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Results for “Propylamines”

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At least 19 recordsLinked to original sources
PubMed1996

Nitrogen-14 NMR Study on Solvent Exchange of the Octahedral Cobalt(II) Ion in Neat 1,3-Propanediamine and n-Propylamine at Various Temperatures and Pressures. Tetrahedral-Octahedral Equilibrium of the Solvated Cobalt(II) Ion in n-Propylamine As Studied by EXAFS and Electronic Absorption Spectroscopy.

Solvated cobalt(II) ions in neat 1,3-propanediamine (tn) and n-propylamine (pa) have been characterized by electronic absorption spectroscopy and extended X-ray absorption fine structure (EXAFS) spectroscopy. The equilibrium between tetrahedral and octahedral geometry for cobalt(II) ion has been observed in a neat pa solution, but not in neat diamine solutions such as tn and ethylenediamine (en). The thermodynamic parameters and equilibrium constant at 298 K for the geometrical equilibrium in pa were determined to be DeltaH degrees = -36.1 +/- 2.3 kJ mol(-1), DeltaS degrees = -163 +/- 8 J mol(-1) K(-1), and K(298) = 6.0 x 10(-3) M(-2), where K = [Co(pa)(6)(2+)]/{[Co(pa)(4)(2+)][pa](2)}. The equilibrium is caused by the large entropy gain in formation of the tetrahedral cobalt(II) species. The solvent exchange of cobalt(II) ion with octahedral geometry in tn and pa solutions has been studied by the (14)N NMR line-broadening method. The activation parameters and rate constants at 298 K for the solvent exchange reactions are as follows: DeltaH() = 49.3 +/- 0.9 kJ mol(-1), DeltaS() = 25 +/- 3 J mol(-1) K(-1), DeltaV() = 6.6 +/- 0.3 cm(3) mol(-1) at 302.1 K, and k(298) = 2.9 x 10(5) s(-1) for the tn exchange, and DeltaH() = 36.2 +/- 1.2 kJ mol(-1), DeltaS() = 35 +/- 6 J mol(-1) K(-1), and k(298) = 2.0 x 10(8) s(-1) for the pa exchange. By comparison of the activation parameters with those for the en exchange of cobalt(II) ion, it has been confirmed that the kinetic chelate strain effect is attributed to the large activation enthalpy for the bidentate chelate opening and that the enthalpic effect is smaller in the case of the six-membered tn chelate compared with the five-membered en chelate.

Journal Article↗
PubMed1972

Metabolism of Propane, n-Propylamine, and Propionate by Hydrocarbon-Utilizing Bacteria.

Studies were conducted on the oxidation and assimilation of various three-carbon compounds by a gram-positive rod isolated from soil and designated strain R-22. This organism can utilize propane, propionate, or n-propylamine as sole source of carbon and energy. Respiration rates, enzyme assays, and (14)CO(2) incorporation experiments suggest that propane is metabolized via methyl ketone formation; propionate and n-propylamine are metabolized via the methylmalonyl-succinate pathway. Isocitrate lyase activity was found in cells grown on acetate and was not present in cells grown on propionate or n-propylamine. (14)CO(2) was incorporated into pyruvate when propionate and n-propylamine were oxidized in the presence of NaAsO(2), but insignificant radioactivity was found in pyruvate produced during the oxidation of propane and acetone. The n-propylamine dissimilatory mechanism was inducible in strain R-22, and amine dehydrogenase activity was detected in cells grown on n-propylamine. Radiorespirometer and (14)CO(2) incorporation studies with several propane-utilizing organisms indicate that the methylmalonyl-succinate pathway is the predominant one for the metabolism of propionate.

Journal Article↗
PubMed1982

Mode of action of 3-substituted propylamine cytotoxicity in culture cells.

