Evaluation of Analytical Methods in Biological Systems: Analysis of Biogenic Amines PDF
Preview Evaluation of Analytical Methods in Biological Systems: Analysis of Biogenic Amines
TECHNIQUES AND INSTRUMENTATION IN ANALYTICAL CHEMISTRY Volume 1 Evaluation and Optimization of Laboratory Methods and Analytical Procedures. A Survey of Statistical and Mathematical Techniques by D.L. Massart, A. Dijkstra and L. Kaufman Volume 2 Handbook of Laboratory Distillation by E. Krell Volume 3 Pyrolysis Maas Spectrometry of Recent and Fossil Biomaterials. Compendium and Atlas by H.L.C. Meuzelaar, J. Haverkamp and F.D. Hileman Volume 4 Evaluation of Analytical Methods in Biological Systems Part A. Analysis of Biogenic Amines edited by G.B. Baker and R.T. Coutts a EVALU A T1O N OF ANALYTICAL METHODS IN BIOLOGICAL SYSTEMS general editor: R.A. de Zeeuw PART A ANALYSIS OF BIOGENIC AMINES edited by Glen 6. Baker and Ronald T. Coutts Neurochemical Research Unit, Department of Aychiatry and Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta, Canada E LSEVlE R SClENTlF IC PUBLISHING COMPANY - - Amsterdam Oxford New York 1982 ELSEVIER SCIENTIFIC PUBLISHING COMPANY Molenwerf 1 P.O. Box 21 1,1000 AE Amsterdam, The Netherlands Distributors for the United States and Caneda: ELSEVIER SCIENCE PUBLISHING COMPANY INC. 52, Vanderbilt Avenue New York, NY 10017 Library of Congress Cataloging in Publication Data Main entry under title: Evaluation of analytical methods in biological systems. (Techniques and instrumentation in analytical chemistry chemistry ; v. 4) Bibliography: p. Includes index. Contents: pt. A. Analysis of biogenic mines. 1. !nines--Analysis. 2. Amines in the body. 3. Biological chemistry--Technique. I. Baker, Glen B., . 1947- 11. Coutts, Ronald Thomson. 111. Series. QP8Ol .A48E86 1982 574.19'285 82-11553 ISBN 0-444-42110-6 (v. 1) ISBN 04444211 06 (VOl. 4) ISBN 044441744-3 (Series) 0 Elsevier Scientific Publishing Company, 1982 All rights reserved. No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, mechanical, photocopying, recording or other- wise, without the prior written permission of the publisher, Elsevier Scientific Publishing Company, lo00 AH Amsterdam, The Netherlands Printed in The Netherlands XI11 Contributors Baker, Glen B. Ferkany, John W. Neurochemical Research Unit Departments of Neuroscience, Department of Psychiatry Pharmacology and Psychiatry University of Alberta Johns Hopkins University School Edmonton, Alberta T6G 263, Canada of Medicine Baltimore, Maryland 21205, USA Baker, Judith M. Neurochemical Research Unit Gelpi, Emilio Department of Psychiatry Analytical Neurochemistry Unit University of Alberta Instituto de Quimica Bio-Organica Edmonton, Alberta T6G 263, Canada Consejo Superior de Investigaciones Cie ntif ic a s Candy, John M. Jorge Girona Salgado S/N MRC Neuroendocrinology Unit Barcelona-34, Spain Newcastle General Hospital Newcastle-upon-Tyne NE4 6BE, U.K. Godse, Damodar D. Clarke Institute of Psychiatry Chiu, Andrew S. University of Toronto Clarke Institute of Psychiatry Toronto, Ontario M5T 1R8, Canada University of Toronto Toronto, Ontario M5T 1R8, Canada Hubbard, John W. Faculty of Pharmacy Coutts, Ronald T. University of Manitoba Neurochemical Research Unit Winnipeg, Manitoba R3T 2N2, Canada Faculty of Pharmacy and Pharmaceutical Sciences LeGatt, Donald F. University of Alberta Neurochemical Research Unit Edmonton, Alberta T6G 2N8, Canada Department of Psychiatry and Faculty of Pharmacy and Davis Bruce A. Pharmaceutical Sciences Psychiatric Research Division University of A1 berta University Hospital Edmonton, Alberta T6G 2G3, Canada Saskatoon, Saskatchewan S7N 0x0, Canada Locock, R. Anthony Dayton, Mark A. Faculty of Pharmacy and Medical Sciences Program Pharmaceutical Sciences Myers Hall University of A1 berta Indiana University Edmonton, Alberta T6G 2N8, Canada Bloomington, Indiana 47405, USA Martin, Ian L. Dewhurst, William G. MRC Neurochemical Pharmacology Unit Neurochemical Research Unit Medical Research Council Centre Department of Psychiatry Medical School University of Alberta Cambridge CB2 2QD, U.K. Edmonton, Alberta T6G 2G3, Canada Midha, Kamal K. Dryden, William F. Col 1e ge of Pharmacy Department of Pharmacology University of Saskatchewan University of Alberta Saskatoon, Saskatchewan S7N OWO, Canada Edmonton, Alberta T6G 2E1, Canada Warsh, Jerry J. Durden, David A. ' Clarke Institute of Psychiatry Psychiatric Research Division University of Toronto University Hospital Toronto, Ontario M5T 1R8, Canada Saskatoon, Saskatchewan S7N 0x0, Canada Wightman, R. Mark Enna, S.J. Department of Chemistry Departments of Pharmacology and of Indiana University Neurobiology and Anatomy Bloomington, Indiana 47405, USA University of Texas Medical School Houston, Texas 77025, USA XV PREFACE Analytical chemistry has grown spectacularly over the last two decades. As a result, it has become very difficult, if not impossible for many scientists to keep abreast of the many developments, innovations and new horizons. This does not only hold for specialists involved in the basic aspects, but perhaps even more so for the non-specialists who wish to apply analytical chemistry as a tool to provide answers to the problems that they face in the course of