Mechanism of Action of Antimicrobial and Antitumor Agents

751 Pages·1975·21.91 MB·English

by  Kurt W. Kohn (auth.)

Antibiotics
Volume III
Mechanism of Action
of Antimicrobial
and Antitumor Agents
Edited by
John W. Corcoran and Fred E. Hahn
Assisted by J. F. Snell and K. L. Arora
Springer-Verlag Berlin· Heidelberg· New York 1975
Professor JOHN W. CORCORAN, Ph.D., Northwestern University, Department of
Biochemistry, The Medical and Dental Schools, 303 E. Chicago Avenue, Chicago,
Illinois 60611jUSA
Professor FRED E. HAHN, Ph.D., Department of the Army, Walter Reed Army
Institute of Research, Walter Reed Army Medical Center, Washington, D. C.
20012jUSA
ISBN-13: 978-3-642-46306-8 e-ISBN-13: 978-3-642-46304-4
DOl: lO.lO071 978-3-642-46304-4
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. Under § 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 1975. Library of Congress Catalog Card Number 74-34.
Softcover reprint of the hardcover 1st edition 1975
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: Stiirtz AG, Wiirzburg
Preface
This volume is the third in the series devoted to Antibiotics initiated by
Springer Verlag in 1967. The first two volumes were devoted to the Mode of
Action of Antibiotics and Biogenesis, respectively and were received graciously.
During the intervening years these two works have been used often by research
workers and students alike and have been quoted extensively. Although a number
of other excellent treatises on antibiotics have appeared, the Springer series has
set a standard for thoroughness and quality that meets the need of the scientific
community.
It is against this background that the present Editors set about the preparation
of a third volume in the Series on Antibiotics. Since the appearance of Volume I,
also dealing with Mechanism of Action, tremendous strides have been made in the
depth and breadth of our knowledge of molecular biology, microbial chemistry
and molecular pharmacology and of their direct application to studies on the
mode of action of drugs. The field of molecular biology itself was in its relative
infancy during the preceding decade and the unique role played by many anti
biotics in the development of our understanding of nucleic acid synthesis and
function and its relationship to protein synthesis and cell physiology has led
rapidly to a very precise, understanding of how many of these same antibiotics
inhibit susceptible cells. Thus, a,:, few years since the preparation of Volume I we
feel that a new volume on antibiotic action may be offered which is almost com
pletely new in its content and which may prove useful to student, teacher and
research worker alike.
A definition of classification of antimicrobial agents in terms of their origin is
now largely academic. Accordingly, the selection of topics was based on the state
of our knowledge of mechanisms of action. With few exceptions authors could be
found to write on the major antimicrobial agents meeting this criterion and all
elected are primary authorities on their subject. The Editors' efforts were aimed at
assembling a volume whose various chapters have been prepared within one year
of submission to the publisher and with a very few exceptions this goal has been
achieved. When the first version of a chapter was written much earlier than
desired, the authors have been encouraged to make any necessary revisions and
most have done this. The result offered now is a treatise containing forty-six
separate chapters dealing with both natural and synthetic antimicrobial agents
(here again the distinction is somewhat academic, for at least half a dozen sub
stances are of both natural and synthetic origin). The chapters are well supported
by citations of the original source literature (over 3500) and subject distribution
reflects today's trend toward increased research on anti-tumor agents. Some
thirty-three percent of the chapters deal with this subject. In addition, a broad
spectrum of information is presented in this volume on the mode of action of
certain well-known antimalarial, antitubercular and antiparasitic compounds.
IV Preface
Of the forty-six topics presented, twenty-eight are new to the Springer series on
Antibiotics. Others are dealt with again because there has been a significant
advance in our understanding of their mode of action since the initial treatment.
The editors have attempted only a general organization of the subjects included
in the present Volume. Then guidelines have been suggested by the limited number
of categories of the modes of action known; e.g. 1. inhibitors of nucleic acid bio
synthesis either at the level of the template or by some other mechanisms, 2. inhi
bitors of protein synthesis at the ribosomal or translational level, 3. interference
with the formation or integrity of the cell wall or membrane, 4. inhibition of
specific enzyme reactions in the intermediary metabolism of the cell. Because of
the paucity of subject material, the last two topics are arranged as one unit together
with some miscellaneous subjects where significant knowledge has yet to lead to an
unambiguous decision regarding the mode of action.
The Editors have included, indeed encouraged, consideration of antimicrobial
agents which are not or may never be useful clinical chemotherapeutic agents.
This is done without apology since such agents illustrate general principles of the
interaction of antimicrobial drugs with either the host or infectious cell and indeed
much of our present knowledge of molecular biology and antibiotic action has
come from the study of such substances.
