Methods in Enzymology
Volume 105
Oxygen Radicals in
Biological Systems
EDITED BY
Lester Packer
MEMBRANE BIOENERGETICS GROUP
UNIVERSITY OF CALIFORNIA
BERKELEY, CALIFORNIA
Advisory Board
Bruce Ames
Anthony Diplock
Lars Ernster
Rolf J. Mehlhorn
William A. Pryor
Trevor F. Slater
Irwin Fridovich
FACHBE5?EICH
1984
B I O L O G i E (10)
der Technfecher. icr'ischub Darmstadi
- B i o i: ; . ;.: D - 6 1 0 0 O a r m s i a d t / B. R. D
Inv.-Nr.
ACADEMIC PRESS, INC.
(Harcourt Brace Jovanovich, Publishers)
Orlando San Diego San Francisco New York London
Toronto Montreal Sydney Tokyo Sao Paulo
Table of Contents
CONTRIBUTORS TO VOLUME 105
xi
PREFACE
xvii
VOLUMES IN SERIES
xix
Section I. Ghemistry and Biochemistry of Oxygen and Intermediate
States of Its Reduction
1. Chemistry of Dioxygen
MONIKA J. GREEN AND
H. ALLEN O. HILL
2. Biochemistry of Oxygen Radical Species
M. BRUNORI AND
G. ROTILIO
3. Characterization of Singlet Oxygen
3
22
CHRISTOPHER S. FOOTE,
F. C. SHOOK, AND
R. B. ABAKERLI
4. Role of Iron in Oxygen Radical Reactions
36
BARRY HALLIWELL AND
JOHN M. C. GUTTERIDGE
47
Section II. Isolation and Assays of Enzymes or Substances Resulting in
Formation or Removal of Oxygen Radicals
A. One-Electron Transfer Enzyme Reactions Resulting in
O2~ Production
5. Overview: Biological Sources of O2~
IRWIN FRIDOVICH
6. Overview: Superoxygenase
RYOTARO-YOSHIDA AND
OSAMU HAYAISHI
59
61
7. Methods for the Study of Superoxide Chemistry in JOAN S. VALENTINE,
Nonaqueous Solutions
ANDREW R. MIKSZTAL, AND
DONALD T. SAWYER
Generation of Superoxide Radicals in Aqueous BENON H. J. BIELSKI
and Ethanolic Solutions by Vacuum-UV Photolysis
71
81
VI
TABLE OF CONTENTS
- B. Isolation, Purification, Characterization, and Assay of
Antioxygenic Enzymes
9. Isolation and Characterization of Superoxide Dis- J. V. BANNISTER AND
mutase
W. H. BANNISTER
10. Superoxide Dismutase Assays
L. FLOHE AND
F. OTTING
11. Subcellular Distribution of Superoxide Dismu- BRUCE L. GELLER AND
tases in'Rat Liver
DENNIS R. WINGE
12. Assays of Glutathione Peroxidase
13. Catalase in Vitro
88
93
105
LEOPOLD FLOH£ AND
WOLFGANG A. GUNZLER
114
HUGO AEBI
121
14. Assays of Lipoxygenase, 1,4-Pentadiene Fatty SIMO LAAKSO,
Acids, and O2 Concentrations: Chemilumines- ESA-MATTI LILIUS,
cence Methods
AND PEKKA TURUNEN
126
C. Antioxidants/Prooxidants
15. High-Performance Liquid Chromatography Meth- JUDITH L. BUTTRISS AND
ods for Vitamin E in Tissues
16. Vitamin E Analysis Methods for Animal Tissues
ANTHONY T. DIPLOCK
131
INDRAJIT D. DESAI
138
17. Simultaneous Determination of Reduced and Oxi- MASAHIRO TAKADA,
dized Ubiquinones
SATORU IKENOYA,
TERUAKI YUZURIHA,
AND KOUICHI KATAYAMA
18. Assay of Carotenoids
SUDHAKAR WELANKIWAR
19. Uric Acid: Functions)and Determination
147
NORMAN I. KRINSKY AND
155
PAUL HOCHSTEIN,
LINDA HATCH,
AND ALEX SEVANIAN
162
D. Detection and Characterization of Oxygen Radicals
20. Pulse Radiolysis Methodology
KLAUS-DIETER ASMUS
21. Electron and Hydrogen Atom Transfer Reactions: L. G. FORNI AND
Determination of Free Radical Redox Potentials R. L. WILLSON
167
179
by Pulse Radiolysis
22. Spin Trapping
EDWARD G. JANZEN
188
23. Spin Trapping of Superoxide and Hydroxyl Rad- GERALD M. ROSEN AND
icals
ELMER J. RAUCKMAN
198
TABLE OF CONTENTS
24. Reaction of • OH
.