their daily work, particularly in the area of biomedicine and other life sciences. A1 though the present analytical literature contains various excel lent monographs and review series, appliers of analytical chemistry to biological specimens often find that they focus too much on individual analytical techniques and on their basic aspects, with little or no comparison of the potentials and limitations of a particular technique as compared to others. This leaves a need for a series which will evaluate the various analytical techniques and approaches that can be used in a particular bioanalytical field, taking into account the type of the problem, the type of the answer needed and the impact of the biological matrix in which the measurements are to be performed. Thus, Evaluation of Analytical Systems in Biological Systems will be problem-orientated, rather than technique-orientated with the emphasis on evaluation in that the volumes in the Series will focus on a given bioana- lytical problem and then provide a critical and comprehensive discussion of the particular merits and pitfalls of the various techniques and approaches available for solving that problem. This requires a team of expert authors having not only an in-depth knowledge regarding the techniques as such but also a broad and balanced overview over the entire domain. It is hoped that in this way the reader will be provided the necessary information to select the most suitable methodology for his particular application and also to properly interpret the analytical answers produced by that methodology. It is not surprising that the first volume deals with the analysis of biogenic amines. There exists a heavy demand for reliable, sensitive, selective and accurate analyses of these compounds in biological specimens. On the other hand, major analytical innovations and applications have been reported recently in this area, so that a thorough evaluation seems very timely. We feel fortunate that Drs. Baker and Coutts have been willing to accept the challenge to edit this volume and that they have been able to find a team of outstanding authors to assist in this endeavour. The advice and suggestions of Dr. Karel Macek, Prague, Czechoslovakia during the early stages of this work are gratefully acknowledged. XVI Obviously, analysis in biological systems represents a rather broad field, from which topics will be selected on the basis of their importance, time- liness and feasibility. Books on the analysis of metals in human toxicology and on benzodiazepine analysis are under preparation, whereas volumes on alcohol analysis and on carbon monoxide are being set up. Additional topics will not only be selected from the biomedical sciences, but also from other areas such as environmental analysis, food and agricultural chemistry, etc. Suggestions to this end as well as comments and suggestions for improvements wi1 1 be greatly appreciated. Rokus A. de Zeeuw 1 Chapter 1 AMINES OF BIOLOGICAL INTEREST AND THEIR ANALYSIS GLEN B. BAKER AND RONALD T. COUTTS Neurochemical Research Unit, Department of Psychiatry and Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta T6G 2G3 (Canada) 1.1 INTRODUCTION Biogenic or naturally-occurring amines have been the subject of a great deal of research, particularly in the neurosciences. Much of this research has centered around the catecholamines dopamine and noradrenaline and the indolalkylamine 5- hydroxytryptamine (5-HT; serotonin). There is now a reasonable body of evidence supporting the role of these amines as neurotransmitters, and the term "biogenic amine" has become synonymous with the catecholamines and 5-HT. However, in recent years, there has been increased interest in histamine and the 'trace' amines, and in this book these are also included in the term biogenic amines. 'Trace' amines are defined as a number of naturally-occurring amines which are present in the central nervous system in much lower absolute quantities than the catecholamines and 5-HT, and include 6-phenylethylamine, m- and p-tyramine, phenylethanolamine, -m- and p-octopamine and tryptamine. The role of these substances in neurotrans- mission is unclear, but it is known that their concentrations in brain are affected markedly by a number of psychotropic drugs. They have also been implicated in a variety of psychiatric and neurologic disorders, and this will be discussed in further detail below. There is now a voluminous literature on biogenic amines, and space does not allow for a comprehensive review of the research which has been done on these sub- stances in biological systems. Rather, it is the purpose of this introductory chapter to highlight important aspects of the biogenic amines and to give a brief description of the format of the remainder of the book. 1.2 CATECHOLAMINES AND THEIR 0-METHYLATED AMINE METABOLITES The catecholamines (Fig. 1.1) have been the most extensively studied of the biogenic amines because of interest in their role as neurohumors. A number of excellent books and reviews are available describing the synthesis, metabolism and localization of the catecholamines in nervous tissue (e.9. 