Liquid chromatography in biomedical analysis

309 Pages·1991·13.091 MB·English

by  Toshihiko Hanai

JOURNAL OF CHROMATOGRAPHY LIBRARY- volume 50
liquid chromatography in biomedical analysis
This Page Intentionally Left Blank
JOURNAL OF CHROMATOGRAPHY LIBRARY- volume 50
liquid chromatography
i8n mI =om ecnI =c ai 1
analysis
edited b y
T. Hanai
International Institute of Technological Analysis, Health Research Foundation,
Hyakumanben, Kyoto 606, Japan

ELSEVIER
- - -
Amsterdam Oxford New York Tokyo 1991
ELSEVIER SCIENCE PUBLISHERS B.V.
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Distributors for the United States and Canada:
ELSEVIER SCIENCE PUBLISHING COMPANY INC.
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Llbrary of Congress Cataloging-in-Publication Data
Liquid chromatography in biomedical analysis / edited by T. Hanai.
--
p. cm. (Journal of chromatography library ; v. 50)
Includes bibliographical references and index.
ISBN 0-444-87451-8
1. High performance liquid chromatography. 2. Biomolecules-
-Analysis. I. Hanai, Toshihiko. 11. Series.
[DNLM: 1. Chromatography, Liquid. W1 J05846 v. 50 / OD 79.C454
L76481
OP519.9.H53157 1991
543'.0894--dC20
DNLH/DLC
for Library of Congress 91 -6505
ISBN 0-444-8745 1-8
0 Elsevier Science Publishers B.V.. 1991
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V
CONTENTS
. . . . . . . . . . . . . . . . . . . . . . . . . . . .
List of Contributors I X
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Preface XI
Chapter 1: Liquid chromatography in biomedical analysis: basic approach
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(C.K. Lim) 1
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
1 Introduction 1
. . . . . . . . . . . . . . . . . . . . .
2 Sample collection or sampling 1
. . . . . . . . . . . . . . . . . . . . . . . . . . .
3 Sample preparation 3
4 . High-performance liquid chromatography . . . . . . . . . . . . . . . . 12
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 19
Chapter 2: Optimization of liquid chromatography for biomedically important
. . . . . . . . . . . . . . . . . . . . . . . . . . .
compounds (T Hanai) 21
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
1 Introduction 21
. .
2 Relationships between retention and hydrophobicity of aromatic acids 22
. . . . . . . . .
3 Liquid chromatography of nitrogen-containing compounds 28
4 . Chromatographic behaviour of aromatic acids on ion-exchangers . . . . 29

