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PubMed1987

Simultaneous liquid chromatographic determination of seventeen of the major monoamine neurotransmitters, precursors and metabolites. I. Optimization of the mobile phase using factorial designs and a computer program to predict chromatograms.

Utilizing reversed-phase high-performance liquid chromatography (HPLC) with electrochemical detection and optimization of the mobile phase using factorial designs and a constructed computer program to predict chromatograms, it has been possible to obtain a satisfactory resolution of seventeen of the major monoamine neurotransmitters, precursors and metabolites. A rapid (less than 25 min) isocratic system for the simultaneous determination of 3,4-dihydroxyphenylalanine, dopamine, dihydroxyphenylacetic acid, 3-methoxytyramine, homovanillic acid, norepinephrine, normetanephrine, 3,4-dihydroxyphenylethylene glycol, 3-methoxy-4-hydroxyphenylethylene glycol, epinephrine, metanephrine, vanillylmandelic acid, 5-hydroxytryptophan, serotonin, 5-hydroxytryptophol and 5-hydroxyindoleacetic acid in addition to the internal standard isoproterenol is presented. The optimization strategy included selection of variables to optimize by a reduced factorial design a detailed study of these variables by a complete factorial design, theoretical predictions of chromatograms by a constructed computer program and test on the HPLC system. This optimization strategy can easily be applied to any problem of solute separation by liquid chromatography.

Chromatography, High Pressure Liquid↗
PubMed1997

3,4-Dimethoxybenzylamine as a sensitive pre-column fluorescence derivatization reagent for the determination of serotonin in human platelet-poor plasma.

3,4-Dimethoxybenzylamine is shown to be a highly sensitive pre-column fluorescence derivatization reagent for the determination of serotonin in plasma by high-performance liquid chromatography. The reagent reacts selectively with 5-hydroxyindoles including serotonin in slightly alkaline media in the presence of potassium hexacyanoferrate(III) to give highly fluorescent derivatives. The derivatives of six standard 5-hydroxyindoles (5-hydroxytryptophan, 5-hydroxyindole-3-acetic acid, serotonin, 5-hydroxyindole-3-acetamide, N-acetyl-5-hydroxytryptamine and 5-hydroxytryptophol) are separated within 18 min by isocratic elution using acetonitrile-10 mM phosphate buffer (pH 6.0)-50 mM 1-hexanesulfonic acid on a Wakosil II 5C18RS reversed-phase column. The detection limits (signal-to-noise ratio=3) for the indoles were 1.0-5.7 fmol in a 100-microl injection volume. The method was applied to the measurement of serotonin in human platelet-poor plasma.

Benzylamines↗
PubMed1998

Determination of biological markers for alcohol abuse.

Alcoholism is one of the most frequent addictions and an important subject in forensic medicine and clinical toxicology. Several laboratory abnormalities are associated with excessive alcohol consumption. They are useful in the diagnosis of alcoholism especially during the follow-up of various treatment programs. The biological markers mostly used for diagnosis of alcoholism are presented. Especially, methods for the determination of the following diagnostic tools are reviewed: congener alcohols, gamma-glutamyltransferase, aspartate and alanine aminotransferase, beta-hexosaminidase, erythrocyte aldehyde dehydrogenase, alpha-amino-n-butyric acid to leucine ratio, macrocytosis, carbohydrate-deficient transferrin, (apo)lipoproteins, fatty acid ethyl esters, blood acetate, acetaldehyde adducts, 5-hydroxytryptophol, dolichol and condensation products. No laboratory test exists that is reliable enough for the exact diagnosis of alcoholism. The combination of physician interview, questionnaire and laboratory markers is necessary for the diagnosis of alcoholism.

Alcoholism↗
PubMed2000

4-Dimethylaminobenzylamine as a sensitive chemiluminescence derivatization reagent for 5-hydroxyindoles and its application to their quantification in human platelet-poor plasma.