Vll
GIDON CZAPSKI
209
25. Electron Spin Resonance Spin Destruction Meth- ROLF J. MEHLHORN AND
ods for Radical Detection
LESTER PACKER
215
26. Low-Level Chemiluminescence as an Indicator of ENRIQUE CADENAS AND
- Singlet Molecular Oxygen in Biological Systems HELMUT SIES
221
27. High-Pressure Liquid Chromatography-Electro- ROBERT A. FLOYD,
chemical Detection of Oxygen Free Radicals
C. ANN LEWIS,
AND PETER K. WONG
231
28. Survey of the Methodology for Evaluating Nega- RONALD PETHIG
tive Air Ions: Relevance to Biological Studies
238
E. Genetic Methods for Detection/Assay of Oxygen Radical Species
29. Detection of Oxidative Mutagens with a New Sal- DAVID E. LEVIN,
monella Tester Strain (TA102)
MONICA HOLLSTEIN,
MICHAEL F. CHRISTMAN,
AND BRUCE N. AMES
249
30. Determination of the Mutagenicity of Oxygen HOSNI M. HASSAN AND
Free Radicals Using Microbial Systems
CARMELLA S. MOODY
254
31. Assay of Rate of Aging of Conidia of Neuro- KENNETH D. MUNKRES AND
spora crassa
CHERYL A. FURTEK
263
Section III. Assay of Modes of Biological Damage Imposed by O2 and
Reduced Species
)
A. Lipid Peroxidation '
32. Chemistry of Lipid Peroxidation
N E D A. PORTER
273
33. Overview of Methods Used for Detecting Lipid T. F. SLATER
Peroxidation
283
34. Chemical Methods for the Detection of Lipid Hy- WILLIAM A. PRYOR AND
droperoxides
"
LAWRENCE CASTLE
""
293
35. Comparative Studies on Different Methods of Ma- R. P. BIRD AND
lonaldehyde Determination
H. H. DRAPER
299
36. Concentrating Ethane from Breath to Monitor GLEN D. LAWRENCE AND
Lipid Peroxidation in Vivo
GERALD COHEN
305
37. Assay of Ethane and Pentane from Isolated Or- ARMIN MULLER AND
gans and Cells
HELMUT SIES
311
Vlll
TABLE OF CONTENTS
38. Detection of Malonaldehyde by High-Perfor- HERMANN ESTERBAUER,
mance Liquid Chromatography
JOHANNA LANG,
SYLVIA ZADRAVEC,
AND TREVOR F. SLATER
39. Assay for Blood Plasma or Serum
KUNIO YAGI
319
328
40. Spectrophotometric Detection of Lipid Conju- RICHARD O. RECKNAGEL AND
" gated Dienes
,
.
ERIC A. GLENDE, JR.
