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PubMed1982

Importance of dietary amines in meal-induced gastrin release.

The dietary chemical constituents responsible for initiating the gastrin secretory response to a meal have yet to be identified. The evidence supporting the importance of dietary amino acids in the initiation of the postprandial release of gastrin is both conflicting and unconvincing. In this study we investigated the role of the amino acid breakdown products ammonia and the amines in the regulation of gastrin release both in vivo and in vitro. Lyophilization of standard rat food under alkaline conditions results in the volatilization of both ammonia and the amines, which can be subsequently condensed in a cold trap. The normal postprandial release of gastrin is significantly reduced by approximately 50% when rats are fed this freeze-dried diet. Addition of the amine-containing condensate back to the freeze-dried diet completely restores this response to normal. Analysis of the completely restores this response to normal. Analysis of the condensate by thin-layer chromatography revealed that it contained ammonia, methylamine, ethylamine, dimethylamine, and a fourth unidentified aliphatic amine. All of the above compounds significantly stimulated the release of gastrin from isolated G cells. Similarly, addition of ammonia and a synthetic amine mixture to the freeze-dried diet completely restored the postprandial release of gastrin to normal levels. In conclusion, our results suggest that dietary amines and ammonia may play a key role in initiating the gastrin secretory response to a meal.

Amines↗
PubMed1976

Biogenic amines and affective disorders. A critical analysis.

The evidence linking biogenic amines and affective disorders is critically reviewed. Surveyed are studies on the level of biogenic amines and their metabolites in the brain, blood, urine and cerebrospinal fluid of patients with affective conditions; the effects of biogenic amine precursors, depletors and blockers on affective states and the action of present methods of treatment of these disorders on the level of biogenic amines. Reference is also made to the existence of various disease states where abnormalities of biogenic amines exist in the absence of affective disorders. The review fails to uncover convincing evidence that affective disorders are related to abnormal levels of biogenic amines. Reasons are outlined why the "catecholamine hypothesis" and related theories can neither be proven nor disproven with the available techniques.

5-Hydroxytryptophan↗
PubMed1998

Enhancing the interaction of central nervous system neurons with poly(tetrafluoroethylene-co-hexafluoropropylene) via a novel surface amine-functionalization reaction followed by peptide modification.

Poly(tetrafluoroethylene-co-hexafluoropropylene) (FEP) surfaces were modified with cell adhesive peptides, via a novel amination reaction, to enhance the neuron-substrate interaction. Amination of FEP surfaces was achieved by exposing FEP film samples to a UV-activated mercury/ammonia system for either 3 or 24 h, yielding nitrogen compositions of 3.5 and 13.2%, respectively. By labeling the nitrogen functionality with trichlorobenzaldehyde, the surface amine compositions were calculated to be 14 and 4.3% for the 3 and 24 h amination reactions, respectively. Three oligopeptide sequences derived from laminin (GYIGSR, GRGDS, and SIKVAV) were coupled to the aminated FEP (FEP-NH2) surfaces and found to have almost identical surface concentrations as determined by XPS. Using radiolabeled GYIGSR, three coupling agents were compared and the concentration of peptide per surface area was calculated to be 3 and 6 fmol cm-2 for surfaces aminated for 3 and 24 h, respectively, regardless of the coupling agent. The interaction of embryonic hippocampal neurons with the modified surfaces was compared to that with the positive poly(L-lysine)/laminin control in terms of number and length of extended neurites. After 1 day incubation, neurite extension on the GYIGSR- and SIKVAV-coupled surfaces was similar to that on the positive control but significantly greater than that on FEP and FEP-NH2 control surfaces. These peptide-coupled fluoropolymer surfaces enhance the neuron-fluoropolymer interaction, similar to that observed with PLL/laminin.

Amines↗
PubMed1969

Diagnostic and genetic studies on fibrin-stabilizing factor with a new assay based on amine incorporation.

