Table Of ContentEICOSANOIDS AND OTHER BIOACTIVE LIPIDS IN CANCER,
INFLAMMATION AND RADIATION INJURY
DEVELOPMENTS IN ONCOLOGY
43. M.A. Rich. J.C. Hager and J. Taylor-Papadimitriou. eds.: Breast Cancer: Origins. Detection
and Treatment. 0-89838-792-2.
44. D.G. Poplack. L. Massimo and P. Cornaglia-Ferraris. eds.: The Role of Pharmacology in
Pediatric Oncology. 0-89838-795-7.
45. A. Hagenbeek and B. LOwenberg. eds.: Minimal. Residual Disease in Acute Leukemia.
0-89838-799-X.
46. EM. Muggia and M. Rozencweig. eds.: Clinical Evaluation of Antitumor Therapy.
0-89838-803-1.
47. EA. Valeriote and L. Baker. eds.: Biochemical Modulation of Anticancer Agents:
Experimental and Clinical Approaches. 0-89838-827-9.
48. B.A. Stoll. ed.: Pointers to Cancer Prognosis. 0-89838-841-4; Pb. 0-89838-876-7.
49. KH. Hollmann and J.M. Verley. eds.: New Frontiers in Mammary Pathology. 1986.
0-89838-852-X.
50. DJ. Ruiter. GJ. Fleuren and S.O. Warnaar. eds.: Application of Monoclonal Antibodies in
Tumor Pathology. 1987.0-89838-853-8.
51. A.H.G. Paterson and A.W. Lees. eds.: Fundamental Problems in Breast Cancer. 1987.
0-89838-863-5.
52. M. Chatel. E Darcel and l Pecker. eds.: Brain Oncology. Biology. Diagnosis and Therapy. 1987.
0-89838-954-2.
53. M.P. Hacker. J.S. Lazo and T.R. Tritton. eds.: Organ Directed Toxicities of Anticancer Drugs.1988.
0-89838-356-0.
54. M. Nicolini. ed.: Platinum and Other Metal Coordination Compounds in Cancer
Chemotherapy. 1988.0-89838-358-7.
55. J.R. Ryan and L.O. Baker. eds.: Recent Concepts in Sarcoma Treatment. 1988.0-89838-376-5.
56. M.A. Rich. lC. Hager and D.M. Lopez. eds.: Breast Cancer: Scientific and Clinical Progress. 1988.
0-89838-387-0.
57. B.A. Stoll. ed.: Women at High Risk to Breast Cancer. 1989.0-89838-416-8.
58. M.A. Rich. lC. Hager and I. Keydar. eds.: Breast Cancer. Progress in Biology. Clinical
Management and Prevention. 1989.0-7923-0507-8.
59. P.1. Reed, M. Carboni. BJ. Johnston and S. Guadagni. eds.: New Trends in Gastric Cancer.
Background and Videosurgery. 1990.0-7923-8917-4.
60. H.K Awwad: Radiation Oncology: Radiobiological and Physiological Perspectives. The
Boundary-Zone between Clinical Radiotherapy and Fundamental Radiobiology and
Physiology. 1990.0-7923-0783-6.
61. J.L. Evelhoch, W. Negendank, EA. Valeriote and L.H. Baker. eds.: Magnetic Resonance in
Experimental and Clinical Oncology. 1990.0-7923-0935-9.
62. B.A. Stoll. ed.: Approaches to Breast Cancer Prevention. 1991. 0-7923-0995-2.
63. MJ. Hill and A. Giacosa. eds.: Causation and Prevention of Human Cancer. 1991. 0-7923-1084-5.
64. J.R.w. Masters. ed.: Human Cancer in Primary Culture. A Handbook. 1991. 0-7923-1088-8.
65. N. Kobayashi, T. Akera and S. Mizutani, eds.: Childhood Leukemia. Present Problems and
Future Prospects. 1991. 0-7923-1138-8.
66. P. Paoletti, K Takakura, M.D. Walker, G. Butti and S. Pezzota, eds.: Neuro-Oncology. 1991.
0-7923-1215-5.
