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Effects of angiotensin II on biogenic monoamine uptake in the brain of nonhypoxic and hypoxic mice.

The effects of angiotensin II (ATII) administered intacerebroventricularly (i.c.v.) at a dose of 0.5 microgram per mouse on dopamine (DA), noradrenaline (NA) and 5-hydroxytryptamine (5-HT) high-affinity uptake in mouse forebrain during hypoxia (asphyxic and hemic) were studied. The influence of hypoxia on biogenic monoamine uptake was also investigated. It was found that DA uptake increased, NA uptake decreased and 5-HT uptake was unchanged after asphyxic hypoxia. Hemic hypoxia had no effect on biogenic monoamine uptake. ATII did not affect uptake of biogenic monoamines in normoxic mice after asphyxic and hemic hypoxia. The results suggest that ATII increases the susceptibility of animals to hypoxia through alterations in the brain high-affinity monoamine uptake.

Angiotensin II↗

Biochemistry and molecular biology of receptors for biogenic amines in locusts.

The biochemistry and molecular biology of biogenic amines and their metabotropic receptors in insects, with a focus on locusts, is reviewed. These compounds are known to be responsible for the control of a huge variety of different behaviours. Receptors for these amines usually belong to the class of G-protein coupled receptors (GPCR) and transmit all known functions of these compounds. The physiological significance of biogenic amine neurotransmission in insects, especially in locusts is briefly summarised. Regarding the corresponding receptors, their pharmacological features and the molecular properties are described in detail.

Animals↗

Genomic determinants underlying biogenic amine detoxification phenotypes in food-associated lactic acid bacteria: Mechanism, evolutionary origin, and relevance to fermented food safety.

Biogenic amines (BAs) are toxic metabolites that accumulate in fermented foods and pose significant food safety concerns. Although several lactic acid bacteria (LAB) have previously been reported to exhibit strain-specific BA-degrading phenotypes, the genetic determinants underlying these activities have remained largely uncharacterized. Here, we analyzed 8251 LAB genomes to validate BA-degrading phenotypes. We predicted five BA-associated genes, including two direct biogenic amine-degrading genes (BADGs), mco and patA, and three polyamine-modifying genes (PMGs), speG, paiA, and bltD. Among BADGs, mco was broadly distributed across LAB and strongly enriched across food-associated niches. patA, organized within a conserved potD-glnB-potABC-patA cassette, is a putative, functionally distinct BADG in LAB, revealing a nitrogen-responsive polyamine uptake-catabolism module. Phylogenomics, phylogenetic reconciliation, and synteny analysis established that all five genes entered the LAB through episodic horizontal gene transfer followed by lineage-specific fixation. GC compositional bias and mobile genetic element association further corroborated the horizontal origin of the two BADGs. Structural analysis confirmed the conservation of catalytic core residues of BADGs across LAB, indicating strong purifying selection. Phenotype-to-genotype correlation with experimentally reported LAB suggested mco as a reliable genomic predictor of degrading phenotype. Integration of degradation and biosynthetic profiles predicted multiple LAB species capable of both synthesizing and degrading BA, along with 1823 genomes with degradation potential but lacking detectable BA biosynthesis genes. This study provides the first large-scale genome framework linking BA-degrading phenotypes with their genetic determinants in LAB and offers a rational basis for selecting BA-detoxifying strains for fermented food applications.

Biogenic Amines↗

Microchannel electrophoretic separation of biogenic amines by micellar electrokinetic chromatography.

Fast, efficient separation of most common biogenic amines was successfully performed on a glass microchip capillary electrophoresis device. The amines putrescine, histamine, tyramine, cadaverine, phenethylamine, tryptamine, spermidine and spermine were derivatized prior to fluorescence detection with fluorescein isothiocyanate. Separation was carried out using a channel length of 28 mm, a cross section of 50 x 8 microm, and a field strength of 600 V/cm. After optimization of buffer electrolyte conditions (120 mM boric acid, pH 9.4, modified with 40 mM SDS), fluorescein thiocarbamyl amine derivatives were successfully resolved. Analysis time was as short as 75 s. Determination of the biogenic amines was achieved in soy sauce samples.

