Biological Methylation and Drug Design: Experimental and Clinical Role of S-Adenosylmethionine PDF
Preview Biological Methylation and Drug Design: Experimental and Clinical Role of S-Adenosylmethionine
BiQlogical Met.hylation and Drug Design Experimental Biology and Medicine Biological Methylation and Drug Design: Experimental and Clinical Roles of S-Adenosylmethionine, edited by Ronald T. Borchardt, Cyrus R. Creveling, and Per Magne Ueland, 1986 Retroviruses and Human Pathology, edited by Robert C. Gallo, Dominique Stehelin, and Oliviero E. Varnier, 1985 Directed Drug Delivery, edited by Ronald T. Borchardt, Arnold Repta, and Valentino Stella, 1985 Immune Regulation, edited by Marc Feldmann and N. A. Mitchison, 1985 Human T Cell Clones: A New Approach to Immune Regulation, edited by Marc Feldmann, Jonathan R. Lamb, and James N. Woody, 1985 Inositol and Phosphoinositides: Metabolism and Regulation, edited by John E. Bleasdale, Joseph Eichberg, and George Hauser, 1985 Growth, Cancer, and the Cell Cycle, edited by Philip Skehan and Susan J. Friedman, 1984 Ir Genes: Past, Present, and Future, edited by Carl W. Pierce, Susan E. Cullen, Judith A. Kapp, Benjamin D. Schwartz, and Donald C. Shreffler, 1983 Methods in Protein Sequence Analysis, edited by Marshall Elzinga, 1982 Inflammatory Diseases and Copper, edited by John R. J. Sorenson, 1982 Membrane Fluidity: Biophysical Techniques and Cellular Regulation, edited by Morris Kates and Arnis Kuksis, 1980 Biological Methylation and Drug Design Experimental and Clinical Role of S-Adenosylmethionine Edited by Ronald T. Borchardt, Cyrus R. Creveling, and Per Magne Ueland Humana Press· Clifton, New Jersey Library of Congress Cataloging-In-Publication Data BlOlogical methylation and drug design. (Experimental biology and medicine) "This book has been developed from ... the proceedings of a symposium .. held at the Solstrand Fjord Hotel in Ber-gen, Norway on June 30-July 4, 1985"--Pref. Includes index. 1. Adenosylmethionine--Metabolism--Congresses. 2. Methylation--Congresses. 3. Adenosylmethionine- Therapeutic use--Congresses. 4. Nucleic acids- Metabolism--Congresses. 5. Phospholipids--Metabolism- Congresses. I. Borchardt, Ronald T. II. Creveling, Cyrus R. III. Ueland, Per Magne. IV. Series: Experimental biology and medicine (Clifton, N.J.) QP563.A3B58 1986 574.19'283 86-7212 ISBN-13: 978-1-4612-9398-9 e-ISBN-13: 978-1-4612-5012-8 001: 10.1007/978-1-4612-5012-8 Copyright © 1986 by The Humana Press Inc. Softcover reprint of the hardcover I st edition 1986 Crescent Manor PO Box 2148 Clifton, NJ 07015 All rights reserved. No part of this book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise withour written permission from the Publisher. Preface This book has been developed from its earlier and far less formal presentment as the proceedings of a symposium entitled The Biochemistry of S-Adenosylmethionine as a Basis for Drug Design that was held at the Solstrand Fjord Hotel in Bergen, Norway on June 30-July 4, 1985. The purpose of the symposium was to bring together scientists from various disciplines (biochemistry, pharmacology, virology, immunology, chemistry, medicine, and so on) to discuss the recent advances that have been made in our understanding of the biological roles of S adenosylmethionine (AdoMet) and to discuss the feasibility of utilizing AdoMet-dependent enzymes as targets for drug design. Thus the information provided herein will be of value not only to basic scientists involved in elucidating the role of AdoMet in biology, but also to medicinal chemists who are using this basic knowledge in the process of drug design. The volume should also be of interest to pharmacologists and clinicians involved in biological evaluation of potential therapeutic agents arising from the efforts of the biochemists and medicinal chemists. Each plenary speaker at the symposium was requested to submit a chapter