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PubMed1989

Carcinogenic activity of endogenously synthesized N-nitrosobis(2-hydroxypropyl)amine in rats administered bis(2-hydroxypropyl)amine and sodium nitrite.

The carcinogenic activity of endogenously synthesized N-nitrosobis(2-hydroxypropyl)amine (BHP) was investigated in male Wistar rats administered bis(2-hydroxypropyl)amine (BHPA) mixed in powder diet at a concentration of 1%, and sodium nitrite (SN) dissolved in distilled water at concentrations of 0.15 and 0.3%, for 94 weeks. Urinary excretion of BHP was detected in rats given 1% BHPA and 0.3% SN but not in the groups receiving either of these precursors alone. Nasal cavity, lung, esophagus, liver and urinary bladder tumors were found in animals treated with combinations of 1% BHPA and 0.15 or 0.3% SN, suggesting that the target organs of the endogenously synthesized BHP are similar to those affected when the carcinogen is administered exogenously. The incidences of nasal cavity and lung tumors reached 74 and 58% in rats given 1% BHPA and 0.3% SN, respectively. Tumors at sites other than target organs were only found at levels similar to those previously reported for spontaneous tumors in male Wistars. The present results clearly indicated the tumor inducibility of a nitrosatable amine, BHA, through an endogenous nitrosation by feeding to rats in conjunction with nitrite, and provide further suggestive evidence that endogenous nitrosations of environmental nitrosatable amines can be a potential risk factor in human cancer development.

Animals↗
PubMed1988

Carcinogenic potency of N-nitrosomethyl(2-hydroxypropyl)amine and other metabolic relatives of N-nitrosobis(2-hydroxypropyl)amine by single intraperitoneal injection on the lung of rats.

The carcinogenic effects of a single intraperitoneal injection of N-nitrosobis(2-hydroxypropyl)amine (BHP) or its metabolic relatives, N-nitrosomethyl(2-hydroxypropyl)amine (MHP), N-nitrosobis(2-oxopropyl)amine (BOP), N-nitroso(2-hydroxypropyl)(2-oxopropyl)amine (HPOP) and N-nitroso-2,6-dimethylmorpholine (NDMM), were studied in male Wistar rats. The main target organ of these nitrosamines proved to be the lung, followed by the thyroid. Lung lesions were induced in a dose-dependent manner with total lung tumor incidences reaching 55% to 100%. BHP, MHP, HPOP and NDMM all caused lung carcinomas to develop (22% to 44% incidence), whereas BOP was only associated with adenomas. On the basis of dose administered and incidence of carcinomas, MHP appeared to be the most potent lung carcinogen of the five nitrosamines investigated. Smaller numbers of neoplasms were also induced in the kidney, urinary bladder, esophagus and intestine at differing rates by these nitrosamines.

Animals↗
PubMed1994

Deamination of aliphatic amines by type B monoamine oxidase and semicarbazide-sensitive amine oxidase; pharmacological implications.

Straight and branched chain aliphatic monoamines, which are not normal tissue constituents, are deaminated selectively by type B monoamine oxidase (MAO-B). They exhibit a high affinity towards the active site of MAO-B and this made them very useful pharmacologically. An anticonvulsant prodrug, Milacemide [2-(N-pentyl)glycinamide] is deaminated by MAO-B and this facilitates a mechanism of delivering glycine into the CNS. We have found that 2-propyl-pentylamine (2-propyl-1-aminopentane) and N-(2-propylpentyl)glycinamide are also converted by MAO-B to valproic acid and glycine both in vitro and in vivo; these compounds, however, cause severe tremor. By attaching a propargylamine group the resultant series of aliphatic propargylamine derivatives have been shown to be very potent selective MAO-B inhibitors. They are chemically quite different from most other MAO-B inhibitors, since they do not possess any aromatic structures. The relatively short chain aliphatic propargylamines, i.e. N-2-pentyl-N-methylpropargylamine and N-2-hexyl-N-methylpropargylamine, are 4 to 5 times more potent and more selective than selegiline (1-deprenyl) with respect to the inhibition of MAO-B in brain following oral administration. Semicarbazide-sensitive amine oxidase (SSAO) catalyzes the deamination of not only longer chain aliphatic amines but also short chain aliphatic amines including methylamine. Formaldehyde is produced from methylamine by SSAO. Increased methylamine deamination may cause cellular damage in some pathological conditions, such as uraemia and diabetes. We have observed that cultured human endothelial cells are damaged by methylamine in the presence of SSAO. Inhibition of the SSAO activity completely protects these cells from the methylamine-SSAO induced damage.