Fibrinoligase, the fibrin cross-linking enzyme, transiently appearing during the course of coagulation in normal blood, was shown to catalyze the incorporation of a fluorescent amine, monodansylcadaverine [or N-(5-aminopentyl)-5-dimethylamino-1-naphthalene-sulfonamide] into casein. The reaction provided the basis of a sensitive fluorimetric method for measuring the activity of the enzyme (and also of similar other transpeptidases, such as transglutaminase). In tests involving plasma, certain difficulties had to be overcome which were mainly due to the fact that the enzyme itself does not occur in citrated plasma. Only its precursor (fibrin-stabilizing factor or factor XIII) is present, still requiring limited proteolytic activation by thrombin. Thus, in order to measure amine incorporation with plasma as a source of the factor, thrombin must be added. This necessitated a differential desensitization of the intrinsic fibrinogen so that the latter could not clot and could not thereby interfere with amine incorporation. Also, the thrombin-inactivating capacity of plasma had to be saturated to enable full conversion of the factor to the transpeptidase. Concentrations of casein, monodansylcadaverine, calcium, and hydrogen ions were chosen to permit almost maximal velocity of amine incorporation. A linear relationship with regard to plasma concentration could be obtained only under such conditions. No similar assay is presently available for quantitatively evaluating fibrin-stabilizing factor levels in plasma.The amine incorporation test was applied to a clinical case of hereditary total fibrin-stabilizing factor deficiency. The effect of transfusion therapy was studied, and some of the patient's relatives were examined. Whereas a paternal aunt and uncle gave values well within the normal range, a brother and the mother proved to be partially deficient and could be considered as heterozygous carriers. The father appeared to have a reduced level of fibrin-stabilizing factor, though not quite as low as the other two relatives. Two infusions (1 liter each) of fresh normal plasma, administered about 26 hr apart, brought levels in the patient's plasma close to those found in the mother and brother. The corrective power of the transfusions, however, rapidly declined within 5-6 days. Futility of the last transfusion could be ascribed to the appearance of a neutralizing antibody directed against the precursor stabilizing factor, a serious complication. General diagnostic versatility and potential of the quantitative amine incorporation assay with plasma is discussed.

Adult↗
PubMed1985

Neurohormonal modulation of the Limulus heart: amine actions on neuromuscular transmission and cardiac muscle.

The responses of Limulus cardiac neuromuscular junctions and cardiac muscle cells to four endogenous amines were determined in order to identify the cellular targets underlying amine modulation of heartbeat amplitude. The amines increased the amplitude of the Limulus heartbeat, with dopamine (DA) being more potent than octopamine, epinephrine or norepinephrine. The effect of DA on heartbeat amplitude was not blocked by phentolamine. DA enhanced the contractility of deganglionated heart muscle, with time course and dose-dependence similar to its effect on the intact heart. The amines also enhanced neuromuscular transmission, with time course and dose-dependence similar to their effects upon the intact heart. The amplitude of unitary excitatory junction potentials (EJPs) and frequency of miniature excitatory junction potentials (mEJPs) were increased by DA, while mEJP amplitude was unchanged. Thus DA, and probably the other amines, had a presynaptic effect. Combined actions upon cardiac muscle and cardiac neuromuscular transmission account for the ability of these amines to increase the amplitude of the Limulus heartbeat.

Amines↗
PubMed2004

Antimicrobial activity of saturated fatty acids and fatty amines against methicillin-resistant Staphylococcus aureus.

The objective of this study was to investigate the antimicrobial activities of saturated fatty acids and fatty amines against methicillin-resistant Staphylococcus aureus (MRSA). The antimicrobial activity of saturated fatty acids and fatty amines was determined by oxygen meters with multi-channels and disposable oxygen electrode sensors (DOX-96). Lauric acid, the most effective among the saturated fatty acids, showed antimicrobial activity at 400 microg/ml against methicillin-susceptible Staphylococcus aureus (MSSA) and MRSA. The minimal inhibitory concentration (MIC) of fatty amines depended on each hydrophobic chain length. The MIC of myristylamine was 1.56 microg/ml; most effective of the fatty amines. In time-kill curves, lauric acid and myristylamine produced a bactericidal effect and a bacteriostatic effect at 4-fold the MIC, respectively. The antimicrobial activities of lauric acid and myristylamine were decreased by human plasma. Cytotoxicity of 3 saturated fatty acids and 3 fatty amines was examined in cultured endothelial cells. Although cytotoxicity of fatty amines was severer than that of saturated fatty acids, myristylamine showed the highest value of apparent therapeutic index among them. DOX-96 was useful for screening antimicrobial substances, especially in the case of insoluble substances. We found that myristylamine showed anti-MRSA activity comparable to that of vancomycin and teicoplanin.

