Mechanism of Action

796 Pages·1967·48.654 MB·English

by  Edwin H. Flynn, Carl W. Godzeski (auth.), David Gottlieb, Paul D. Shaw (eds.)

Antibiotics
Volume I
of
Mechanism Action
Edited by
David Gottlieb and Paul D. Shaw
With 197 Figures
Springer-Verlag Berlin· Heidelberg. New York 1967
David Gottlieb
Professor of Plant Pathology
University of Illinois
Urbana, Illinois
PauiD. Shaw
Associate Professor of Biochemistry
University of Illinois
Urbana, Illinois
ISBN 978-3-642-46053-1 ISBN 978-3-642-46051-7 (eBook)
DOI 10.1007/978-3-642-46051-7
All rights, especially that of translation into foreign languages, reserved. It is also forbidden to reproduce this book, either whole
or in part~ by photomechanical means (photostat, microfilm and/or microcard) or by other procedure without written permission
from Springer-Verlag. © by Springer-Verlag Berlin· Heidelberg 1967. Library of Congress Catalog Card Number 67-21462.
Softcover reprint of the hardcover 1s t edition 1967
The use of general descriptive names, trade names, trade marks, etc. in this publication. even if the fonner
are not especially identified, is not to be taken as a sign that such names, as understood by the Trade Marks and Merchandise
Marks Act, may accordingly be used freely by anyone. Title No. 1410
Dedication
For most areas of scientific pursuit, there is usually that rare investigator who
has the imagination to conceive ideas, who has faith in his visions, and who has
the ability to critically test his concepts in the laboratory. Almost invariably, this
scientist also inspires younger men to enthusiastically enter into his research
program. To him should go the accolades and the recognitions of the esteem in
which he is held. As only a small part of this esteem, we wish to dedicate these
books to Professor SELMAN A. WAKSMAN in appreciation of his leadership and
contributions in all facets of antibiotic research.
Preface
The idea for publishing these books on the mechanism of action and on the
biosynthesis of antibiotics was born of frustration in our attempts to keep
abreast of the literature. Gone were the years when we were able to keep a biblio
graphy on antibiotics and feel confident that we could find everything that was
being published on this subject. These fields of investigation were moving for
ward so rapidly and were encompassing so wide a range of specialized areas in
microbiology and chemistry that it was almost impossible to keep abreast of
developments. In our naivete and enthusiasm, however, we were unaware that
we were toying with an idea that might enmesh us, that we were creating an
entity with a life of its own, that we were letting loose a Golom who instead of
being our servant would be our master.
That we set up ideals for these books is obvious; they would be current guides
to developments and information in the areas of mechanism of action and bio
synthesis of antibiotics. For almost every subject, we wished to enlist the aid of
an investigator who himself had played a part in determining the nature of the
phenomena that were being discussed. One concept for the books was that they
include only antibiotics for which a definitive, well-documented mechanism of
action or biosynthetic pathway was known. Yet, such an approach would not
entirely serve the purpose we projected, for it would not encompass all of the
information available in these fields of antibiotic investigations and blind searches
for the original literature would still have to be made. We therefore chose to
include any and all antibiotics about which some pertinent information had been
published. It was obvious even at the start that such a compilation, integration,
and analysis of information could never be complete unless scientific investi
gations ceased at the moment the last manuscript was submitted-an end that
was neither desirable nor possible. An addendum was therefore included at the
end of the volume and left open for the addition of new information until the
last pages of the regular articles had been printed.
The original concept has also been further expanded as the authors of several
papers found it advisable to elaborate on their subject. Some of the articles in
cluded discussions of compounds that were not strictly antibiotics, but were vital
in giving a more comprehensive picture of the biosynthesis of an entire series of
natural products. In other cases, the antibiotics have served as tools for the elu
cidation of metabolic pathways and the contributions included clear and current
descriptions of various phases of cellular metabolism.
The clinical and industrial aspects of antibiotics have not been emphasized
and for most of them only enough information has been given to allow an evalu
ation of the studies. There is one notable exception, the chapter on the in vivo
behavior of penicillin. This exposition highlights the important fact that anti
biotics have been sought primarily for their use in controlling diseases. The action
VI Preface
of antibiotics in a diseased animal are far more complex than in our in vitro
systems. To understand the mechanism of action of an antibiotic in disease, data
from in vitro studies must be considered in light of the effects of the compound
in the natural, multifaceted system in which it is used.
