Anticancer Agents from Natural Products PDF
Preview Anticancer Agents from Natural Products
ANTICANCER AGENTS from NATURAL PRODUCTS Edited by Gordon M. Cragg David G.I. Kingston David J. Newman Boca Raton London New York Singapore A CRC title, part of the Taylor & Francis imprint, a member of the Taylor & Francis Group, the academic division of T&F Informa plc. Copyright © 2005 CRC Press, LLC 1863_Discl.fm Page 1 Thursday, May 12, 2005 10:43 AM Published in 2005 by CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2005 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group No claim to original U.S. Government works Printed in the United States of America on acid-free paper 10 9 8 7 6 5 4 3 2 1 International Standard Book Number-10: 0-8493-1863-7 (Hardcover) International Standard Book Number-13: 978-0-8493-1863-4 (Hardcover) Library of Congress Card Number 2004065568 This book contains information obtained from authentic and highly regarded sources. Reprinted material is quoted with permission, and sources are indicated. A wide variety of references are listed. Reasonable efforts have been made to publish reliable data and information, but the author and the publisher cannot assume responsibility for the validity of all materials or for the consequences of their use. No part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information storage or retrieval system, without written permission from the publishers. For permission to photocopy or use material electronically from this work, please access www.copyright.com (http://www.copyright.com/) or contact the Copyright Clearance Center, Inc. (CCC) 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that provides licenses and registration for a variety of users. For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged. Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe. Library of Congress Cataloging-in-Publication Data Kingston, David. Anticancer agents from natural products / David Kingston, Gordon Cragg, David Newman. p. cm. ISBN 0-8493-1863-7 1. Antineoplastic agents. 2. Pharmacognosy. 3. Natural products. I. Cragg, Gordon M. L. II. Newman, David J. III. Title. RS431.A64K545 2005 616.99'4061--dc22 2004065568 Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com Taylor & Francis Group and the CRC Press Web site at is the Academic Division of T&F Informa plc. http://www.crcpress.com Copyright © 2005 CRC Press, LLC 1863_C000.fm Page v Thursday, May 12, 2005 10:12 AM Preface Natural products have made an enormous contribution to cancer chemotherapy, and over half of the current anticancer agents in clinical use are natural products or are derived from natural products. In spite of this fact, no book published in recent years has brought together the disparate information on anticancer natural products that is currently scattered throughout the chemical, biological, and medical literature. The most recent book to do this was Anticancer Agents Based on Natural Product Models, edited by John Cassady and John Douros, but this text was published in 1980 and is now sadly out of date. The present book covers the current clinically used anticancer agents that are either natural products or are clearly derived from natural product leads. In addition, a number of drug candidates that are in clinical development are also covered, albeit more briefly, as many of these will be clinically used drugs in the future. It is expected that this volume will appeal to several classes of reader. It will be of interest to natural products chemists, medicinal chemists, and pharmacognosists as an important reference work in their area of interest. It will appeal to synthetic organic chemists as a source of information on challenging synthetic targets. It will also appeal to oncologists as a source of background information on the drugs they use, although it is not intended as a primary clinical text. Some of the key features of the book include up-to-date coverage of a field that is scattered among many different journals and review articles, inclusion of information on drugs in clinical development, and authorship by leading scientists on each drug; in some cases the drug developer or a close associate is the chapter author. These features should give the book real value for scientists looking for information on the next generation of anticancer drugs. The editors express their appreciation to the staff of Taylor & Francis for their excellent help, especially Randi Cohen, Erika Dery, Lindsey Hofmeister, and Jay Margolis. The volume is dedicated to the memory of those scientists who have