Redox Chemistry and Interfacial Behavior of Biological Molecules PDF
Preview Redox Chemistry and Interfacial Behavior of Biological Molecules
REDOX CHEMISTRY AND INTERFACIAL BEHAVIOR OF BIOLOGICAL MOLECULES REDOX CHEMISTRY AND INTERFACIAL BEHAVIOR OF BIOLOGICAL MOLECULES Edited by Glenn Dryhurst The University oj Oklahoma Norman, Oklahoma and Katsumi Niki Yokohama National University Yokohama, Japan PLENUM PRESS • NEW YORK AND LONDON Library of Congress Cataloging in Publication Data International Symposium on Redox Mechanisms and Interfacial Properties of Molecules of Biological Importance (3rd: 1987: Honolulu, Hawaii) Redox chemistry and interfacial behavior of biological molecules / edited by Glenn Dryhurst and Katsumi Niki. p. cm. "Proceedings of the Third International Symposium on Redox Mechanisms and Interfacial Properties of Molecules of Biological Importance, held October 19-23, 1987, in Honolulu, Hawaii" - T.p. verso. Includes index. ISBN·13: 978·1·4615·9536·6 e·ISBN·13: 978-1·4615·9534-2 DOl: 10.1007/978-1·4615-9534-2 1. Bioelectrochemistry - Congresses. 2. Oxidation-reduction reaction - Con gresses. 3. Biomolecules - Surfaces - Electric properties - Congresses. 1. Dryhurst, Glenn, 1939- . II. Niki, Katsumi. III. Title. QP517.B53I58 1987 88-29382 574.19'283-dc19 CIP Proceedings of the Third International Symposium on Redox Mechanisms and Interfacial Properties of Molecules of Biological Importance, held October 19-23, 1987, in Honolulu, Hawaii © 1988 Plenum Press, New York Softcover reprint of the hardcover 1st edition 1988 A Division of Plenum Publishing Corporation 233 Spring Street, New York, N.Y. 10013 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, without written permission from the Publisher PREFACE The papers in this book were presented at the Third International Symposium on Redox Mechanisms and Interfacial Properties of Molecules of Biological Importance held in Honolulu, Hawaii between October 19-23, 1987. This Symposium was held as part of the 172nd Meeting of The Electrochemical Society which was cosponsored by The Electrochemical Society of Japan with the cooperation of The Japan Society of Applied Physics. The aim of the Symposium was to bring together a group of electrochemists and bio-medical scientists with interests in electrochemistry from around the world to present their most current research results and/or to present up-to-date reviews of current areas of research activity. It is quite clear from the diversity of topics covered in the various papers that electrochemistry and electrochemical techniques and principles have much to contribute to our under standing of many important biochemical phenomena. For example, electrochemical studies are providing important insights into the redox properties of biomolecules ranging from relatively small organic molecules such as indoleamine neurotransmitters to very large organic/organometallic molecules which include various redox enzymes or model enzyme systems. Many of the most powerful analytical techniques are now being coupled to electrodes to monitor potential-controlled behaviors of bio logical molecules at charged interfaces. Electrochemical techniques are now being developed which permit extraordinarily small electrodes to be inserted into single cells to monitor electroactive biomolecules. Other microelectrodes are being employed to control cell growth and to manipulate single cells. Electrochemical techniques utilizing modified electrodes are now being employed for very sensitive and selective analytical measurements. All of these topics and many more are covered in the forty six papers presented in this book. We hope that there is much here to interest not only electrochemists and electro analytical