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Progress in Medicinal Chemistry 14 This Page Intentionally Left Blank Progress in Medicinal Chemistry 14 Progress in Medicinal Chemistry 14 This Page Intentionally Left Blank Progress in Medicinal Chemistry 14 Edited by G.P. ELUS, D.SC., PH.D., F.R.I.C. Department of Chemistry, University of Wales Institute of Science and Technology, King Edward VII Avenue, Cardiff, CFI 3NU and G.B. WEST, B.PHARM., D.SC., PH.D., F.I.BIOL. Department of Paramedical Sciences North East London Polytechnic, Romford Road, London El 5 4LZ 1977 NORTH-HOLLAND PUBLISHING COMPANY AMSTERDAM - NEW YORK . OXFORD 0 I:lsevier/North-HoUand Biomedical Press - 1977 AN righls reserved. No part of this publication may be reproduced, stored in a retrieval sjstem, or transmitted in any form or by any means; electronic, mechanical, photocopying, recording or otherwise. without the prior permission of the copyright owner. ISBN for the series: 0 7204 7400 0 ISBN for this volume: 0 7204 0645 5 PUBLISHERS: North-Holland Publishing Company 335 Jan van Galenstraat, P.O. Box 211 Amsterdam, The Netherlands SOLE DISTRIBUTORS FOR THE U.S.A. AND CANADA: Elsevier/North-Holland Inc. 52 Vanderbilt Avenue New York,N.Y. 10017, USA. LIBRARY OF CONGRESS CATALOGING IN PUBLICATION DATA Main entry under title: Progress in medicinal chemistry. London, Buttenvorths, 1961-1973 (Vols. 1-9). Amsterdam, North-Holland Publishing Co., 1974- (Vols. 10- ). Editors: 1961- G.P. Ellis and G.B. West. Includes bibliography. 1. Pharmacology - Collected works. 2. Chemistry, Medical and pharmaceutical. I. Ellis, Gwynn Pennant, ed. 11. West, Geoffrey Buckle, 1961- ed. 111. Title: Medicinal chemistry. RM30.P7 6 15.19082 62-2712 ISBN 0 7204 0645 5 Printed in The Netherlands Preface There are six reviews in this volume, two on membranes, two on antibiotics and one each on flavonoids and opiates. The review of Dr A.W. Cuthbert discusses the properties of model membranes and epithelia, particularly in relation to sodium channels and the transfer of ions across cell membranes. This exciting new field involving ionophores is being extensively studied by biological chemists at the present time. The second review by Dr G.J. Moody and Dr J.D.R. Thomas describes some applications of ion- selective electrodes in medicine, an area in which membranes may lead to impor- tant advances. Antibiotics continue to attract attention and the antifungal polyene antibi- otics are discussed in Chapter 3 (by Dr S.M. Hammond). Nuclear analogues of the @-lactamantibiotics are considered in Chapter 4 (Dr J.Cs. Jriszberinyi and Dr E.T. Gunda), structure-activity relationships, which were briefly discussed in Volume 12, now being of great significance for further advances. Professor P.S.J. Spencer and Dr R.D.E. Sewell discuss in Chapter 5 important changes in brain amines that occur during analgesia with narcotic and non- narcotic opiates and compounds with similar properties. Finally, Dr R.E. Hughes and Dr H.K. Wilson (Chapter 6) expand on the physiological and nutritional sig- nificance of flavonoids on the stability and action of ascorbic acid in the tissues. In conclusion, we wish to thank our authors for their reviews and their patience, owners of the copyright of