Biogenic Amines↗

Biogenic amines in chicken meat products in relation to bacterial load, pH value and sodium chloride content.

Exogenous biogenic amines may present food poisoning hazards, especially when coupled with additional risk factors. In recent years, consumption of poultry meat and poultry meat products has increased. Therefore, the goals of this work were to estimate biogenic amines in chicken meat products and to find a correlation to bacterial quality, pH value and/or NaCl content. A total number of 60 random samples of chicken frankfurter, luncheon and keshta were collected from Cairo and Assiut supermarkets and groceries. The samples were analyzed for estimation of histamine, tyramine, cadaverine and puerscine. The results were in low levels and varied in each product. The bacterial quality was evaluated with respect to total colony, Enterobacteriaceae, coliforms, Lactobacillaceae and Pseudomonas aeruginosa counts. These amineproducering bacteria were detected in low amounts. Such findings as well as pH value and NaCl content correlated with amines levels.

Animals↗

Poly(dimethylsiloxane) microchip for precolumn reaction and micellar electrokinetic chromatography of biogenic amines.

We have demonstrated that precolumn derivatization and capillary electrophoresis separation on a poly(dimethylsiloxane) (PDMS) microchip can be realized as efficient as those on glass microchips. In an optimized condition of micellar electrokinetic chromatography (MEKC), using 25 mM sodium borate buffer (pH 10.0) with 25 mM sodium dodecyl sulfate (SDS) and 5% v/v methanol, the electroosmotic flow in an oxidized PDMS microchip is stabilized within 3% for days. By employing a fluorometric derivatization with o-phthaldialdehyde (OPA) in an optimally designed reaction chamber, four most important biogenic amines occurring in foods, histamine, tyramine, putrescine, and tryptamine, are quantitatively determined in less than 1 min at the levels applicable to real samples. The migration behaviors of anionic OPA-derivatized biogenic amines under the MEKC conditions are analyzed, and it has been found that under our separation conditions, the electrophoretic mobility of the SDS micelles is significantly greater than those of the anions in the aqueous phase. The channel manifold in a PDMS substrate is fabricated using replica molding against a thick photoresist, SU-8, pattern generated by photolithography. The plate with the microchannel pattern is strongly, irreversibly bonded to another PDMS plate by using a new bonding technique, which employs surface oxidation by corona discharge generated from a cheap, handy source, Tesla coil.

Biogenic Amines↗

A polydimethylsiloxane/glass capillary electrophoresis microchip for the analysis of biogenic amines using indirect fluorescence detection.

A polydimethylsiloxane-glass capillary microchip is fabricated for the rapid analysis of a mixture of common biogenic amines using indirect fluorescence detection. Using a running buffer of phosphate and 2-propanol, and Rhodamine 110 as a background fluorophore, both co-ionic and counter-ionic systems are explored. Studies demonstrate the separation and analysis of cations using indirect fluorescence detection for the first time in a chip-based system. Resulting electrophoretic separations are achieved within a few tens of seconds with detection limits of approximately 6 microM. The reduced sample handling and rapid separations afforded by the coupling of indirect fluorescence detection with chip-based capillary electrophoresis provide a highly efficient method for the analysis and detection of molecules not possessing a chromophore or fluorophore. Furthermore, limits of detection are on a par with reported chip-based protocols that incorporate precolumn derivatisation with fluorescence detection. The current device circumvents lengthy sample preparation stages and therefore provides an attractive alternative technique for the analysis biogenic amines.

Animals↗

In-capillary derivatization and analysis of amino acids, amino phosphonic acid-herbicides and biogenic amines by capillary electrophoresis with laser-induced fluorescence detection.

