Clinical chemistry of serotonin and metabolites.

Analyses of serotonin and other 5-hydroxyindoles, such as its precursor 5-hydroxytryptophan and major metabolite 5-hydroxyindoleacetic acid (5-HIAA), are indispensable for the elucidation of their (patho)physiological roles. In clinical chemistry attention is mainly focused on the diagnosis and follow-up of carcinoid tumours. For this most laboratories routinely measure urinary 5-HIAA. More recently, measurements of serotonin in platelets and urine have been advocated. Platelet serotonin may be the most sensitive indole marker for the detection of carcinoid tumours that secrete only small amounts of serotonin and/or its precursor 5-hydroxytryptophan. Although several chromatographic techniques have emerged for the analysis of tryptophan-related indoles, HPLC with either electrochemical or fluorometric detection have become the methods of choice for their quantification. HPLC-based methods combine selectivity, sensitivity and high precision, and enable the simultaneous investigation of several metabolically related indoles. This review aims to place the analysis of indoles in biological matrices in a biochemical, physiological and clinical perspective and highlights several important steps in their chromatographic analysis and quantification.

[1]  Grahame-Smith Dg Serotonin (5-hydroxytryptamine, 5-HT). , 1988 .

[2]  V. E. Davis,et al.  Free and conjugated serotonin excretion in carcinoid syndrome. , 1965, The Journal of laboratory and clinical medicine.

[3]  H. Nohta,et al.  Fluorescence derivatizing procedure for 5-hydroxytryptamine and 5-hydroxyindoleacetic acid using 1,2-diphenylethylenediamine reagent and their sensitive liquid chromatographic determination. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[4]  E. Wilander,et al.  Malignant Carcinoid Tumors An Analysis of 103 Patients with Regard to Tumor Localization, Hormone Production, and Survival , 1987, Annals of surgery.

[5]  J. Glowinski,et al.  Regulation of serotonin synthesis. , 1974, Life sciences.

[6]  Y. Mori,et al.  Revised method for the quantitative determination of 5-hydroxytryptamine in human plasma by gas chromatography--mass spectrometry--selected ion monitoring. , 1984, Journal of chromatography.

[7]  G. Anderson,et al.  Signal-to-noise optimization of HPLC-fluorometric systems and their application to the analysis of indoles. , 1991, Advances in experimental medicine and biology.

[8]  H. Weissbach,et al.  Purification and properties of hydroxyindole-O-methyl transferase. , 1961, The Journal of biological chemistry.

[9]  B. Karger,et al.  Analysis for indole compounds in urine by high-performance liquid chromatography with fluorometric detection. , 1976, Clinical chemistry.

[10]  E. D. de Vries,et al.  Improved diagnosis of carcinoid tumors by measurement of platelet serotonin. , 1992, Clinical chemistry.

[11]  L. Siever,et al.  Critical issues in defining the role of serotonin in psychiatric disorders. , 1991, Pharmacological reviews.

[12]  F. Engbaek,et al.  Radioimmunoassay of serotonin (5-hydroxytryptamine) in cerebrospinal fluid, plasma, and serum. , 1982, Clinical chemistry.

[13]  A. Sjoerdsma,et al.  A unique syndrome associated with secretion of 5-hydroxytryptophan by metastatic gastric carcinoids. , 1962, The American journal of medicine.

[14]  I. Hindberg An improved specific and sensitive radioenzymatic method for determination of serotonin concentrations in biological fluids (radioenzymatic serotonin method). , 1984, Scandinavian journal of clinical and laboratory investigation.

[15]  J. Martineau,et al.  Determination of urinary serotonin using liquid chromatography with electrochemical detection. , 1986, Journal of chromatography.

[16]  X. Páez,et al.  Plasma serotonin monitoring by blood microdialysis coupled to high-performance liquid chromatography with electrochemical detection in humans. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[17]  J. Feldman Increased dopamine production in patients with carcinoid tumors. , 1985, Metabolism: clinical and experimental.

[18]  I. Page,et al.  New metabolites of serotonin in carcinoid urine. , 1958, Science.