blazed the trail to successful natural products-based anticancer drug development, including Drs. John Douros, John Faulkner, Jonathan Hartwell, Morris Kupchan, Paul Scheuer, Matthew Suffness, and Monroe Wall. May their tribe increase! Gordon M. Cragg, David G. I. Kingston, and David J. Newman Frederick, MD, and Blacksburg, VA Copyright © 2005 CRC Press, LLC 1863_C000.fm Page vii Thursday, May 12, 2005 10:12 AM Editors Gordon M. Cragg was born in Cape Town, South Africa, and obtained his undergraduate training in chemistry at Rhodes University before proceeding to Oxford University, where he obtained his D. Phil. in organic chemistry in 1963. After 2 years of postdoctoral research in natural products chemistry at the University of California, Los Angeles, he returned to South Africa to join the Council for Scientific and Industrial Research. In 1966, he was appointed to the staff of the Department of Chemistry at the University of South Africa and transferred to the University of Cape Town in 1972. In 1979, he returned to the United States to join the Cancer Research Institute at Arizona State University, working with Professor G. Robert Pettit on the isolation of potential anticancer agents from plant and marine invertebrate sources. In 1985, he moved to the National Cancer Institute in Bethesda, Maryland, and was appointed Chief of the Natural Products Branch in 1989. His major interests lie in the discovery of novel natural product agents for the treatment of cancer and AIDS. He has been awarded National Institutes of Health Merit Awards for his contributions to the development of the drug, taxol (1991), leadership in establishing international collaborative research in biodiversity and natural products drug discovery (2004), and contributions to developing and teaching NIH technology transfer courses (2004). In 1998–1999 he served as President of the American Society of Pharmacognosy, and was elected to honorary membership of the society in 2003. He has established collaborations between the National Cancer Institute and organizations in many countries promoting drug discovery from their natural resources. He has given over 100 invited talks at conferences in many countries and has published more than 140 papers related to these interests. David G. I. Kingston was born in London, England, and obtained both his undergraduate and graduate training in chemistry at Cambridge University. His graduate supervisors were Lord Todd and Dr. D. W. Cameron, and his Ph.D. research was on the chemistry of the aphid pigments; he completed his Ph.D. degree in 1963. He then did 3 years of postdoctoral research; one in the Division of Biochemistry at MIT under Professor J. M. Buchanan and two back at Cambridge, where he was a Research Fellow of Queens College and worked with Lord Todd, Franz Sondhe- imer, and Dudley Williams. He moved to the State University of New York at Albany in 1966 and then to Virginia Polytechnic Institute and State University in 1971, where he currently holds the rank of University Distinguished Professor. He served as President of the American Society of Pharmacognosy in 1988–1989. His research interests are on the isolation and structure elucidation of novel natural products, especially those with anticancer activity, and on the chemistry and mechanism of action of tubulin-binding natural anticancer agents such as taxol, epothilone, and discodermolide, and he currently serves as the principal investigator of the Madagascar Interna- tional Cooperative Biodiversity Group. He received the Research Achievement Award of the American Society of Pharmacognosy in 1999 and was named Virginia Scientist of the Year in 2002. He has published over 280 papers and holds 14 patents. He is also an Elder in his church, the Blacksburg Christian Fellowship. David J. Newman was born in Grays, Essex. Initially he trained as a chemical analyst (Grad. RIC), followed by his being awarded an M.Sc. in organic chemistry (University of Liverpool), and then after time in the U.K. chemical industry, he obtained a D. Phil. in microbial chemistry from the University of Sussex in 1968. Following two years of postdoctoral studies on the structure of electron transport proteins at the University of Georgia, he worked for Smith Kline and French in Copyright © 2005 CRC Press, LLC 1863_C000.fm Page viii Thursday, May 12, 2005 10:12 AM Philadelphia, Pennsylvania, as a biological chemist predominantly in the area of antibiotic discovery. During this time, he obtained an M.S. in information sciences in 1977 from Drexel University, Philadelphia. He has worked for a