67. K.V. Honn, LJ. Marnett, S. Nigam and T. Walden Jr. (eds.): Eicosanoids and Other Bioactive Lipids
in Cancer and Radiation Injury. 1991. 0-7923-1303-8.
68. EA. Valeriote, T.H. Corbett and L.H. Baker (eds.): Cytotoxic Anticancer Drugs. Models and
Concepts for Drug Discovey and Development. 1992.0-7923-1629-0.
69. L. Dogliotti, A. Sapino and G. Bussolati (eds.): Breast Cancer. Biological and Clinical Progress.
1992.0-7923-1655-X.
70. E. Benito, A. Giacosa and MJ. Hill (eds.): Public Education on Diet and Cancer. 1992.
0-7923-8997-2.
71. S. Nigam. K.V. Honn, LJ. Marnett, and T.L. Walden (eds.): Eicosanoids and Other Bioactive
Lipids in Cancer, Inflammation and Radiation Injury. 1993.0-7923-1870-6.
EICOSANOIDS AND OTHER
BIOACTIVE LIPIDS IN CANCER,
INFLAMMATION AND
RADIATION INJURY
Proceedings of the 2nd International Conference
September 17-21, 1991
Berlin, FRG
edited by:
Santosh Nigam
Oepartment of Gynecological Endocrinology
Klinikum Steglitz, Free University Berlin
Berlin, Germany
Kenneth V. Honn
Oepartment of Radiation Oncology
Wayne State University
Oetroit, MI USA
Lawrence J. Marnett
Oepartment of Biochemistry
Vanderbilt University
Nashville, TN USA
Thomas L. Waiden, Jr.
formerly of:
Oepartment of Radiation Biochemistry
Armed Forces Radiobiology Research Institute
Bethesda, MD USA
....
"
Springer Science+Business Media, LLC
Library of Congress CataIoging-in-Publication Data
Eicosanoids and other bioactive lipids in cancer, inflammation, and
radiation injury : proceedings of the 2nd international conference,
September 17-21, 1991, Berlin, FRG / edited by Santosh Nigam '" let
al.].
p. cm. - (Developments in oncology: 71)
Includes bibliographical references and index.
ISBN 978-1-4613-6562-4 ISBN 978-1-4615-3520-1 (eBook)
DOI 10.1007/978-1-4615-3520-1
1. Carcinogenesis-Congresses. 2. Radiation injuries
-Pathophysiology-Congresses. 3. Inflammation-Mediators-
-Congresses. 4. Eicosanoic acid-Derivatives-Congresses.
5. Radiation-protective agents-Congresses. I. Nigam, S. K.
(Santosh K.) H. Series.
[DNLM: 1. Eicosanoids-metabolism-congresses. 2. Inflammation
-physiopathology-congresses. 3. Lipid Peroxides-metabolism-
-congresses. 4. Neoplasms-physiopathology-congresses.
5. Radiation Injuries-physiopathology-congresses. 6. Radiation
-Protective Agents-therapeutic use-congresses. Wl DE998N v. 71/
QZ 202 E3374 1991]
RC268.5.E323 1993
616.99'4071-dc20
DNLMlDLC
for Library of Congress 92-23659
CIP
Copyright © 1993 by Springer Science+Business Media New York
Originally published by Kluwer Academic Publishers in 1993
Softcover reprint of the hardcover 1s t edition 1993
All rights reserved. No part of this publication may be reproduced, stored in a retrieval system or
transmitted in any form or by any means, mechanicaI. pbotocopying, recording, or otherwise. without the
prior written permission of the publisher. Springer Science+Business Media, LLC.
Printed on acid-free paper.
