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PubMed1991

Stereospecific HPLC method for the quantitation of the enantiomers of MK-0571, a potent leukotriene D4 receptor antagonist, in biological specimens.

A stereospecific HPLC bioanalytical method was developed for quantitation of the enantiomers of MK-0571, a leukotriene D4 receptor antagonist. The procedure involves the addition of an internal standard analog to the biological matrix followed by extraction of the free acids into ethyl acetate. The acids are subsequently reacted with the homochiral reagent, (+)-(R)-alpha-(1-naphthyl)ethylamine (NEA) to form diastereomers. Following removal of excess reagent and side products by a dilute acid wash, the NEA-MK-0571 diastereomers are separated on a phenyl urea chiral column using a mobile phase containing hexane, isopropanol, and acetonitrile and are detected with a fluorescence detector. The sensitivity of the method is such that 50 ng of each enantiomer can be quantitated. In the 0.05 to 10 micrograms range the recoveries of the enantiomers of MK-0571 from plasma were 100.4 +/- 7.9% and 100.0 +/- 7.2%. NMR and mass spectral data confirmed the structure of the derivative. The method has been utilized in drug safety evaluation studies to demonstrate enantioselectivity in disposition of the enantiomers of MK-0571 in rats and monkeys but not in mice.

Animals↗
PubMed1983

Stimulation of tyrosinase activity of cultured melanoma cells by lysosomotropic agents.

The tyrosinase (EC 1.14.18.1) activity of cell-free extracts (TyH) of B16 melanoma cells cultured in the presence of 5 to 10 mM ammonium chloride was considerably higher than that of cells from control cultures. This increase in TyH in the presence of ammonium chloride seemed to be due to de novo synthesis of the enzyme, because it was inhibited by 1 microgram/ml of cycloheximide. In the presence of the latter, however, ammonium chloride did increase the tyrosinase activity of living cells in culture (TyC) resulting in about threefold increase in the TyC/TyH ratio, a measure of the extent of tyrosinase reaction exerted by the enzyme present in living cells. This higher TyC/TyH ratio induced by ammonium chloride was also observed in the absence of cycloheximide. Similar increases in TyH, TyC, and TyC/TyH occurred in the presence of methylamine or ethylamine instead of ammonium chloride, but not in the presence of tetraethylammonium chloride, and also in culture medium of higher pH. The apparently similar effects of lysosomotropic bases and medium of higher pH on the TyC/TyH ratio suggest that there are some mechanisms that control the intramelanosomal pH lower than the cytoplasmic pH.

Ammonium Chloride↗
PubMed1994

Ion pair formation involving methylated lysine side chains: a theoretical study.

Lysine residues with one, two, or three methyl groups substituted on the epsilon-nitrogen atom are found in many proteins. To evaluate the effect of the posttranslational methylation on ion-pair formation we have performed semiempirical and ab initio molecular orbital calculations, using the AM1 method and the 6-31G* basis set, respectively. Combinations of various methylated forms of methylamine and ethylamine with formate, acetate, and dimethyl phosphate were studied as model compounds. This approach allowed us to obtain information relevant to the interaction of the modified Lys residues with carboxylate groups of proteins, and the backbone of nucleic acids. We have found that the interaction energy decreases with an increasing number of methyl groups. Inclusion of a solvent reaction field in the semiempirical calculations gave reasonable values for the interaction energy in aqueous solution, when formate and acetate were the counterions. These studies suggest that, in addition to other factors, a weakening of ionic interactions contributes to the various physiological effects of lysine methylation.

Acetates↗
PubMed2006

Reduction of nitriles to amines in positive ion electrospray ionization mass spectrometry.

Some compounds readily form [M+46]+ adduct ions during positive ion electrospray ionization mass spectrometry ((+)ESI-MS) analysis. These [M+46]+ ions were characterized as [M+CH3CH2NH2+H]+ by accurate mass determination. Ethylamine involved in the adduct was proposed to be the reduction product of acetonitrile and this was confirmed using deuterated acetonitrile. Other nitrile-containing compounds tested, including isobutyronitrile and benzonitrile, also formed the adduct ions of the respective amine forms under (+)ESI-MS conditions. Hydrogen/deuterium exchange experiments demonstrated that the reductive hydrogen originated from water. Reduction of nitriles (R-CN) to their respective amines (R-CH2NH2) under (+)ESI-MS conditions expands the ability to identify nitrile-containing chemical unknowns.