In summary, the Editors wish to thank their throughout-the-world colleagues
for innumerable instances of help and advice during the conception, planning
and preparation of Volume III in the series Antibiotics. They apologize for the
obvious omissions of desirable new chapters (e.g. quinine, nitrofurans, para
aminosalicylic acid etc.) and for the lack of updated treatments of certain more
familiar substances (e.g. actinomycin, chromomycin, hadacidin, rubiflavin,
streptonigrin etc.). When primary authorities could not be enlisted we have
decided in favor of deferral to a future new volume on the Mode of Action of
Antibiotics. Like the editors of Volumes I and II we have attempted to maintain
the highest standards for authorship and editorial review. It is for you, the intended
recipient of this our most sincere effort to evaluate the result.
JOHN W. CORCORAN
Chicago/Washington, Summer 1974 FRED E. HAHN
Acknowledgements
Preparation of this third volume in the series on antibiotics published by
Springer Verlag was begun under the editorship of Professor J. F. SNELL. With
his being unable to continue in this effort, the responsibility was assumed by the
present editors. They wish to express their deep appreciation to Dr. KONRAD
F. SPRINGER for his continued interest, encouragement and understanding during
the long period of planning and the recent period of manuscript pleparation.
Above all, the editors wish to thank their colleague Dr. KAsTURI LAL ARORA for
his extraordinary support in the detailed preparation of this volume. Dr. ARORA
carefully surveyed the abstract and original literature and advised them during the
planning phase for this work and again during the period of manuscript prepara
tion and review he helped immeasurably in the maintenance of contact with both
authors and publisher. His painstaking and scholarly review of each manuscript
prior to submission to one or the other of the editors made their task much
simpler and permitted the review process to focus on the scientific aspects of each
chapter. The support of Dr. ARORA has made this volume a reality.
Contents
Section I. Interference with Nucleic Acid Biosynthesis
Anthramycin. KURT W. KOHN. (With 6 Figures). . . . . . . . . 3
3'-Amino-3'-Deoxyadenosine. HAROLD T. SHIGEURA. (With 1 Figure) 12
Bleomycin. HAMAO UMEZAWA. (With 2 Figures). . . . . . . . . . 21
Berenil: A Trypanocide with Selective Activity against Extranuclear DNA.
B. A. NEWTON. (With 7 Figures) . . . . . . . . . . 34
Camptothecin. SUSAN B. HORWITZ. (With 3 Figures). . . . . 48
Chloroquine (Resochin). FRED E. HAHN. (With 3 Figures) . . 58
Distamycin A and Netropsin. FRED E. HAHN. (With 5 Figures) 79
Daunomycin (Daunorubicin) and Adriamycin and Structural Analogues:
Biological Activity and Mechanism of Action. A. DI MARCO, F. ARCAMONE,
and F. ZUNINO. (With 12 Figures) . . . . . . . " . . 101
Edeines. Z. KURYLO-BoROWSKA. (With 6 Figures). . . . . . 129
Ethidium and Propidium. MICHAEL WARING. (With 7 Figures) 141
Kanchanomycin. IRVING H. GOLDBERG. (With 9 Figures) . 166
Nalidixic Acid - Mode of Action. WILLIAM A. Goss and THOMAS M.
COOK. (With 8 Figures). . . . . . . . . . . . . . . . . . . . . . 174
Olivomycin, Chromomycin, and Mithramycin. G. F. GAUSE. (With 2 Figures) 197
Quinacrine and Other Acridines. ALAN DAVID WOLFE. (With 1 Figure) ... 203
Quinoxaline Antibiotics. KEN KATAGIRI, TADASHI YOSHIDA, and KOSABURO
SATO. (With 5 Figures). . . . . . . . . . . . . . . . . . . 234
Rifamycins and Other Ansamycins. W. WEHRLI and M. STAEHELIN. (With
4 Figures). . . . . . . . . . . . . . . . . . . . . . . . . 252
Sibiromycin. G. F. GAUSE. (With 2 Figures) . . . . . . . . . . . 269
Thiaxanthenones: Miracil D and Hycanthone. ERICH HIRSCHBERG. (With
2 Figures). . . . . . . . . . . . . . . . . . . . . . . . . .. 274
Trimethoprim and Pyrimethamine. JAMES J. BURCHALL. (With 3 Figures) . 304
n.