chemists but also the biomedical research community in general. It is always of very great importance to the success of any major symposium to have the participation of established scientists from throughout the world and, equally importantly, v young investigators at the beginning of their independent scientific careers. We are thus very pleased to acknowledge the financial support provided by the following organizations which permitted many such people to attend the Symposium: Office of Naval Research EE&G Princeton Applied Research Corporation Eli Lilly Corporation The Organic and Biological Electrochemistry Division of The Electrochemical Society We would also like to express our thanks to Melanie Yelity and Lisa Honski of Plenum Publishing Corporation for help and advice concerning the preparation of the manuscript. Finally, we would like to thank Susan Kyncl who typed the entire manuscript and provided help in numerous other ways. Glenn Dryhurst Konstanz Katsumi Niki Yokohama May 1988 CON'l'EN'rS Supramolecular Effects in the Redox and Coordination 1 Chemistry of Superstructured Porphyrins D. Lexa and J.M. Saveant Electrochemistry of Metalloporphyrins Containing a 27 Metal-Metal or Metal-Carbon Bond K.M. Kadish A study of the Effects of Ionic Strength and Anion 47 Binding on the Reduction Potential of Cytochrome c Using Microelectrodes S. Sun, D.E. Reed and F.M. Hawkr~dge Electrochemical Reactivity of Strongly Adsorbed 63 Cytochrome c J.L. Willit and E.F. Bowden Redox Reactivity of Manganese "Capped" Metalloporphyrins 77 L.A. Bottomley, J.F. Luck, F.L. Neely and J.S. Quick Metalloporphyrin Films on Solid Electrodes: Reflectance 87 Spectroscopy and AC Impedance Studies in Aqueous and Nonaqueous Media T. Malinski and J.E. Bennett Bacterial Cytochrome P-450 Enzymes and Reactions on 105 Immobilized Electrodes. I. Preliminary Studies V.L. Vilker, F. Khan, D. Shen, M.M. Baizer and K. Nobe Interfacial Electrochemistry of Promoter-Modified 113 Electrodes for the Rapid Electron-Transfer of Cytochrome c I. Taniguchi SERS Studies on the Electrode Reaction of 125 Cytochrome c at Silver Electrodes in the Presence of Pyridine Derivatives F. Ke-jun, I. Satake, K. Ueda, H. Akutsu and K. Niki vii The Electrochemical Characterization of Oxene Adducts 139 of PFe (Cl04 ), PFeI I, and PFeI I (SR) [P = Tetrakis (2,6-Dichlorophenyl)porphinato Dianion] in Acetonitrile: Models for Compounds I and II of Horseradish Peroxidase and for Activated Cytochrome P-450 D.T. Sawyer, H. Sugimoto, H.-C. Tung and P.K.S. Tsang Direct Electrical Communication Between Chemically 151 Modified Enzymes and Metal Electrodes: III. Electron-Transfer Relay Modified Glucose Oxidase and D-Amino Acid Oxidase A. Heller and Y. Degani Potential-Controlled Enzymatic Activity of Conducting 173 Enzyme Membrane M. Aizawa, So-ichi Yabuki and H. Shinohara Electro-Enzymatic Studies of the Interfacial Behavior 181 of Proteins F.W. Scheller, R. Hintsche, V. Bogdanovskaja and P. Ohlsson Catalytic Oxidation of D-Glucose at an Enzyme- 193 Modified Electrode with Entrapped Mediator I. Ikeda, H. Hiasa and M. Senda Electrochemistry of the Iron-Molybdenum Cofactor 203 of Nitrogenase: Evidence for Multiple Speciation and ElectrocatalyticBehavior F.A. Schultz, S.F. Gheller and W.E. Newton SERRS as a Probe of Electrode Processes: 217 Interaction of Glucose Oxidase and FAD at Silver Electrodes R.E. Holt and T.M. Cotton Surface Electrochemistry of Amino Acids: 229 Voltammetry Assisted by EELS, Auger Spectroscopy and LEED A.T. Hubbard, D.G. Frank, M.J. Tarlov, N. Batina, N. Walton, E. Wellner and J.W. McCarger Electrochemistry and Spectroelectrochemistry 247 of Adenine and Adenosine Complexes with 3d Transition Metals T. Malinski, J.R. Fish, C.N. Mikulski and