Amines↗
PubMed1985

Metabolism of aromatic amines by prostaglandin H synthase.

The metabolism of aromatic amines by the peroxidase activity of prostaglandin H synthase (PHS) has been studied in this laboratory by use of two model compounds, the carcinogenic primary amine 2-aminofluorene (2-AF) and the substituted amine aminopyrine (AP). 2-AF is oxidized by PHS to 2, 2-azobisfluorene, 2-aminodifluorenylamine, 2-nitrofluorene, polymeric material, and products covalently bound to macromolecules. In the presence of phenolic compounds, 2-AF oxidation results in the formation of amine/phenol adducts. The data are consistent with a one-electron mechanism of 2-AF oxidation by PHS; furthermore, an N-hydroxy intermediate is not involved in 2-AF metabolism by PHS. PHS also catalyzes the binding of 2-AF to DNA in vitro. Unique 2-AF/DNA adducts were isolated and are distinct from the N-(deoxyguanosin-8-yl)-2-AF adduct formed from the reaction of N-hydroxy-2-AF with DNA. These new adducts represent a marker unique to peroxidative activation of 2-AF. AP is oxidized by the peroxidase activity of PHS to the cation radical, with one molecule of hydroperoxy fatty acid reduced for every two molecules of AP free radical formed. The decay of the AP radical follows second order kinetics, supporting the proposed mechanism in which the AP radical disproportionates to an iminium cation, followed by hydrolysis of this species to the demethylated amine and formaldehyde. In the presence of glutathione, the cation radical is reduced to the parent amine, resulting in the formation of the glutathione thiyl radical. It thus appears that both primary and substituted aromatic amines may undergo one-electron oxidation by PHS.

Amines↗
PubMed2005

Aging of triazine amine in soils demonstrated through sorption, desorption, and bioavailability measurements.

The aging of triazine amine in soil was studied during a time course of 119 d by measuring bioavailability in terms of mineralization after inoculation of the triazine amine-degrading bacterium Rhodococcus erythropolis TA57. The bioavailability was measured in four soil samples: A-, B-, and C-horizons from an agricultural soil profile and in a peat soil. The sorption of triazine amine in the soil samples was quantified during the period of aging in terms of sorption distribution coefficients (Kd) and desorption distribution coefficients (Kd,des). Measures of bioavailability and triazine amine concentration in the nonavailable fraction showed effects of aging in the soils that were rich in organic matter. The triazine amine bioavailability declined significantly during the aging period in soils containing greater than 2% organic carbon, whereas the B- and C-horizons showed no signs of aging, in agreement with their low content of organic material. Corresponding to this, desorption decreased significantly in the A-horizon but, surprisingly, not in the peat soil. Analyses by thin-layer chromatography indicated an association of aqueous triazine amine and dissolved organic matter in the peat soil. This gives an explanation for both the significant decrease in bioavailability and the noncorresponding stability of the nonavailable (i.e., nondesorbed) fraction.

Adsorption↗
PubMed2002

Production of amines in equine cecal contents in an in vitro model of carbohydrate overload.

Acute laminitis can be induced experimentally in horses by the administration of carbohydrate, resulting in fermentation within the cecum and ischemia-reperfusion of the digits. The products of fermentation that trigger acute laminitis are as yet unknown; however, compounds such as amines might play a role due to their potential vasoactive properties. The objectives of this study were to quantify the amines present in equine cecal contents and to use a model of carbohydrate overload in vitro to test the hypothesis that carbohydrate fermentation is associated with increased amine production. Cecal contents from each horse were divided into aliquots and incubated anaerobically with either cornstarch or inulin (a form of fructan carbohydrate; both 1 g/100 mL). The pH was measured and samples were taken at the same time for amine measurement by HPLC at 2-h intervals over a 24-h period. In a second set of experiments, the effects of the antibiotic virginiamycin (1 mg/100 mL), calcium (CaPO4; 0.3 g/100 mL), and plant steroidal saponin (Yucca schidigera extract; 0.1 g/100 mL) were examined on pH and amine concentrations in cecal contents incubated with starch or inulin. Both starch and inulin caused significant time-dependent falls in pH, from 6.7 +/- 0.1 at 0 h to 5.2 +/- 0.1 (starch) and 5.0 +/- 0.1 (inulin) at 24 h. Fermentation of carbohydrate was also associated with increased production of phenylethylamine and isoamylamine (two- to threefold increases) as well as putrescine and cadaverine (1.5- to twofold increases). Virginiamycin inhibited the fall in pH and increases in production of phenylethylamine and isoamylamine, while calcium phosphate moderated the changes in pH only. Yucca schidigera extract was without effect. These data show that fermentation of carbohydrate by equine cecal microbiota may lead to increased production of amines.

