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C o p p e r A m i n e O x i d a s e s Structures, Catalytic Mechanisms, and Role in Pathophysiology C o p p e r A m i n e O x i d a s e s Structures, Catalytic Mechanisms, and Role in Pathophysiology Edited by Giovanni Floris Bruno Mondovì Boca Raton London New York CRC Press is an imprint of the Taylor & Francis Group, an informa business CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2009 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business 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-13: 978-1-4200-7680-6 (Hardcover) This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish reliable data and information, but the author and publisher can- not assume responsibility for the validity of all materials or the consequences of their use. The authors and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained. If any copyright material has not been acknowledged please write and let us know so we may rectify in any future reprint. Except as permitted under U.S. Copyright Law, 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.copy- right.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 pro- vides 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 Copper amine oxidases : structures, catalytic mechanisms, and role in pathophysiology / edited by Giovanni Floris and Bruno Mondovì. p. ; cm. Includes bibliographical references and index. ISBN-13: 978-1-4200-7680-6 (hardcover : alk. paper) ISBN-10: 1-4200-7680-9 (hardcover : alk. paper) 1. Amine oxidase. 2. Copper enzymes. I. Floris, Giovanni, 1945- II. Mondovì, Bruno. [DNLM: 1. Amine Oxidase (Copper-Containing)--metabolism. 2. Amine Oxidase (Copper-Containing)--pharmacology. QU 140 C785 2009] QP603.M6C67 2009 572’.548--dc22 2008038892 Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Contents Acknowledgments .....................................................................................................ix Introduction: The Dawn of Pink Enzymes ...............................................................xi Editors ......................................................................................................................xv Contributors ...........................................................................................................xvii Abbreviations ..........................................................................................................xxi Chapter 1 History ..................................................................................................1 Franca Buffoni Chapter 2 Nomenclature and Potential Functions of Copper Amine Oxidases................................................................................................5 Sinéad Boyce, Keith F. Tipton, Michael I. O’Sullivan, Gavin P. Davey, Martha Motherway Gildea, Andrew G. McDonald, Aldo Olivieri, and Jeff O’Sullivan Chapter 3 Cofactors of Amine Oxidases: Copper Ion and Its Substitution and the 2,4,5-Trihydroxylphenylalanine Quinone ..............................................................................................19 Shinnichiro Suzuki, Toshihide Okajima, Katsuyuki Tanizawa, and Minae Mure Chapter 4 Copper Amine Oxidases from Plants.................................................39 Rosaria Medda, Andrea Bellelli, Pavel Pecˇ, Rodolfo Federico, Alessandra Cona, and Giovanni Floris Chapter 5 Soluble Copper Amine Oxidases from Mammals..............................51 Paola Pietrangeli, Laura Morpurgo, Bruno Mondovì, Maria Luisa Di Paolo, and Adelio Rigo Chapter 6 Membrane-Bound Copper Amine Oxidases ......................................69 Andrew Holt Chapter 7 Copper Amine Oxidase Genes ...........................................................87 Ivo Frébort and Hubert G. Schwelberger v vi Contents Chapter 8 Mechanism of TPQ Biogenesis in Prokaryotic Copper Amine Oxidase ....................................................................103 Toshihide Okajima and Katsuyuki Tanizawa Chapter 9 Copper Amine Oxidase Crystal Structures ......................................119 J. Mitchell Guss, Giuseppe Zanotti, and Tiina A. Salminen Chapter 10 Plasma Amine Oxidases in Various Clinical Conditions and in Apoptosis .............................................................................143 Frans Boomsma, Anton H. van den Meiracker, and Antonio Toninello Chapter 11 Copper Amine Oxidases in Intestinal Diseases .............................159 Wieslawa Agnieszka Fogel, Ewa Toporowska-Kowalska, and Anna Stasiak Chapter 12 Copper Amine Oxidases in Adipose Tissue-Related Disorders .........................................................................................177 Christian Carpéné Chapter 13 Copper Amine Oxidases in Adhesion Molecules in Renal Pathology and in Alzheimer’s Disease and VAP-1 in Leukocyte Migration ......................................................................195 Peter Boor, Mercedes Unzeta, Marko Salmi, and Sirpa Jalkanen Chapter 14 Inhibitors of Copper Amine Oxidases: Past, Present, and Future .........................................................................219 Marek Šebela and Lawrence M. Sayre Chapter 15 Pharmacological Applications of Copper Amine Oxidases..........................................................................................239 Emanuela Masini and Laura Raimondi Chapter 16 Copper Amine Oxidases as Antioxidant and Cardioprotective Agents .................................................................253 Mircea Alexandru Mateescu and Réginald Nadeau Contents vii Chapter 17 Biotechnological Aspects of Copper Amine Oxidases ..................261 Roberto Stevanato Chapter 18 Concluding Remarks ......................................................................275 David M. Dooley References ..............................................................................................................279 Index ......................................................................................................................325 Acknowledgments The editors wish to thank Drs. Francesca Pintus and Delia Spanò of the Department of Applied Sciences in Biosystems, Cagliari University, Italy, for their valuable help in the preparation of this book. ix

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