Though the ideals for this book became clear, their realization proved more
difficult. We had to deal with a real world, one in which people are very much
involved in their own enterprises. Our colleagues were all busy, with their own
research and teaching. There were commitments for lectures, for committee
meetings, for surveys of the state of science, and for almost any other concievable
phase of scientific activities. We pleaded, we cajoled, we called attention to their
debt to science in this matter. We bullied some acquaintances and praised others.
We called on their aid for friendship's sake until we finally had commitments to
all our topics.
Soon we became aware that editing these books was teaching us more than
scientific facts; we were also learning how individualistic our colleagues were. No
editor could indicate to them how to write their papers, nor could he dragoon
them to a time schedule or insist on a general style of organization. Instead, we
were told how the books should be organized, how individual papers should be
written, and what topics should be covered. Under such conditions, the best
plan was to retreat and allow the authors as much leeway as possible to express
their individual approaches and styles of writing. Each retreat was not without
resistance from the editors and battle lines were always set beyond which further
withdrawal could not go. Many friendships hung in balance during the process,
but in the end these relationships persevered.
Finally, there were the many colleagues who helped us and whom we wish to
thank. This book would not have existed if it were not for the cooperative effort of
our students who gave much time to searching the literature and making certain
that our records of antibiotics were complete. We wish to thank them for this aid.
Our gratitude goes also to the authors of the papers who were invariably coopera
tive and understanding during the many trials through which their manuscripts
have gone. Finally, we wish to thank Dr. KONRAD F. SPRINGER of Springer-Verlag
for his humanistic approach to the project and for his sensitive discernment of the
relationship between the publishing media and the sciences which they serve.
Urbana, Illinois, 1967 DAVID GOTTLIEB
PAUL D. SHAW
Contents
Penicillins and Cephalosporins, 1. In Vitro: E. H. FLYNN and C. W. GODZESKI 1
Penicillins and Cephalosporins, II. In the Host: C. W. GODZESKI and
E. H. FLYNN ........................ . 20
Addendum - Penicillin-Cephalosporin: E. H. FLYNN and C. W. GODZESKI 748
D-Cycloserine and O-Carbamyl-D-serine: F. C. NEUHAUS 40
Ristocetin: D. C. JORDAN ......... . 84
Bacitracin: E. D. WEINBERG ........ . 90
Vancomycin: D. C. JORDAN and P. E. REYNOLDS 102
Pyocyanine: P. G. CALTRIDER ... 117
Polyene Antibiotics: S. C. KINSKY 122
Addendum - Polyenes: S. C. KINSKY 749
Polymyxins and Circulin: O. K. SEBEK 142
Addendum - Polymyxins and Circulin: O. K. Sebek 750
Albomycin: B. K. BHUYAN ..... 153
Sarkomycin: S. C. SUNG. . . . . . . 156
Addendum - Sarkomycin: S. C. SUNG 751
Pluramycin: N. TANAKA ...... . 166
Edeine and Pactamycin: B. K. BHUYAN 169
Phleomycin, Xanthomycin, Streptonigrin, Nogalamycin, and Aurantin:
B. K. BHUYAN. . . . . . . . . . . . 173
Griseofulvin: F. M. HUBER ....... . 181
Daunomycin and Related Antibiotics: A. DI MARCO 190
The Mitomycins and Porfiromycins: W. SZYBALSKI and V. N. hER 211
Chromomycin, Olivomycin and Mithramycin: G. F. GAUSE 246