A selective and sensitive high-performance liquid chromatographic method with chemiluminescence detection for the determination of 5-hydroxyindoles is described, based on the reaction of 5-hydroxyindoles with 4-dimethylaminobenzylamine. Serotonin, 5-hydroxyindole-3-acetic acid, 5-hydroxytryptophol, 5-hydroxyindole-3-acetamide and N-acetyl-5-hydroxytryptamine were used as model compounds to optimize the derivatization and chemiluminescent reaction. The reagent reacts with 5-hydroxyindoles in slightly alkaline media in the presence of potassium hexacyanoferrate(III) to give the corresponding derivatives, which can be separated on a reversed-phase column, Wakosil-II 5C18RS, with aqueous acetonitrile as an eluent. The derivatives were detected by peroxyoxalate chemiluminescence detection. The detection limits are in the range of 0.5-1.2 fmol per 100-microl injection. The method was applied to the simultaneous determination of serotonin and 5-hydroxyindole-3-acetic acid in human platelet-poor plasma.

Aniline Compounds↗
PubMed2000

Are there possibilities for the detection of chronically elevated alcohol consumption by hair analysis? A report about the state of investigation.

The analysis of suitable ethanol markers in hair would be an advantageous tool for chronic alcohol abuse control because of the wide diagnostic window allowed by this specimen and the possibility of segmental investigation. Between the markers practically used or thoroughly investigated in blood or urine, ethylglucuronide, fatty acid ethylesters, phosphatidylethanol, acetaldehyde adducts to protein and 5-hydroxytryptophol can be regarded as possible candidates also in hair, but preliminary data were found in the literature only for ethylglucuronide and acetaldehyde modified proteins. By using headspace gas chromatography and headspace solid phase microextraction in combination with gas chromatography-mass spectrometry (SPME-GC/MS), in alkaline hydrolysates of hair it was possible to determine between 17 and 135 ng/mg of ethanol beside acetone and several other volatile compounds with slightly higher ethanol values for alcoholics than for social drinkers and teetotalers. A part of this is ethanol only absorbed in the hair matrix from the surrounding environment and consequently is not applicable as a diagnostic criterion. By extraction with aqueous buffer, methanol or a methanol/chloroform mixture and subsequent alkaline hydrolysis it was found that another part is generated from ethylesters, which are preferentially deposited in the lipid fraction of hair. In a specific search for ethylesters of 17 carboxylic acids by GC/MS-SIM in most cases ethyl 4-hydroxybenzoate (0.1 to 5.9 ng/mg, a preservative in hair cosmetics) and in four cases traces of indolylacetic acid ethylester were found. Furthermore, diethyl phthalate (a softening agent, present also in many cosmetic products) was identified in the hair of alcoholics as well as of children. As potential markers of alcohol intake, ethyl palmitate, ethyl stearate and ethyl oleate were detected in hair samples of alcoholics by headspace SPME-GC/MS of the chloroform/methanol extracts.

Acetaldehyde↗
PubMed2000

Monoamines and their metabolites in the freshwater snail Biomphalaria glabrata.

Metabolism of the major monoamines and their functions were studied in the freshwater snail Biomphalaria glabrata. In both juvenile and adult snails, the plasma (cell-free hemolymph) appears to act as a reservoir for most of these monoamines and their metabolites including among others, L-dopa and dopamine as major constituents. Significant quantities of L-tryptophan, precursor of indoleamines, also was found in the plasma. L-dopa, serotonin, homovanillic acid and dopamine were prominently represented in the central nervous system of the snail, while serotonin and its metabolites, 5-hydroxyindole acetic acid and 5-hydroxytryptophol were found in the ovotestis. Catecholamines such as L-dopa, dopamine and homovanillic acid were identified in the albumen gland. Functional aspects of both dopamine and serotonin were studied using in vitro cultures of albumen glands, the site of perivitelline fluid and galactogen synthesis in B. glabrata. Dopamine was found to stimulate the release of secretory proteins when exogenously added to gland cultures and this process was inhibited by chlorpromazine, a dopamine receptor antagonist. Similarly, exogenous serotonin stimulated in vitro protein secretion by albumen glands. Thus, these results suggest that monoamines may play important roles in regulating reproductive activity of this snail and provides an excellent model for studying neurotransmitter function and metabolism in molluscs.

