Mechanism of Action of Antibacterial Agents

388 Pages·1979·12.79 MB·English

by  D. R. Storm

Antibiotics
Volume V IPart 1
Mechanism of Action
of Antibacterial Agents
Edited by Fred E. Hahn
Springer-Verlag
Berlin Heidelberg New York 1979
Professor Fred E. Hahn, Ph.D
Department of the Army
Walter Rced Army Institute o f Re~arch
Walter Reed Army Medical Ccnter
Wa~hington, O.C. 20012, USA
With 80 Figures
ISllN-13: 978-3·642-46405-8 e-ISBN-13: 978-3-642-46403-4
001: 10.1007/978-3-642-46403·4
Library of Congress Ca(aloging in Publicalion Oa( •. Main entry under title: M..::hnism of action or antibaclerial
agcms. (Antibiotics; v. 5. pt. I). Includes bibliographies and index. I. Amibiotics. l. Hahn. Fred Ernest. 1916·
II. Seri• •. [DNLM: I. Antibiotics _ Pharmacodynamics. WI AN854H v_ 5 pI. I/QV350.3 M4861. RM267.M4.
61S'329,79.12471.
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Preface
The first volume of Antibiotics was published in 1967 and contained a series
of review papers on antibiotic actions. The editors, Drs. GOTTLIEB and SHAW,
were aware of the rapid development of this field of study and provided a
number of addenda in an effort to keep knowledge up to date while the book
was in production.
One year after the publication of Antibiotics I, this editor had a conference
with Dr. KONRAD F. SPRINGER in which it became clear that another volume
on actions of antibiotics would be necessary. For a variety of reasons, this
was delayed until 1975 and became Antibiotics III. It did not contain addenda
since it was recognized by the editors, Drs. CORCORAN and HAHN, that still
another volume would have to follow and that in a moving field, such as
the study of the actions of antibacterial drugs, no publication can be definitive
or remain current, except for a limited period of time.
The editors of Volume III grouped the contributions into sections: 1. Inter
ference with nucleic acid biosyntheses, 2. Interference with protein biosynthesis,
and 3. Interference with cell wall/membrane biosynthesis, specific enzyme sys
tems, and those in which the mode of action was not known with certainty.
We now present Volume V, Part 1 of Antibiotics, the third volume on
the actions of antibacterial compounds, with contributions selected either because
the active compounds have not previously been reviewed in this series, or because
further progress has been made in knowledge of such actions during the interven
mg years.
The problem of grouping the contributions into logically coherent sections
has again arisen. Realizing that no set of criteria can satisfactorily organize
the knowledge, this editor finally resigned himself to presenting the contributions
alphabetically.
Another problem in assembling and editing such a series of articles lies
in the disparity of the existing knowledge. For some substances, either new
or studied only to limited extents, the knowledge does not significantly exceed
a level which is conventionally referred to as mode ofa ction, i. e., a documentation
that a particular physiological process or overall biochemical event is affected.
For other substances, for example chloramphenicol, aminoglycosides, or nali
dixic acid, just to name a few, the mechanisms of their actions at the molecular
level approach resolution in detail. The field no longer possesses the relative
homogeneity in the level of knowledge which still existed in 1967 when Antibiotics
I was published. The Editor of a future volume may have to cope with this
emerging problem through categorizing articles as to (1) mode of action and
(2) mechanism of action.
A review of the contents of this Volume V, Part 1 might suggest that certain
topics have been omitted. This is especially true for the lactam antibiotics,
VI Preface
the penicillins, and cephalosporins. They have not been reviewed for the follow
ing reasons: In terms of enzymology, the inhibition of peptidoglycan biosynthesis
is known and has been reviewed on numerous occasions. There has emerged,
however, an element of doubt that the anatomical changes induced by these
drugs in bacteria, as well as the attendant bactericidal effects, can be fully
explained by known enzyme inhibitions. The physiological/biochemical basis
of the bacterial destruction by these antibiotics is currently under study, but
has not yet attained a level of understanding at which it would lend itself
to a systematic review. This editor felt, therefore, that such updated treatment
of the actions of the lactam antibiotics should be deferred to a future volume.
In Antibiotics I, Drs. GOTTLIEB and SHAW made a highly successful begin
ning, and a deliberate effort has been made in this Volume V, Part 1 to maintain