Amine Oxidase (Copper-Containing)↗
PubMed1994

Several aspects on the amine oxidation by semicarbazide-sensitive amine oxidase (SSAO) from bovine lung.

The lung has been shown to be potentially important in the metabolism of amines. Since SSAO has been demonstrated to be active towards some volatile short-chain aliphatic amines in other tissues, the current study determined the specificity and kinetic constants for the metabolism by bovine lung SSAO, of several aliphatic and aromatic amines some of which have been suggested to be physiological substrates (e.g. methylamine, aminoacetone and beta-phenylethylamine), and others (e.g. benzylamine) which are non-physiological. In the case of benzylamine, an inhibition at high substrate concentration was observed. Kinetic assays ruled out the possibility that this inhibition was caused by products of the deamination of benzylamine, and consequently it is suggested that these results may indicate the presence of two binding sites for the interaction of benzylamine with SSAO.

Amine Oxidase (Copper-Containing)↗
PubMed1981

Arthrobacter P1, a fast growing versatile methylotroph with amine oxidase as a key enzyme in the metabolism of methylated amines.

A facultative methylotrophic bacterium was isolated from enrichment cultures containing methylamine as the sole carbon source. It was tentatively identified as an Arthrobacter species. Extracts of cells grown on methylamine or ethylamine contained high levels of amine oxidase (E.C. 1.4.3) activity. Glucose- or choline-grown cells lacked this enzyme. Oxidation of primary amines by the enzyme resulted in the formation of H2O2; as a consequence high levels of catalase were present in methylamine- and ethylamine-grown cells. The significance of catalase in vivo was demonstrated by addition of 20 mM aminotriazole (a catalase inhibitor) to exponentially growing cells. This completely blocked growth on methylamine whereas growth on glucose was hardly affected. Cytochemical studies showed that methylamine-dependent H2O2 production mainly occurred on invaginations of the cytoplasmic membrane. Assimilation of formaldehyde which is generated during methylamine oxidation was by the FBP variant of the RuMP cycle of formaldehyde fixation. The absence of NAD-dependent formaldehyde and formate dehydrogenases indicated the operation of a non-linear oxidation sequence for formaldehyde via hexulose phosphate synthase. Enzyme profiles of the organism grown on various substrates suggested that the synthesis of amine oxidase, catalase and the enzymes of the RuMP cycle is not under coordinate control.

Amine Oxidase (Copper-Containing)↗
PubMed2004

Elusive amines and cluster headache: mutational analysis of trace amine receptor cluster on chromosome 6q23.

Cluster headache (CH) is characterised by unilateral pain and ipsilateral autonomic features. To date, no molecular genetic evidence has been shown for CH. Small pedigrees and low penetrance render the identification of the CH-gene quite difficult. Nonetheless the association of CH and migraine to a new class of amine, namely trace or elusive amines such as tyramine, octopamine and synephrine, has recently been demonstrated. In particular, in comparison to healthy control subjects, all these neurotransmitters have been found to be greatly elevated in CH sufferers in plasma and platelets both in active and remission periods. A cluster of gene-encoding G-protein-coupled receptors that bind and are activated by trace amines was identified in the long arm of chromosome 6q23. We evaluated two families with CH by linkage analysis to 6q23 region and the mutation scanning of the TAR 1, TAR 3, TAR 4, TAR 5, PNR and GPR58 genes by denaturing high liquid chromatography is in progress in 16 familial cases.

Biogenic Amines↗
PubMed2005

Nuclear amination catalyzed by fungal laccases: reaction products of p-hydroquinones and primary aromatic amines.

[reaction: see text] Nuclear amination of p-hydroquinones with primary aromatic amines was catalyzed by fungal laccases (EC 1.10.3.2) from Trametes spec. and Myceliophthora thermophila. This is the first report of laccase-catalyzed synthesis of aminoquinones. Incubation of two compounds with laccase in the presence of oxygen resulted in the formation of the corresponding monoaminated or diaminated quinones. No hydroquinonoids were formed. Observed differences in the reaction courses for different p-hydroquinones and aromatic amines with different laccases are discussed.

Amination↗
PubMed2007

Saturated amine oxides: Part 8. Hydroacridines: Part 27. Effects of N-oxidation and of N-quaternization on the 15N NMR chemical shifts of N-methylpiperidine-derived mono-, bi-, and tricycloaliphatic tertiary amines.