Acetonitriles↗
PubMed1984

Catalytic and ligand binding properties of bovine trypsinogen and its complex with the effector dipeptide Ile-Val. A comparative study.

Steady-state and pre-steady-state kinetic data for the trypsinogen catalyzed hydrolysis of a series of synthetic substrates (i.e. p-nitrophenyl esters of N-alpha-carbobenzoxy-L-amino acids) have been obtained as a function of pH (3.4-8). Moreover, the effect of ethylamine on the hydrolysis of a neutral substrate and benzamidine binding have been extensively studied. In order to obtain direct information on the transition of trypsinogen to a beta-trypsin-like structure, the role of the effector dipeptide Ile-Val on the catalytic and ligand binding properties of the zymogen has been investigated. Kinetic and thermodynamic data for beta-trypsin and alpha-chymotrypsin are also reported for the purpose of an homogeneous comparison of the various (pro)enzymes. Under all the experimental conditions, kinetic data for (pro)enzyme catalysis are consistent with the minimum three-step mechanism: (formula; see text) involving the acyl intermediate E X P. In the presence of Ile-Val dipeptide, trypsinogen assumes catalytic and ligand binding properties that are reminiscent of activated beta-trypsin. This is at variance with free trypsinogen, which shows a alpha-chymotrypsin-like behavior. The large differences in the results of kinetic and thermodynamic measurements for free trypsinogen, as compared to its binary adduct with Ile-Val, can be ascribed to the substantial differences in the two molecular species, which include the spatial orientation of Asp189.

Animals↗
PubMed1986

Oxidation of amines by yeasts grown on 1-aminoalkanes or putrescine as the sole source of carbon, nitrogen and energy.

The maximum growth rate of Trichosporon cutaneum CBS 8111 in chemostat cultures was 0.185 h-1 on ethylamine and 0.21 h-1 on butylamine, that of Candida famata CBS 8109 was 0.32 h-1 on putrescine. The amine oxidation pattern of the ascomycetous strains studied, viz. Candida famata CBS 8109, Stephanoascus ciferrii CBS 4856 and Trichosporon adeninovorans CBS 8244 was independent of the amine that had been used as the growth substrate. It resembled that of benzylamine/putrescine oxidase found in other ascomycetous yeasts. However, differences in pH optimum and substrate specificity were observed between the amine-oxidizing systems of these three species. The amine oxidation pattern of cell-free extracts of Trichosporon cutaneum CBS 8111 varied with the amine that was used as growth substrate. The enzyme system produced by Cryptococcus laurentii CBS 7140 failed to oxidize isobutylamine and benzylamine, and showed a high pH optimum. The synthesis of amine oxidase in the four yeast strains studied was not repressed by ammonium chloride and was weakly repressed by glucose but was strongly repressed if both compounds were present in the growth medium.

Amines↗
PubMed1987

Permeability of ammonia and amines in Rhodobacter sphaeroides and Bacillus firmus.