number of United States-based pharmaceutical companies in natural products-based discovery programs in antiinfective and cancer treatments and joined the Natural Products Branch of the National Cancer Institute in 1991. He is responsible for the marine and microbial collection programs of the National Cancer Institute and, in concert with Gordon Cragg, for the National Cancer Institute’s Open and Active Repository programs. In 2003 he was awarded the National Institutes of Health Merit Award for his contributions to the development of potential anticancer agents from marine and microbial sources. His scientific interests are in the discovery and history of novel natural products as drug leads in the antiinfective and cancer areas and in the application of information technologies to drug discovery. In conjunction with Gordon Cragg, he has established collaborations between the National Cancer Institute and organizations in many countries promoting drug discovery from their natural resources. He has published over 60 papers, presented over 60 abstracts, holds 17 patents that are related to these interests, is both a UK Chartered Chemist and a UK Chartered Biologist, and is also an adjunct full professor at the Center of Marine Biotechnology, University of Maryland. Copyright © 2005 CRC Press, LLC 1863_C000.fm Page ix Friday, May 13, 2005 7:26 PM Contributors Dr. Rima Al-awar Dr. Gordon M. Cragg Eli Lilly and Company Natural Products Branch Lilly Corporate Center Developmental Therapeutics Program Discovery Chemistry Research Division of Cancer Treatment and Diagnosis and Technology National Cancer Institute Drop Code 2810 NCI-Frederick Indianapolis, IN 46285 Fairview Center, Room 206 [email protected] P.O. Box B Frederick, MD 21702-1201 [email protected] Professor Raymond J. Andersen Dr. Carmen Cuevas Dept of Chemistry PharmaMar University of British Columbia Av. de los Reyes, 1, P.I. La Mina Vancouver, BC 28770 Colmenar Viejo Canada V6T 1Z1 Madrid, Spain [email protected] [email protected] Dr. Klaus Edvardsen Dr. Federico Arcamone Department of Cell and Molecular Biology Via Quattro Novembre 26 Section for Tumor Immunology Nerviano University of Lund 20014 I12, 221 84 Milano, Italy Lund, Sweden [email protected] Dr. Jacques Fahy Division de Chimie Médicinale 5 Dr. Kathryn A. Bixby Centre de Recherches Pierre F. Department of Bacteriology 17, avenue Jean Moulin University of Wisconsin-Madison 81106 CASTRES, France 777 Highland Avenue [email protected] Madison, WI 53705-2222 Dr. Glynn T. Faircloth PharmaMar USA, Inc. 320 Putnam Avenue Dr. Don Borders Cambridge, MA 02139 13 Heatherhill Lane [email protected] Suffern, NY 10901 [email protected] Dr. Erik Flahive Pfizer Global Research and Development - La Jolla Labs Dr. David J. Chaplin 10578 Science Center Drive Oxigene Inc. San Diego, CA 92109 230 Third Avenue Erik.flahive@pfizer.com Waltham, MA 02451 efl[email protected] Copyright © 2005 CRC Press, LLC 1863_C000.fm Page x Thursday, May 12, 2005 10:12 AM Professor Heinz G. Floss Professor Hideji Itokawa University of Washington Department of Medicinal Chemistry, School of Department of Chemistry Pharmacy Campus Box 351700 Beard Hall CB7360 Seattle, WA 98195-1700 University of North Carolina [email protected] Chapel Hill, NC 27599-7360 Dr. (Mrs) Françoise Guéritte Dr. Christopher Jelinek I.C.S.N./C.N.R.S. Department of Chemistry and Biochemistry Avenue de la Terrasse P.O. Box 97348 91198 Gif-sur-Yvette, France Baylor University [email protected] Waco, Texas 76798-7348 Dr. Sarath P. Gunasekera David G. I. Kingston Harbor Branch Oceanographic Institution Department of Chemistry, M/C 0212 5600 US 1 North Virginia Polytechnic Institute and State Fort Pierce, FL 34946 University [email protected] Blacksburg, VA 24061 [email protected] Dr. Philip R. Hamann Chemical and Screening Sciences Professor Yoshita Kishi Wyeth Research Laboratories Dept. of Chemistry 401 N. Middletown Road Harvard University Pearl River, NY 10965 Cambridge, MA 02138 [email protected] [email protected] Professor Sidney M. Hecht Dr. Rohtash Kumar Department of Chemistry Department of Chemistry University of Virginia University of Alberta McCormick Road, PO Box 400319 Edmonton Charlottesville, VA 22904-4319 Alberta T6G 2G2 [email protected] Canada Dr. Rubén Henríquez Professor Helmut Lackner PharmaMar Institut für Av. de los Reyes, 1, P.I. La Mina Universität Göttingen 28770 Colmenar Viejo Tammannstraße 2 Madrid, Spain D-37077 [email protected] Göttingen, Germany [email protected] Dr. Gerhard Höfle Bereich Naturstoffe Profesor K. H. Lee GBF – Gesellschaft für Biotechnologische