The (15)N chemical shifts of 13 N-methylpiperidine-derived mono-, bi- and tricycloaliphatic tertiary amines, their methiodides and their N-epimeric pairs of N-oxides were measured, and the contributions of specific structural parameters to the chemical shifts were determined by multilinear regression analysis. Within the examined compounds, the effects of N-oxidation upon the (15)N chemical shifts of the amines vary from +56 ppm to +90 ppm (deshielding), of which approx. +67.7 ppm is due to the inductive effect of the incoming N(+)--O(-) oxygen atom, whereas the rest is due to the additive shift effects of the various C-alkyl substituents of the piperidine ring. The effects of quaternization vary from -3.1 ppm to +29.3 ppm, of which approx. +8.9 ppm is due to the inductive effect of the incoming N(+)--CH(3) methyl group, and the rest is due to the additive shift effects of the various C-alkyl substituents of the piperidine ring. The shift effects of the C-alkyl substituents in the amines, the N-oxides and the methiodides are discussed.

Acridines↗
PubMed2006

Correlation between microbial flora, sensory changes and biogenic amines formation in fresh chicken meat stored aerobically or under modified atmosphere packaging at 4 degrees C: possible role of biogenic amines as spoilage indicators.

This study evaluated the formation of biogenic amines (BAs) in breast chicken meat during storage under aerobic and modified atmospheric packaging (MAP) conditions at 4 degrees C, the correlation of microbial and sensory changes in chicken meat with formation of BAs and the possible role of BAs as indicators of poultry meat spoilage. Poultry breast fillets were stored aerobically or under MAP (30%, CO(2), 70% N(2)) at 4 degrees C for up to 17 days. Quality evaluation was carried out using microbiological, chemical and sensory analyses. Total viable counts, Pseudomonads and Enterobacteriaceae, were in general higher for chicken samples packaged in air whereas lactic acid bacteria (LAB) and Enterobacteriaceae were among the dominant species for samples under MAP. Levels of putrescine and cadaverine increased linearly with storage time and were higher in aerobically stored chicken samples. Spermine and spermidine levels were also detected in both aerobically and MAP stored chicken meat. Levels of tyramine in both chicken samples stored aerobically and or under MAP were low (< 10 mg kg(-1)) whereas the formation of histamine was only observed after day 11 of storage when Enterobacteriaceae had reached a population of ca. 10(7) CFU g(-1). Based on sensory and microbiological analyses and also taking into account a biogenic amines index (BAI, sum of putrescine, cadaverine and tyramine), BAI values between 96 and 101 mg kg(-1) may be proposed as a quality index of MAP and aerobically-packaged fresh chicken meat. Spermine and spermidine decreased steadily throughout the entire storage period of chicken meat under aerobic and MAP packaging, and thus these two amines cannot be used as indicators of fresh chicken meat quality.

Aerobiosis↗
PubMed1983

Conversion of a primary amine to a labeled secondary amine by the addition of phenolic group and radioiodination.

To preserve the nucleophilicity of amino compounds during conjugative radioiodination, a new method for converting primary amines to phenolic secondary amines was developed. Amino acids were used as model compounds for establishing optimal conditions for the reductive amination. In the first step of the reaction, the aldehyde group of 4-hydroxybenzaldehyde (formylphenol) was reacted reversibly with an amino group to form an imine. The irreversible attachment of formylphenol to the amino group was accomplished by reduction of the imine with sodium cyanoborohydride. The pH optimum for the reaction was 5.0. Higher temperature has favorable effects on the rate and extent of the conjugation. Phenolic derivatives of amino compounds suitable for radioiodination are produced by the reactions described.

Amines↗
PubMed1988

Formation of quaternary amines by N-methylation of azaheterocycles with homogeneous amine N-methyltransferases.

Catalytic activities of two amine N-methyltransferases were documented for the following azaheterocycles: isomeric phenyl- and bispyridyls; 2-, 3- and 4-mono-substituted pyridines; and a miscellaneous group of azaheterocycles that included mono- and diazabenzenes and mono- and diazanaphthalenes. The broad substrate specificities of the two amine N-methyltransferases for primary and secondary amines are here extended to a large number of aromatic azaheterocycles in which N-methylation results in the formation of quaternary ammonium metabolites. Pyridine was the best substrate for both enzymes. Substitution in the ring at the 2-position sterically hindered methylation of the pyridyl nitrogen; 2-phenylpyridine and 2,2'-bispyridyl were not substrates.

Amines↗
PubMed2003

Determination of biogenic amines as dansyl derivatives in alcoholic beverages by high-performance liquid chromatography with fluorimetric detection and characterization of the dansylated amines by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry.