diagrams for permission to reproduce them, and, by no means least, the publishers for their co-operation and understanding. Februaty I977 G.P. Ellis G.B. West V This Page Intentionally Left Blank Contents 1. Aspects of the Pharmacology of Passive Ion Transfer Across Cell Membranes 1 A.W.Cuthbert, B.Sc., B. Pharm., M.A., Ph.D. Department of Pharmacology, University of Cambridge, Hills Road, Cambridge CB2 2QD, England 2. The Bio-Medical and Related Roles of IonSelective Membrane Electrodes 51 G.J. Moody, BSc., Ph.D. and J.D.R. Thomas, D.Sc., C.Chem., F.R.I.C. Chemistry Department, University of Wales Institute of Science and Technology, Cardiff CFI 3NU, Wales 3. Biological Activity of Polyene Antibiotics 105 S.M. Hammond, B.Sc., Ph.D. Department of Biological Sciences, Arrdue University, W. Lafayette, Indiana 4 790 7, II.S.A. 4. Functional Modifications and Nuclear Analogues of p-Lactam Antibiotics - Part I1 181 E.T. Gunda, Ph.D. Antibiotics Research Group of the Hungarian Acadamy of Sciences, Institute of Organic chemistry, L. Kossuth University,H-4010 Debrecen, Hungary J.Cs. JiszberCnyi, Ph.D. Institute of Organic Chemisny, L. Kossuth Univeristy. H-4010 Debrecen, Hungary 5. The Role of Biogenic Agents in the Actions of Centrally-Acting Analgesics 249 R.D.E. Sewell, B. Pharm., Ph.D., M.P.S. and P.S.J. Spencer, B. Pharm., Ph.D., F.I. Biol., M.P.S. Welsh School of Pharmacy, University of Wales Institute of Science and Technology, ardvf CFI 3NU, Wales 6. Flavonoids: Some Physiological and Nutritional Considerations 28 5 R.E. Hughes, M.A., FkD., F.I. Biol. and H.K. Wilson, M.Sc., Ph.D., M.I. Biol. Lkpartment of Applied Biology. University of Wales Institute of Science and Technology, Grdiff CFl3NU, Wales Index 303 viii Contents of earlier volumes VOLUME 7 1 SOME RECENTLY INTRODUCED DRUGS-A.P. Launchbury 2THE BIOCHEMICAL BASIS FOR THE DRUG ACTIONS OF PURINES-John H. Montgomery 3 THE CHEMISTRY OF GUANIDINES AND THEIR ACTIONS AT ADRENERGIC NERVE ENDINGS-G.J. Durant, A.M. Roe and A.L. Green 4 MEDICINAL CHEMISTRY FOR THE NEXT DECADE-W. S. Peart 5 ANALGESICS AND THEIR ANTAGONISTS: RECENT DEVELOPMENTS-A.F. Casy 6 SOME PYRIMIDINES OF BIOLOGICAL AND MEDICINAL INTERST-Part 11-C. C. Cheng and Barbara Roth VOLUME 8 1 ORGANOPHOSPHORUS PESTICIDES: PHARMACOLOGY-Ian L. Natoff 2 THE MODE OF ACTION OF NOVOBIOCIN-A. Morris and A.D. Russell 3 SOME PYRIMIDINES OF BIOLOGICAL AND MEDICINAL INTEREST-Part 111-C. C. Cheng and Barbara Roth 4 ANTIVIRAL AGENTS-D.L. Swallow 5 ANTIFERTILITY AGENTS-V. Petrow 6 RECENT ADVANCES IN THE CHEMOTHERAPY OF MALARIA-R.M. Pinder 7 THE PROSTAGLANDINS-M.P.L. Caton VOLUME 9 1 NATURALLY-OCCURRING ANTITUMOUR AGENTS-K. Jewers, A.H. Machanda and MIS. H.M. Rose 2 CHROMONE-2- AND -3CARBOXYLIC ACIDS AND THEIR DERIVATIVES-G.P. Ellis and G. Barker 3 4-OXOPYRANOAZOLES AND 4-OXOPYRANOAZINES-Misbahul Ah Khan 4 ISOTOPE TECHNIQUES IN THE STUDY OF DRUG METABOLISM-Y. Kobayashi and D.V. Maudsley 5 THE PHARMACOTHERAPY OF PARKINSONISM-R.M. Pinder 6 ADRENOCHROME AND RELATED COMPOUNDS-R.A. Heacock and W.S. Powell VOLUME 10 1 MEDLARS COMPUTER INFORMATION RETRIEVAL-A.J. Hartley 2 THE USE OF ENZYMOLOGY IN PHARMACOLOGICAL AND TOXICOLOGICAL INVESTIGATIONS-W.G. Smith 3 THE METABOLISM AND BIOLOGICAL ACTIONS OF COUMARINS-G. Feuer 4 CARCINOGENICITY