[19]  D. Olichon,et al.  Determination of serotonin in plasma by liquid chromatography with electrochemical detection. , 1985, Journal of chromatography.

[20]  J. Chin Determination of six indolic compounds, including melatonin, in rat pineal using high-performance liquid chromatography with serial fluorimetric-electrochemical detection. , 1990, Journal of chromatography.

[21]  V. Erspamer,et al.  Identification of Enteramine, the Specific Hormone of the Enterochromaffin Cell System, as 5-Hydroxytryptamine , 1952, Nature.

[22]  S. Pang,et al.  Analysis of 5-methoxytryptamine at the femtomole level in the rat and quail brain by gas chromatography-electron-capture negative-ion chemical ionization mass spectrometry. , 1996, Journal of chromatography. B, Biomedical applications.

[23]  P. Kissinger,et al.  I. Minireview: Neurochemical applications of liquid chromatography with electrochemical detection , 1981 .

[24]  H. Tsai,et al.  Capillary electrophoresis of monoamines and catechol with indirect chemiluminescence detection , 1999, Electrophoresis.

[25]  M. Rodríguez,et al.  Determination of monoamines and indoles in amniotic fluid by high-performance liquid chromatography-electrochemical detection. , 1990, Journal of chromatography.

[26]  P. Kissinger,et al.  Determination of serotonin in serum and plasma by liquid chromatography with precolumn sample enrichment and electrochemical detection. , 1980, Analytical chemistry.

[27]  M. Weg,et al.  A specific assay for urinary 5-hydroxyindole-3-acetic acid by gas chromatography. , 1975, Clinica chimica acta; international journal of clinical chemistry.

[28]  D. Tonelli,et al.  Thin-layer chromatographic determination of indolic tryptophan metabolites in human urine using Sep-Pak C18 extraction. , 1982, Journal of chromatography.

[29]  J. Weller,et al.  Indole Metabolism in the Pineal Gland: A Circadian Rhythm in N-Acetyltransferase , 1970, Science.

[30]  M. Rapport,et al.  Serum vasoconstrictor, serotonin; isolation and characterization. , 1948, The Journal of biological chemistry.

[31]  E. Korpi Serotonin determined in whole blood by liquid chromatography with electrochemical detection. , 1984, Clinical chemistry.

[32]  Y. Sagara,et al.  Determination of plasma 5-hydroxytryptophan, 5-hydroxytryptamine, 5-hydroxyindoleacetic acid, tryptophan and melatonin by high-performance liquid chromatography with electrochemical detection. , 1988, Journal of chromatography.

[33]  A. Pletscher Metabolism, transfer and storage of 5-hydroxytryptamine in blood platelets. , 1968, British journal of pharmacology and chemotherapy.

[34]  Y. Michotte,et al.  New antioxidant mixture for long term stability of serotonin, dopamine and their metabolites in automated microbore liquid chromatography with dual electrochemical detection. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

[35]  J. Chauveau,et al.  Rapid and specific enzyme immunoassay of serotonin. , 1991, Clinical chemistry.

[36]  J. Naschitz,et al.  Crohn's disease associated with pellagra and increased excretion of 5-hydroxyindolacetic acid. , 1997, The American journal of the medical sciences.

[37]  D. Cohen,et al.  Steady-state model for plasma free and platelet serotonin in man. , 1987, Life sciences.

[38]  V. E. Davis,et al.  The alteration of serotonin metabolism to 5-hydroxytryptophol by ethanol ingestion in man. , 1967, The Journal of laboratory and clinical medicine.

[39]  T. Masujima,et al.  Enrichment and high-performance liquid chromatography analysis of tryptophan metabolites in plasma. , 1981, Analytical biochemistry.

[40]  R. Williams,et al.  Williams Textbook of endocrinology , 1985 .

[41]  E. Yeung,et al.  Capillary electrophoretic study of individual exocytotic events in single mast cells. , 1998, Journal of chromatography. A.