N.M. Karayannis viii Electrochemical Study of the Mechanism and 267 Kinetics of Oxygen Reduction Mediated by Anthracycline Antibiotics Adsorbed on Electrode Surface K. Kano, T. Konse, B. Uno and T. Kubota Studies on Redox Phototransformations of Reduced 281 Forms of Coenzyme RADP+ and Related Compounds B. Czochralska, E. Bojarska and K. Pawlicki Anticancer Quinones and Quinolines: Mode of Action 295 via Electron Transfer and Oxidative Stress P. Kovacic, J.R. Ames, J.W. Grogan, B. Hazra and M.D. Ryan Oxidation Pathways of Purine Drugs: 309 Electrochemical, Liquid Chromatographic and Mass Spectrometric Insights K.J. Volk, T. Peterson, K. McKenna, P.J. Kraske and A. Brajter-Toth Electron Transfer Mechanism for Cocaine Action 323 P. Kovacic, J.R. Ames, M. Jawdosiuk and M.D. Ryan Studies of Acid-Base, Hydration-Dehydration and 333 Keto-Enol Equilibria in Aqueous Solutions of a-Ketoacids by Polarography, Linear Sweep Voltammetry and Spectroscopy J. Kozlowski and P. Zuman Electron Transfer Oxy-Radical Mechanism for 345 Anticancer Agents: Etoposide, Cu DIPS, and Bis(9-aminoacridines) P. Kovacic, J.R Adams and M.D Ryan Surface Enhanced Raman Scattering (SERS) 359 Spectroscopy of Guanine Derivatives E. Koglin and J.-M. Sequaris Electrochemistry in Cancer: Applications to 369 Pharmacological Studies and Quinone-Containing Antitumor Agents P.L. Gutierrez and B. Nguyen On the Electrocatalytic Oxidation of D-Glucose 383 and Related Polyols on Large Pt and Au Electrodes o. Enea Electrochemistry of Some Synthetic Oxygen Carrier 397 Molecules in Water J.P. Ciccone, L.A. Deardurff, E.S. DeCastro, J.B. Kerr and B.D Zenner Electrochemical Studies on the Generation of 407 Active Oxygen Species in Biological Systems with the Use of Mediators S. Kwee Intracellular Voltammetry with Ultrasmall Carbon 417 Ring Electrodes J.B. Chien, R.A. Saraceno and A.G. Ewing Oxidation Chemistry of CNS Indoles 425 M.Z. Wrona, K. Humphries and G. Dryhurst Organic Electrochemistry IV: Electrochemical 447 Desulfurization Reactions of Thiolumazines W. Pfleiderer and B.S. Schulz Determination of Cationic Drugs on a Nafion 457 Coated Electrode T. Matsue, A. Aoki and I. Uchida Adsorptive Stripping Voltammetric Studies of 469 Biologically-Significant Compounds J. Wang Modified Electrodes Used to Elucidate Electro 479 chemical Behaviors of Biologically Significant Molecules G.J. Patriarche, J.-M. Kauffmann and J.-C. Vire Studies of the Kinetics of Mediated Electrochemical 499 Oxidation at Polymer-Coated Electrodes M. Sharp Electrochemical Preparation of Metallophthalocyanine 515 Films S.-i. Iijima, F. Mizutani, Y. Tanaka and K. Ichimura Selective Determination of Phosphate with PhoE 521 Porin-Lecithin Membrane Electrode T. Matsunaga, A. Shigematsu, Y. Asakura, H. Abe and S. Takezawa x Membrane Bioenergetics as Viewed from Reconstitution 529 Experiments H. Ti Tien Surface Charge Determines the Aggregation of Hemoglobin 557 Subunits as Predicted by the Surface Free Energy M. Blank Electrocatalysis in Membrane Mimetic Media 565 J.F. Rusling, C.-N. Shi and E.C. Couture Some Techniques for Investigation of Electrochemical 583 and Ion Transport Properties of Biological Cell Membranes: The Case of Chara Corallina F. Homble, A. Jenard and H.D. Hurwitz Vectorial Control of Cell Growth with Microelectrodes 613 H. Matsuoka, S. Matsumoto and M. Kinoshita Electrochemical Manipulation of Single Cell with a 623 Microelectrode M. Yaoita, J. Kojima, H. Shinohara and M. Aizawa Y. Ikariyama Introduction of New Alcohol Binding Sites at the 631 Lipid/Water Interface by the Incorporation of Monosialogangliosides into DPPC Liposomes G.P. Kreischman, C. Grahame-Brittain, H.E. Schueler and R.J. Hitzemann Index 641
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