Table of Contents
PREFACE xvii
ACKNOWLEDGEMENTS xix
CONTRIBUTORS xxi
ENZYMES OF EICOSANOID BIOSYNTHESIS
Mutagenesis of Six Conserved Histidines in Human 5-Lipoxygenase, Effects 3
on Enzyme Activity
Y. Zhang, O. Rildmark and B. Samuelsson
2 Arachidonate 12-Lipoxygenases: Enzymology and Molecular Biology 7
S. Yamamoto, T. Yoshimoto, N. Ueda, Y. Takahashi, S. Matsuda, H. Suzuki,
T. Oshima, H. Ikawa, T. Hada, G.R. Reddy, Y. Yamamoto, K. Kishimoto, T. Arakawa,
K. Ishimura, S. Arase, C. Yokoyama, T. Tanabe, H. Toh, M. Nishiyama, H. Okamoto,
T. Watanabe, and T. Hori
3 Cytochrome P-450 Epoxygenase Dependent Formation of Novel Endogenous 11
Epoxyeicosatrienoyl-Phospholipids
J. H. Capdevila, Y. Jin, A. Karara, and J. R. Falck
4 The Significance of the Peroxide Tone in the Arachidonic Acid Cascade 17
V. Ullrich, G. Hecker, F. Meisch, and M. Schatz-Munding
5 Properties and Functions of an Epidermal 8-Lipoxygenase 23
G. FOrstenberger, T. Jacobi, B. Schurich, M. Loschke, W. D. Lehmann,
M. Stephan and F. Marks
6 On the Biological Role of Mammalian 15-Lipoxygenases 27
T. Schewe
7 Studies on Expression and Regulation of 5-Lipoxygenase in Human B 31
Lymphocytes
P. -J. Jakobsson, B. Odlander, D. Steinhilber, A. Rosen, H. -E. Claesson,
and B. Samuelsson
8 Platelet-Activating Factor Induces Receptor Mediated Leukocyte 35
5-Lipoxygenase Activation Through its Translocation to the Membrane
J. Sola and L. Vila
9 Leukotriene ~ Hydrolase: A Zinc Metalloenzyme with Dual Enzymatic Activities 39
J.z. Haeggstrom, A. Wetterholm, and B. Samuelsson
10 Mutations of the Three Zinc-Ligands of Leukotrienes ~ Hydrolase: Effects 43
on Zinc Content and Enzyme Activities
J. F. Medina, A. Wetterholm, 0. R~dmark, R. Shapiro, J. Z. Haeggstrom, B. L. Vallee
and B. Samuelsson
11 Effects of Anions on the Peptidase Activity of Leukotriene A4 Hydrolase 47
A. Wetterholm and J.z. Haeggstrom
vi
12 ESR Investigation of Tyrosyl Radicals of Prostaglandin H Synthase; Relation 51
to Enzyme Catalysis
G. Lassmann, R. Odenwaller, J. F. Curtis, J. A. Degray, R. P. Mason,
L. J. Marnett, and T. E. Eling
13 Histadine Residues Involved in Heme Binding by Prostaglandin Endoperoxide 55
Synthase
T. Shimokawa and W. L. Smith
14 Chemical Modifications of Prostaglandin Endoperoxide Synthase with 59
N-Acetylimidazole and Tetranitromethane
H. -J. Scherer, R. Karthein, S. Strieder, and H. H. Rut
15 Rous Sarcoma Virus Induces a New Form of Prostaglandin GlH Synthase 63
(Cyclooxygenase)
D. L. Simmons, W. Xie, and G. E. Evett
16 3-Hydroxy-5,8,11 ,14 (All Cis)-Eiscosatetraenoic Acid (3-HETE) -A New 67
Aspirin Sensitive Arachidonic Acid Metabolite from Yeast
M. S. van Dyk, J.L.F. Kock, A. Botha, D. J. Coetzee, P. J. Botes
O.P.H. Augustyn, and S. Nigam
17 Gestational Age Related Changes in Platelet Activating Factor Acetylhydrolase 71
Activity in Matemal Plasma
N.M. Khan and S.A. Saeed
18 Phospholipid Hydroperoxide Glutathione Peroxidase: A Selenoprotein Distinct 75
from Glutathione Peroxidase
R. Brigelius-FloM, R. Schuckelt, W. StrafJburgher, F. Ursini, B. Wolf, and I. L. FloM
LIPID PEROXIDATION