reviewing recent contributions of their discipline to our base of knowledge about the biological role of AdoMet. Topics covered in this volume include protein and phospholipid methylations (Section A), nucleic acid methyl ations (Section B), the regulation of AdoMet, S-adenosylhomocysteine, and methylthioadenosine metabolism (Section C), clinical aspects of AdoMet (Section D), and the design, synthesis, and biological evaluation of trans methylation inhibitors (Section E). The individual chapters in this volume represent comprehensive, up-to-date reviews of the subject material. However, to gain maximum appreciation for the pivotal role of AdoMet in biology, the editors suggest a thorough reading of the entire volume. Ronald T. Borchardt Cyrus R. Creveling Per Magne Ueland v In Honor of Giulio Cantoni The Executive Committee for the International Symposium entitled The Biochemistry of S-Adenosylmethionine as a Basis for Drug Design was privileged to select Dr. Giulio Cantoni as Honorary Chainnan of the Symposium. The contributions of Dr. Cantoni to science began at the University of Milan, and continued at Oxford, The University of Michigan, New York University, Long Island College of Medicine, Western Reserve University, and the National Institute of Mental Health, where he has been the Chief of the Laboratory of General and Comparative Biochemistry since 1954. His initial studies on the methylation of nicotinamide were reported in 1951. In the same year he published a paper in the Journal of the American Chemical Society entitled The Nature of the Active Methyl Donor Formed Enzymatically from L-Methionine and Adenosine-Triphosphate. The crucial work appeared in the Journal ofB iological Chemistry in 1953, S-Adenosyl L-Methionine and ATP-and a new era in biochemistry began! Dr. Cantoni has made many contributions since this seminal discovery, including the identification of S-adenosylhomocysteine, studies on S adenosylhomocysteine hydrolase, studies on the enzymatic synthesis and decarboxylation of S-adenosylmethionine, the preparation of many unique and useful inhibitors of transmethylation, and studies on the role of methyltransferases in chemotaxis viral multiplication, cellular differenti ation, and phospholipid methylation. Dr. Cantoni has materially contributed to many of the previous conferences on S-adenosylmethionine both as a speaker, a session chairman, and a valued member of organizing committees. We have rightfully selected Dr. Cantoni as Honorary Chainnan in recognition of the importance of his creative, persistent, and successful pursuit of the "active methyl donor." It is now clearly evident that S adenosylmethionine ranks with ATP as one of the few truly pivotal molecules in biology. The Editors vii In Memory of Earl Us din We are all saddened by the recent death, on May 26, 1984, of Dr. Earl U sdin. The absence of his special leadership will be keenly felt in the many groups that he was instrumental in establishing, including our own "Conference on Transmethylation." Dr. Usdin began his career at the Johns Hopkins University. Then, upon receiving his doctorate in chemistry from the University of Ohio, he was a research fellow at the University of Pennsylvania; a research fellow at the Institute for Cancer Research, Philadelphia; Associate Professor at the University of New Mexico Highlands; Chief of Psychosomatic and Psychiatric Research at the Michael Reese Hospital; and worked for Melpar, Inc. Hazelton Laboratories, and Atlantic Research Corp. In 1968 he joined the National Institute of Mental Health, first as an Executive Secretary of the Preclinical Psychopharma cological Research Section and then Chief of the Pharmacology Section of Psychopharmacology Branch, NIMH. In 1981 Dr. Usdin was appointed Professor of Psychiatry at the California College of Medicine, University of California. In 1982 he became Chief of the Center for