Evaluation of Analytical Methods in Biological Systems Analysis of Biogenic Amine part A

325 Pages·1982·14.67 MB·English

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TECHNIQUES AND INSTRUMENTATION IN ANALYTICAL CHEMISTRY VOLUME 4
EVALUATION OF ANALYTICAL METHODS IN BIOLOGICAL SYSTEMS
PART A
ANALYSIS OF BlOGENlC 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
V
CONTENTS
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Contri butors XIi i
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Preface XV
.
Chapter 1 Amines of biological interest and their analysis
. . . . . . . . . . . . . . .
(Glen B Baker and Ronald T Coutts) 1
. . . . . . . . . . . . . . . . . . . . . . . . . . .
1.1. Introduction 1
. . . . . . . .
1.2. Catecholamines and their D-methylated metabolites 1
. . . . . . . . . . . . . . . . . . . . . . .
1.3. 5-Hydroxytryptamine 3
. . . . . . . . . . . . . . . . . . . . . . . . . . . .
1.4. Trace amines 4
. . . . . . . . . . . . . . . . . . . . .
1.4.1. B-Phenylethylamine 4
m- . . . . . . . . . . . . . . . . . . .
1.4.2. and para-tyramine 6
m- . . . . . . . .
1.4.3. Phenylethanolamine. and para-octopamine 6
. . . . . . . . . . . . . . . . . . . . . . . . .
1.4.4. Tryptamine 7
. . . . . . . . . . . . . . . . . . . . . . . . . . . .
1.5. Histamine 7
. . . . . . . . . . . . . . . . . . . . . . .
1.6. Purpose of the book 8
. . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 9
Chapter 2 . Biological assay methodology (William F . Dryden) . . . . . . . 15
. . . . . . . . . . . . . . . . . . .
2.1. General problems in bioassay 15
. . . . . . . . . . . . . . . . . . . . . .
2.2. Design of experiments 17
. . . . . . . . . . . . . . . . . . . . . . . .
2.3:Choice of tissues 23
. . . . . . . . . .
2.3.1. Smooth muscle contraction and relaxation 25
. . . . . . . . . .
2.3.2. Cardiac muscle contraction and frequency 26
. . . . . . . . . . . . . . . . .
2.3.3. Skeletal muscle contraction 27
. . . . . . . . . . .
2.3.4. Parameters from non-contractile tissues 28
. . . . . . . . . . . . . . . . . . . . . . . . .
2.4. Methods of assay 28
. . . . . . . . . . . . . . . .
2.4.1. Catecholamines and congeners 29
. . . . . . . . . . . . . . . . .
2.4.2. Acetylcholine and congeners 31
. . . . . . . . . . . . . . . . . . .
2.4.3. Histamine and congeners 32
. . . . . . . . . . . . . . . . . . .
2.4.4. Serotonin and conqeners 33
. . . . . . . . . . . . . . . . . .
2.4.5. Assay of complex mixtures 33
. . . . . . . . . . . . . . . . . . . . . . . . . . .
2.5.Conclusions 35
. . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 36
.
Chapter 3 Thin-layer chromatography of biogenic amines
. . . . . . . . . . . . . . . . . . . . . .
(R Anthony Locock) 37
. . . . . . . . . . . . . . . . . . . . . . . . . .
3.1. Introduction 37
3.1.1. Brief history of the development of thin-layer
chromatography (TLC) and its application to the
. . . . . . . . . . . . . .
separation of biogenic amines 37
VI
. . . . . . . . .
3.1.2. High-performance thin-layer chromatography 38
. . . . . .
3.1.3. Multiple development in thin-layer chromatography 39
. . . . . . . . . . .
3.1.4. Recent developments in TLC technology 41
. . . . . . . . . . . . . .
3.2. TLC as applied to the biogenic amines 41
. . . . . . .
3.2.1. TLC systems for underivatized biogenic amines 41
3.2.2. TLC systems for 3-0-methyl derivatives of catecholamines . . 50
3.2.3. TLC systems for DNS derivatives of biogenic amines . . . . . 50
3.2.4. TLC systems for other derivatives of biogenic amines . . . . 56
. . . . . . . . . . . . . . . . . .