19 Disturbances of Lipid Peroxidation in Rat Liver Cancer Cells and in Normal 81
Regenerating Rat Liver
T. F. Slater, K. H. Cheeseman, M. -L. Carrie, L. Li, S. Clutton, S. Nigam,
S. Emery, and K. U. Ingold
20 Identification of Novel Prostaglandin-Containing Glycerophospholipids ~ 85
J. D. Morrow, J. A. Awad, T. A. Duckworth, W. E. Zackert, H. J. Boss, I. A. Blair,
and L. J. Roberts /I
21 Susceptibility to Lipid Peroxidation of Rat Hepatoma Cells Enriched with 89
Arachidonic Acid
M. U. Dianzani, G. Muzio, M. E. Biocca and R. A. Canuto
22 Human Reperfusion Injury: The Role of Free Radicals 99
W. D. Flitter, J. G. Coghlan, C. D. Isley, and T. F. Slater
23 Hydrogen Peroxide as Inflammatory Mediator 103
v. R. Muzykantov
24 Relationships Between Ascorbic Acid and Glutathione in Antioxidant Defense 107
A. F. Casini, E. Mael/aro, B. Del Bel/o, L. Sugherini, M. Comporti
25 Antioxidant and Hepatoprotective Properties of IdB 1016, A New
Flavanolignan Complex 111
R. Carini. A. Comoglio, H. Basaga, E. Albano, and G. Poli
vii
26 Absorption and Transport of Vitamin E 115
K. U. Ingold and G. W. Burton
27 Protection against Lipid Peroxidation by Vitamin E-Acetate is Higher in 119
Liver than in Kidney
A. Wolf, M. Broadhurst, M. Tschopp, and T. Singer
28 Enhancement of Hydroxyl Radical Induced Methionine Oxidation to Methionine 125
Sulfoxide by the Vitamine E Analogue Trolox C
C. SchOneich, A. Aced, A. Willnow, D. L. Thomas, and K. -D. Asmus
29 Plasma Membrane Structure, Calcium and Microfilaments in Anoxia 129
A. J. Sowerby, S.A.E. Finch and A. Stier
EICOSANOID RECEPTORS
30 Prostanoids, Prostanoid Receptors and Tumor Progression 135
R. A. Coleman
31 Pharmacological Characterization of the Prostanoid FP-Receptor 143
A. H.-P. Krauss, C. E. Fairbairn, C. E. Protzman, L. S. Williams,
and D. F. Woodward
32 PGE2 Receptors: Involvement of EP2 and EP3 Subtypes in the Chick Spinal 147
Cord
M. F. Vesin, C. Bil/otte, and E. Pra/ong
33 Thromboxane A2 Receptors: Characterization and Regulation 151
P. V. Halushka, D. E. Mais, A. Masuda, K. Matsuda, T. Morinelli and J. E. Oates, Jr.
34 The Second Leukotriene Receptor in Human Lung 155
C. Labat, J. L. Ortiz, I. Gorenne, X. Norel, P. Gardiner, and C. Brink
SIGNAL TRANSDUCTION
35 Molecular Diversity and Functional Considerations in Transmembrane Signalling 161
by G Proteins
L. Birnbaumer
36 Function of Sphingolipid Metabolites in Cell Regulation 175
R. M. Bell, B. Buehrer, A. Kalen, R. Borchardt, T. Okazaki, and Y. Hannun
37 Cell Signaling in LPS Primed and PAF Stimulated P388D, Macrophage-Like 183
Cells
R. Asmis and E. A. Dennis
38 Cellular Phospholipases A2 in Inflammatory Processes 187
R. Levistre, P. Pernas, J. Masliah, and G. Bereziat
39 Regulation of Eicosanoid Formation in Liver Macrophages: Role of 191
Phospholipase A2
P. Dieter
40 Enhancement by Staurosporine of PLA2-Activity and PAF-Biosynthesis in 195
FMLP-Stimulated Human Neutrophils: Specific Role of Endogenously
Synthesized PAF
S. MOiler and S. Nigam
viii
41 Phosphorylation/Dephosphorylation Possibly Regulate Cellular PLA2 and 201
PI-PLC-y1 Activity: Irnplicaiton for the Mechanism of H202 and Glucocorticoid