A sensitive high-performance liquid chromatographic method for the simultaneous determination of 11 biogenic amines has been developed. The method involves addition of an internal standard (1,7-diaminoheptane), pre-column dansylation of the amines and subsequent solid-phase extraction of the derivatives through C18 cartridges. The dansylamides were separated on an Inertsil ODS-3 column (250 x 4 mm I.D., 5 microm) using a 35-min gradient elution with a binary system of acetonitrile-water, a flow-rate of 1 ml min(-1) and fluorescence detection at excitation and emission wavelengths of 320 and 523 nm, respectively. The identity of the dansyl derivatives was confirmed by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. Linearity of derivatization was obtained for concentrations ranging from 0.008 to 40.0 mg l(-1). The within- and between-day relative standard deviations ranged from 0.2 to 7.6% and 0.3 to 8.6%, respectively. The overall process was successfully applied to identify and quantify biogenic amines in white-, red- and Retsina Greek wines and Greek beers, after treatment with polyvinylpyrrolidone.

Alcoholic Beverages↗
PubMed1998

Novel (N-ferrocenylmethyl)amines and (N-ferrocenylmethylen)imines derived from vicinal steroid amino alcohols and amines: synthesis, molecular structure, and biological activity.

Novel steroidal (N-ferrocenylmethyl)amines with potential biologic activity and of potential interest as chiral ligands for metal complexation were synthesized. The new compounds were screened in vitro for their potential as antimicrobial agents. The synthesis of the new steroidal ferrocenes, including two X-ray crystal structures and biologic assays, are described. The 16-(ferrocenylmethyl)amino-estratrienes 4a-d, 7b, and 10b exhibited outstanding broad antimicrobial activity particularly against mycobacteria and multi-resistant staphylococci. Thus, they can be considered as new lead structures. In contrast, the analogous 3 alpha-(ferrocenylmethyl)amino-cholestanes 12 possessed only weak activity. The reaction of the four isomeric amino alcohols 1a-d (Scheme 1) with ferrocenecarbaldehyde was studied. 1b and 1c with 16/17-trans configuration yielded nearly quantitatively the (E)-Schiff bases 2b and 2c (Scheme 2). In contrast to the trans-compounds, condensation of the cisconfigurated amino alcohols 1a and 1d furnished tautomeric mixtures of the Schiff bases (2a and 2d, respectively) and their corresponding 1,3-oxazolidines (3a and 3d, respectively). The novel (N-ferrocenylmethyl)amines 4a-d were obtained in excellent yields by reduction of the tautomer mixtures and the uniform Schiff bases with sodium borohydride in ethanol. Starting with the 16 beta-hydroxy compound 5a, the synthesis of 16 beta- and 16 alpha-amino-3-methoxy-estra-1,3,5(10)-triene (6b, 9b) is described. The corresponding 16-(N-ferrocenylmethyl)amines 7b and 10b and the 3 alpha-(N-ferrocenylmethyl)amino-cholestanes 12 were synthesized (Scheme 3) for comparison in biologic tests.

Alcohols↗
PubMed2000

Electromigration methods for amino acids, biogenic amines and aromatic amines.

Methods of electromigration in laboratory apparatus of small-bore size have recently undergone development at a remarkably rapid pace, leading to a variety of new analytical techniques. One such technique is called "capillary electrophoresis" (CE), which is further classified on the basis of electromigration mode, viz., "capillary zone electrophoresis" (CZE), which, in turn, has several variations. This review aims to give a short overview of the various electromigration methods for amino compounds by using CE. Firstly, this review briefly summarizes the detection methods employed for detection of monoamines and polyamines by CE for both native and derivative forms. Next, current CE methods are described, and their applications to detection of amino acids, biogenic amines, aromatic amines, including heteroaromatic amines and their enantiomers, are introduced from representative papers. Finally, new methods for single-cell analysis and microchip CE techniques are focused on.

Amines↗
PubMed2000

Haemoglobin adducts of aromatic amines: diamines and polyaromatic amines.