Animals↗
PubMed2002

Demonstration of antifungal and anti-human immunodeficiency virus reverse transcriptase activities of 6-methoxy-2-benzoxazolinone and antibacterial activity of the pineal indole 5-methoxyindole-3-acetic acid.

6-methoxy-2-benzoxazolinone (6-MBOA), a naturally occurring progonadal compound present in grasses with structural resemblance to melatonin, was tested for antifungal activity against Fusarium oxysporum, Rhizoctonia solani and Coprinus comatus. A variety of pineal products was also examined for the sake of comparison, including 5-methoxytryptamine, melatonin, 5-methoxytryptophol, 5-hydroxytryptamine, 5-methoxyindole-3-acetic acid and 5-hydroxytryptophol. The assay for antifungal activity was carried out in Petri plates containing potato dextrose agar. It was found that 6-MBOA most potently inhibited the growth of C. comatus, R. solani and F. oxysporum. When 6-MBOA and pineal indoles were tested for antibacterial activity against the bacterium Agrobacterium tumefaciens, 5-methoxyindole-3-acetic acid was found to be the most potent. 6-MBOA most potently inhibited human immunodeficiency virus-1 reverse transcriptase.

Agrobacterium tumefaciens↗
PubMed2002

Chromatographic methods for the determination of markers of chronic and acute alcohol consumption.

The development in chromatographic methods for the determination of markers of alcohol consumption is summarized in this review. The markers included in this article are ethanol in body fluids, ethanol congeners, fatty acid ethyl esters (FAEEs), ethyl glucuronide (EtG), cocaethylene (CE), carbohydrate-deficient transferrin (CDT), phosphatidylethanol (PEth), 5-hydroxytryptophol (5-HTOL), dolichol, ketone bodies, acetaldehyde-protein adducts, and salsolinol (SAL). Some of these markers for alcohol consumption do not only indicate previous ethanol ingestion, but also approximate the amount of intake and the time when ethanol ingestion last occurred. Basic information about the procedures, work-up, and chromatographic conditions are summarized in tables. Also the main metabolic pathways and reaction schemes are demonstrated in figures. Some examples of typical applications are presented. The author points out that in many of the reviewed papers validation data of the procedures as well as specificities and sensitivities were not clearly presented and consequently were not comparable.

Acute Disease↗
PubMed1993

High-performance liquid chromatographic determination of 5-hydroxyindoles by post-column fluorescence derivatization.

A selective and sensitive high-performance liquid chromatographic method with post-column fluorescence detection has been developed for the determination of 5-hydroxyindoles. Five biogenic 5-hydroxyindoles (5-hydroxytryptophan, 5-hydroxytryptamine, 5-hydroxyindol-3-ylacetic acid, 5-hydroxytryptophol and N-acetyl-5-hydroxytryptamine) were separated by isocratic elution on a reversed-phase column, TSKgel ODS-80Tm, and then converted into fluorescent derivatives by post-column reaction with benzylamine and potassium hexacyanoferrate(III) reagents. The detection limits (signal-to-noise ratio = 3) for the indoles were in the range 140-470 fmol per injection volume (100 microliters). The method was applied to the determination of 5-hydroxyindol-3-ylacetic acid in human urine, with direct sample injection.

Adult↗
PubMed1965

5-HYDROXYTRYPTAMINE METABOLISM BY THE NUCLEAR FRACTION OF RAT-LIVER HOMOGENATE.