Action
U. Zor and N. Reiss
42 Hydra Tentacle Regeneration: A Model for the Study of the Involvement of 209
Protein Kinase C and Phospholipase A2 in Cell Differentiation
V. Di Marzo, L. De Petrocellis and G. Cimino
43 Concerted Mitogenic Signals Control Mammalian DNA Replication Protein 213
Kinase C Role
L. Jiminez De Asua, A. G. Estevez and M. Goin
44 12(S)-HETE-lnduced Microvascular Endothelial Cell Retraction is Mediated 219
by Cy10skeletal Rearrangement Dependent on PKC Activation
D. G. Tang, C. A. Dig/io, and K V. Honn
45 Inhibition of Human Platelet Aggregation by Novel2-Aminochromone 231
Phospholipase C Inhibitors
C. W. Benjamin, A. H. Lin, J. Morris, D. G. Wishka, R. B. Gammill, R. J. Shebuski
and R. R. Gorman
46 Arachidonic Acid is Involved in Catecholamine Release Mechanism of PGE2 in 235
Bovine Adrenal Chromaffin Cells
S. Ito, M. Negishi, K Sugama, and O. Hayaishi
47 Effect of A23187 Stimulation on Subcellular Redistribution of 15-Lipoxygenase 239
Activity in Human Leukocy1es
M. Bongrazio and S. Nigam
48 Enhancement of Phospholipase C and Phospholipase D Activity by 243
Staurosporine in N-Formyl-Methionin-Leucin-Phenylalanine-Stimulated
Human Neutrophils
B. Walzog, S. Muller, and S. Nigam
49 Hepoxilins Activate Phospholipase D in the Human Neutrophil 249
S. Nigam, S. Muller and C. R. Pace-Asciak
INFLAMMATION
50 Regulation of Eosinophil Programmed Cell Death and the Subsequent Priming 255
of Ligand Mediated Functions by the Eosinophil-Directed Hematopoietins
K F. Austen and W. Owen
51 In Vivo Desensitization to LT B4-lnduced Neutrophil Sequestration in Rabbit 261
Lungs
S. Marleau, C. Fortin, and P. Borgeat
52 Synthesis of 20-Hydroxy Arachidonic Acid by the Human Neutrophil and 265
Platelet Metabolism
E. Hill and R. C. Murphy
53 Leukotoxin, a Linoleate Epoxide, and Severe Inflammation 271
T. Ozawa, M. Hayakawa, K Kosaka, S. Sugiyama, K Yokoo, H. Aoyama,
andY.lzawa
ix
54 Epidermal Cell-Polymorphonuclear Leukocyte Cooperation in the Formation 275
of Leukotreine B4 by Transcellular Biosynthesis
L. Vila, N. Godessart and J. Sola
55 Contribution of Bidirectional Transcellular Routes to Lipoxin Biosynthesis 279
C. N. Seman, S. Fiore, and M. Romano
56 The Effect of Lipoxin on the Binding of [3Hl LT B4to Guinea Pig Eosinophils 283
C.F. Ng, F.F. Sun and P. Y-K Wong
57 Stimulus Dependent Formation of Leukotriene B4 in Human Alveolar 291
Macrophages
M. Kumlin, A. Eklund, J. Hed and S. -E. Dahlen
58 Transport and Elimination of Cysteinyl Leukotrienes 295
M. MOiler, A. Guhlmann, K. Krauss, T. Schaub, C. KlOnemann, U. Berger
and D. Keppler
59 Mast Cells are Essential for the Formation of Leukotrienes InHiating Early 299
Inflammatory Responses
B. A. Jakschik, Y. Zhang, B. F. Ramos, and R. Malaviya
60 Importance of Prostanoids for Bronchial Smooth Muscle Tone 303
J. C. FrtJlich, S. Duff, A. Becker, F. M. Kuhn, J. H. Wilkens, D. Tsikas, M. Emura,
and M. Riebe-Imre
61 Neuropeptides and Airway-Inflammation 307
G. Kunkel, K. Nieber, K. Graf. J. Niehus, and C. R. Baumgarten
62 PAF and Related Lipids Regulate Events in the Vascular Wall 313