[42]  T. J. Panholzer,et al.  Coupled-column liquid chromatographic analysis of catecholamines, serotonin, and metabolites in human urine. , 1999, Clinical chemistry.

[43]  R. Wurtman,et al.  The pharmacology of the pineal gland. , 1976, Annual review of pharmacology and toxicology.

[44]  L. Cubeddu,et al.  Use of intravenous microdialysis to monitor changes in serotonin release and metabolism induced by cisplatin in cancer patients: comparative effects of granisetron and ondansetron. , 1999, The Journal of pharmacology and experimental therapeutics.

[45]  P. Vanhoutte Serotonin and the cardiovascular system , 1985 .

[46]  B. Renaud,et al.  Determination of reference values for serotonin concentration in platelets of healthy newborns, children, adults, and elderly subjects by HPLC with electrochemical detection. , 1990, Clinical chemistry.

[47]  D. Cohen,et al.  Determination of serotonin in whole blood, platelet-rich plasma, platelet-poor plasma and plasma ultrafiltrate. , 1987, Life sciences.

[48]  Mühlbauer Hd Human aggression and the role of central serotonin. , 1985 .

[49]  N. Mulder,et al.  Effects of peripheral stem-cell or bone-marrow reinfusion on peripheral serotonin metabolism , 1999, The Lancet.

[50]  M. Airaksinen,et al.  Excretion of histamine and metabolites of 5-hydroxytryptamine in a case of metastasized carcinoid tumour. , 2009, Acta medica Scandinavica.

[51]  Y. Yi,et al.  Simultaneous determination of tryptophan, 5-hydroxytryptophan, 5-hydroxytryptamine, 5-hydroxyindoleacetic acid, 4-hydroxy-3-methoxyphenylacetic acid and 3-methoxy-4-hydroxyphenylglycol in human cerebrospinal fluid. , 1994, Journal of chromatography. B, Biomedical applications.

[52]  N. Crawford Serotonin absorption by normal and "carcinoid" platelets. , 1967, Clinica chimica acta; international journal of clinical chemistry.

[53]  F. Artigas,et al.  Evaluation of the potential of thermospray liquid chromatography-mass spectrometry in neurochemistry. , 1987, Journal of chromatography.

[54]  E. Kwarts,et al.  A Simple Paired-Ion Liquid Chromatography Assay for Serotonin in Cerebrospinal Fluid, Platelet-Rich Plasma, Serum and Urine , 1984, Annals of clinical biochemistry.

[55]  P. Hjemdahl,et al.  On the accurate measurement of serotonin in whole blood. , 1998, Scandinavian journal of clinical and laboratory investigation.

[56]  S. Peroutka 5‐Hydroxytryptamine Receptors , 1993, Journal of neurochemistry.

[57]  J. Feldman Urinary serotonin in the diagnosis of carcinoid tumors. , 1986, Clinical chemistry.

[58]  A. V. van Kuilenburg,et al.  High-performance liquid chromatographic analysis of biogenic amines in cells and in culture media using on-line dialysis and trace enrichment. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[59]  A. Nobin,et al.  Increased levels of plasma 5-hydroxytryptamine in patients with coeliac disease. , 1985, Scandinavian journal of gastroenterology.

[60]  D. Cohen,et al.  Serotonin in human lumbar cerebrospinal fluid: a reassessment. , 1990, Life sciences.

[61]  J. Oates The carcinoid syndrome. , 1986, The New England journal of medicine.

[62]  A. Pearse The APUD concept and hormone production. , 1980, Clinics in endocrinology and metabolism.

[63]  T. O'Dorisio,et al.  Role of neuropeptides and serotonin in the diagnosis of carcinoid tumors. , 1986, The American journal of medicine.

[64]  H. Yoshida,et al.  Determination of tryptophan and its metabolites in human plasma and serum by high-performance liquid chromatography with automated sample clean-up system. , 1990, Journal of chromatography.

[65]  F. Michal,et al.  Relative activities on and uptake by human blood platelets of 5‐hydroxytryptamine and several analogues , 1972, British journal of pharmacology.