1-14). It has been proposed that one or more of the catecholamines are involved in the etiology and/ or symptomatology of a number of neurological and psychiatric disorders, includ- ing migraine, schizophrenia, anxiety, depression, aggression, pheochromocytoma and parkinsonism (1-3,7,9,14,15-22). In addition, a wide variety of psychotropic 2 HO a b HO OH C Yb.,,,, H3ch HO OH d e Fig. 1.1. Structures of the catecholamines and their 0-methylated amine derivatives: a) dopamine, b) noradrenaline, c) adrenaline, d) 3-methoxytyramine, e) normetanephrine and f) metanephrine. 3 and cardiac drugs are thought to interact with the synthesis, storage, metabolism and/or receptor activity of the catecholamines (1-4,7,11,13,15,19-30). The ability to form fluorescent derivatives of catecholamines with relative ease and specificity has meant that much is now known about the localization of nerve tracts containing these substances (see Chapter 5 of this volume). Electrolytic or chemical lesions of these tracts as well as the administration of catecholamine- depleting drugs have been used in animal models to study the involvement of the catecholamines in a number of behavioural and physiological functions such as loco- motion, exploratory activity, hunger, thirst and sexual activity (1-3,7-9,15,18, 21,26,31). The distribution of the catecholamines dopamine (DA), noradrenaline (NA) and adrenaline (A) and the ratios of each one to the others vary widely between the peripheral and central nervous system, within the central nervous system itself and amongst various species (1,2,6,7). 3-Methoxytyramine (3-MTA), normetanephrine (NMN) and metanephrine (MN) (Fig. 1. are produced by the enzymatic action of catechol 0-methyl transferase (COMT) on DA NA and A respectively. These 0-methylated amines have been identified in various tissues and body fluids (32-39). Concentrations of these compounds in these loca- tions can be altered dramatically in certain disease states and after administration of a number of psychotropic drugs. 1.3 5-HYDROXYTRYPTAMINE 5-Hydroxytryptamine (Fig. 1.2), a substance which possesses strong vasocon- strictive properties on smooth muscle, is found in many parts of the body, and is located in nonneuronal sites (platelets, mast cells, enterochromaffin cells) as well as in neurones (7,40,41). Although only 1-2% of this indolealkylamine in the body is located in the brain (7), 5-HT has been of interest to neuroscientists for some time because of its putative role as a neurotransmitter and its apparent CH2CH2NH2 H Fig. 1.2. Structure of 5-hydroxytryptamine. 4 involvement i n a number of psychological and physiological functions, including emotion, sleep, hunger, thirst and sexual activity (5,7,8,15,26,31,40-45). As with the catecholamines, a wide variety of psychotropic drugs affect the synthesis, metabolism, storage and receptor activity of 5-HT (7,ll-13,15,21-25,30,40-45). The localization of 5-HT-containing nerve tracts has also been investigated ex- tensively (4,7,8,15,41-44). The involvement of 5-HT in a number of nervous dis- orders, including migraine, depression and schizophrenia has been suggested (15, 16,21,22,41-49). 1.4 TRACE AMINES The trace amines (Fig. 1.3) have not been investigated as thoroughly as the catecholamines or 5-HT. The primary reason for this is the very low concentration of these substances in the nervous system, which has necessitated the development of highly sensitive and specific analytical techniques. The amount of literature on these amines has increased enormously in recent years as these methods have been applied to brain and body fluids. Although they are present in the CNS in minute quantities, the turnover rate of most of the trace amines is very rapid (50-53) and 8-phenylethylamine and tryptamine can cross the blood-brain-barrier with ease (54); these two factors may be very important from a physiological standpoint. Boulton (55) has pointed out that the trace amines, like the catecholamines and 5-HT, are distributed hetero- genously amongst brain areas. Most of the trace amines exert rather strong effects on uptake and release of the catecholamines and 5-HT (56-59) and metabolic conversions between some of the trace amines and the catecholamines have been reported (60-63). Recent micro- iontophoretic studies in brain have revealed that application of trace amines at currents insufficient to affect baseline firing rates of neurones can alter drama- tically the response of cells to DA, NA or 5-HT which are applied subsequently (64,65). Although much yet remains to be known about the role of trace amines in the CNS, the above findings and structural similarities to the putative neuro- transmitter amines suggest that their function may be associated intimate y with OA, NA and 5-HT. 1 .4.1 6-Phenyl ethyl ami ne The neurochemistry, metabolism and. pharmacology of B-phenylethylamine PEA) and its effects on animal behaviour have been reviewed extensively (66,67 . A number of monoamine oxidase inhibitors are known to cause dramatic increases in brain concentrations of PEA (68-72). One of the biochemical abnormalities result- ing from phenylketonuria is an increased production of PEA and hence a greatly elevated urine level of PEA and its major metabolite, phenylacetic acid (PAA) (73,741.
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