Puromycin: D. NATHANS . . . . . . . . . . . . . . . 259
Gougerotin: J. M. CLARK, Jr.. . . . . . . . . . . . . 278
Cycloheximide and Other Glutarimide Antibiotics: H. D. SISLER and
M. R. SIEGEL . . . . . . . . . . . . 283
Chloramphenicol: F. E. HAHN ..... . 308
Addendum - Chloramphenicol: F. E. HAHN 751
Addendum - Chloramphenicol: P. D. SHAW 751
Tetracyclines: A. 1. LASKIN . . . . . . 331
Addendum - Tetracyclines: A. 1. LASKIN . 752
Tenuazonic Acid: H. T. SHIGEURA . . . . 360
Macrolide Antibiotics - Spiramycin, Carbomycin, Angolamycin, Methy-
mycin and Lancamycin: D. VAZQUEZ .......... . 366
VIn Contents
Addendum - Streptogramin and Macrolide Antibiotics: D. VAZQUEZ 754
Erythromycin and Oleandomycin: F. E. HAHN. . . . 378
Addendum - Erythromycin: F. E. HAHN . . . . . . . . . . . . 755
The Streptogramin Family of Antibiotics: D. VAZQUEZ . . . . . . 387
Addendum - Streptogramin and Macrolide Antibiotics: D. VAZQUEZ 754
Fucidin: C. L. HARVEY, C. J. SIR, and S. G. KNIGHT 404
Sparsomycin: L. SLECHTA . . . . . . . 410
Addendum - Sparsomycin: D. GOTTLIEB 756
Rifamycins: L. FRONTALI and G. TECCE 415
Nuc1eocidin: J. R. FLORINI . . . . . 427
Blasticidin S: T. MISATO ..... 434
Lincomycin: F. N. CHANG and B. WEISBLUM 440
Chalcomycin: D. C. JORDAN 446
Hadacidin: H. T. SHIGEURA . . 451
Psicofuranine: L. J. HANKA . . 457
Angustmycin A: A. J. GUARINO 464
Cordycepin: A. J. GUARINO . . 468
Addendum - Cordycepin: A. J. GUARINO 756
Azaserine and 6-Diazo-5-0xo-L-Norleucine (DON): R. F. PITTILLO and D. E.
HUNT ............................. 481
Tubercidin and Related Pyrrolopyrimidine Antibiotics: G. Acs and E. REICH 494
Sideromycins: J. NUESCH and F. KNUSEL . . . . . . 499
Addendum - Sideromycins: J. NUESCH and F. KNUSEL 757
Antimycin A: J. S. RIESKE . . . . . . . . . . . . 542
Addendum - Antimycin A: J. S. RIESKE . . . . . . 757
Oligomycin Complex, Rutamycin and Aurovertin: P. D. SHAW 585
Usnic Acid: P. D. SHAW. . . 611
Nigericin: P. D. SHAW 613
Flavensomycin: D. GOTTLIEB 617
Patulin: J. SINGH. . . . . . 621
Valinomycin: F. E. HUNTER, Jr. and L. S. SCHWARTZ 631
Addendum - Valinomycin: P. D. SHAW. . . . . . 758
Tyrocidines and Gramicidin S (Jv J2): F. E. HUNTER, Jr. and L. S. SCHWARTZ 636
Gramicidins: F. E. HUNTER, Jr. and L. S. SCHWARTZ. 642
Nonactin and Related Antibiotics: P. D. SHAW. 649
Addendum - Nonactin: P. D. SHAW 758
Novobiocin: T. D. BROCK . . . . . . 651
Addendum - Novobiocin: D. GOTTLIEB 760
Actithiazic Acid: P. G. CALTRIDER 666
Minomycin: P. G. CALTRIDER 669
Protoanemonin: P. G. CALTRIDER. 671
Trichothecin: P. G. CALTRIDER. 674
Viomycin: P. G. CALTRIDER . . . 677
Contents IX
Addendum - Viomycin: P. D. SHAW 760
Actinomycetin: P. G. CALTRIDER 681
Bacteriocins: 1. B. HOLLAND 684
Megacins: 1. B. HOLLAND . . . 688
Colicin: M. NOMURA ..... 696
Addendum - Colicin: D. GOTTLIEB 761
Enzymatic Reactions in Bacterial Cell Wall Synthesis Sensitive to Penicillins,
Cephalosporins and Other Antibacterial Agents: J. L. STROMINGER ... 705
Actinomycin: E. REICH, A. CERAMI, and D. C. WARD .......... 714
The Effect of Streptomycin and Other Aminoglycoside Antibiotics on
Protein Synthesis: G. A. JACOBY and L. C. GORINI .......... 726
Addenda
Antibiotic U-20,661: F. REUSSER . . . . . . 761
Antibiotic 6270 (Echinomycin-like): D. GOTTLIEB. 761
Amicetin: D. GOTTLIEB . . 762
Bruneomycin: D. GOTTLIEB 763
Phytoactin: D. GOTTLIEB . 763
List of Antibiotics According to Their Sites of Action . 764
Subject Index 766
Contributors