1. The metabolism of 5-hydroxy[1'-(14)C]tryptamine creatinine sulphate in the nuclear fraction of rat-liver homogenate was studied. In the incubation mixture five metabolites were found. 2. Two metabolites were not radioactive; one of them was identified as 5-hydroxyindole-3-carboxylic acid and the second tentatively as 5-hydroxyindole-3-aldehyde. 3. 5-Hydroxyindol-3-ylacetic acid, 1'-N-acetyl-5-hydroxytryptamine and 5-hydroxytryptophol were not precursors of 5-hydroxyindolealdehyde and 5-hydroxyindolecarboxylic acid. 4. It was shown that the metabolism of 5-hydroxytryptamine in the nuclear fraction involves monoamine oxidase, the precursor of 5-hydroxyindolealdehyde and 5-hydroxyindolecarboxylic acid being most probably 5-hydroxyindol-3-ylacetaldehyde.

Aldehydes↗
PubMed2003

Characterization of the serotoninergic system in the C57BL/6 mouse skin.

We showed expression of the tryptophan hydroxylase gene and of tryptophan hydroxylase protein immunoreactivity in mouse skin and skin cells. Extracts from skin and melanocyte samples acetylated serotonin to N-acetylserotonin and tryptamine to N-acetyltryptamine. A different enzyme from arylalkylamine N-acetyltransferase mediated this reaction, as this gene was defective in the C57BL6 mouse, coding predominantly for a protein without enzymatic activity. Serotonin (but not tryptamine) acetylation varied according to hair cycle phase and anatomic location. Serotonin was also metabolized to 5-hydroxytryptophol and 5-hydroxyindole acetic acid, probably through stepwise transformation catalyzed by monoamine oxidase, aldehyde dehydrogenase and aldehyde reductase. Activity of the melatonin-forming enzyme hydroxyindole-O-methyltransferase was notably below detectable levels in all samples of mouse corporal skin, although it was detectable at low levels in the ears and in Cloudman melanoma (derived from the DBA/2 J mouse strain). In conclusion, mouse skin has the molecular and biochemical apparatus necessary to produce and metabolize serotonin and N-acetylserotonin, and its activity is determined by topography, physiological status of the skin, cell type and mouse strain.

Animals↗
PubMedDate not supplied

Sequestration of serotonin in stored platelets.

A high-pressure liquid chromatographic procedure was used for the determination of 5-hydroxytryptamine (serotonin, 5HT) in platelets. The method, which is based on the separation on a reverse-phase column and measurement of native fluorescence in an acidified mobile phase, had a detection limit of femtomol quantities of 5HT. The mean contents of 5HT extracted from the Triton X-100-lysed platelets in random-donor platelet concentrates (PCs) were 0.39 +/- 0.19 mumol per 10(11) platelets (n = 5), the value of which was almost equal to 0.40 +/- 0.09 mumol per 10(11) platelets (n = 15) of platelets prepared by cytapheresis. The fate of platelet 5HT during storage of PCs at 22 degrees C with agitation was investigated for 5 days. Nearly all amounts of 5HT were sequestered within platelets after 5-day storage. No increased amounts of major metabolites of 5HT, 5-hydroxytryptophol and 5-hydroxy-3-indoleacetic acid, were detected in plasma. These data suggest that 5HT stored in dense granules of platelets is not metabolized during storage of PCs at 22 degrees C for 5 days.

Blood Platelets↗
PubMed1979

Formation of 5-hydroxykynurenine and 5-hydroxykynurenamine from 5-hydroxytryptophan in rabbit small intestine.