Department of Medicinal Chemistry, School of Forschung Pharmacy Mascheroder Weg 1 Beard Hall CB7360 D-38124 University of North Carolina Braunschweig, Germany Chapel Hill, NC 27599-7360 [email protected] [email protected] Copyright © 2005 CRC Press, LLC 1863_C000.fm Page xi Thursday, May 12, 2005 10:12 AM Dr. Bruce A. Littlefield Dr. Michelle Prudhomme Eisai Research Institute Université Blaise Pascal One Corporate Drive Laboratoire de Synthèse et Etude de Systèmes Andover, MA 01810 à Intérêt Biologique bruce_littlefi[email protected] UMR 6504 du CNRS URA 485 du CNRS Professor J. W. Lown 63177 Department of Chemistry Aubière, France University of Alberta [email protected] Edmonton Alberta T6G 2G2 Dr. Nicholas J. Rahier Canada Department of Chemistry [email protected] University of Virginia McCormick Road, PO Box 400319 Dr. Anthony Mauger Charlottesville, VA 22904-4319 10206 Frederick Ave Kensington, MD 20891-3304 Professor Hans Reichenbach [email protected] Bereich Naturstoffe Gesellschaft für Biotechnologische Forschung Dr. David J. Newman Mascheroder Weg 1 Natural Products Branch D-38124 Developmental Therapeutics Program Braunschweig, Germany Division of Cancer Treatment and Diagnosis [email protected] National Cancer Institute NCI-Frederick Dr. William Remers Fairview Center, Room 206 AmpliMed Corporation P.O. Box B 4280 N. Campbell Avenue Frederick, MD 21702-1201 Tucson, AZ 85718 [email protected] [email protected] Professor George R. Pettit Professor Michel Roberge Cancer Research Institute Department of Biochemistry and Molecular Arizona State University, Main Campus Biology P.O. Box 872404 University of British Columbia Tempe, AZ 85287-2404 Vancouver, BC Canada V6T 1Z1 Professor Kevin G. Pinney [email protected] Department of Chemistry and Biochemistry P.O. Box 97348 Professor Ben Shen Baylor University Division of Pharmaceutical Sciences Waco, TX 76798-7348 School of Pharmacy [email protected] University of Wisconsin-Madison 777 Highland Avenue Madison, WI 53705-2222 [email protected] Copyright © 2005 CRC Press, LLC 1863_C000.fm Page xii Thursday, May 12, 2005 10:12 AM Dr. Chuan Sih Dr. Janis Upeslacis Eli Lilly and Company Chemical and Screening Sciences Lilly Corporate Center Wyeth Research Laboratories Discovery Chemistry Research and Technology 401 N. Middletown Road Indianapolis, IN 46285 Pearl River, NY 10965 [email protected] [email protected] Dr. Kenneth Snader Dr. Amy E. Wright 1346 34th Avenue Harbor Branch Oceanographic Institution Vero Beach, FL 32960 5600 US 1 North [email protected] Fort Pierce, FL 34946 [email protected] Dr. Jay Srirangam Chemical Research & Development Ms. Zhiyan Xiao Pfizer Global R&D - La Jolla Labs Department of Medicinal Chemistry, School of 10578 Science Center Drive Pharmacy San Diego, CA 92109 Beard Hall CB7360 Jay.srirangam@pfizer.com University of North Carolina Chapel Hill, NC 27599-7360 Dr. Craig J. Thomas Department of Chemistry Dr. Melvin Yu University of Virginia Eisai Research Institute McCormick Road, PO Box 400319 4 Corporate Drive Charlottesville, VA 22904-4319 Andover, MA 01810 [email protected] Dr. Michael G. Thomas Department of Bacteriology Dr. Tin-Wein Yu. University of Wisconsin-Madison Department of Biological Sciences 777 Highland Avenue Louisiana State University Madison, WI 53705-2222 Baton Rouge, LA 70803-1715 [email protected] Copyright © 2005 CRC Press, LLC 1863_C000.fm Page xiii Friday, May 13, 2005 4:06 PM Contents Chapter 1 Introduction Gordon M. Cragg, David G. I. Kingston, and David J. Newman Chapter 2 Camptothecin and Its Analogs Nicolas J. Rahier, Craig J. Thomas, and Sidney M. Hecht Chapter 3 The Discovery and Development of the Combretastatins Kevin G. Pinney, Christopher Jelinek, Klaus Edvardsen, David J. Chaplin, and George R. Pettit Chapter 4 Homoharringtonine and Related Compounds Hideji Itokawa, Xihong Wang, and Kuo-Hsiung Lee Chapter 5 Podophyllotoxins and Analogs Kuo-Hsiung Lee and Zhiyan Xiao Chapter 6 Taxol and Its Analogs David G. I. Kingston Chapter 7 The Vinca Alkaloids Françoise Guéritte and Jacques Fahy Chapter 8 The Bryostatins David J. Newman Chapter 9 The Isolation, Characterization, and Development of a Novel Class of Potent Antimitotic Macrocyclic Depsipeptides: The Cryptophycins Rima S. Al-awar and Chuan Shih Chapter 10 Chemistry and Biology of the Discodermolides, Potent Mitotic Spindle Poisons Sarath P. Gunasekera and Amy E. Wright Chapter 11 The Dolastatins: Novel Antitumor Agents from Dolabella auricularia Erik Flahive and Jayaram Srirangam Copyright © 2005 CRC Press, LLC
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