This paper describes a general approach for the in-capillary derivatization of amino compounds and the subsequent sensitive determination of the derivatives by micellar electrokinetic chromatography (MEKC) or capillary zone electrophoresis (CZE) with laser-induced fluorescence (LIF) detection. Amino acids, biogenic amines and amino phosphonic acid-herbicides were chosen as model analytes to evaluate the analytical potential of this approach. Fulfilment of the in-capillary reaction of the analytes using LIF detection hinged on the excellent labeling chemistry of 5-(4,6-dichloro-s-triazin-2-ylamino)fluorescein (DTAF) and the good resolution achieved in the separation of derivatized analytes. Careful optimization of the electrophoretic conditions in the mixing step of this protocol allowed the determination of amino acids, biogenic amines and phosphorus-containing amino acid-herbicides with concentration limits of detection at the nug/L level and relative standard deviations from 3.5 to 5.8%. The whole analysis is carried out within 20 min, resulting in a very simple, fast and practical approach for the fully automated analysis of amino acids and related compounds in low-volume and low-concentration samples.

Amino Acids↗

Diurnal patterns in brain biogenic amines of rats exposed to 60-Hz electric fields.

Levels of brain neurotransmitters and their metabolites, as well as concentrations of enzymes associated with their synthesis and metabolism, fluctuate during the day in patterns defined as circadian. The present study examined these rhythms in albino rats exposed to 60-Hz electric fields. Thirty-six animals were exposed to a 39 kV/m field for 4 weeks, 20 h/day, in a parallel-plate electrode system. A group of 36 sham animals was similarly handled and housed in a nonenergized exposure system. On the sampling day, animals were sacrificed at 4-h intervals throughout the 24-h day. Brains were removed, dissected, and kept frozen until chemically analyzed. The levels of biogenic amines and their acidic metabolites in the striatum, hypothalamus, and hippocampus were determined by high-performance liquid chromatography with electrochemical detection (HPLC-ECD) methods. Repeated exposure to 60-Hz electric fields produced significant alterations in the diurnal rhythms of several biogenic amines: dihydroxyphenylacetic acid (DOPAC, the primary metabolite of dopamine in the rat) in the striatum, and norepinephrine, dopamine, and 5-hydroxyindoleacetic acid (5-HIAA; serotonin metabolite) in the hypothalamus. Levels of serotonin in the striatum and hypothalamus showed clear circadian patterns that was not affected by the field. No diurnal or field-related changes were observed in the hippocampal amines.

Animals↗

Profiling and quantification of biogenic amines in wine by constant B2E linked scan mass spectrometry.

The constant B2E linked scan is shown to be an excellent tool for the profiling of biogenic amines in wine samples. The fragment ion at m/z 169 of the dansylated amines is used for the precursor ion search in combination with direct sample evaporation. Besides the profile a semi-quantification may be achieved when using suitable amines as internal standards with standard deviations of 12-17%. More accurate results with standard deviations of 3-5% are obtained when using deuterated analogues as internal standards. Both methods are applied to the analysis of biogenic amines in synthetic mixtures and actual wine samples.

Biogenic Amines↗

An extraction-derivatization method suitable for the analysis of biogenic amines by gas chromatography negative ion mass spectrometry.

An extraction-derivatization method suitable for the analysis of subnanogram amounts of biogenic amines in aqueous solution has been developed. The most satisfactory procedure for the analysis of these compounds was reaction with 3,5-ditrifluorobenzoylchloride (DTFMBCl) in phosphate buffer at pH 7.2 followed by extraction of the resultant amide esters into ethyl acetate. This was followed by hydrolysis of the phenolic ester functionalities by shaking the organic layer with 10 M ammonium hydroxide. The phenolic and alcoholic hydroxyl groups were then reacted with bistrimethylsilylacetamide and the trimethylsilyl-DTFMB amides were then analysed by gas chromatography/mass spectrometry in the negative ion chemical ionization mode with methane as reagent gas. The limits of detection for these derivatives was less than 1 pg and the method was readily applicable to the extraction and analysis of 0.5 ng of a given biogenic amine.

Biogenic Amines↗

Ligand-binding modes in cationic biogenic amine receptors.

