Mechanism of Action of Antieukaryotic and Antiviral Compounds

483 Pages·1979·9.48 MB·English

by  A. Jiménez

Antibiotics
Volume V / Part 2
Mechanism of Action
of Antieukaryotic
and Antiviral Compounds
Edited by Fred E. Hahn
Springer-Verlag
Berlin Heidelberg New York 1979
Professor Fred E. Hahn, Ph.D.
Department of the Army
Walter Reed Army Institute of Research
Walter Reed Army Medical Center
Washington, D.C. 20012, USA
With 138 Figures
ISBN 978-3-642-46409-6 ISBN 978-3-642-46407-2 (eBook)
DOI 10.107/978-3-642-46407-2
Library of Congress Cataloging in Publication Data. Main entry under title: Mechanism of actions of antieukaryo
tic and antiviral compounds. (Antibiotics; v. 5, pt. 2). Includes bibliographical references and index. I. Antibiotics.
2. Antiviral agents. 3. Eukaryotic cells -Drug effects. 1. Hahn, Fred Ernest, 1916- . H. Series. III. Title: Antieukaryo-
tic and antiviral compounds. RM267.M42. 615'.329. 79-12228.
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©by Springer-Verlag Berlin·Heidelberg 1979.
Softcover reprint of the hardcover 1s t edition 1979
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Preface
When Antibiotics I was published in 1967, the teleological view was held
by some that" antibiotics" were substances elaborated by certain microorgan
isms for the purpose of competing with other microorganisms for survival in
mixed ecological environments. However, not only had J. EHRLICH and his
associates shown 15 years earlier that chloramphenicol was produced by Strepto
myces venezuelae in cultures of sterilized soils but not in parallel cultures of
the same soils which were not sterilized, but operationally, the search for anti
cancer antibiotics was actively under way (Antibiotics I reporting on numerous
such substances), although the concept of antibiosis could not logically justify
such undertakings.
This editor hesitates to accept the use of the term "antibiotic" for anti
microbial agents of non microbiological origins which is sometimes encountered,
but neither does he subscribe to the view that antibiotics are in some fundamental
manner different from chemotherapeutic substances of other origins. Modes and
mechanisms of action of chemotherapeutic compounds are not systematic
functions of their origins nor of the taxonomical position of the target
organisms. Consequently, in the selection of topics for Antibiotics III (published
in 1975), synthetic drugs and natural products of higher plants (alkaloids) were
represented, along with antibiotics in the strict sense of the definition.
We now present Antibiotics V, for whose assembly the same selection criteria
were applied as for Antibiotics Ill. The aggregate length of the contributions
rendered it impractical to place the entire text between the covers of one book.
Antibiotics V is, therefore, published in two volumes: Part 1, dealing with
the actions of antibacterial compounds and Part 2, with the actions of antieuka
ryotic and antiviral substances. For antieukaryotic substances of natural origin,
we present for the first time reviews of the actions of certain bacterial toxins,
as well as of toxins from higher plants.
The separation of Antibiotics V into two volumes for practical reasons does
not imply that there exist fundamental scientific differences between the contents
of the two books. Many substances that inhibit molecular processes in eukaryotic
cells also produce inhibitions in prokaryotes. The reverse statement can also
be made, although the frequency of such instances is less. This is not surprising
because antibacterial drugs are chosen according to their selective toxicity for
bacteria. It is also of interest that certain antiviral drugs, for example, 5-iodode
oxyuridine and ara-A were originally developed as potential anticancer sub
stances before it was discovered that they possess valuable activities against
virus infections. The fact remains that the partition of Antibiotics V into two
separate volumes does not signify systematic scientific differences but rests essen
tially on a descriptive distinction.
VI Preface
Our book does not aspire to encyclopedic completeness. This editor did
not select certain substances for review at this time, for example mefloquin,
nifurtimox, interferons and their inducers, ara-C, or 9-(2-hydroxyethoxymethyl)
guanine since he felt that knowledge of the mechanisms of action of these
substances should be left to mature before reviews are necessary. Even at the
time of publication of this book, it is apparent that new chemotherapeutic
drugs and much new information on the actions of existing drugs continue
to be discovered and reported. Within a few years still another volume of
Antibiotics will be required to review these current and impending developments.
This should not detract from the usefulness of Antibiotics V. It presents
a series of reviews of actions of substances which have been studied in sufficient
detail and depth to yield bodies of scientific knowledge which are more easily
accessible through review articles than through the retrieval and study of the
source literature.
There remains the pleasant task of thanking my publisher, Dr. KONRAD
F. SPRINGER, for his unwavering interest in, and support of, this undertaking
and for having once again provided for the production of such a well-appointed
and handsome book.
Washington, D.C., Spring 1979 FRED E. HAHN
Contents of Part 2
Anisomycin and Related Antibiotics. A. JIMENEZ and D. VAZQUEZ
(With 6 Figures) . . . . . . . . . . . . . . . . . . . .