Education and International Research, International Institute on Brain and Behavior, University of California at Irvine. Dr. Usdin's personal vision of his role in science was as a creator of "colleges." He saw the value and need for providing dynamic forums where scientists could meet, discuss, and subject their latest investigations to the critical eyes of knowledgeable colleagues. His own personal energy, humor, and sense of urgency was the moving force that made these groups function-finding the chairpersons, writing endless letters in his own piquant style to encourage their prompt action, forcefully maintaining discipline with authors to submit abstracts and manuscripts on time, and enforcing not only good but prompt editorial scholarship. The extent to which his efforts were successful is attested to by the number, more than sixty, of published proceedings of congresses, symposia, and conferences that bear his name. Earl Usdin has left a legacy of friendships between scientists that extends across both disciplinary lines and national borders. His influence was truly international-he was at home in Scandian via, in Europe, in Eastern Europe, the Orient, as well as throughout the United States. Many of those persons who had the privilege of working with Earl Usdin have not only acquired his techniques, but more important, his sense of mission and as such constitute a continuing memorial to this unique individual. The Editors viii Acknowledgments The symposium entitled The Biochemistry of S-Adenosylmethionine as a Basis for Drug Design was organized and sponsored by the Department of Pharmaceutical Chemistry, School of Pharmacy, The University of Kansas, Lawrence, Kansas, USA and the Clinical Pharmacology Unit, University of Bergen, Bergen, Norway. We acknowledge with pleasure the assistance of Nancy Helm, Svein Helland, Asbjom Svardal, Helga Refsum, and Halvard Bergesen in the organization of the symposium. The symposium was made possible by the financial support provided by the following organizations: AFI A/SFarmaceutisk Industri AL A/S Apothekernes Laboratorium for Special Preparater Astra Lakemede1 AB Beckman Instruments BioResearch Boehringer-Ingelheim, Ltd. Burroughs Wellcome Company CIBA-Geigy Pharma NS GlaxoNS Hewlett Packard ICI-Pharma Janssen Division ab Cikad Lederle NAF-Laboratoriene A/S Norsk Pharmacia NS N orske Hoechst NS The Norwegian Cancer Society (LMK) The Norwegian Society for Fighting Cancer (NftKB) Norwegian Society for Science and the Humanities (NA VF) Nyegaard & Co. A/S Perkin-Elmer Schering AG G. D. Searle & Co. Toyo Jozo Co. The Upjohn Company ix Contributors V. Nambi Aiyar, Duke University Medical Center. Durham. North Carolina Maqsudul Alam, Biochemistry/Biophysics Program. Washington State University. Pullman. Washington R. D. Alarcon, University of Alabama at Birmingham. Birmingham. Alabama R. Albers, Department of Molecular Biology and Microbiology. Case Western Reserve University. Cleveland. Ohio *J ean-Herve AIix,Institut de Biologie Physico-Chimique. Paris. France Vitauts Alks, Grace Cancer Drug Center. Roswell Park Memorial Institute. Buffalo. New York D. Ayers, Department of Molecular Biology and Microbiology. Case Western Reserve University. Cleveland. Ohio Carey D. Balaban, Milton S. Hershey Medical Center. Pennsylvania State University. Hershey. Pennsylvania A. J. Bancroft, University of Alabama at Birmingham. Birmingham. Alabama K. Benes, Institute of Experimental Botany. Praha. Czechoslovakia Ralph J. Bernacki, Grace Cancer Drug Center. Roswell Park Memorial Institute. Buffalo. New York *Melvin L. Billingsley, Milton S. Hershey Medical Center. Pennsylvania State University. Hershey. Pennsylvania Pal Bjornstad, Institute of Medical Biochemistry. University of Oslo. Oslo. Norway P. Blanchard, Institut de Chimie des Substances Naturelles. CNRS. Gif-sur-Yvette. France Craig A. Bloch, Howard Hughes Medical Institute Laboratories. Duke University Medical Center. Durham. North Carolina J. Blusztajn, Massachusetts Institute of Technology. Cambridge. Massachusetts L. Boccassini, Rheumatology Service. L. Sacco Hospital. Milan. Italy John Bollinger, Biochemistry/Biophysics Program. Washington State University. Pullman. Washington *Ronald T. Borchardt, Pharmaceutical Chemistry Department. The University of }(ansas.Lawrence.