Cytotoxic effects on MDBK cells of various 3-substituted propylamines, including spermine and spermidine, were tested in culture in the presence of calf serum, and the possible mode of action was studied from the viewpoint of oxidative deamination leading to acrolein formation. The compounds were roughly classified in two groups with IC50 values of 0.1 and 0.4 mM under the conditions used. Phenyl derivatives of 3-substituted propylamines, 3-benzylaminopropylamine, and polyamines were included in the first group with IC50 values of 0.1 mM, and acrolein was liberated from these compounds after incubation with bovine plasma amine oxidase. Alkyl derivatives of 3-substituted propylamines (with IC50 values of 0.4 mM), on the other hand, were unable to release acrolein after the oxidative deamination, which was further confirmed by a lack of liberation of acrolein from the authentic 3-butoxypropanal. These observations indicated that both the acrolein originating from the 3-substituted propanals, and the propanal as such, were possibly involved in manifestation of the cytotoxicity of the 3-substituted propylamines. Thus, spermine and spermidine may exert their cytotoxic effects on the cells in vitro by a combination of two mechanisms involving acrolein and oxidized polyamines.

1-Propanol↗
PubMed1985

Metabolism of N-nitrosodi-n-propylamine and N-nitrosodiallylamine by isolated rat hepatocytes.

Isolated rat hepatocytes were incubated with approximately equimolar amounts of N-nitrosodi-n-propylamine (NDPA) and N-nitrosodiallylamine (NDAA) in order to compare their metabolism. The principal metabolite of NDPA was N-nitroso-(2-hydroxypropyl)propylamine, which was present as a glucuronide. N-Nitroso-(3-hydroxypropyl)propylamine and N-nitrosopropyl-(carboxyethyl)amine were minor metabolites; no N-nitrosomethylpropyl-amine (NMPA) was detected. A single N-nitroso metabolite of NDAA was found and identified as N-nitroso-(2,3-dihydroxypropyl)allylamine. These data indicate that the allyl group of N-nitrosodiallylamine is readily oxidized by hepatocytes in vitro. It appears unlikely that N-nitrosomethylpropylamine is an intermediate in N-nitrosodi-n-propylamine metabolism.

Animals↗
PubMed1986

Purification and characterization of propylamine transferase from Sulfolobus solfataricus, an extreme thermophilic archaebacterium.

The enzyme propylamine transferase, catalyzing the transfer of the propylamine moiety from S-adenosyl(5')-3-methylthiopropylamine to several amine acceptors, has been purified 643-fold in 20% yield from Sulfolobus solfataricus, an extreme thermophilic archaebacterium optimally growing at 87 degrees C. The purified enzyme (specific activity 2.05 units/mg protein), is homogeneous by criteria of gel electrophoresis, gel filtration, isoelectric focusing and ultracentrifugation analysis. The molecular mass of the native enzyme was estimated to be about 110 kDa by gel permeation and ultracentrifugation analysis. The protein migrates on SDS/polyacrylamide gel electrophoresis as a single band of 35 kDa, suggesting that the enzyme is a trimer composed by identical subunits. An optimum pH of 7.5 and an acidic isoelectric point of 5.3 have been calculated. The optimum temperature was 90 degrees C and no loss of activity is observable even after exposure of the purified enzyme to 100 degrees C for 1 h. No reducing agents are required for enzymatic activity. Substrate specificity towards the amine acceptors is rather broad in that 1,3-diaminopropane (Km = 1675 microM), putrescine (Km = 3850 microM), sym-norspermidine (Km = 954 microM) and spermidine (Km = 1539 microM) are recognized as substrates. Conversely S-adenosyl(5')-3-methylthiopropylamine is the only propylamine donor (Km = 7.9 microM) and the deamination of the sulfonium compound prevents the recognition by the enzyme. The reaction is irreversible and initial-rate kinetic studies indicate that the propylamine transfer is operated through a sequential mechanism. 5'-Methylthioadenosine, a product of the reaction, acts as a powerful competitive inhibitor with a Ki of 3.7 microM. Enzyme-substrate binding sites have been investigated with the aid of several substrate analogs and products. Among the compounds assayed, 5'-methylthiotubercidin, S-adenosyl(5')-3-thiopropylamine and S-adenosyl-3-thio-1,8-diaminooctane are the most active inhibitors.