In order to clarify the role of indoleamine 2,3-dioxygenase [indole:oxygen 2,3-oxidoreductase (decyclizing), EC 1.13.11.17] in the metabolism of serotonin, DL-5-hydroxy[methylene-(14)C]tryptophan, a precursor of serotonin, was incubated with slices of rabbit ileum. Resulting metabolites were separated by DEAE-cellulose column and polyamide column chromatography and identified by various chromatographic techniques and enzymatic analysis. Metabolites obtained in significant amounts were serotonin, 5-hydroxyindoleacetic acid, 5-hydroxytryptophol, 5-hydroxykynurenine, 5-hydroxykynurenamine, and 4,6-dihydroxyquinoline, representing 13.2, 15.8, 7.0, 21.9, 1.3, and 2.6% of the total metabolites, respectively. The first three compounds were previously reported to be major metabolites produced from 5-hydroxytryptophan by the action of aromatic L-amino acid decarboxylase and monoamine oxidase, whereas the last three are formed by the cleavage of the indole ring by the action of indoleamine 2,3-dioxygenase. In the presence of pargyline, a monoamine oxidase inhibitor, the major metabolites obtained were serotonin, 5-hydroxykynurenine, and 5-hydroxykynurenamine, representing 29.6, 26.6, and 5.4% of the total metabolites, respectively. In the presence of RO4-4602, an aromatic amino acid decarboxylase inhibitor, 5-hydroxykynurenine was the sole major product. These results strongly suggest that the newly discovered metabolic pathway involving the cleavage of the indole ring of 5-hydroxytryptophan operates in vivo to a significant extent and that indoleamine 2,3-dioxygenase plays an important role in the regulation of serotonin levels in the small intestine of the rabbit.

5-Hydroxytryptophan↗
PubMed1986

Stimulation of aortic smooth muscle cell mitogenesis by serotonin.

Bovine aortic smooth muscle cells in vitro responded to 1 nM to 10 microM serotonin with increased incorporation of [3H]thymidine into DNA. The mitogenic effect of serotonin was half-maximal at 80 nM and maximal above 1 microM. At a concentration of 1 microM, serotonin stimulated smooth muscle cell mitogenesis to the same extent as human platelet-derived growth factor (PDGF) at 12 ng/ml. Tryptamine was approximately 1/10th as potent as serotonin as a mitogen for smooth muscle cells. Other indoles that are structurally related to serotonin (D- and L-tryptophan, 5-hydroxy-L-tryptophan, N-acetyl-5-hydroxytryptamine, melatonin, 5-hydroxyindoleacetic acid, and 5-hydroxytryptophol) and quipazine were inactive. The stimulatory effect of serotonin on smooth muscle cell DNA synthesis required prolonged (20-24 hr) exposure to the agonist and was attenuated in the presence of serotonin D receptor antagonists. When smooth muscle cells were incubated with submaximal concentrations of serotonin and PDGF, synergistic rather than additive mitogenic responses were observed. These data indicate that serotonin has a significant mitogenic effect on smooth muscle cells in vitro, which appears to be mediated by specific plasma membrane receptors.

Animals↗
PubMed1980

Tryptophan and indolic tryptophan metabolites in chronic renal failure.

Tryptophan and indolic tryptophan metabolites were measured in the serum of normal subjects and chronic renal failure patients. The tryptophan free/total ratio was 0.07 in the normal serum, but the other tryptophan metabolite values were below detectable levels. The free/total ratio was 0.66 in patients with chronic renal failure, and both increase of free tryptophan and decrease of total tryptophan were observed. At the same time, 5-hydroxyindoleacetic acid, indole acetic acid, 5-hydroxytryptophol, and N-acetyltryptophan also increased in the serum of chronic renal failure patients, existing not only in free form but in protein-bound form. In the serum samples, following hemodialysis the indolic tryptophan metabolites showed a tendency to decrease, and the tryptophan free/total ratio of 0.42 a approached the normal value. When indolic tryptophan metabolites were added to normal serum in vitro, the free tryptophan level rose, and competition for binding to albumin between tryptophan and indolic tryptophan metabolites was observed. These findings suggested that the cause of the decrease in protein-bound tryptophan in uremic serum may be an accumulation of indolic tryptophan metabolites which complete for binding to albumin in uremia.

Humans↗
PubMed1996

Longitudinal comparison of carbohydrate-deficient transferrin and gamma-glutamyl transferase: complementary markers of excessive alcohol consumption.

