz--Induced Lipid Peroxidation in Hepatoma Microsomes
Tornrnaso Galeotti and Silvia Borrello
Generation of Superoxide by the Microsomal Mixed-Function Oxidase System . . . . . . . . . . . . .
Lee A. Morehouse and Steven D. Aust
OXIDATIVE STRESS
Membrane Permeability and Oxidant Induced Injury. Henry Jay Forman, Dianne C. Skelton, George A. Loeb, and Raymond J. Dorio
The Measurement of Protein Degradation in Response to Oxidative Stress . . . . . . . . . . . . . . . . . .
Robert E. Pacifici, Sharon W. Lin, and Kelvin J. A. Davies
Oxidative Modification of Enzymes during Aging and Acute Oxidative Stress . . . . . .
Pamela E. Starke-Reed and Cynthia N. Oliver
Oxidative Modification of Glutamine Synthetase: Covalent and Conformational Changes which Control Susceptibility to Proteolysis. . . . . . ....... .
Rodney L. Levine and A. Jennifer Rivett
Role of Hemin in Oxidative Stress Induced by Divicine in Vitamin E-Deficient Rats ....
M. D'Aquino and G. Tomassi
The Isolation and Partial Characterization of Stable HzOz-Resistant Variants of Chinese Hamster Fibroblasts
D. R. Spitz, G. C. Li, M. L. McCormick, Y. Sun, and L. W. Oberley
Reactive Oxygen Metabolites and Hyperoxic Toxicity .. Dana Jamieson
ANTIOXIDANT DEFENSE
Inhibition of Peroxidation of Membranes Etsuo Niki and Erika Komuro
491
501
509
513
517
523
531
537
541
545
549
553
561
xvii
Cellular Protection Against Damage by Hydroperoxides: Role of Glutathione ............. .
John E. Biaglow, Marie E. Varnes, Edward R. Epp, Edward P. Clark, Steve Tuttle, and Kathryn D. Held
567
A Secondary Antioxidant Defense Role for Proteolytic Systems. 575 Kelvin J. A. Davies
Radioprotection of Mice with Ascorbic Acid, Desferal and Mercaptoethylamine . . . . . . . . . . . . . 587
Ajit Singh, Harwant Singh, James S. Henderson, Robert D. Migliore, Jacques Rousseau, and Johan E. Van Lier
Antiinflammatory, Analgesic, and Antiulcer Activities of Copper Complexes Suggest Their Use in a Physiologic Approach to Treatment of Arthritic Diseases . . . .
John R. J. Sorensen
Tocopherol Behavior and Membrane Constituents in Erythrocytes
591
with Oxidant Stress. . . . . . . . . . . . . . . 595 Masayuki Miki, Tadashi Motoyama, Yoshito Takenaka, and Makoto Mino
Porcine Stress Syndrome, Free Radicals and Vitamin E. . . . . . . . 605 Garry Duthie, John Arthur, and Peter Hoppe
Increased Oxidation of Tocopherols in Chickens with Inherited Muscular Dystrophy . . . . . . . .
Michael E. Murphy and James P. Kehrer
Vitamin E and Immune Functions. Adrianne Bendich
Beneficial Effect of Dietary Antioxidants on the Aging Immune System ................. .
S. Nikbin Meydani, T. Furukawa, M. Meydani, and J. B. Blumberg
611
615
621
Inclusion of Antioxidants in Resuscitation Fluids . . . . . . . . . 627 Bo E. Hedlund
Serum Antioxidant Activity as a Determinant of Pulmonary Dysfunction in Cigarette Smokers . . . . . . . . .
Raymond B. Bridges and Stanley R. Rehm
ENZYMATIC DEFENSE
Probing Enzyme-Substrate Recognition and Catalytic CU,Zn Superoxide Dismutase ....... .