Antitumor Platinum Compounds. J.J. ROBERTS (With 30 Figures) 20
9-p-D-Arabinofuranosyladenine (AraA). C.E. CASS (With 3 Figures) 85
8-Azaguanine. D. GRUNBERGER and G. GRUNBERGER (With 5 Figures) 110
Bleomycin. C.W. HAIDLE and R.S. LLOYD (With 4 Figures) . . . .. 124
Diphtheria Toxin and Exotoxin A from Pseudomonas aeruginosa. R. COLLIER
(With 4 Figures) . . . . . . . . . . . . . . . . . . . . . . . . 155
Echinomycin, Triostin, and Related Antibiotics. M.J. WARING
(With 10 Figures) ............ . . . . . . 173
Ellipticine. K.W. KOHN, W.E. Ross, and D. GLAUBIGER (With 7 Figures) 195
2-Hydroxy-3-Alkyl-l,4-Naphthoquinones. J.G. OLENICK · 214
Hydroxystilbamidine. B. FESTY (With 1 Figure) . . . . · 223
5-Iodo-2/-Deoxyuridine. W.H. PRUSOFF, M.S. CHEN, P.H. FISCHER, T.S. LIN,
and G.T. SHIAU (With 2 Figures). . . . . . . 236
Neocarzinostatin. I.H. GOLDBERG (With 10 Figures) . . . 262
Nitracrine. M. GNIAZDOWSKI, J. FILIPSKI, and M. CHORJ\ZY
(With 14 Figures) ........... . 275
Phleomycin. CH.F. EARHART, JR. (With 1 Figure) · 298
Polyene Antibiotics: Nystatin, Amphotericin B, and Filipin. R.W. HOLZ
(With 4 Figures) . . . . . . . . . . . . . . . . . . . . . . . . 313
Protein and Glycoprotein Toxins That Inactivate the Eukaryotic Ribosome.
D. VAZQUEZ (With 2 Figures) 341
Quinine. F.E. HAHN (With 6 Figures) . . . . . . . . . . . . 353
Showdomycin. D.W. VISSER and S. Roy-BuRMAN (With 1 Figure) 363
Streptonigrin. N.S. MIZUNO (With 2 Figures) . . . . . . . . . 372
Tilorone Hydrochloride. P. CHANDRA, M. WOLTERSDORF, and G.J. WRIGHT
(With 17 Figures) ................... . . . . 385
VIII Contents of Part 2
The Vinca Alkaloids. W.A. CREASEY (With 3 Figures) 414
Virazole (Ribavirin). F.E. HAHN (With 6 Figures) 439
Subject Index. . . . . . . . . . . . . . . . 459
Contents of Part 1
Bacitracin. D.R. STORM and W.A. TOSCANO, JR. (With 4 Figures)
Bicyclomycin. N. TANAKA (With 1 Figure) . 18
Chloramphenicol. O. PONGS (With 6 Figures) 26
Ethambutol. W.H. BEGGS (With 3 Figures) . 43
Ionophore Antibiotics. E.P. BAKKER (With 4 Figures) 67
Isonicotinic Acid Hydrazide. K. TAKAYAMA and L.A. DAVIDSON
(With 6 Figures) . . . . . . . . . . . . . . . . . . . . 98
Kidamycin and Acetyl Kidamycin. H. TAKESHIMA and I. UMEZAWA
(With 4 Figures) . . . . . . . . . . 120
Lincomycin. F.N. CHANG (With 4 Figures) . . . . . . . . . . . 127
Moenomycin and Related Phosphorus-Containing Antibiotics. G. HUBER
(With 2 Figures) . . . . . . . . . . . . l35
Nalidixic Acid. A.M. PEDRINI (With 5 Figures) 154
Nitrofurans. D.R. MCCALLA (With 1 Figure) . 176
Novobiocin and Coumermycin At. M.J. RYAN (With 1 Figure) 214
Phenomycin and Enomycin. N. TANAKA . . . . . . . . . . . 235
Quinone Antibiotics. A. OGILVIE and W. KERSTEN (With 18 Figures) . . 243
Sparsomycin. I.H. GOLDBERG (With 5 Figures) . . . . . . . . . 264
Streptomycin and Related Antibiotics. B.J. WALLACE, P.-C. TAl,
and B.D. DAVIS (With 2 Figures) . . . . . . . 272
Tetracycline. A. KAJI and M. RYOJI (With 2 Figures) . . . . . . 304
Thiostrepton and Related Antibiotics. E. CUNDLIFFE (With 3 Figures) . 329
Tiamulin and Pleuromutilin. G. HOGENAUER (With 5 Figures) . . 344
Tirandamycin. F. REUSSER (With 4 Figures) . . 361
Subject Index. . . . . . . . . . . . . . . 371
Contributors
CASS, CAROL E., Cancer Research Laboratory (McEachern Laboratory), 5-75
Medical Sciences Building, Edmonton, Alberta T6G 2H7, Canada
CHANDRA, PRAKASH, Klinikum der Johann Wolfgang Goethe-Universitat,
Gustav-Embden-Zentrum der Biologischen Chemie, Abteilung fUr Mole
kularbiologie, Theodor-Stern-Kai 7, 6000 Frankfurt/Main 70, FRG