Acute Disease↗
PubMed1986

N-sulphoconjugation of alicyclic, alkyl- and aryl-amines in vivo and in vitro.

Radioactive 35S in 3'-phosphoadenosine 5'-phosphosulphate was incorporated into alicyclic, alkyl- and aryl- amines in the presence of hepatic 105 000 g supernatants of female rats. 4-Phenylpiperazine, 4-phenyl-1,2,3,6-tetrahydropyridine (PTHP), 1,2,3,4-tetrahydroisoquinoline, N-methylbenzylamine, desmethylzotepine and desmethylzimeldine showed the highest conjugation with 35SO3 among the amines tested. Incorporation of 35SO3 into alicyclic and alkyl-amines was higher at pH 10.0 than at pH 7.4 but the incorporation into arylamines was the opposite. A greater amount of 35SO3 was incorporated into the secondary alkylamines than the corresponding primary amines. Radioactive reaction products were identified as N-sulphoconjugates of amines by comparison on t.l.c. with synthetic authentic compounds. Reaction products of desmethylimipramine (DMI) and PTHP in vitro were isolated as their sulphoconjugates, identified by comparison of field desorption mass spectra, u.v. spectra, retention time on h.p.l.c. and RF values on t.l.c. with synthetic standards. DMI N-sulphonate and PTHP N-sulphonate were detected in the body of female rats treated orally with DMI and PTHP, respectively. These results indicate that N-sulphoconjugation is a common metabolic pathway of alicyclic, alkyl- and aryl-amines in vivo and in vitro.

Adenine Nucleotides↗
PubMed1998

Competitive inhibition of Lens culinaris L. copper amine oxidase by amiloride, p-aminobenzamidine, clonidine, 4',6-diamidino-2-phenylindole and gabexate mesylate: a comparative study.

The competitive inhibition of Lens culinaris L. copper amine oxidase by amiloride (Ki = 4.1 x 10(-4) M), p-aminobenzamidine (Ki = 6.0 x 10(-4) M), clonidine (Ki = 5.0 x 10(-4) M), 4',6-diamidino-2-phenylindole (DAPI; Ki = 1.9 x 10(-5) M) and gabexate mesylate (Ki = 2.5 x 10(-4) M) has been investigated, at pH 7.0 and 25 degrees C. The affinity of p-aminobenzamidine, clonidine and DAPI for plant and mammalian copper amine oxidase is closely similar. However, values of Ki for amiloride and gabexate mesylate binding to swine kidney copper amine oxidase are lower than those observed for inhibitor binding to Lens culinaris L. cooper amine oxidase. Thus, amiloride and gabexate mesylate may represent useful model compounds for the development of selective inhibitors of mammalian copper amine oxidase, which may be important in view of the potential use of plant copper amine oxidase as drugs.

Amiloride↗
PubMed1980

Mastitis: II. Evaluation of antimicrobial amines for use as teat dips.