John A. Tainer, Robert A. Hallewell, Victoria Hans E. Parge, and Elizabeth D. Getzoff
Bacterial Superoxide Dismutases Howard M. Steinman
xviii
Mechanism in
A. Roberts,
631
635
641
Extracellular-Superoxide Dismutase Association with Cell Surface-Bound Sulfated Glucosaminoglycans. . . . . . 647
Kurt Karlsson and Stefan L. Marklund
Catalases--With and Without Heme. . . . . 651 Wayne F. Beyer, Jr., and Irwin Fridovich
Glutathione Peroxidase. 663 L. Flohe
The Role of Glutathione Transferase in the Detoxication and Repair of Lipid and DNA Hydroperoxides . . 669
Brian Ketterer, David J. Meyer, and Kia Hong Tan
n-3 Fatty Acids and Hydroperoxide Activation of Fatty Acid Oxygenases . . . . . . . . . . 675
William E. M. Lands and Robert B. Pendleton
Sequence of Complementary DNA Encoding Human Extracellular-Superoxide Dismutase and Production of Recombinant Enzyme. 683
Stefan L. Marklund, Lena Tibell, Karin Hjalmarsson, Gunnar Skogman, Ake Engstrom, and Thomas Edlund
A cSOD-Null Mutant of Drosophila Confers Sensitivity to Paraquat and Reduced Longevity. . . . . . . . . . . . 689
J. P. Phillips
Induction of Superoxide Dismutase Activity by Paraquat or EDU in Human Gingival Fibroblasts . . . . . . . 695
Janet S. Kerr, George A. Boswell, Jr., Neil R. Ackerman, and Theresa M. Stevens
Superoxide Dismutase in Cultured Benign and Malignant Tumors of the Colon. ........ ..... 699
Richard L. Nelson
Microinjection of Antioxidant Enzymes to Protect Cells from Oxygen Derived Free Radicals . . . . . . . . .
Carine Michiels and Jose Remacle
Human Fibroblast Antioxidant Defense Response to Alteration in Oxygen Tension. . . . . . .
Arthur K. Balin, Robert G. Allen, and Richard Reimer
Relationship between the Antioxidant Enzyme DT-Diaphorase and Tumor Response to Mitomycin C Treatment ....
Chris A. Pritsos, Lani L. Pardini, Andrew J. Elliott, and Ronald S. Pardini
Microsomal Fatty Acid Composition and Ca2 + Uptake Modifications
703
707
713
Induced by SOD Depletion in Rat Liver. . . . . . 717 G. M. Bartoli, P. Palozza, E. Piccioni, B. Giannattasio, G. Calviello, A. M. Guerrera, D. Bossi, G. Maccauro, and A. Cittadini
xix
The Use of Oxygen Free Radical Scavengers in the Rat Peritonitis Model. . . . . . . . . . . . . . . . . . . . . . . . . .. 721
Whitney M. Limm, Susan N. Ishikawa, Thomas Grover, J. Judson McNamara, and Lawrence H. Piette
Adaptations to Plant Pro-Oxidants in a Phytophagous Insect Model: Enzymatic Protection from Oxidative Stress
Ronald S. Pardini, Chris A. Pritsos, Susan M. Bowen, Sami Ahmad, and Gary J. Blomquist
PHARMACOLOGY AND TOXICOLOGY
725
Mechanisms for the Generation of Oxygen Radicals by Drugs . . . . . 729 Daniel M. Ziegler
Enhancement of Chemical Activation via Radical-Dependent Mechanisms: An Emerging Concept in Chemical-Chemical Interactions . . . . . . . . . . . .
Michael A. Trush and David C. Thompson
Roles of Oxygen and Oxygen Substitutes in DNA Sugar Damage by Antitumor Antibiotics. . . . . . ....
Irving H. Goldberg, Lizzy Kappen, and Der-Hang Chin
Reduction of 5-Nitroimidazoles, Nitrofurazone, and 2,4-Dinitrophenol to Their Free Radical Metabolites by Tritrichomonas foetus Hydrogenosomes ....... . Silvia N. J. Moreno and Roberto Docampo
739
745
759
Role of Free Radicals in Etoposide (VP-16,213) Action. . . . . . . 765 Birandra K. Sinha
The Mechanism of Quinone Formation from Benzo[a]Pyrene Mediated by Lipid Liposomal Suspension . . . . . .