M. Kozak, G. A. Zimmerman, T. M. Mcintyre, and S. M. Prescott
63 Use of PCR-Technique for Determination of Cell Adhesion Molecule 317
Transcription in Human Endothelial Cells
W. Luttmann and K-H Thierauch
RADIATION-INDUCED INJURY & RADIOPROTECTION
64 Cytokines Interaction in Innate and Immunornodulator-Induced Radioprotection 323
R. Neta, J. J. Oppenheim, G. D. Looney and T. J. Macvittie
65 Variations in the Profiles of Radioprotective Eicosanoids 329
W. R. Hanson and L. A. Duffner
66 Radiation Injury and Antioxidant Mechanisms of Protection 333
K. S. Kumar, Y. N. Vaishnav, C. Smith, and E. P. Clark
67 Reduction of Short-and Long-Term Lethality by Prostaglandins Given 341
Alone or in Association With Other Protectors
J.R. Maisin, C. Albert and M. Lambiet-Collier
68 The Effects of SO-1100 in Reducing the Severity of Radiation-Induced 345
Damage to Pig Skin
J. W. Hopewell, M. E. C. Robbins and C. A. Scott
69 Protection of Thymocytes from Radiation-Induced Interphase Death by 349
Dihydrolipoic Acid and Wr-1065
N. Ramakrishnan and G. N. Catravas
x
70 Protective Roles of MnSOD, TNF-a, TNF-~ and D-Factor in Radiation Injury 353
G. H. W. Wong, R. Neta, and D. V. Goeddel
71 Radioprotective Efficacy of Platelet Activating Factor in Mice 359
T.L. Walden, Jr., L.K. Steel, and H.N. Hughes
72 Low Level Radiation Effects on Endothelial Cell Eicosanoid Biosynthesis 369
J.M. Onoda, S. Kantak, M.P. Piechocki, and C.A. Diglio
73 Capsaicin and Its Protective Effect Against UV-Induced Lipid Peroxidation on 377
Liposomal Preparations
AK. De and J.J. Ghosh
MULTISTAGE CARCINOGENESIS
74 Chronic Inflammation is a Major Cause of Preventable Cancer 383
B. N. Ames, T. M. Hagen, and M. K. Shigenaga
75 Inflammation and Oxidative Stress in Carcinogenesis 387
P. Cerutti and P. Amstad
76 Intracellular Signal Transduction and Skin Tumor Promotion (A Minireveiw) 391
F. Marks, G. FOrstenberger, and M. Gschwendt
77 Oxidant Generation in Mouse Skin in Response to Phorbol Ester Tumor 395
Promoters
L. J. Marnett and C. Ji
78 Antioxidant-Proxidant Status of Murine Skin During the Ontogeny of Chemically- 401
Induced Skin Cancer
J.J. Reiners, Jr., G. Thai, A Cantu, E. Kodari, and H. Gilbert
79 Profiling of Monohydroxylated Fatty Acids in Normal, Hyperplastic and Neoplastic 405
Mouse Epidermis by Gas Chromotography-Mass Spectrometry
W. D. Lehmann, M. Stephen, G. FOrstenberger, and F. Marks
80 Free Radical Metabolism and DNA Damage by Organic Peroxide Tumor 409
Promoters
T. Kensler, P. Do/an, P. Egner, S. Lesko, J. Swauger, J. Zweier and S. Akman
81 Does Superoxide Anion Have a Role in Phorbol Ester Tumor Promotion? 415
S. M. Fischer, K. E. Patrick and K. VA
82 Ovine Seminal Vesicle Cell Cultures, A Tool for Studies of Carcinogen Activation 419
by Prostaglandin H Synthase
G. H. Degen
83 Defective Heme Biosynthesis as the Initiating Lesion in Carcinogenesis 423
A BatJ/e, and P. A Riley
84 Inhibitors of Prostaglandin Synthesis in Cancer Chemoprevention 427
B. S. Reddy, DVM, Ph.D.
85 Sphingolipids Inhibij Protein Kinase C and Multistep Transformation 431
C. Borek and A H. Merrill, Jr.