3.3. Summary and Conclusions 59
. . . . . . . . . . . . . . . . . . . . . . . . . .
References 59
.
Chapter 4 Fluorescence techniques for detection and quant tation of
amines (Judith M . Baker and William G . Dewhurst . . . . . . . 63
. . . . . . . . . . . . . . . . . . . . . . . . .
4.1. Introduction 63
. . . . . . . . . . . . . . . .
4.1.1. Theory and instrumentation 63
. . . . . . . . . . . . . . .
4.1.2. Common methodological problems 65
4.2. Fluorescence techniques for detection of amines . . . . . . . . . 66
. . . . . . . . . . . . . . . . . . . . . . .
4.2.1. Derivatization 66
4.3. Fluorescence techniques for quantitation of amines . . . . . . . 68
. . . . . . . . . . . . . . . . . . . . . . .
4.3.1. Derivatization 68
. . . . . . . . . . . .
4.3.1.1. Catecholamines and metabolites 68
. . . . . . . . . . . . . . . . . . . . .
4.3.1.2. Indoleamines 74
. . . . . . . . . . . . . . . . . . . . .
4.3.1.3. Other amines 75
. . . . . . . . . . . . . . . . . . . .
4.3.2. Native fluorescence 75
4.3.3. Fluorescence detection combined with another quantitation
. . . . . . . . . . . . . . . . . . . . . . . . . . .
method 76
. . . . . . . . . . . . . . . . . . . . . . . .
4.3.4. Micromethods 76
4.4. Comparison of fluorescence techniques and other analytical
. . . . . . . . . . . . . . . . . . . . . . . . . . . . .
methods 77
. . . . . . . . . . . . . . . . . . . . . . . . . . . . .
4.5. Summary 78
. . . . . . . . . . . . . . . . . . . . . . . . . . .
References 78
.
Chapter 5 Histochemical approaches to the detection of biogenic amines
(John M . Candy) . . . . . . . . . . . . . . . . . . . . . . . 83
. . . . . . . . . . . . . . . . . . . . . . . . . .
5.1. Introduction 83
5.1.1. Validation of histochemical approach . . . . . . . . . . . . 83
5.1.2. Outline of history of development of histochemical methods
. . . . . . . . . . . .
for the detection of the monoamines 83
5.1.3. Fluorescence microscopy and microspectrofluorimetry in the
. . . . . . . . . . . . . . . .
detection of the monoamines 84
5.2. Chemical background to the formaldehyde and glyoxylic acid
. . . . . . . . . . . . . . . . . . . . . . . . . . . . .
method 85
VII
5.2.1. Reaction mechanisms in the formaldehyde method . . . . . . 85
5.2.2. Reaction mechanisms in the glyoxylic acid method . . . . . . 85
5.2.3. Fluorescence and microspectrofluorimetric analysis in the
detection of the monoamines . . . . . . . . . . . . . . . . 87
5.3. Practical aspects of the histochemical detection of the
monoamines . . . . . . . . . . . . . . . . . . . . . . . . . . . 95
5.3.1. Tissue preparation . . . . . . . . . . . . . . . . . . . . . 95
5.3.2. Methods of fluorophore formation . . . . . . . . . . . . . . 99
. . . .
5.3.3. Fluorescence microscopy and microspectrofluorimetry 100
.
5.4. Evaluation of the formaldehyde and glyoxylic acid techniques . 102
. . . . . . . .
5.4.1. Formation and extraction of the fluorophores 102
5.4.2. Fluorescence yield and photodecomposition of the
. . . . . . . . . . . . . . . . . . . . . . . .
fluorophores 103
5.4.3: Quantitation of the fluorescence . . . . . . . . . . . . . . 104
. . . . . . . . . . . . . . . .
5.4.4. Specificity and sensitivity 104
. . . . . . . . . .
5.4.5. Comparison with other analytical methods 105
Reference s . . . . . . . . . . . . . . . . . . . . . . . . . . 106
Chapter 6 . Gas chromatographic analysis of amines in biological systems
. . . . . . .