Junji Terao and Setsuro Matsushita
Carcinogenic Peroxidation in
Lipid Peroxidation, Protein Thiols and Calcium Homeostasis in Bromobenzene-Induced Liver Damage . . . . . .
A. F. Casini, E. Maellaro, A. Pompella, M. Ferrali, and M. Comporti
Vanadate Stimulation of Pyridine Nucleotide Oxidation in Mammalian Liver Microsomal Membranes . . . . . . .
Roger A. Coulombe, Jr., David W. Reif, Randal J. Keller, Donald P. Briskin, Steven D. Aust, and Raghubir P. Sharma
Mechanism of Oxidation of 1-Methyl-4-Phenyl-3,3-Dihydropyridinium (MPDP+) ..
B. Kalyanaraman, W. Korytowski, and C. C. Felix
Reduction of Nitroheterocyclic Drugs by Ascorbate and Catecholamines: A Possible Mechanism for the Neurotoxicity of Nitroheterocyclic Drugs
D. N. Ramakrishna Rao and Ronald P. Mason
Role of Active Oxygen in Paraquat and 1-Methyl-4-Phenyl-1,2,3,6-
769
773
777
781
787
Tetrahydropyridine (MPTP) Cytotoxicity . . . . . . . . .. 795 Martha S. Sandy, Donato Di Monte, Phyllis Cohen, and Martyn T. Smith
xx
Free Radical Formation by Cytotoxic Alkylaminoanthraquinones in Liver Microsomes . . . . . . . . . . . . . . . . 803
Laurence H. Patterson, Jaspel Basra, and Jeffrey R. Brown
Lipid Peroxidation and Haloalkylation in CCl 4 -Induced Liver Fatty Degeneration and Necrosis. . . . . . . . . . . 807
Giuseppe Poli, Elena Chiarpotto, Fiorella Biasi, Emanuele Albano, Rita Carini, Umberto M. Marinari, and Mario U. Dianzani
Paraquat-Resistant HeLa Cells . . . . . . . . . . . . . . 811 J. Krall, A. C. Bagley, G. M. Mullenbach, R. A. Hallewell, and R. E. Lynch
NEUTROPHILS AND PHAGOCYTOSIS
The Respiratory Burst Oxidase . . . . . . . . . . Bernard M. Babior
Reactions of Myeloperoxidase with Superoxide and Hydrogen Peroxide: Significance for Its Function in the Neutrophil ......... .
Christine C. Winterbourn and Anthony J. Kettle
Bacterial Killing by Phagocytes: Potential Role(s) of Hypochlorous Acid and Hydrogen Peroxide in Protein Turnover, DNA Synthesis, and RNA Synthesis ....
Susan M. McKenna and Kelvin J. A. Davies
Cellular Targets of H2 02 and HOCl Induced Injury. I. U. Schraufstatter, P. A. Hyslop, J. Jackson, and C. G. Cochrane
815
823
829
833
Oxidative Modification of Enzymes by Stimulated Neutrophils . . . . 839 Cynthia N. Oliver
Oxidative Inactivation of Neutrophil Granule Proteinases: Implications for Neutrophil-Mediated Proteolysis
Margret C. M. Vissers and Christine C. Winterbourn
Effects of Alpha,Beta-Unsaturated Aldehydes on Macrophage Neutrophil Membrane Function, Fluidity and Sulfhydryl Status ............... .
Gisela Witz, Nancy J. Lawrie, Bernard D. Goldstein, Jill Ryer-Powder, and Marie A. Amoruso
and
Latex Beads as Vehicles for the Study of Free Radical Processes
845
849
in Phagocytic Cells .. , ..... 853 Michael J. Thomas and Catherine C. Hedrick
Superoxide Generation of Phagocytizing Polymorphonuclear Leukocytes from Patients with Chronic Renal Failure.