Section Interference with Protein Biosynthesis
Althiomycin. SIDNEY PESTKA. (With 1 Figure) ............. 323
Aurintricarboxylic Acid. A Non-Antibiotic Organic Molecule that Inhibits
Protein Synthesis. DAVID APIRION and DENNIS DOHNER. (With 1 Figure) 327
Aminoglycoside Antibiotics. NOBUO TANAKA. (With 11 Figures) 340
Borrelidin. K. PORALLA. (With 2 Figures) . . . . 365
Chloramphenicol. SIDNEY PESTKA. (With 6 Figures) . . . . . . 370
VIII Contents
The Erythromycins. NANCY L. OLEINICK. (With 1 Figure) . . . . . . . . 396
Emetine and Related Alkaloids. ARTHUR P. GROLLMAN and ZELDA J ARKOVSKY.
(With 5 Figures). . . . . . . . . . . . . . 420
Fusidic Acid. NOBUO TANAKA. (With 4 Figures) 436
Gougerotin. MUNEHIKO YUKIOKA. (With 6 Figures) . . . 448
The Macrolide Antibiotics. D. VAZQUEZ. (With 2 Figures) 459
Micrococcin and Micrococcin P. SIDNEY PESTKA. (With 2 Figures) . 480
Mikamycin. NOBUO TANAKA. (With 5 Figures) . . . 487
Pactamycin. IRVING H. GOLDBERG. (With 12 Figures) . . . . . . 498
Primaquine. JOHN G. OLENICK. (With 1 Figure) . . . . . . . . . 516
The Streptogramin Family of Antibiotics. D. VAZQUEZ. (With 2 Figures) . 521
Streptomycin, Dihydrostreptomycin, and the Gentamicins. DAVID
SCHLESSINGER and GERALD MEDOFF. (With 2 Figures). . . . . . .. 535
The Thiostrepton Group of Antibiotics. SIDNEY PESTKA and JAMES W. BODLEY.
(With 6 Figures). . . . . . . . . . . . . . . . . . . . . . . . . 551
Section ID. Interference with Cell Wall/Membrane Biosynthesis, Specific Enzyme
Systems and Those in Which Mode of Action Not Known with Certainty
Berberine. FRED E. HAHN and JENNIE OAK. (With 1 Figure) 577
Boromycin. W. PACHE. (With 2 Figures) . . . . 585
Colicins 1972. LOUIS W. WENDT. . . . . . . . . . . . . 588
Griseofulvin. FLOYD M. HUBER. (With 1 Figure) . . . . . 606
Irehdiamine and Malouetine. SIMON SILVER, LOUIS WENDT, and PINAKILAL
BHATTACHARYYA. (With 1 Figure) . . . . . . . . . . . . . . 614
Isonicotinic Acid Hydrazide. C. R. KRISHNA MURTI. (With 4 Figures) 623
Sideromycins. F. KNUSEL and W. ZIMMERMANN. (With 11 Figures) . 653
Sulfonamides and Sulfones. NITYA ANAND. (With 12 Figures) 668
Suramin. JOHN G. OLENICK. (With 1 Figure) . . . . . . . . . . 699
Vancomycin. D. C. JORDAN and P. E. REYNOLDS. (With 3 Figures) 704
Subject Index . . . . . . . . . . . . . . . . . . . . . . . 719
Contributors
NITYA ANAND, Division of Medicinal Chemistry, Central Drug Research Institute,
Lucknow/India
DAVID APIRION, Department of Microbiology, Washington University Medical
School, St. Louis, Missouri 63110/USA
F. ARCAMONE, Istituto Ricerche Di Base Farmitalia, Milano/Italy
PINAKILAL BHATTACHARYYA, Department of Biology, Washington University,
St. Louis, Missouri 63130/USA
JAMES W. BODLEY, Department of Biochemistry, University of Minnesota, Min
neapolis, Minnesota 55455/USA
JAMES J. BURCHALL, The Wellcome Research Laboratories, Burroughs Wellcome
Co., 3030 Cornwallis Road, Research Triangle Park, North Carolina 27709/USA
JENNIE CIAK, Department of the Army, Walter Reed Army Institute of Research,
Walter Reed Army Medical Center, Washington, D. C. 200l2/USA
THOMAS M. COOK, Department of Microbiology, University of Maryland, College
Park, Maryland 20742/USA
A. DI MARCO, Division of Experimental Oncology B, Istituto Nazionale Per Lo
Studio E La Cura Dei Tumori, Via Venezian, 1,20133 Milano/Italy
DENNIS DOHNER, Department of Microbiology, Washington University Medical
School, St. Louis, Missouri 631l0/USA
G. F. GAUSE, Institute of New Antibiotics, Bolshaia Pirogovskaia, 11, Moscow/
USSR
IRVING H. GOLDBERG, Department of Pharmacology, Harvard Medical School,
25 Shattuck Street, Boston, Massachusetts 02115/USA