331
41. Fluorescence Damage Products of Lipid Peroxi- CORA J. DILLARD AND
dation
AL L. TAPPEL
337
42. Calibration of Microspectrophotometers as It Ap- WILLIAM S. STARK,
plies to the Detection of Lipofuscin and the GREGORY V. MILLER,
Blue- and Yellow-Emitting Fluorophores in Situ AND KENDALL A. ITOKU
43. Detection of the Metabolism of Polycyclic Aro- THOMAS A. Dix AND
matic Hydrocarbon Derivatives to Ultimate LAWRENCE J. MARNETT
Carcinogens during Lipid Peroxidation
341
347
44. Detection of Picomole Levels of Lipid Hydroper- RICHARD CATHCART,
oxides Using a Dichlorofluorescein Fluorescent ELIZABETH SCHWIERS,
Assay
AND BRUCE N. AMES
352
B. Plasma Membrane
45. Measurement of O2~ Production by Human Neu- MICHELE MARKERT,
trophils. The Preparation and Assay of NADPH PATRICIA C. ANDREWS,
Oxidase-Containing Particles from Human Neu- AND BERNARD M. BABIOR
trophils
46. Measurement of O2~ Secreted by Monocytes and RICHARD B. JOHNSTON, JR.
358
365
Macrophages
47. Superoxide Production
,
PETER J. O'BRIEN
48. Endothelial Culture, Neutrophil or Enzymic Gen- CHARLES F. MOLDOW AND
eration of Free Radicals: In Vitro Methods for HARRY S. JACOB
370
378
the Study of Endothelial Injury
49. Systemic Consequences of O2~ Production
ROLANDO DEL MAESTRO
386
50. Calcium and Calmodulin in Neutrophil Activation HAROLD P. JONES AND
JOE M. MCCORD
389
51. Measurement of Oxidizing Radicals by Polymor- DENNIS P. CLIFFORD AND
phonuclear Leukocytes
52. Antimicrobial Activity of Myeloperoxidase
JOHN E. REPINE
393
SEYMOUR J. KLEBANOFF,
ANN M. WALTERSDORPH,
AND HENRY ROSEN
399
TABLE OF CONTENTS
53. Determination of Microbial Damage Caused by HOSNI M. HASSAN
Oxygen Free Radicals, and the Protective Role
of Superoxide Dismutase
IX
404
C. Microsomal Membranes
54. Oxidizing Radical Generation by Prostaglandin H PAUL H. SIEDLIK AND
Synthase
LAWRENCE J. MARNETT
55. Assay of in Situ Radicals by Electron Spin Reso- RONALD P. MASON
nance
412
416
D. Organelles
56. Chloroplasts: Formation of Active Oxygen and Its Kozi ASADA
Scavenging
422
57. Determination of the Production of Superoxide ALBERTO BOVERIS
Radicals and Hydrogen Peroxide in Mitochondria
429
58. Hydroperoxide Effects on Redox State of Pyridine CHRISTOPH RICHTER
Nucleotides and Ca2+ Retention by Mitochondria
435
Section IV. Pathology, Cancer, Aging
59. Glutathione Disulfide (GSSG) Efflux from Cells HELMUT SIES AND
and Tissues
.
60. Stable Tissue Free Radicals
.,
'
.
THEO P. M. AKERBOOM
445
W. LOHMANN AND
H. NEUBACHER
451
61. Assay of Superoxide Dismutase Activity in Tumor LARRY W. OBERLEY AND
Tissue
DOUGLAS R. SPITZ
457
62. In Vitro Cell Cultures as Tools in the Study of CARMIA BOREK
Free Radicals and Free Radical Modifiers in
Carcinogenesis
464
63. Radicals in Melanin Biochemistry
479
ROGER C. SEALY
64. Assay of Lipofuscin/Ceroid Pigment in Vivo dur- R. S. SOHAL
ing Aging
484
TABLE OF CONTENTS
Section V. Enzymes, Viral Activity, and Cell Viability as End Points for
Study of Free Radical Damage
65. The Use of Selective Free Radical Probes to Study J. LESLIE REDPATH
491
Active Sites in Enzymes and Viruses
Section VI. Drugs: Environmental Induction of Radical Formation and
Radical Species
66. Detection and Measurement of Drug-Induced Ox- MARTYN T. SMITH,
ygen Radical Formation
HJORDIS THOR,
AND STEN ORRENIUS
505
67. Alloxan and 6-Hydroxydopamine: Cellular Toxins GERALD COHEN AND
RICHARD E. HEIKKILA
510
68. Microsomal Oxidant Radical Production and Eth- ARTHUR I. CEDERBAUM AND
anol Oxidation
GERALD COHEN
516
69. Exacerbation of Superoxide Radical Formation by HOSNI M. HASSAN
Paraquat
523
70. Ethidium Binding Assay for Reactive Oxygen J. WILLIAM LOWN
Species Generated from Reductively Activated
Adriamycin (Doxorubicin)
532
71. Chemical Carcinogenesis: Benzopyrene System
539
STEPHEN A. LESKO
AUTHOR INDEX
551
SUBJECT INDEX
577