(Glen B Baker. Ronald T Coutts and Donald F LeGatt) 109
. . . . . . . . . . . . . . . . . . . . . . . . . .
6.1. Introduction 109
. . . . . . . . . . . . . . . . . . . . . . . . .
6.1.1. GC columns 109
. . . . . . . . . . . . . . . . . . . . . . . . .
6.1.2. Detectors 110
. . . . . . . . . . . . .
6.1.2.1. Thermal conductivity detector 110
. . . . . . . . . . . . . . .
6.1.2.2. Flame ionization detector 111
. . . . . . . . . . . . . . .
6.1.2.3. Electron-capture detector 111
. . . . . . . . . . . . .
6.1.2.4. Nitrogen-phosphorous detector 111
. . . . . . . . . . . . .
6.1.2.5. Mass spectrometric detection 111
. . . . . .
6.1.3. Derivatization for gas chromatographic analysis 112
. . . . . . . . . . . . . . . . . . .
6.2. Analysis of specific amines 113
. . . . . . .
6.2.1. Catecholamines and their 0-methyl metabolites 113
. . . . . . . . . . .
6.2.2. 5-Hydroxytryptamine (5-HT; serotonin) 117
6.2.3. Trace amines: phenylethylamine (PEA). tyramine (TA),
octopamine (OA), phenylethanolarnine (PEOH) and
. . . . . . . . . . . . . . . . . . . . . . .
tryptamine (T) 118
. . . . . . . . . . . . . . . . . . . . . . . . .
6.2.4. Histamine 123
6.3. Advantages and limitations of GC compared to other analytical
. . . . . . . . . . . . . . . . . . . . . . . . . . . . .
methods 124
. . . . . . . . . . . . . . . . . . . . . . . .
6.4. Acknowledgements 125
. . . . . . . . . . . . . . . . . . . . . . . . . . .
References 125
VIII
.
Chapter 7 Quantitative high resolution mass spectrometry of biogenic
amines (Bruce A . Davis and David A . Durden) . . . . . . . . . 129
. . . . . . . . . . . . . . . . . . . . . . . . . .
7.1. Introduction 129
7.1 . 1. Historical background and development . . . . . . . . . . . 129
. . . . . . . . .
7.1.2. Mass spectrometric quantitative techniques 131
. . . . . . . . . . . . . . . . . . . . . . . . . . . .
7.2. Procedure 132
7.2.1. Chemical and biochemical preparation of the sample for
. . . . . . . . . . . . . . . . . . . . .
mass spectrometry 132
7.2.2. Mass spectrometric procedure for the quantitation of
. . . . . . . . . . . . . . . . . . . . . .
biogenic amines 132
.
7.3. Evaluation of high resolution mass spectrometry vs other
. . . . . . . . . . . . . . . . . . . . . .
analytical techniques 135
. . . . . . . . . . . . . . . . . . . . . . . .
7.3.1. Specificity 135
(i) Comparison of values for trace amines measured by
. . . . . . . . . . . . . .
different analytical techniques 135
(ii) Evaluation of the specificity of the different analytical
. . . . . . . . . . . . . . . . . . . . . . . .
techniques 136
. . . . . . . .
a Thin-layer chromatography-mass spectrometry 136
b . Radioenzymatic assay . . . . . . . . . . . . . . . . . . . 137
c . Gas chromatography-mass spectrometry . . . . . . . . . . . 137
. . . . . . . . . . . . . . . . . . . . .
d Gas chromatography 138
. . . . . . . . . . .
e High-performance 1 iquid chromatography 138
. . . . . . . . . . . . . . . . . .
f Spectrophotofluorimetry 139
. . . . . . . . . . . . . . . . . . . . . . . .
7.3.2. Sensitivity 139
. . . . . . . . . . . . . . . . . . . . . . . . .
(i) Definition 139
. . . . . . . . . . . . . . . . . . . . . . .
(ii) Trace amines 139
. . . . . . . . . . . . . . .
(iii) Catecholamines and serotonin 141
. . . . . . . . . . . . . . . . . . . . . . .
(iv) Other arnines 141
. . . . . . . . . . . . . . . . .