their editorial style and approach to the treatment of subject matter. The most
important feature in this striving for continuity has been that only such scientists
have been invited to authorship who have materially and originally contributed
to the bodies of knowledge which they were asked to review. Every contribution
is based on first-hand knowledge of the treated subject matter. The editor
hopes that such a policy has provided for an element of actuality and currency
which should distinguish Volume V, Part 1 from academic textbooks.
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 1
Bacitracin. D.R. STORM and W.A. TOSCANO, JR. (With 4 Figures) 1
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 L UMEZAWA
(With 4 Figures) . . . . . . . . . . 120
Lincomycin. F.N. CHANG (With 4 Figures) . . . . . . . . . . . 127
Moenomycin and Related Phosphorus-Containing Antibiotics. G. HUBER
(With 2 Figures) . . . . . . . . . . . . 135
Nalidixic Acid. A.M. PEDRINI (With 5 Figures) 154
Nitrofurans. D.R. MCCALLA (With 1 Figure) . 176
Novobiocin and Coumermycin A1. 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. LH. 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. RYon (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
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-fJ-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. SmAu (With 2 Figures). . . . . . . 236
Neocarzinostatin. LH. GOLDBERG (With 10 Figures) . . .. · 262
Nitracrine. M. GNIAZDOWSKI, J. FILIPSKI, and M. CHORt\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
x 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
Contributors
BAKKER, EVERT P., National Jewish Hospital and Research Center, Division
of Cellular and Molecular Biology, Denver, CO 80206, USA. Present address:
Ruhr-UniversiUit Bochum, Lehrstuh1 fUr Biochemie der Pflanzen, Postfach
102148,4630 Bochum 1, FRG
BEGGS, WILLIAM H., General Medical Research Service, Veterans Administration
Medical Center, Minneapolis, MN 55417, USA
CHANG, FONG N., Department of Biology, Temple University, Philadelphia,
PA 19122, USA
CUNDLIFFE, ERIC, Department of Biochemistry, University of Leicester, Leicester
LE 1 7RH, Great Britain
DAVIDSON, LESLIE A., Tuberculosis Research Laboratory, William S. Middleton
Memorial Veterans Hospital, 2500 Overlook Terrace, Madison, WI 53705, USA
DAVIS, BERNARD D., Bacterial Physiology Unit, Harvard Medical School,
Boston, MA 02115, USA
GOLDBERG, IRVING H., Department of Pharmacology, Harvard Medical School,
250 Longwood Avenue, Boston, MA 02115, USA
HAHN, FRED E., Department of the Army, Walter Reed Army Institute of
Research, Walter Reed Army Medical Center, Washington, D.C. 20012, USA
HOGENAUER, GREGOR, Sandoz Forschungsinstitut GmbH, Brunner Str. 59,
1235 Wien, Austria
HUBER, GERHARD, Hoechst AG, 6230 Frankfurt/Main 80, FRG
KAJI, AKIRA, Department of Microbiology, School of Medicine, University
of Pennsylvania, Philadelphia, PA 19174, USA
KERSTEN, WALTER, Institut fUr Physio1ogische Chemie der Universitat Erlangen
Niirnberg, Fahrstra13e 17, 8520 Er1angen, FRG
MCCALLA, DENNIS R., Department of Biochemistry, McMaster University,
Hamilton, Ontario L8S 4J9, Canada
OGILVIE, ADALING, Institut fUr Physio1ogische Chemie der Universitat Erlangen
Niirnberg, Fahrstra13e 17, 8520 Erlangen, FRG
PEDRINI, ANTONIA M., Laboratorio di Genetica, Biochimica et Evo1uzionistica,
Via S. Epifanio 14, Pavia, Italy
PONGS, OLAF, Ruhr-Universitat Bochum, Lehrstuh1 fUr Biochemie der Pflanzen,
4630 Bochum, FRG
XII Contributors
REUSSER, FRITZ, The Upjohn Company, Kalamazoo, MI 49001, USA
RYAN, MICHAEL J., Microbiological Sciences, Schering Corporation, 60 Orange
Street, Bloomfield, NJ 07003, USA
Ryon, MASARU, Department of Microbiology, University of Pennsylvania School
of Medicine, 36th Hamilton Walk, Philadelphia, PA 19174, USA
STORM, DANIEL R., Department of Pharmacology, School of Medicine SJ-30,
University of Washington, Seattle, WA 98195, USA
TAl, PHANG-CHENG, Bacterial Physiology Unit, Harvard Medical School, Boston,
MA 02115, USA
TAKAYAMA, KUNI, Tuberculosis Research Laboratory, William S. Middleton
Memorial Veterans Hospital, 2500 Overlook Terrace, Madison, WI 53705, USA
TAKESHIMA, HIDEO, 25-11 Yanagich6 Kanazawa-ku, Yokohama-Shi, Kanaga
waken 236, Japan
TANAKA, NOBUO, Institute of Applied Microbiology, University of Tokyo,
Bunkyo-ku, Tokyo 113, Japan
TOSCANO, WILLIAM A., JR., Department of Pharmacology, School of Medicine
SJ-30, University of Washington, Seattle, WA 98195, USA
UMEZAWA, IWAO, 6-22-8 Komagome Toshima-ku, Tokyo 170, Japan
WALLACE, BRIAN J., School of Microbiology, Faculty of Biological Sciences,
University of New South Wales, Kensington, N.S.W. 2033, Australia