The utility of carbohydrate-deficient transferrin (CDT) and gamma-glutamyl transferase (GGT) as biochemical markers of excessive alcohol consumption was studied in alcohol-dependent subjects. Serum samples were collected once weekly from 10 male out-patients undergoing a 6-month alcohol treatment programme. Frequency of relapse into drinking (defined as any intake of alcoholic beverage) was assessed by self-reports during patient interviews three times per week and by daily determination of the 5-hydroxytryptophol level in urine. A marked decrease in mean CDT and GGT values was observed during the initial month. Only one patient remained totally abstinent throughout the observation period, while four had sporadic relapses (2-5 days with alcohol consumption). Both CDT and GGT remained below the respective reference limits in those patients. The other five patients drank more frequently (range 22-57 days) and increased their mean levels of CDT and GGT after the initial decrease. As determined from the values at admission and during the course of the study, CDT appeared to be the most sensitive marker in six out of the 10 patients. In one patient, both markers were affected in a parallel way, whereas two of those with frequent relapses responded to alcohol consumption with a marked increase in GGT, but with no or only a slight increase in CDT. One patient did not show any abnormal CDT or GGT values. In 54 female and 60 male serum samples collected at random from patients during admission at an alcohol detoxification unit, 35% and 58% of the CDT values exceeded the reference limits for females and males, respectively. For GGT, 59% of the female and 67% of the male values were above cut-off. Carbohydrate-deficient transferrin and GGT were not significantly correlated. Taken together, the present results indicate that measurement of both CDT and GGT will increase the possibility of identifying excessive alcohol consumption. By following changes in CDT and GGT values during a period of alcohol withdrawal, the most sensitive individual marker can be determined. This in turn allows for improved detection of relapse into heavy drinking during long-term monitoring of out-patients.

Adult↗
PubMed1985

Inhibitory action of exogenous melatonin, 5-methoxytryptamine, and 6-hydroxymelatonin on sexual maturation of male rats: activity of 5-methoxytryptamine might be due to its conversion to melatonin.

The effect on sexual maturation of 6 different pineal indoles, including melatonin, and of the metabolite 6-hydroxymelatonin was studied in the male rat after daily injections from 20 to 40 days of age. Only 5-methoxytryptamine (5MT) and 6-hydroxymelatonin (6M), in addition to melatonin, inhibited the neuroendocrine-reproductive axis during sexual maturation. Their potencies when injected in the afternoon were in the range of one-twentieth to one-fifth that of melatonin. Like melatonin these two indoles had no effect when injected in the morning. N-acetylserotonin, serotonin, 5-hydroxytryptophol and 5-methoxytryptophol did not influence sexual maturation either when injected in the morning or in the afternoon. Chromatographic separation was performed on plasma extracts from rats injected daily with the biologically active indoles and killed 10-120 min after the last injection. This procedure confirmed that 6M injections did not increase plasma melatonin levels. In contrast, plasma melatonin levels in 5MT-treated rats were increased 1 h after the 5MT injection. These results suggest that 5MT or part of it might be acetylated to melatonin; thus inhibition of sexual maturation might be mainly due to melatonin. These results indirectly support the contention that melatonin is the principal pineal indoleamine playing a role during sexual maturation.

5-Methoxytryptamine↗
PubMed1985

Rapid nocturnal increase in ovine pineal N-acetyltransferase activity and melatonin synthesis: effects of cycloheximide.

Thirty minutes after the onset of darkness, ovine pineal arylalkylamine N-acetyltransferase, N-acetylserotonin, and melatonin increase 5- to 10-fold. No significant changes in hydroxyindole-O-methyltransferase, 5-hydroxytryptamine, 5-hydroxyindoleacetic acid, 5-hydroxytryptophol, 5-methoxyindoleacetic acid, and 5-methoxytryptophol are detected at this time. Administration of cycloheximide inhibits the rise in N-acetyltransferase and N-acetylserotonin, but not melatonin. Unexpectedly, 5-methoxytryptophol increases after cycloheximide treatment. Taken together, these results, although consistent in part with a role for serotonin N-acetylation in the regulation of melatonin synthesis in sheep, indicate that an N-acetyltransferase-independent mechanism may also be involved.

Acetylserotonin O-Methyltransferase↗