Recent proposals by the Food and Drug Administration to regulate teat dips as drugs have led to a search for safer teat dip ingredients. Primary, secondary, and tertiary alkyl amines (carbon-10 to -18 chain length) inhibit growth of mastitic bacteria (Streptococcus agalactiae, Streptococcus uberis, Staphylococcus aureus, Escherichi coli, Klebsiella pneumoniae) in a broth tube culture assay. Since carbon-13 compounds were active, a carbon-13 primary (tridecanamine hydrochloride), secondary methyl (N-methyltridecanamine), secondary ethyl (N-ethyltridecanamine), tertiary dimethyl amine (N, N-dimethyltridecanamine), and carbon-12 quaternary amine (N, N, -trimethyldodecaneammonium chloride) were tested for their ability to reduce experimentally applied populations of S. agalactiae or E. coli on the bovine teat surface. The five compounds were compared at concentrations of 100, 500, 1,000, 3,000, 7,000, and 10,000 ppm. Activity was greater against the gram-positive S. agalactiae than against the gram-negative E. coli. The tertiary amine was most active, producing a log reduction of 4 (reduction of bacterial number from 10(6) to 10(2)) at a concentration of 3,000 ppm in the teat dip. The relative order of effectiveness for the amines was: dimethyl tertiary greater than methyl secondary greater than ethyl secondary greater than primary = quaternary. The results suggest that these amines may be useful as potent, effective antibacterial agents for incorporation into teat dips.

Amines↗
PubMed2000

Reduction of biogenic amine formation using a negative amino acid-decarboxylase starter culture for fermentation of Fuet sausages.

The ability of Lactobacillus sakei CTC494, a negative amino acid-decarboxylase starter culture, to reduce biogenic amine accumulation during sausage fermentation and storage at 4 and 19 degrees C was studied. The effect on the amine formation of the tyramine producer Lactobacillus curvatus CTC371, as a positive strain, was also examined in comparison to a spontaneous fermentation process without starter culture (control batch). The polyamines spermine, spermidine, and diaminopropane were not influenced by the ripening, and their levels slightly decreased in all the batches throughout the storage. Tyramine, cadaverine, and putrescine were the main amines formed during the ripening. The addition of starter culture resulted in a decrease on the biogenic amine formation, depending on the strain inoculated. A great reduction in tyramine content was achieved when L. sakei CTC494 was inoculated, whereas L. curvatus CTC371 only attenuated tyramine accumulation compared with the control batch. Both starters were able to significantly limit the production of putrescine and cadaverine, and they inhibited tryptamine and phenylethylamine formation by the wild microbial flora. Tyramine levels of the control sausages rose during the storage at both temperatures, whereas those of cadaverine only increased at 19 degrees C. On the contrary, sausages manufactured through the starter controlled fermentation did not show changes of amine contents during the storage. The addition of a proper selected starter culture is advisable to produce safer sausages with low contents of biogenic amines.

Animals↗
PubMed2001

Effectiveness of a Lactobacillus sakei starter culture in the reduction of biogenic amine accumulation as a function of the raw material quality.

The effectiveness of an amine-negative starter culture (Lactobacillus sakei CTC494) in the reduction of biogenic amine production during the ripening of fermented sausages was examined. Four batches were manufactured in parallel: spontaneously fermented and starter-mediated sausages were manufactured from two lots of raw materials of different hygienic quality. Besides the biogenic amine contents, changes in the microbial counts, nitrogenous fractions, pH, and water content were measured at several sampling points during the ripening process. In sausages manufactured from good quality meat, the starter strain of L. sakei reduced and even inhibited biogenic amine accumulation during sausage fermentation, the end products showing extremely low biogenic amine contents (tyramine levels less than 15 mg/kg of dry matter and putrescine and cadaverine levels less than 5 mg/kg of dry matter). Nevertheless, starter-mediated sausages made from poorer-quality raw materials showed much higher amine contents (308, 223, and 36 mg/kg of dry matter of cadaverine, tyramine, and putrescine, respectively), which were only slightly lower than those of the spontaneously fermented sausages made from the same raw materials. The relatively high bacterial numbers of raw materials of poorer-hygienic quality diminished the beneficial effect of the starter strain. Therefore, the effectiveness of the starter was strongly dependent on the hygienic quality of the raw materials used.

Animals↗
PubMed2003

Monitoring volatile and nonvolatile amines in dried and salted roes of tuna (Thunnus thynnus L.) during manufacture and storage.