[66]  Stig Allenmark Evaluation of analytical methods in biological systems. Part A: Analysis of biogenic amines , 1983 .

[67]  A. Deacon,et al.  The Measurement of 5-Hydroxyindoleacetic Acid in Urine , 1994, Annals of clinical biochemistry.

[68]  G. Anderson,et al.  Applications of liquid chromatographic-fluorometric systems in neurochemistry. , 1981, Life sciences.

[69]  O. Naesh,et al.  Serotonin concentrations in plasma and variations during the menstrual cycle. , 1992, Clinical chemistry.

[70]  A. Moir Interaction in the cerebral metabolism of the biogenic amines: Effect of intravenous infusion of l‐tryptophan on the metabolism of dopamine and 5‐hydroxyindoles in brain and cerebrospinal fluid , 1971, British journal of pharmacology.

[71]  E. D. de Vries,et al.  Serotonin, catecholamines, histamine, and their metabolites in urine, platelets, and tumor tissue of patients with carcinoid tumors. , 1994, Clinical chemistry.

[72]  G. Bertaccini,et al.  URINARY EXCRETION OF 5-HYDROXYINDOLE-ACETIC ACID AFTER REMOVAL OF THE LARGE INTESTINE IN MAN , 1960 .

[73]  J. Vane,et al.  5-Hydroxytryptamine in the Circulation of the Dog , 1967, Nature.

[74]  S. Pavel,et al.  Chromatography of urinary indole derivatives. , 1988 .

[75]  A. Sjoerdsma,et al.  SEROTONIN IN PLATELETS: ITS UPTAKE AND DISAPPEARANCE AFTER ADMINISTRATION OF THE AMINE BY MOUTH. , 1963, Lancet.

[76]  P. Jaynes,et al.  Determination of urinary 5-hydroxyindole-3-acetic acid using solid-phase extraction and reversed-phase high-performance liquid chromatography with electrochemical detection. , 1985, Journal of chromatography.

[77]  T. Harumi,et al.  Simultaneous determination of serotonin, N-acetylserotonin and melatonin in the pineal gland of the juvenile golden hamster by high-performance liquid chromatography with electrochemical detection. , 1996, Journal of chromatography. B, Biomedical applications.

[78]  I. Kopin,et al.  Catecholamine metabolism: basic aspects and clinical significance. , 1985, Pharmacological reviews.

[79]  J. Alvarez,et al.  Simultaneous measurement of dopamine, serotonin, their metabolites and tryptophan in mouse brain homogenates by high-performance liquid chromatography with dual coulometric detection. , 1999, Biomedical chromatography : BMC.

[80]  E. Endert,et al.  Improved method for the determination of serotonin in plasma by high-performance liquid chromatography using on-line sample pre-treatment. , 1991, Journal of chromatography.

[81]  I. Kema,et al.  Influence of a serotonin- and dopamine-rich diet on platelet serotonin content and urinary excretion of biogenic amines and their metabolites. , 1992, Clinical chemistry.

[82]  R. Mailman,et al.  Analytical considerations for quantitative determination of serotonin and its metabolically related products in biological matrices. , 1985, Clinical chemistry.

[83]  M. S. Lee,et al.  Determination of plasma serotonin and 5-hydroxyindoleacetic acid in healthy subjects and cancer patients. , 2000, Clinical chemistry.

[84]  S. S. Brown,et al.  Chemical Diagnosis of Disease , 1979 .

[85]  L. Price,et al.  Serotonin transporter-blocking properties of nefazodone assessed by measurement of platelet serotonin. , 1998, Journal of clinical psychopharmacology.

[86]  E. Mertz,et al.  Effect of a Tryptophan Deficient Diet on Brain Serotonin and Plasma Tryptophan Level.∗ , 1963, Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine.

[87]  S. Hourani,et al.  Pharmacological receptors on blood platelets. , 1991, Pharmacological reviews.

[88]  E. D. de Vries,et al.  High performance liquid chromatographic profiling of tryptophan and related indoles in body fluids and tissues of carcinoid patients. , 1993, Clinica chimica acta; international journal of clinical chemistry.