Aromatic amines and nitroarenes are important antioxidants and intermediates in the synthesis of dyes, pesticides and plastics. In the present paper we introduce methods for the synthesis of deuterated standards: 3-[2H8]aminofluoranthene, 3,3'-dimethyl-[2H4]benzidine, [2H4]benzidine, N'-acetyl-[2H4]benzidine, 2,4-[2H6]toluenediamine, 2,6-[2H6]toluenediamine. These standards have been used for the quantification of haemoglobin adducts of diamines and polyaromatic amines. Haemoglobin was hydrolysed in 0.1 M sodium hydroxide and the hydrolysate extracted with dichloromethane. The extracts were derivatised with heptafluorobutyric anhydride and analysed by GC-MS with negative chemical ionisation. In one run up to 15 aromatic amines can be determined: 6-aminochrysene, 3-aminofluoranthene, 2-aminofluorene, 1-aminopyrene, benzidine, 3,3'-dichlorobenzidine, 3,3'-dimethoxybenzidine, 3,3'-dimethylbenzidine, 3,3'-methylenedianiline, 4,4'-methylenedianiline, N'-acetyl-benzidine, N'-acetyl-4,4'-methylenedianiline, 4,4'-methylene bis(2-chloroaniline), 2,4-toluenediamine and 2,6-toluenediamine.

Amines↗
PubMed2005

Role of the interactions between the active site base and the substrate Schiff base in amine oxidase catalysis. Evidence from structural and spectroscopic studies of the 2-hydrazinopyridine adduct of Escherichia coli amine oxidase.

2-Hydrazinopyridine (2HP) is an irreversible inhibitor of copper amine oxidases (CAOs). 2HP reacts directly at the C5 position of the TPQ cofactor, yielding an intense chromophore with lambda(max) approximately 430 nm (adduct I) in Escherichia coli amine oxidase (ECAO). The adduct I form of wild type (WT-ECAO) was assigned as a hydrazone on the basis of the X-ray crystal structure. The hydrazone adduct appears to be stabilized by two key hydrogen-bonding interactions between the TPQ-2HP moiety and two active site residues: the catalytic base (D383) and the conserved tyrosine residue (Y369). In this work, we have synthesized a model compound (2) for adduct I from the reaction of a TPQ model compound (1) and 2HP. NMR spectroscopy and X-ray crystallography show that 2 exists predominantly as the azo form (lambda(max) at 414 nm). Comparison of the UV-vis and resonance Raman spectra of 2 with adduct I in WT, D383E, D383N, and Y369F forms of ECAO revealed that adduct I in WT and D383N is a tautomeric mixture where the hydrazone form is favored. In D383E adduct I, the equilibrium is further shifted in favor of the hydrazone form. UV-vis spectroscopic pH titrations of adduct I in WT, D383N, D383E, and 2 confirmed that D383 in WT adduct I is protonated at pH 7 and stabilizes the hydrazone tautomer by a short hydrogen-bonding interaction. The deprotonation of D383 (pKa approximately 9.7) in adduct I resulted in conversion of adduct I to the azo tautomer with a blue shift of the lambda(max) to 420 nm, close to that of 2. In contrast, adduct I in D383N and D383E is stable and did not show any pH-dependent spectral changes. In Y369F, adduct I was not stable and gradually converted into a new species with lambda(max) at approximately 530 nm (adduct II). A detailed mechanism for the adduct I formation in WT has been proposed that is consistent with the mechanism proposed for the oxidation of substrate by CAOs but addresses some key differences in the active site chemistry of hydrazine inhibitors and substrate amines.

Amine Oxidase (Copper-Containing)↗
PubMedDate not supplied

Directed covalent immobilization of aminated DNA probes on aminated plates.

A new protocol that enables the immobilization of DNA probes on aminated micro-titer plates activated with aldehyde-dextran via an amino group artificially introduced in the 3' end of the oligonucleotide probe is reported in this work. The method is based on the use of hetero-functional-dextran as a long and multifunctional spacer arm covalently attached to an aminated surface capable of immobilizing DNA oligonucleotides. The immobilization occurred only via the amino introduced in the 3' end of the probe, with no implication of the DNA bases in the immobilization, ensuring that the full length of the probe is available for hybridization. These plates having immobilized oligonucleotide probes are able to hybridize complementary DNA target molecules. The tailor-made hetero-functional aldehyde-aspartic-dextran together with the chemical blocking of the remaining primary amino groups on the support using acetic anhydride avoid the nonspecific adsorption of DNA on the surface of the plates. Using these activated plates, (studying the effect of the probe concentration, temperature, and time of the plate activation on the achieved signal), thus, the covalent immobilization of the aminated DNA probe was optimized, and the sensitivity obtained was similar to that achieved using commercial biotin-streptavidin systems. The new DNA plates are stable under very drastic experimental conditions (90% formamide, at 100 degrees C for 30 min or in 100 mM NaOH).

Adsorption↗