Toru Tanigawa, Toshikazu Yoshikawa, Norimasa Yoshida, Shigeru Sugino, and Motoharu Kondo
857
xxi
ISCHEMIA - REPERFUSION
Clastogenic Factor in Ischemia-Reperfusion Injury. Protective Effect of Allopurinol . . . . . .
Ingrid Emerit and Jean-Noel Fabiani
Inactivation of Creatine Phosphokinase by Superoxide during Reperfusion Injury . . . . . . . . . . . . . . . . .
Joe M. McCord and William J. Russell
The Post-Treatment Experiment: Reperfusion Injury
Charles F. Babbs
An Operational Definition of
Mechanisms of Oxidant-Mediated Microvascular Injury Following Reperfusion of the Ischemic Intestine. . . . ..
Barbara J. Zimmerman, Matthew B. Grisham, and D. Neil Granger
The Amplificative Role of PAF-Acether in the Oxidative Stress Following Reperfusion of Ischemic Stomach. . . . . . .
Marie-Therese Droy-Lefaix, Yvette Drouet, Gerard Geraud, and Pierre Braquet
Equieffective Protection by Human and Bovine SOD Against Renal
863
869
875
881
887
Reperfusion Damage in Rats . . .. ....... 891 Johannes Schneider, Elmar Friderichs, and Hubert Giertz
Potential of Methylene Blue to Block Oxygen Radical Generation in Reperfusion Injury. . . . . . . . . . . . . . . 895
Michael J. Kelner, Richard Bagnell, Braden Hale, and Nicholas M. Alexander
CARDIOVASCULAR SYSTEM
Superoxide Radical Release into the Cytoplasm of Heart Cells by an NADH-Driven Oxygen Activator. . . . . . . . . . . . . 899
Hans Nohl
Detection and Measurement of Free Radical Generation during Cardiovascular Injury .............. .
Carmen M. Arroyo, Benjamin F. Dickens, Jay H. Kramer, Roy H. Leiboff, Gertrud W. Mergner, I. Tong Mak, and William B. Weglicki
Evidence That Free Radicals Result in Reperfusion Injury in Heart Muscle . . . . . . . . . . . . . . . . . .
Myron L. Weisfeldt, Jay Zweier, Giuseppe Ambrosio, Lewis C. Becker, and John T. Flaherty
905
911
Identification of Free Radical Species in the Myocardium. 921 Hiroe Nakazawa, Kazunobu Ban, Kohji Ichimori, Yoshiro Sinozaki, Haruka Okino, Takashi Masuda, Nobuo Aoki, Shingo Hori, and Masahiro Kono
Abnormal Electrical Activity Induced by HzOz in Isolated Canine
xxii
Myocytes . . . . . . . . . . . . . . .. ...... 927 Peggy L. Barrington, Charles F. Meier, Jr., and William B. Weglicki
Role of Oxygen Radicals in Endotoxin Shock and Disseminated Intravascular Coagulation. . . . . . . . . . . .
T. Yoshikawa, N. Yoshida, H. Miyagawa, T. Tanigawa, T. Takemura, Y. Morita, S. Sugino, and M. Kondo
Plasma Lipid Peroxidation and Atherosclerosis in Restricted Ovulator Chickens. . . . .. . ..... .
Terrance L. Smith and Fred A. Kummerow
Enzymatic Lipid Peroxidation: A Step in the Breakdown of Mitochondria during the Maturation of Red Blood Cells.
Hartmut Kuhn, Tankred Schewe, Samuel M. Rapoport, and Alan R. Brash
Myocardial Salvage by the Free Radical Scavenging Actions of Xanthine Oxidase Inhibitors .......... .
Dipak K. Das, Richard M. Engelman, Ronald Clement, Hajime Otani, M. Renuka Prasad, and Parinam S. Rao
Oxygen Radical Scavengers and Myocardial Preservation during Transplantation: Role of Xanthine Oxidase . . .