. . . . . . . . . . . . . . .
5 Liquid chromatography of biological fluids 31
6 . Advanced optimization techniques in liquid chromatography . . . . . . 39
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
7 Conclusion 46
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 46
. . . . . . . . . . . . . . . . . . . . . .
Chapter 3: Amino acids [Y Ishida) 47
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
1 Introduction 47
. . . . . . . . . . . . . . .
2 Post-column derivatization using ninhydrin 47
. . . . . . . . . . . . . . . . . .
3 Post-column derivatization using OPA 52
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
4 Reactor 62
. . . . . . . . . . . . . . . . . . . . . . .
5 Pre-column derivatization 63
. . . . . . . . . . . . . . . . . . . . . . . . . . . . .
6 Related topics 73
7 . Clinical applications . . . . . . . . . . . . . . . . . . . . . . . . 75
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 79
VI
. . . . . . . . . . . . . . . . .
Chapter 4: Bile acids (J Goto and T Nairbara) 81
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
1 Introduction 81
. . . . . . . . . . . . .
2 Extraction of bile acids in biological fluids 82
. . . . . . . . . . . . . . . . . . . . . . . .
3 Separation of bile acids 87
. . . . . . . . . . . . . . . . . . . . . .
4 Determination of bile acids 98
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 107
. . . . . . . . . . . . . . . . . . . . .
Chapter 5: Carbohydrates (S Honda) 109
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
1 Introduction 109
. . . . . . . .
2 Principle of the liquid chromatography of carbohydrates 110
. . . . . . . . . . . . . . . .
3 Liquid chromatography of monosaccharides 115
. . . . . . . . . . . . . . . .
4 Liquid chromatography of oligosaccharides 128
. . . . . .
5 Liquid chromatography in structural studies of carbohydrates 131
.
6 Liquid chromatographic assay of the activities of enzymes related to
. . . . . . . . . . . . . . . . . . . . . . . . . . . .
carbohydrates 135
. . .
7 Automated analysis of carbohydrates and its clinical applications 136
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 138
. . . . . . . . . . . . . . . . . . . . .
Chapter 6: Catecholamines (K Mori) 141
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
1 Introduction 141
. . . . . . . . . . . . . . . .
2 Post-column fluorescence derivatization 142
. . . . . . . . . . . . . . . . .
3 Pre-column fluorescence deri vatization 160
. . . . . . . . . . . . .
4 Amperometric electrochemical detector for HPLC 163
. . . . . . . . . . . . . . . . . . . . . . . . . .
5 Coulometric detector 163
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
6 Conclusion 165
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 165
. . . . . . . . . . . . . . . . . . . . . .
Chapter 7: Fatty acids (T Hirai) 169
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
1 Introduction 169
. .
2 Pretreatment of fatty acids in biological samples for HPLC analysis 172
.
3 Separation and determination of fatty acids by HPLC using refractive
. . . . . . . . . . . . . . . . . . . . . . . . . . .
index detection 173
.
4 Separation and determination of fatty acids by HPLC using UV detection 174
.
5 Various fluorescence-labelling techniques for the determination of
. . . . . . . . . . . . . . . . . . . . . . . . .
fatty acids by HPLC 179
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 188
VI I
. . . . . . . . . . . . . . . . . . . . .
Chapter 3: Nucleotides (C.K. Lim) 191
. . . . . . . . . . . . . . . . . . . . . . . . . . . . .
1 Introduction 191
. . . . . . . . . . . . . . . .
2 High-performance liquid chromatography 191
. . . . . . . . . . .
3 Extraction of nucleotides from cells and tissues 202
. . . . . . . . . . . . . . . . . . . .
4 HPLC detectors for nucleotides 205
. . . . . . . . . . . . . . . . . . . . .
5 Quantification of nucleotides 206
. . . . . . . . . . . . . . . . . . . . . . . . . .
6 Peak identification 206
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 207
. . . . . . . . . . . . . . . . . . . . .
Chapter 9: Porphyrins (C.K. Lim) 209
. . . . . . . . . . . . . . . . . . . . . . . . . . . . .
1 Introduction 209
. . . . . . . . .
2 High-performance liquid chromatography of porphyrins 210
. . . . . . .
3 High-performance liquid chromatography of porphyrinogens 219
. . . . . . . . . . .
4 HPLC detectors for porphyrins and porphyrinogens 222
. . . . . . . . . . . . . . . . . . .
5 HPLC quantification of porphyrins 222
. . . . . . . . . . . . . . .
6 Sample preparation for HPLC of porphyrins 222
. . . . . . . . . . . . . . . . . . . . . . . .
7 Biomedical applications 225
. . . . . . .
8 Assay of enzymes of the haem biosynthetic pathway by HPLC 228
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 230
Chapter 10: Prostaglandins (T. Hirai) . . . . . . . . . . . . . . . . . . .23 3
. . . . . . . . . . . . . . . . . . . . . . . . . . . . .
1 Introduction 233
.
2 Direct UV detection in the s eparation and determination of PGs. TXB2
. . . . . . . . . . . . . . . . . . . . . . . . . . .
and LTs by HPLC 237
.
3 UV-labelling techniques for the determination of PGs and their
. . . . . . . . . . . . . . . . . . . . . . . . .
metabolites by HPLC 241
.
4 Fluorescent-labelling techniques for the determination of PGs and
. . . . . . . . . . . . . . . . . . . . . . . . . . . .
TXB2 by HPLC 242
.
5 Simultaneous separation of several closely related prostanoids by
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
HPLC 243
.
6 Application of HPLC and GC-MS to the determination of prostanoids in
. . . . . . . . . . . . . . . . . . . . . . . . .
biological samples 247
.
7 Application of HPLC and RIA to the determination of prostanoids in
. . . . . . . . . . . . . . . . . . . . . . . . .
biological samples 250
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 252
Vlll
. . . . . . . . . . . . . . . . . . .
Chapter 11: Steroid hormones (T Hirai) 255
. . . . . . . . . . . . . . . . . . . . . . . . . . . .
1.Introduction 255
. 5
2 Simultaneous determination of pregnenolone (A -pathway) and
4 . . . . . . . . . . . .
progesterone (A -pathway) metabolites by HPLC 259
. . . . . . . . . . . . . . . . . .
3 HPLC determination of C19 steroids 263
. . . . . . . . . . . . . . . . .
4 HPLC determination of corticosteroids 267
. . . . . . . .
5 Determination of estrogens in biological fluids by HPLC 272
.
6 Application of HPLC and RIA to the determination of steroid hormones
. . . . . . . . . . . . . . . . . . . . . . . .
in biological samples 275
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 279
. . . . . . . . . . . . . . . . . . . .
Chapter 12: Miscellaneous (T Hanai) 283
. . . . . . . . . . . . . . . . . . . . . . . . . . . . .
1 Introduction 283
. . . . . . . . . . . . . . . . . . . . . . .
2 Catecholamine metabolites 283
. . . . . . . . . . . . . . . . . . . . . . . . . . .
3 Indoleacetic acid 285
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References 286
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Subject Index 289
. . . . . .
Journal of Chromatography Library (other volumes in the series) 293
IX
LIST OF CONTRIBUTORS
Dr. J. Goto Dr. Y. Ishida
Pharmaceutical Institute Analytical Instruments Division
Tohoku University Shimadzu Corporation
Aobayama 1 Nishinokyo-kuwabaracho
Sendai 980 Nakagyo- ku
Japan Kyoto 604
Japan
Dr. T. iianai
Internatiorial Institute of Dr. C.K. Lim
Techrloloqi cal Aria1 vsi s Division of Clinical Cell Biology
tlml th Research Foundation Clinical Research Centre
Instiiut 2asieur de Kvoto 5F Watford Road
Hyakumariben Harrow
i<votO 606 Middlesex HA1 3UJ
Janan U.K.
Jr. T. Hirai Dr. K. Mori
Analytical Research & Services The Institute for Science of Labour
Chci;iical 5 Formulation Laboratories 2-8-14 Sugao
L2derlc (Japan) Ltd. Miyamae-ku
1-G-34 Kashiwacho Kawasaki 213
Shi ki-shi Japan
Sai taiila 353
Japan Professor T. Nambara
Pha rmaceuti cal Inst it ute
Professor S. Honda Tohoku University
Faculty of Pharmaceutical Sciences Aobayama
Kinki University Sendai 980
3-4- 1 Kowakae Japan
Higashi-Osaka 577
Japan