Mechanism of Action of Antieukaryotic and Antiviral Compounds PDF
Preview Mechanism of Action of Antieukaryotic and Antiviral Compounds
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. This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machine or similar means, and storage in data banks. Unter § 54 of the German Copyright Law where copies are made for other than private use, a fee is payable to the publisher, the amount of the fee to be determined by agreement with the publisher. ©by Springer-Verlag Berlin·Heidelberg 1979. Softcover reprint of the hardcover 1s t edition 1979 The use of registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. Typesetting, printing, and bookbinding: Universitätsdruckerei H. Stürtz AG, Würzburg 2131/3130-543210 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
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