The binding site in G protein-coupled cationic biogenic amine receptors is formed in the cleft of the seven transmembrane segments. Upon binding the ligand, the receptors are activated or inactivated through the conformational changes of the transmembrane segments. G protein-coupled receptors bind four functionally distinct ligands; inverse agonists, antagonists, partial agonists, and full agonists. Hence, putative structural models for biogenic amine receptors corresponding to the ligand function (inverse agonist-, antagonist-, partial agonist-, and full agonist-bound receptor models) were built by using photointermediate models in the rhodopsin photocascade (M. Ishiguro et al. ChemBioChem. 2004, 5, 298-310). The ligand-receptor recognition of each was examined by modeling receptor-ligand complexes with functional ligands. The complex models suggested that each functional ligand binds the corresponding receptor structure and that ligand-specific interactions contribute to stabilization of the corresponding receptor structure.

Amino Acids↗

Molecular genetics of dopa decarboxylase and biogenic amines in Drosophila.

The gene Ddc encodes two isoforms of the enzyme dopa decarboxylase in Drosophila. These gene products catalyze the final steps in the synthesis of the biogenic amines serotonin and dopamine. This article summarizes recent progress in understanding the tissue- and cell-specific regulation of Ddc, which occurs at both the transcription and alternate splicing levels. In addition, results that are pertinent to understanding the roles of biogenic amines in the neurophysiology of Drosophila are discussed.

Animals↗

Direct automatic determination of biogenic amines in wine by flow injection-capillary electrophoresis-mass spectrometry.

A capillary electrophoresis-electrospray mass spectrometry (CE-ESI-MS) method for the separation and determination of nine biogenic amines is proposed. Operational variables, such as the voltage, temperature, sheath liquid composition, flow-rate, and MS parameters, were optimized. Samples are injected in the hydrodynamic mode into a 75 cm x 50 microm ID coated capillary and separated by using 25 mM citric acid at pH 2.0. Heptylamine is used as internal standard. The experimental setup includes a flow manifold coupled to the CE system for automatic insertion of samples into the CE vials. The proposed method allows amines to be determined with limits of detection from 0.018 to 0.09 microg x mL(-1) and relative standard deviation (RSD) values from 2.4% to 5.0% (except 6.8% for histamine). The method was successfully used to determine biogenic amines in red and white wines.

Biogenic Amines↗

Capillary electrophoresis determination of biogenic amines by field-amplified sample stacking and in-capillary derivatization.

A sensitive CE method for determining biogenic amines in wines based on in-capillary derivatization with 1,2-naphthoquinone-4-sulfonate is presented. In this method, reagent and buffer solutions are introduced hydrodynamically into the capillary whereas the sample is injected electrokinetically, thus, allowing a selective preconcentration of the analytes by field-amplified sample stacking. Amines are labeled inside the capillary using a zone-passing derivatization approach in mixed tandem mode. The most relevant variables influencing on the derivatization and separation as well as significant interactions have been evaluated using experimental design. Multi-criteria decision making is utilized for the simultaneous optimization of interacting variables through overall desirability response surfaces. The validation of the method has proven an excellent separation performance and accuracy for the determination of biogenic amines such as histamine, tryptamine, phenylethylamine, tyramine, agmatine, ethanolamine, serotonin, cadaverine, and putrescine in red wines. Detection limits range from 0.02 mg/L for ethanolamine to 0.91 mg/L for serotonin. The RSDs for migration time and peak area are around 1.2 and 6.2%, respectively. Red wines from different Spanish regions have been analyzed using the proposed method.

Biogenic Amines↗

A proteomic approach to studying biogenic amine producing lactic acid bacteria.