GEORGE Acs, Institute of Muscle Disease, 515 East 71 St., New York, N.Y./USA
B. K. BHUYAN, Biochemical Research, The Upjohn Company, Kalamazoo, Michi
gan/USA
THOMAS D. BROCK, Department of Bacteriology, Indiana University, Blooming
ton, Indiana/USA
PAUL G. CALTRIDER, Eli Lilly and Company, Indianapolis, Indiana/USA
A. CERAMI, Rockefeller University, New York, N.Y./USA
F. N. CHANG, Department of Pharmacology, University of Wisconsin, Medica
School, Madison, Wisconsin/USA
JOHN M. CLARK, Jr., Biochemistry Division, Department of Chemistry and
Chemical Engineering, University of Illinois, Urbana, Illinois/USA
A. DI MARCO, Istituto Nazionale per 10 Studio e la Cura dei Tumori, Piazzale
Gorini 22, Milano/Italia
JAMES R. FLORINI, Department of Zoology, Syracuse University, Syracuse,
New York/USA
EDWIN H. FLYNN, The Lilly Research Laboratories, Eli Lilly and Company,
ndianapolis, Indiana/USA
LAURA FRONTALI, Istituto di Fisiologia Generale, Cattedra di Chimica delle
Fermentazioni, Universita di Roma, Roma/Italia
G. F. GAUSE, Institute of New Antibiotics, Academy of Medical Sciences of
USSR, Bolshaia Pirogovskaia 11, Moscow G 21/USSR
CARL W. GODZESKI, The Lilly Research Laboratories, Eli Lilly and Company,
Indianapolis, Indiana/USA
LUIGI C. GORINI, Department of Bacteriology and Immunology, Harvard Medical
School, Boston 15, Massachusetts/USA
DAVID GOTTLIEB, Department of Plant Pathology, University of Illinois, Urbana,
Illinois/USA
ARMAND J. GUARINO, Department of Biochemistry, Woman's Medical College of
Pennsylvania, Philadelphia, Pennsylvania/USA
Contributors XI
FRED E. HAHN, Department of Molecular Biology, Walter Reed Army
Institute of Research, Washington, D. C./USA
LADISLAV J. HANKA, Department of Microbiology, The Upjohn Company,
Kalamazoo, Michigan/USA
C. L. HARVEY, Hoffman-La Roche, Inc., Nutley, New Jersey/USA
1. B. HOLLAND, Department of Genetics, University of Leicester, Leicester/
England
FLOYD M. HUBER, Eli Lilly and Company, Indianapolis, Indiana/USA
D. E. HUNT, Kettering-Meyer Laboratories, Southern Research Institute
Birmingham, Alabama/USA
F. EDMUND HUNTER, Jr., Department of Pharmacology, Washington University,
St. Louis 10, Missouri/USA
V. N. IYER, Microbiology Research Institute, Canada Department of Agri
culture, Ottawa/Canada
G. A. JACOBY, Department of Bacteriology and Immunology, Harvard Medical
School, Boston 15, Massachusetts/USA
D. C. JORDAN, Microbiology Department, University of Guelph, Ontario/Canada
STEPHEN C. KINSKY, Washington University, School of Medicine, St. Louis,
Missouri/USA
S. G. KNIGHT, Department of Bacteriology, University of Wisconsin, Madison,
Wisconsin/U SA
F. KNUSEL, Research Laboratories, Pharmaceutical Division, CIBA Ltd.,
Basel/Switzerland
ALLEN 1. LASKIN, The Squibb Institute for Medical Research, New Brunswick,
New Jersey/ U SA
TOMOMASA MISATO, Rikagaku Kenkyusho, The Institute of Physical and Chemica
Research, Honkomagome Bunkyo-ku, Tokyo/Japan
DANIEL NATHANS, Department of Microbiology, The John Hopkins University,
School of Medicine, Baltimore, Maryland/USA
FRANCIS C. NEUHAUS, Biochemistry Division, Department of Chemistry,
Northwestern University, Evanston, Illinois/USA
MASAYASU NOMURA, Laboratory of Genetics, University of Wisconsin, Madison,
Wisconsin/USA
JACOB NUESCH, Research Laboratories, Pharmaceutical Division, CIBA Ltd.,
Basel/Switzerland
R. F. PITTILLO, Kettering-Meyer Laboratories, Southern Research Institute,
Birmingham, Alabama/USA