}(ansas *T. Bottiglieri, }(ing's College Hospital. London. U)( *J on Bremer, Institute of Medical Biochemistry. University of Oslo. Oslo. Norway C. Cabrero, Metabolismo. Nutricion Y Hormonas. Fundacion Jimenez Diaz. Madrid. Spain S. Camper, Department of Molecular Biology and Microbiology. Case Western Reserve University. Cleveland. Ohio *Giulio L. Cantoni, Laboratory of General and Comparative Biochemistry. National Institute of Mental Health. Bethesda. Maryland xi xii Contributors M. W. P. Carney, King's College Hospital, London, UK Carlos J. Carrera, Scripps Clinic and Research Foundation. La Jolla, California "'Dennis A. Carson, Scripps Clinic and Research Foundation, La Jolla, California Maria Carteni.Farina, Department ofB iochemistry of Macrorrwlecules. University ofN aples, Napoli. Italy "'I. Caruso, Rheumatology Service, L. Sacco Hospital, Milan, Italy Sara Chaffee, Duke University Medical Center, Durham, North Carolina "'Peter K. Chiang, Division of Biochemistry, Walter Reed Army Institute of Research. Washington. DC "'Steven Clarke, Department of Chemistry and Biochemistry and the Molecular Biology Institute. University of California, Los Angeles. California "'James K. Coward, Department of Chemistry, Rensselaer Polytechnic Institute, Troy, New York Cyrus R. Creveling, NIADDK. National Institutes of Health, Bethesda, Maryland Sylvia Curtis, Duke University Medical Center, Durham, North Carolina E. DeClerq, REGA Instituut. Leuven, Belgium N. Dodic, Institut de Chimie des Substances Naturelles. CNRS, Gif-sur-Yvette, France Walter Doerfler, Institute of Genetics, University of Cologne, Cologne. Germany J. Edeh, King's College Hospital. London, UK J. Ferro, Department of Microbiology, Oregon State University, Corvallis, Oregon "'J. H. Fitchen, Medical Research Service, Portland. Oregon J. L. Fourrey, Institut de Chimie des Substances Naturelles, CNRS, Gif-sur-Yvette, France M. Fumagalli, Rheumatology Service, L. Sacco Hospital, Milan, Italy Deborah Campano German, Howard Hughes Medical Institute Laboratories, Duke University Medical Center. Durham, North Carolina M. Geze, Institut de Chimie des Substances Naturelles, CNRS, Gif-sur-Yvette, France Robert N. Golden, Laboratory of Clinical Science, National Institutes of Mental Health, Bethesda, Maryland R. Goodwin, Department of Molecular Biology and Microbiology, Case Western Reserve University, Cleveland, Ohio Michael L. Greenberg, Duke University Medical Center, Durham, North Carolina Masakazu Hatanaka, Institute of Virus Research. Kyoto University, Kyoto, Japan "'Gerald L. Hazelbauer, Biochemistry/Biophysics Program and Program in Genetics and Cell Biology, Washington State University, Pullman, Washington S. Helland, Department of Pharmacology, University of Bergen, Bergen, Norway "'Michael S. Hershfield, Duke University Medical Center. Durham, North Carolina "'Fusao Hirata, Laboratory of Cell Biology, National Institute of Mental Health, Bethesda, Maryland "'Robert M. Hoffman, Department of Pediatrics. University of California, San Diego, La Jolla, California P. Holbrook, Massachusetts Institute of Technology, Cambridge, Massachusetts "'A. Holy, Institute of Biochemisty and Organic Chemistrty. Praha, Czechoslovakia S. Horowitz, Department of Molecular Biology and Microbiology, Case Western Reserve University. Cleveland, Ohio Marie A. Iannone, Wellcome Research Laboratories, Burroughs Wellcome Co., Research Triangle, North Carolina
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