Archaea↗
PubMed1978

Identification of ejaculate derived propylamine found in collagen sponge contraceptives.

Propylamine is identified as one of the compounds present in odoriferous intravaginal contraceptive sponges from sexually active women. This compound also appears in samples of human ejaculate incubated at 37 degrees C for seven days. We have identified propylamine by gas liquid chromatography, mass spectroscopy and as N-propylbenzoylamide. Evidently the compound forms enzymatically from spermine and spermidine. We believe that this is the first time that propylamine has been identified as forming from human tissue.

Collagen↗
PubMed2006

Adsorption behavior of propylamine on activated carbon fiber surfaces as induced by oxygen functional complexes.

In this study, the surfaces of activated carbon fibers (ACFs) were modified by nitric acid to introduce surface oxygen complexes and to observe the influence of those complexes on the propylamine adsorption of the ACFs. It was found that the oxygen complexes including carboxylic and phenolic groups were predominantly increased, resulting in the increase of total surface acidity. However, the specific surface areas and the total pore volumes of the modified ACFs were decreased by 5-8% due to the increased blocking (or demolition) of micropores in the presence of newly introduced complexes. Despite the decrease of textural properties, it was found that the amount of propylamine adsorbed by the modified ACFs was increased by approximately 17%. From the XPS results, it was observed that propylamine reacted with strong or weak acidic groups, such as COOH or OH, on the ACF surfaces, resulting in the formation of pyrrolic-, pyridonic-, or pyridine-like structures.

Adsorption↗
PubMed1997

A novel class of potent gamma-aminobutyric acid aminotransferase inhibitor, 3-(hydroxyamino)propylamine and analogues.

Hydroxyamino analogues of gamma-aminobutyric acid (GABA) were synthesized and evaluated for inhibitory activity toward gamma-aminobutyric acid aminotransferase (GABA-T). The title compound, 3-(hydroxyamino)propylamine (HPA), showed a potent inhibitory activity. The inhibition is competitive with respect to GABA and the Ki value of GABA-T for HPA is 0.4 mmol. The activity of inhibition is comparable to those of aminoxyacetic acid and valproic acid. 3-(Hydroxyaminomethyl)piperidine (3HMP), a cyclic analogue of HPA, also showed a potent inhibitory activity, whereas 3-(methoxyamino)propylamine (OMe-HPA), 3-(N-hydroxy-N-methylamino)propylamine (NMe-HPA) and 4-(hydroxyamino)piperidine (4HP) showed weak activity.

4-Aminobutyrate Transaminase↗
PubMed1980

Mechanism of propylamine-transfer reactions. Kinetic and inhibition studies on spermidine synthase from Escherichia coli.

Spermidine synthase (EC 2.5.1.16) purified from Escherichia coli has been subjected to a kinetic analysis including initial velocity and substrate analogs inhibition studies. Evidence is reported for a ping-pong mechanism, indicating that a propylaminated form of the enzyme is an obligatory intermediate in the reaction mechanism. S-Adenosyl(5')-3-methylthiopropylamine exerts a competitive substrate inhibition by combining with the improper stable enzyme form, while putrescine does not show any inhibitory effect. In order to investigate the substrate binding sites, new sulfonium-deaminated analogs of S-adenosyl(5')-3-methylthiopropylamine have been synthesized and assayed as substrates and as inhibitors of the reaction. The replacement of the amino group of adenine, or propylamine moiety of the sulfonium compound by the hydroxyl group, or both, resulted in a complete loss of activity as substrate. On the other hand, the deaminated analogs exert a competitive inhibition with respect to putrescine. On the basis of these results and in analogy with methyltransfer reactions, three recognition sites for S-adenosyl(5')-3-methylthiopropylamine on propylamine transfer enzymes are proposed.