WILLIAM A. Goss, Sterling-Winthrop Research Institute, Division of Sterling
Drug Inc., Rensselaer, New York 12144/USA
x
Contributors
A. P. GROLLMAN, Department of Pharmacology, Albert Einstein College of Medi
cine of Yeshiva University, 1300 Morris Park Avenue, Bronx, New York 10461/
USA
FRED E. HAHN, Department of Molecular Biology, Walter Reed Army Institute
of Researt;:h, Walter Reed Army Medical Center, Washington, D. C. 20012/USA
ERICH HIRSCHBERG, College of Medicine and Dentistry of New Jersey, New Jersey
Medical School, 100 Bergen Street, Newark, New Jersey 07l03/USA
SUSAN B. HORWITZ, Albert Einstein College of Medicine of Yeshiva University,
1300 Morris Park Avenue, Bronx, New York 1046l/USA
FLOYD M. HUBER, Antibiotic Fermentation Technology, Eli Lilly and Company,
Indianapolis, Indiana 46206/USA
Z. JARKOVSKY, Department of Pharmacology, Albert Einstein College of Medicine
of Yeshiva University, 1300 Morris Park Avenue, Bronx, New York 10461/USA
D. C. JORDAN, Department of Microbiology, College of Biological Science, Univer
sity of Guelph, Guelph, Ontario/Canada
KEN KATAGIRI, Shionogi Research Laboratory, Shionogi and Co., Ltd.,
Fukushima-ku, Osaka 553/Japan
F. KNUSEL, Biological Research Laboratories, Pharmacology Division, Ciba
Geigy, Ltd., 4002 Basel/Switzerland
KURT W. KOHN, National Cancer Institute, Department of Health, Education,
and Welfare, Public Health Service, National Institutes of Health, Bldg. 37, Rm.
5B27, Bethesda, Maryland 200l4/USA
C. R. KRISHNA MURTI, Division of Biochemistry, Central Drug Research Institute,
Lucknow/India
Z. KURYLO-BoROWSKA, Department of Biochemistry, The Rockefeller University,
New York, 1002l/USA
GERALD MEDOFF, Departments of Microbiology and Medicine, Infectious Disease
Division, Washington University School of Medicine, S. Louis, Missouri 63110/
USA
B. A. NEWTON, Medical Research Council, Biochemical Parasitology Unit,
Molteno Institute, University of Cambridge, Cambridge/Great Britain
Contributors XI
NANCY L. OLEINICK, Departments of Radiology and Biochemistry, Case Western
Reserve University, School of Medicine, 2220 Circle Drive, Cleveland, Ohio 44106/
USA
JOHN G. OLENICK, Department of Molecular Biology, Department of the Army,
Walter Reed Army Institute of Research, Walter Reed Army Medical Center,
Washington, D. C, 20012/USA
W. PACHE, Pharmaceutical Division, Chemical Research, Sandoz Ltd. 4002 Basel/
Switzerland
SIDNEY PESTKA, Roche Institute of Molecular Biology, Nutley, New Jersey 07110/
USA
KARL PORALLA, Lehrstuhl fUr Mikrobiologie II der Universitat Tiibingen, Berg
hof, 7400 Tiibingen-Lustenau/Fed. Rep. Germany
P. E. REYNOLDS, Sub-department of Chemical Microbiology, Department of
Biochemistry, University of Cambridge/Great Britain
KOSABURO SATO, Shionogi Research Laboratory, Shionogi and Co., Ltd.,
Fukushima-ku, Osaka 553/Japan
DAVID SCHLESSINGER, Departments of Microbiology and Medicine, Infectious
Disease Division, Washington University School of Medicine, st. Louis, Missouri
63110/USA
HAROLD T. SHIGEURA, Merck Institute for Therapeutic Research, Rahway,
New Jersey 07065/USA
SIMON SILVER, Department of Biology, Washington University, St. Louis, Missouri
63130/USA
M. STAEHELIN, Ciba-Geigy AG, Bau 125/717 Klybeck, 4000 Basel/Switzerland
NOBUO TANAKA, Institute of Applied Microbiology, The University of Tokyo,
Bunyko-ku, Tokyo/Japan
HAMAO UMEZAWA, Microbial Chemistry Research Foundation, Institute of
Microbial Chemistry, 14-23 Kamiosaki 3-Chrome, Shinagawa-ku, Tokyo/Japan
DAVID VAZQUEZ, C.S.I.e. Centro De Investigaciones Bioiogicas, Instituto De
Biologia Celular, Velazquez, 144, Madrid-6/Spain