[89]  G. Dekker,et al.  Platelet-poor plasma serotonin in normal and preeclamptic pregnancy. , 1993, Clinical chemistry.

[90]  W. C. Purdy Quantitative analysis of catecholamines and related compounds : A. M. Krstulovic (Ed.), Ellis Horwood, Chichester, 1986 (ISBN 0-85312-824-3). 384 pp. Price £47.50. , 1987 .

[91]  S. Parvez,et al.  Simple purification of aromatic L-amino acid decarboxylase from human pheochromocytoma using high-performance liquid chromatography. , 1985, Analytical biochemistry.

[92]  C. Palmerini,et al.  Determination of plasma serotonin by high-performance liquid chromatography with pre-column sample enrichment and fluorimetric detection. , 1987, Journal of chromatography.

[93]  P. Maton The carcinoid syndrome. , 1988, JAMA.

[94]  I. Sakuma,et al.  Simultaneous determination of catecholamines, their basic metabolites and serotonin in urine by high-performance liquid chromatography using a mixed-mode column and an eight-channel electrochemical detector. , 1995, Biomedical chromatography : BMC.

[95]  P. Winocour,et al.  Platelet and Plasma Vasoactive Amines in Type 1 (Insulin-Dependent) Diabetes Mellitus with and without Vascular Disease , 1990, Annals of clinical biochemistry.

[96]  B. Claustrat,et al.  Platelet serotonin content and free and total plasma tryptophan in healthy volunteers during 24 hours. , 1993, Clinical chemistry.

[97]  J. Lennard-jones,et al.  Humoral effects of metastasising carcinoid tumours. , 1955, Lancet.

[98]  R. Deitrich,et al.  Brain aldehyde dehydrogenase. Localization, purification, and properties. , 1966, The Journal of biological chemistry.

[99]  T. Kuurne,et al.  Indole levels in human lumbar and ventricular cerebrospinal fluid and the effect of L‐tryptophan administration , 1985, Acta neurologica Scandinavica.

[100]  M. H. Aprison,et al.  Fluorometric assay for 5-hydroxytryptophan with sensitivity in the picomole range. , 1975, Analytical chemistry.

[101]  S. Borg,et al.  Determination of urinary 5-hydroxytryptophol by high-performance liquid chromatography with electrochemical detection. , 1992, Journal of chromatography.

[102]  M. Sandler,et al.  THE CLASSIFICATION OF CARCINOID TUMOURS , 1963 .

[103]  V. Devita,et al.  Cancer : Principles and Practice of Oncology , 1982 .

[104]  B. Brodie,et al.  Identification and assay of serotonin in brain. , 1956, The Journal of pharmacology and experimental therapeutics.

[105]  M. Farthing 5-Hydroxytryptamine and 5-hydroxytryptamine-3 receptor antagonists. , 1991, Scandinavian journal of gastroenterology. Supplement.

[106]  S. Steindel,et al.  Liquid-chromatographic separation of urinary 5-hydroxy-3-indoleacetic acid, with measurement at 254 nm. , 1980, Clinical chemistry.

[107]  M. H. Mills,et al.  Determination of melatonin and monoamines in rat pineal using reversed-phase ion-interaction chromatography with fluorescence detection. , 1991, Journal of chromatography.

[108]  G. M. Halliday,et al.  Loss of brainstem serotonin- and substance P-containing neurons in Parkinson's disease , 1990, Brain Research.

[109]  G. Seghieri,et al.  Simultaneous liquid-chromatographic determination of urinary vanillylmandelic acid, homovanillic acid, and 5-hydroxyindoleacetic acid. , 1988, Clinical chemistry.

[110]  A. Cleare,et al.  A Case of Coeliac Disease Detected via Raised 5-Hydroxytryptamine and 5-Hydroxyindoleacetic Acid , 1997, Annals of clinical biochemistry.

[111]  J. Shear,et al.  Measurements of serotonin and related indoles using capillary electrophoresis with multiphoton-induced hyperluminescence. , 1998, Analytical biochemistry.