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