CHEN, M.S., Department of Pharmacology, Yale University School of Medicine,
New Haven, CT 06510, USA
CHORJ\ZY, MIECZYSLAW, Department of Tumor Biology, Institute of Oncology,
ul. Armii Czerwonej 15,44--100 Gliwice, Poland
COLLIER, R. JOHN, Department of Microbiology, College of Letters and Science,
University of California, Los Angeles, CA 90024, USA
CREASEY, WILLIAM A., Department of Pharmacology, University of Pennsyl
vania, School of Medicine, Philadelphia, PA 19104, USA
EARHART, CHARLES F., JR., Department of Microbiology, The University of
Texas at Austin, Austin, TX 78712, USA
FESTY, BERNARD, 4, avenue de l'Observatoire, 75006-Paris, France
FILIPSKI, JAN, Department of Tumor Biology, Institute of Oncology, ul. Armii
Czerwonej 15,44--100 Gliwice, Poland
FISHER, T.H., Department of Pharmacology, Yale University School of
Medicine, New Haven, CT 06510, USA
GLAUBIGER, DANIEL, Pedriatric Oncology Branch, National Cancer Institute,
National Institutes of Health, Building 10, Room 3B04, Bethesda, MD 20014,
USA
GNIAZDOWSKI, MAREK, Department of General Chemistry, Institute of
Physiology and Biochemistry, Medical School in LOdz, Lindleya 6,90-131 L6dz,
Poland
GoLDBERG, IRVING H., Department of Pharmacology, Harvard Medical School,
250 Longwood Avenue, Boston, MA 02115, USA
GRUNBERGER, DEZIDER, Cancer Center/Institute of Cancer Research, Columbia
University, 701 West 168 Street, New York, NY 10032, USA
XII Contributors
GRUNBERGER, GEORGE, Department of Medicine, Case Western Reserve
University, University Hospitals of Cleveland, 2074 Abington Road, Cleveland,
OH 44106, USA
HAHN, FRED E., Department of the Army, Walter Reed Army Institute of
Research, Walter Reed Army Medical Center, Washington, DC 20012, USA
HAIDLE, CHARLES W., The University of Texas System Cancer Center, M.D.
Anderson Hospital and Tumor Institute, Houston, TX 77030, USA
HOLZ, RONALD W., Department of Pharmacology, University of Michigan
Medical School, Ann Arbor, MI 48109, USA
JIMENEZ, ANTONIO, Centro de Biologia Molecular, Instituto de Bioquimica de
Macromoleculas, Universidad Aut6noma de Madrid, Facultad de Ciencias,
Canto Blanco, Madrid 34, Spain
KOHN, KURT W., Laboratory of Molecular Pharmacology, Developmental
Therapeutics Program, Division of Cancer Treatment, National Cancer Institute,
National Institutes of Health, Building 37, Room 5D18, Bethesda, MD 20205,
USA
LIN, T.S., Department of Pharmacology, Yale University School of Medicine,
New Haven, CT 06510, USA
LLOYD, R. STEPHEN, Department of Biological Sciences, Stanford University,
Stanford, CA 94305, USA
MIZUNO, NOBUKO S., 3628 Lorna Way, San Diego, CA 92106, USA
OLENICK, JOHN G., Department of Applied Biochemistry, Division of
Biochemistry, Walter Reed Army Institute of Research, Walter Reed Army
Medical Center, Washington, DC 20012, USA
PRUSOFF, WILLIAM H., Department of Pharmacology, Yale University School
of Medicine, New Haven, CT 06510, USA
ROBERTS, JOHN J., Institute of Cancer Research, Pollards Wood Research
Station, Chalfont St. Giles, Bucks, Great Britain
Ross, WARREN E., Medical Oncology, Medical Science Building, Room M433,
University of Florida, Gainesville, FL 32601, USA
Roy-BURMAN, SUMITRA, Department of Biochemistry, University of Southern
California, School of Medicine, 2025 Zonal Avenue, Los Angeles, CA 90033,
USA
SHIAU, G.T., Department of Pharmacology, Yale University School of Medicine,
New Haven, CT 06510, USA
VAZQUEZ, DAVID, Centro de Biologia Molecular, Instituto de Bioquimica de
Macromoleculas, Universidad Aut6noma de Madrid, Canto Blanco, Facultat
de Ciencias, Madrid 34, Spain