AND STRUCTURE IN POLYCYCLIC HYDROCARBONS- D.W. Jones and R.S. Matthews 5 LINEAR FREE ENERGY RELATIONSHIPS AND BIOLOGICAL ACTION-K.C. James 6 RECENT ADVANCES IN THE SYNTHESIS OF NITRILES-G.P. Ellis and I.L. Thomas ix VOLUME 11 1 STEREOCHEMICAL ASPECTS OF PARASYMPATHOMIMETICS AND THEIR ANTAGONISTS: RECENT DEVELOPMENTS-A.F. Casy 2 QUANTUM CHEMISTRY IN DRUG RESEARCH-W.G. Richards and M.E. Black 3 PSYCHOTOMIMETICS OF THE CONVOLVULACEAE-R.A. Heacock 4 ANTIHYPERLIPIDAEMIC AGENTS-E.C. Witte 5 THE MEDICINAL CHEMISTRY OF LITHIUM-E. Bailey, P.A. Bond, B.A. Brooks, M. Dimitrakoudi, F.D. Jenner, A. Judd, C.R. Lee, E.A. Lenton, S. McNeil, R.J. Pollitt, G.A. Sampson and E.A. Thompson VOLUME 12 1 GAS-LIQUID CHROMATOGRAPHY-MASS SPECTROMETRY IN BIOCHEMISTRY, PHARMACOLOGY AND TOXICOLOGY -A.M. Lawson and G.H. Draffan 2 RECENT ADVANCES IN COLUMN CHROMATOGRAPHY-K.W. Williams and R.C. Smith 3 NMR SPECTROSCOPY IN BIOLOGICAL SCIENCES-P.J. Sadler 4 ELECTRON SPIN RESONANCE IN MEDICINAL CHEMISTRY-D.L. Williams-Smith and S.J. Wyard 5 POLAROGRAPHY IN BIOCHEMISTRY, PHARMACOLOGY AND TOXICOLOGY- M. Bfezina and J. Volke 6 METHODS RELATED TO CYCLIC AMP AND ADENYLATE CYCLASE-B.G. Benfey 7 RESISTANCE OF PSEUDOMONAS AERUGINOSA TO ANTIMICROBIAL DRUGS- R.B. Sykes and A. Morris 8 FUNCTIONAL MODIFICATIONS AND NUCLEAR ANALOGUES OF 8-LACTAM ANTIBIOTICS-Part I-J.Cs. Jdszberhnyi and T.E. Gunda VOLUME 13 1 CLINICAL ENZYMOLOGY-David M. Goldberg 2 THE RELEASE OF PHARMACOLOGICALLY ACTIVE SUBSTANCES IN PARASITIC INFECTIONS-P.F.L. Boreham and I.G. Wright 3 THE MEDICINAL CHEMISTRY OF 1,2,3-TRIAZINES-Malcolm F.G. Stevens 4 THE BIOLOGICAL USES AND IMPORTANCE OF GLUTARALDEHYDE-A.D. Russell and D. Hopwood 5 THE CHEMISTRY AND BIOCHEMISTRY OF C-NUCLEOSIDES-G. Doyle Daves, Jr. and C.C. Cheng X Progress in Medicinal Chemistry - Vol. 14, edited by G.P. Ellis and G.B. West Q Elsevier/North-HollandBiomedical Press - 1977 1 Aspects of the Pharmacology of Passive Ion Transfer Across Cell Membranes A.W. CUTHBERT, B.Sc., B.Pharm., M.A.,Ph.D. Department of Pharmacology, University of Cambridge, Hills Road, Cambridge CB2QD, England INTRODUCTION 2 MODEL MEMBRANES 3 General properties 3 Channel (pore) formation 4 Gramicidin 4 Polyenes 7 Alamethicin 9 EIM (excitability-inducing material) and BWS V (black widow spider venom) 9 Synthetic pore formers 10 Channel formation in biologkal membranes 10 Carriers 12 Lipid-soluble ions 12 Ionophores 12 Natural ionophores 19 SODIUM CHANNELS 20 Voltagedependent sodium channels 20 Selectivity 22 Chemistry of channel blockers 23 Mechanism of action of channel blockers 26 Density of sodium channels 27 Substances increasing sodium permeability 29 Local anaesthetics 31 Sodium channels in epithelia 32 Occurrence of sodium channels in epithelia 35 Chemistry and mechanism of action of channel blockers 35 Density of sodium channels in epithelia 41 The effects of hormones 42 Sodium channels in tight junctions 43 CONCLUDING REMARKS 44 REFERENCES 45 2 PASSIVE ION TRANSFER ACROSS CELL MEMBRANES INTRODUCTION Most writers of reviews, and this one is no exception, find it necessary to intro- ducc their work with a few paragraphs describing the limits within which they intcnd to contain their discussion.
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