7.3.3. Convenience and efficiency 142
. . . . . . . . . . . . . . . . . . . . . . .
7.3.4. Other factors 143
. . . . . . . . . . . . . . .
7.4. Summary and promising developments 143
. . . . . . . . . . . . . . . . . . . . . . . .
Acknowledgements 145
. . . . . . . . . . . . . . . . . . . . . . . . . . .
References 146
Chapter 8 . Gas chromatography-mass spectrometry and selected ion
monitoring of biogenic amines and related metabolites
. . . . . . . . . . . . . . . . . . . . . . . .
(Emilio Gelpi) 151
. . . . . . . . . . . . . . . . . . . . . . . . . .
8.1. Introduction 151
. . . . . . . . . . . . . . . . . . .
8.1.1. Historical perspective 151
. . . .
8.1.2. Conventional GC-MS and selected ion monitoring (SIM) 155
IX
.
8.1.3. Metabolic profiling assays vs single component
. . . . . . . . . . . . . . . . . . . . . . .
determinations 157
. . . . . . . . . . . . . . . . . . . . .
8.2. Experimental approaches 158
. . . . . . . . . . . . .
8.2.1. Sample preparation for GC-MS work 158
. . . . . . . . . . . . . . . . . . . . .
(i) Sample collection 159
. . . . . . . . . . . . . . .
(ii) Homogenization and extraction 160
. . . . . . . . . . . . . . . . .
(iii) Hydrolysis of conjugates 160
. . . . . . . . . . . . . . . . . .
8.2.2. Specific derivatizations 161
. . . .
8.2.3. Some practical considerations and neglected aspects 163
(i) The stability of compounds during storage prior to
. . . . . . . . . . . . . . . . . . . . . . . . . .
analysis 163
(ii) The catalytic effects of residual impurities in the
. . . . . . . . . . . . . . . . .
solvents or reagents used 164
(iii) Contamination of enzymes used in the hydrolysis of
conjugates of biogenic amines and incomplete
. . . . . . . . . . . . . . . . . . . . . . . .
hydrolysis 164
. . . . . . . . . . .
(iv) Variability of extraction efficiency 164
(v) Carrier effects in the extraction. derivatization and
. . . . . . . . . . . . . . . . . . . . .
clean-up processes 164
(vi) Derivative reproducibility and stability . . . . . . . . . 165
. . . . . . . . . . . . . . . . .
(vii) Other important effects 166
. . . . . . . . . . . . . . . .
8.2.4. Specificity and sensitivity 166
. . . . . . . . . . . . . . . . . . . . .
8.2.5. General equipment 167
. . . . . . . . . . . . . . . . . . . . . . .
8.3. Special techniques 168
. . . . . . . . . . . . . . . . . . . . . .
8.3.1. Capillary GC-MS 168
. . . . . . . . . . . . . . . . .
8.3.2. New ionization techniques 170
(i) Positive chemical ionization . . . . . . . . . . . . . . . . 170
. . . . . . . . . . . . . . .
(ii) Negative chemical ionization 172
. . . . . . . . . . . . . . . . .
8.3.3. GC-High resolution MS/SIM 172
. . . . . . . . . . . . . . . . . . . . . .
8.4. Selected applications 173
. . . . . . . . . . . . . . . . . . . . . . . .
8.4.1. Trace amines 173
. . . . . . . . . . . . . . . . . .
8.4.2. Polyamines and histamine 175
8.4.3. Studies of metabolic pathways with stable isotope
. . . . . . . . . . . . . . . . . . . . . . . . . .
tracers 176
. . . . . . . . . . . .
8.5. Comparison with other analytical procedures 176
. . . . . . . . . . . . . . . . . . . . . . . . . . . . .
8.6. Summary 178
. . . . . . . . . . . . . . . . . . . . . . . . . . .
References 179
.
Chapter 9 Analysis of biogenic amines using radioenzymatic procedures
. . . . . . . . . . . . . . . . . . . . . . . .
(Ian L Martin) 183
. . . . . . . . . . . . . . . . . . . . . . . . . .
9.1. Introduction 183