Binding Sites↗
PubMed1994

Experimental vitreous replacement with perfluorotri-n-propylamine.

OBJECTIVE: To evaluate perfluorotri-n-propylamine, a perfluorocarbon oil, as a temporary vitreous replacement in rabbits. METHODS: After undergoing gas compression vitrectomy, rabbits were injected with perfluorotri-n-propylamine for 24 hours or 2 weeks. The rabbits were evaluated clinically and with electroretinography. The globes were then enucleated and processed for histological evaluation. RESULTS: Clinical results showed droplet dispersion in the 2-week but not in the 24-hour group. Histological evaluation showed no changes in the retinal pigment epithelium or photoreceptor outer segments. Foam cells were seen in the 2-week but not in the 24-hour group. There was a marked dampening of the electroretinographic response that normalized after the removal of the oil. CONCLUSIONS: Perfluorotri-n-propylamine demonstrated no retinal toxic side effects in rabbits and is a promising liquid perfluorocarbon oil.

Animals↗
PubMed1995

Synthesis of uridine-5-propylamine derivatives and their use in affinity chromatography of N-acetylglucosaminyltransferases I and II.

The C-5 substituted uridine derivatives UDP-5-propylamine (7) and UDP-GlcNAc-5-propylamine (8) were synthesized in good yields by Heck alkylation of the 5-mercuriuridines, followed by hydrogenation. The products were characterized by 1H and 13C NMR spectroscopy, electrospray mass spectrometry and UV spectrophotometry. The amines are of interest for the preparation of affinity probes for glycosyltransferases. The benzoylbenzamides of 7 and 8 show strong competitive inhibition of N-acetylglucosaminyltransferase I and II with Ki values ranging from 30 to 100 microM (without irradiation) and may be useful as active site-directed photoaffinity labels. A conjugate of 8 and Sepharose was used for affinity chromatographic purification of N-acetylglucosaminyltransferases I and II. The results indicate that this affinity gel is a stable alternative to the commonly used but unstable UDP-GlcNAc-5-Hg-thiopropyl conjugate.

Affinity Labels↗
PubMedDate not supplied

Estrogen quinones: reaction with propylamine.

Reaction of propylamine with 2,3-estrone o-quinone (2,3-EQ) and 3,4-estrone o-quinone (3,4-EQ) gave a complex mixture of mostly unidentifiable products. Several reaction products were isolated and identified using spectroscopic techniques. With 3,4-EQ, both 1,2- and 1,6-Michael addition reactions were observed in which 4-hydroxyestradiol, an estrogen oxazole, and a violet compound identified as the iminoquinone adduct that was obtained by condensation of one molecule of an estrogen o-aminophenol with the 1,6-Michael addition product of propylamine to 3,4-EQ were identified. Unlike reactions of 3,4-EQ, only 1,2-Michael addition reactions were observed with 2,3-EQ leading to the formation of 2-hydroxyestradiol, two monoiminoquinone compounds, and a bisiminoquinone product.

Estrenes↗
PubMed2004

Allergic contact dermatitis from cocamidopropyl betaine, cocamidoamine, 3-(dimethylamino)propylamine, and oleamidopropyl dimethylamine: co-reactions or cross-reactions?

We present the case of a patient with facial dermatitis caused by sensitization to cocamidopropyl betaine. The patient also had positive patch-test reactions to cocamidoamine, 3-(dimethylamino)propylamine, and oleamidopropyl dimethylamine. The presence of 3-(dimethylamino)propylamine as an impurity in all of these substances can be hypothesized to explain these simultaneous reactions.

Adult↗
PubMed1983

Carcinogenesis in F344 rats by N-nitrosomethyl-n-propylamine derivatives.