All fermented foods are subject to the risk of biogenic amine contamination. Histamine and tyramine are among the most toxic amines for consumers' health, exerting undesirable effects on the central nervous and vascular systems, but putrescine and cadaverine can also compromise the organoleptic properties of contaminated foods. These compounds are produced by fermenting microbial flora that decarboxylate amino acids to amines. Little is known of the factors which induce biosynthesis of decarboxylating enzymes and/or which modulate their catalytic activity: the accumulation of amines is generally considered to be a mechanism that contrasts an acidic environment and/or that produces metabolic energy through coupling amino acid decarboxylation with electrogenic amino acid/amine antiporters. Two Lactobacillus strains, Lactobacillus sp. 30a (ATCC 33222), and a Lactobacillus sp. strain (w53) isolated from amine-contaminated wine, carrying genetic determinants for histidine decarboxylase (HDC) and ornithine decarboxylase (ODC), were studied and the influence of some environmental and nutritional parameters on amine production and protein biosynthesis was analyzed through a proteomic approach; this is the first report of a proteomic analysis of amine-producing bacteria. HDC and ODC biosynthesis were shown to be closely dependent on the presence of high concentrations of free amino acids in the growth medium and to be modulated by the growth phase. The stationary phase and high amounts of free amino acids also strongly induced the biosynthesis of an oligopeptide transport protein belonging to the proteolytic system of Lactic Acid Bacteria. At least two isoforms of glyceraldehyde-3-phosphate dehydrogenase, with different M(r), pI and expression profiles, were identified from Lactobacillus sp. w53: the biosynthesis of one isoform, in particular, is apparently repressed by high concentrations of free amino acids. Other proteins were identified from the Lactobacillus proteome, affording a global knowledge of protein biosynthesis modulation during biogenic amine production.

Amino Acid Sequence↗

Biogenic amine-stimulated adenylate cyclase and spiroperidol-binding sites in rabbit brain: evidence for selective loss of receptors with aging.

Evidence for selective decreases in biogenic amine receptor function with age in the rabbit has been obtained. Dopamine-stimulated adenylate cyclase activity in the striatum (caudate-putamen) of rabbit brain declined by about 50 percent as rabbits aged from less than 1 to 4 to 5 years of age. Similar decreases in transmitter-stimulated adenylate cyclase activity were found for histamine as well as for dopamine and norepinephrine in hypothalamus, frontal cortex and anterior limbic cortex. Isoproterenol-stimulated activity was also decreased with age in frontal cortex. These changes appeared to represent decreases in maximal response and not alteration in affinity for amine. In contrast, dopamine-stimulated adenylate cyclase of retina and transmitter-independent (basal or Gpp(NH)p-stimulated) activity in each of the regions studied were not altered with age. Dopamine receptors in striatum directly assessed by measurement of [3H]-spiroperidol binding revealed a comparable decrease in the number of binding sites without change in ligand affinity. Preliminary data also indicated decreased spiroperidol binding sites in the cortical regions of older animals. These changes in striatum and cortex were evident in the absence of decreases in either dopamine content or choline acetylase activity, an activity presumed to be present in neurons containing dopamine receptors. It is proposed that selective age-dependent decreases in postsynaptic biogenic amine receptor content occur in the absence of, or independent from, neuronal cell loss, possibly by a mechanism involving receptor desensitization. These changes occur in the animal model in those brain regions which in man are thought to be of importance in the loss of cerebral function that is found with senscence.

Adenylyl Cyclases↗

Monoamine oxidase A deficiency: biogenic amine metabolites in random urine samples.

We have recently described an association between abnormal behaviour and monoamine oxidase A (MAO-A) deficiency in several males from a single large Dutch kindred. A characteristically abnormal excretion pattern of biogenic amine metabolites was present in 24-hour urine of affected males. Because of this strikingly abnormal metabolite pattern observed in 24 hour urine samples of MAO-A deficient males we hypothesized that it should be possible to diagnose this condition by examining random urine samples. We therefore studied multiple urine samples obtained over a two-week study period from two males with selective MAO-A deficiency. The results demonstrate that the characteristic abnormalities in the excretion of biogenic amines and their metabolites were faithfully present in every one of 12 independent samples obtained from the MAO-A deficient males over the two-week study period. We conclude that MAO-A deficiency can be reliably diagnosed by measuring the ratio of normetanephrine (NMN) to VMA (or that of NMN to MHPG) in random urine samples.

Biogenic Amines↗