James R. Stewart, Walter H. Merrill, and William H. Frist
GENERAL MEDICINE
933
941
945
951
957
Endothelial Cells: A Source and Target of Oxidant Damage . . . . . 963 Una S. Ryan and James M. Vann
The Role of Iron in Injury of Endothelial Cells in vitro and in vivo ................. .
Peter A. Ward, Gerd O. Till, David E. Gannon, James A. Varani, and Kent J. Johnson
Alterations in Cultured Rat Pulmonary Artery Endothelial Cells
969
with Hyperoxia; Effect of Age. . . . . . . . . . . . . . 975 R. S. Chuknyiska and R. E. Ratych
Lung Energy Metabolism Following Twenty-Four Hours Exposure to One Hundred Percent Oxygen . . . . . . . . . 979
D. J. P. Bassett, E. Bowen-Kelly, and S. S. Reichenbaugh
Prostaglandins and Leukotrienes in Pulmonary O2 Toxicity. . . 983 Morris D. Faiman and Lavonne M. Patton
Lipid Peroxidation, Free Radicals and Experimental Inflammation 987 Andrew M. Symons, Ewa J. Dowling, and Dennis V. Parke
Inhibition by Prostacyclin Analogs of .02- Production in Human Polymorphonuclear Leukocytes . . . . . . . . . . 991
H. J. Stahlberg, G. Loschen, and L. Flohe
Kawasaki Disease, Oxygen Radicals and High Dose Gammaglobulin Therapy. . . . . . . . . . . . . . . . . . . . . . . . 997
Tadatoshi Kuratsuji, Noriaki Shinomiya, Noboru Kobayashi, Kunihisa Takagi, Shunichi Shimizu, Tadashi Ojima, Eisuke Takahashi, and Hideji Hanabusa
xxiii
An Endogenous Source of the Superoxide Anion in the Central Nervous System . . . . . . . . . . . . . . . . . . 1005
Carol A. Colton and Daniel L. Gilbert
Hydrogen Peroxide Production in Dopamine Neurons .......... 1011 Mary Beth Spina and Gerald Cohen
Oxygen Radical-Mediated Damage to Brain Tissue. . . . . . . . . . . 1015 Robert A. Floyd
Oxygen-Induced Retinopathy in the Rat . . . . . . . . . . . . . . . 1025 John S. Penn and Lisa A. Thum
Selective Inhibition of Membrane ATPases by Hydrogen Peroxide in the Lens of the Eye . . . . . . . . . . . . . . . . . . . 1029
Douglas Borchman, Christopher Paterson, and Nicholas Delamere
Anterior Chamber Hydrogen Peroxide: Effects of 3-Aminotriazole on Peroxide Kinetics and on the Status of Glutathione. .. 1035
Stephen Csukas, Anastasios Costarides, Michael V. Riley, and Keith Green
Morphological Sequelae of Anterior Segment Hydrogen Peroxide in Young and Adult Rabbits with or without 3-Aminotriazole Treatment. . . . . . . . . . . . . . . . . . . . .. .. 1039
Anastasios Costarides, David Birnbaum, Stephen Csukas, Elizabeth Forbes, and Keith Green
Corneal Oxygen Scavenging Systems: Lysis of Corneal Epithelial Cells by Superoxide Anions . . . . . . . . . . . . . 1043
Rosalie Crouch, Zhu Ling, and Betty J. Hayden
The Role of Allopurinol and Oxygen Free Radical Scavengers in Liver Preservation . . . . . . . . . . . . . . . . . . . . . 1047
Luis H. Toledo-Pereyra
Prevention of Acute Renal Failure by SOD and Sucrose ........ 1053 M. Wolgast, A. Bayati, O. Hellberg, o. Kallskog, and G. Ojteg
The Aging Process . . . . . . . . . . . . . . . . . . . . . . . . . 1057 Denham Harman
Influence of Life-Prolonging Food Restriction on Membrane Lipoperoxidation and Antioxidant Status. . . . .... 1067
Byung Pal Yu, Serge Laganiere, and Jae-Won Kim
Author Index. 1075
Subject Index 1081
xxiv