The carcinogenicity of N-nitrosomethyl-n-propylamine and five of its derivatives, including N-nitrosomethyl-n-butylamine, was compared by oral administration of the compounds to inbred F344 rats. N-Nitromethyl-n-propylamine and N-nitrosomethyl-n-butylamine given in drinking water induced tumors of the upper gastrointestinal tract, mainly carcinomas of the esophagus, and appeared to be of comparable potency. N-Nitrosomethyl(2-hydroxypropyl)amine also mainly induced esophageal carcinomas (100% incidence) and lung tumors, whereas N-nitrosomethyl(2,3-dihydroxypropyl)amine mainly induced nasal cavity tumors and gave rise to a high incidence of esophageal tumors; however, it appeared to be less potent than the monohydroxy compound. N-Nitrosomethyl(2-oxopropyl)amine, the ketone corresponding to N-nitrosomethyl(2-hydroxypropyl)amine, was a more potent carcinogen than the latter at comparable doses in drinking water and gave rise to a high incidence of esophageal tumors and tumors of the trachea; female rats had a high incidence (15/20) of angiosarcomas of the liver, but only 2 male rats died with this tumor. When N-nitrosomethyl(2-oxopropyl)amine was administered at a lower dose in drinking water or at the same dose given by gavage, the incidence of esophageal tumors was lower and there were fewer carcinomas. After administration of large doses in drinking water to male and female rats, N-nitrosomethyl(3-carboxypropyl)amine, a urinary metabolite of several N-nitrosomethyl-n-alkylamines that induce tumors of the urinary bladder in rats, gave rise to a high incidence of transitional cell carcinomas of the bladder. The time to death of animals with these tumors was long, and there were few other tumors.

Administration, Oral↗
PubMed1977

Mechanism of alkylation by N-nitroso compounds: detection of rearranged alcohol in the microsomal metabolism of N-nitrosodi-n-propylamine and base-catalyzed decomposition of N-n-propyl-N-nitrosourea.

Metabolism of N-nitrosodi-n-propylamine by an isolated rat liver microsomal fraction yielded 17% isopropanol and 83% n-propanol (expressed as a percentage of total propanol formed). Base-catalyzed decomposition of N-n-propyl-N-nitrosourea yielded 39% isopropanol and 61% n-propanol. The values provide evidence for involvement of carbocations in both of these reactions.

Alcohols↗
PubMed2004

Synthesis of 4-methyl-thio-phenyl-propylamine and the evaluation of its interaction with different amine oxidases.

A new molecule, the 4-methyl-thio-phenyl-propylamine (PrNH(2)) was synthesized and its biological interaction with different amine oxidases such as semicarbazide sensitive amine oxidase (SSAO) [E.C.1.4.3.6], and monoamine oxidase [E.C.1.4.3.4] under its two isoforms, MAO A and MAO B, has been assessed. The substrate specifities of MAO and SSAO overlap to some extent. In this context, the search of new molecules, able to discriminate between these different amine oxidases is very important as it will allow greater elucidation of the SSAO's role in physiological and pathological conditions. We report for the first time, the synthesis and evaluation of a new molecule which has a high affinity towards the SSAO family of enzymes, more so than previously described and furthermore an ability to discriminate between the different amine oxidases.

Amine Oxidase (Copper-Containing)↗
PubMed2004

Synthesis and biological evaluation of novel propylamine derivatives as orally active squalene synthase inhibitors.

Squalene synthase inhibitors are potentially superior hypolipidemic agents. We synthesized novel propylamine derivatives, as well as evaluated their ability to inhibit squalene synthase and their lipid-lowering effects in rats. 1-Allyl-2-[3-(benzylamino)propoxy]-9H-carbazole (YM-75440) demonstrated potent inhibition of the enzyme derived from HepG2 cells with an IC(50) value of 63 nM. It significantly reduced both plasma total cholesterol and plasma triglyceride levels following oral dosing to rats with a reduced tendency to elevate plasma transaminase levels.

Administration, Oral↗