Dried and salted roe, obtained from the reproductive organs of female tuna (Thunnus tynnus L.), is a typical fish-based food in the Mediterranean area of Spain. In the present study, we monitored the formation of volatile amines (trimethyamine nitrogen [TMA-N] and total basic volatile nitrogen [TBVN]) and nonvolatile amines (biogenic amines) in dried and salted tuna roe after processing and storage for 8 weeks at 4, 20, and 30 degrees C. The salting and drying process significantly increased the TBVN, cadaverine, tyramine, phenylethylamine, and tryptamine contents, and bacteria with histamine decarboxylase activity were detected both in raw and in dried and salted tuna roes. During storage of tuna roe, TMA-N and TBVN levels increased significantly after the fourth week of storage at 30 degrees C, whereas biogenic amine contents remained more or less constant. However, samples stored at 30 degrees C showed histamine formation after the first week of storage, with a concentration of < 50 ppm. The volatile and nonvolatile amine concentrations in tuna roe were below the consumer safety limit, with the exception of the total biogenic amine level in roe stored at 30 degrees C, which exceeded the European Community's recommended limit (300 ppm). These results indicate that in properly stored tuna roe, histamine formation will not represent a serious health risk to consumers unless the tuna roe has previously been mishandled.

Animals↗
PubMed2004

Comparison of biogenic amine profile in cheeses manufactured from fresh and stored (4 degrees C, 48 hours) raw goat's milk.

In this study, the evolution of microbial counts, biogenic amine contents, and related parameters (pH, moisture, and proteolysis) in goat cheese made from fresh raw milk or raw milk stored for 48 h at 4 degrees C was examined. In both cases the milk was nonpasteurized. This study was designed to evaluate the effect of milk quality on the profile of biogenic amines in relation to the evolution of the microbial population during cheese making. Cheese made from raw milk stored for 48 h at 4 degrees C showed the highest microbial counts and biogenic amine levels. The storage of milk under refrigeration caused significant increases in the levels of some microbial and biogenic amines during ripening, but not initially. Tyramine was the main biogenic amine in the two cheeses tested, followed by cadaverine. However, the main differences in amine contents between batches were found for putrescine, histamine, and beta-phenylethylamine, whose levels were more than twofold higher in samples from raw milk refrigerated for 48 h than in samples from fresh milk.

Animals↗
PubMed1985

Cytotoxicity of spergualin and amine oxidase activity in medium.

The cytotoxicity of spergualin on cultured L5178Y cells is dependent on the kind of serum contained in culture media. Spergualin has stronger cytotoxicity to L5178Y cells in calf serum (IC50 = 2 micrograms/ml) than in horse serum (IC50 = 60 micrograms/ml). This was thought to be caused by amine oxidase in sera. Because calf serum was rich in amine oxidase and horse serum was very poor. Spergualin was found to be oxidized by either calf serum or amine oxidase purified from beef plasma. Aminoguanidine, an amine oxidase inhibitor suppressed the spergualin effect to inhibit the growth of L5178Y cells in calf serum to the level in horse serum. On the other hand, in horse serum the spergualin cytotoxicity was enhanced by addition of amine oxidase. These results suggested to us that spergualin might be inactive in itself and that the amine oxidase-oxidized product might play an essential role in inhibiting the growth of cells.

Amine Oxidase (Copper-Containing)↗
PubMed1999

Elevated activity of semicarbazide-sensitive amine oxidase in blood from patients with skeletal metastases of prostate cancer.

The semicarbazide-sensitive amine oxidases constitute a group of copper-containing enzymes whose physiological function is unclear. The enzymes are present in various tissues, including blood plasma. At present, the source of the plasma enzyme in humans is not known. Results of a recent study suggested that semicarbazide-sensitive amine oxidase is expressed in the skeleton, e.g. in the spine. Using an indirect autoradiographic method in mice, we provide evidence that semicarbazide-sensitive amine oxidase is present in high abundance in bone tissue. Specific activities of semicarbazide-sensitive amine oxidase were estimated in blood samples from subjects with femoral bone fractures. Moreover, enzyme activities were also measured in patients suffering from prostate cancer with skeletal metastases. The level of specific semicarbazide-sensitive amine oxidase activity in serum was significantly elevated in patients with skeletal metastases compared with both healthy controls and patients having prostate cancer without signs of skeletal metastases. Based on the results of the present study, we propose that semicarbazide-sensitive amine oxidase in blood plasma may originate, at least in part, from the skeleton.

Aged↗