Permeabilities of uncharged ammonia (NH3), methylamine (CH3NH2), and ethylamine (CH3CH2NH2) in the gram-negative phototrophic bacterium Rhodobacter sphaeroides were measured directly in cells grown heterotrophically under aerobic conditions. The permeability of NH3 was 2.55 +/- 0.73 microns s-1 (n = 20), but the permeabilities of CH3NH2 (MA) and CH3CH2NH2 (EA) were higher, PMA = 17.8 +/- 2.8 microns s-1 (n = 50), PEA = 24.7 +/- 3.9 microns s-1 (n = 44). The relative permeabilities of amines were also determined from their effect on the pH gradient across the cell membrane at alkaline external pH. In aerobically grown R. sphaeroides, both techniques indicated that the permeability of CH3CH2NH2 was about 30% greater than that of CH3NH2 but that the permeability of NH3 was only about 1/5 that of CH3NH2. The relative permeabilities of NH3 (A) and CH3NH2 were different in R. sphaeroides cells grown under three different physiological conditions: (a) cells grown aerobically with ammonium sulfate (PA/PMA about 0.20), (b) cells grown anaerobically with ammonium sulfate as their nitrogen source (PA/PMA about 0.29), and (c) diazotrophic cells (PA/PMA about 0.38). NH3 was also found to be only about 1/3 as permeable as CH3NH2 in the alkalophilic gram-positive bacterium Bacillus firmus. The findings that permeability properties of NH3 and CH3NH2 are very different in different bacteria and vary according to the conditions under which the organism is grown need to be taken into account in the interpretation of experiments where [14C]methylamine is used as an ammonia analog.

Aerobiosis↗
PubMed1980

Photosensitized cross-linking of erythrocyte membrane proteins. Evidence against participation of amino groups in the reaction.

Exposure of human erythrocyte ghosts (pH 8, 10 degrees C) to visible light in the presence of the photosensitizer, methylene blue, results in a relatively rapid loss of spectrin (bands 1 and 2 on sodium dodecyl sulfate gel electropherograms) and the appearance of high molecular weight cross-linked derivatives. Isolated spectrin also undergoes photosensitized cross-linking, indicating that the reaction is not lipid-dependent. Extensive cross-linking was neither reversed by dithiothreitol nor prevented by prior blocking of SH groups with N-ethylmaleimide, suggesting that cysteine residues are not crucial bridging sites. The possible requirement for NH2 groups, as suggested by previous model studies (Dubbelman, T.M.A.R., de Goeij, A.F.P.M. and van Steveninck, J. (1978) Biochim. Biophys. Acta 511, 141--151), was tested. Succinylation of spectrin protected against cross-linking, but this effect is attributed to the disruption of quaternary structure, as deduced from sedimentation measurements. However, virtually complete blocking of NH2 groups by amidination perturbed overall structure relatively little, and had no effect on cross-linking. Moreover, exogenous amines such as ethylamine, added in large excess to spectrin prior to irradiation, did not interfere with cross-link formation. These results suggest that NH2 groups are not involved in the reaction.

Cross-Linking Reagents↗
PubMed1985

Permeability of alkylamines across phosphatidylcholine vesicles as studied by 1H-NMR.

The exchange rate and enthalpy and entropy of activation of the diffusion of the first five n-alkylamines across egg phosphatidylcholine vesicles has been measured by 1H-NMR spectroscopy employing the 1:2 Gd3+-EDTA complex as a relaxation reagent. The permeability determined from the exchange rate of the ethyl through the pentyl derivatives increased sequentially with increasing chain length from 7.10(-7) to 4.10(-4) cm/s, respectively, at 25 degrees C. The permeability of methylamine was similar to that of ethylamine (1.10(-6) cm/s at 25 degrees C) and exhibited a relatively smaller entropy increase. The enthalpy of activation for the transfer reaction was high for all amine derivatives (20 kcal/mol). The entropy of activation increased with increasing chain length. The results indicate that the rate of diffusion is dominated by the partition into the membrane. Methylamine, being the smallest molecule in this series, can probably diffuse also through vacancies formed by the internal motions of the lipid chains.

Amines↗
PubMed1979

An essential carboxylic acid group in human prostate acid phosphatase.

Treatment of homogenous human prostatic acid phosphatase (orthophosphoric-monoester phosphohydrolase (acid optimum), EC 3.1.3.2) with low concentrations of Woodward's reagent K (N-ethyl-5-phenylisoxazolium-3'-sulfonate) leads to a rapid loss of enzymic activity. The rate of inactivation of the enzyme is reduced in the presence of the competitive inhibitors phosphate and L-(+)-tartrate, but not in the presence of non-inhibitory D-tartrate. Measurement of the ethylamine produced upon hydrolysis of enzyme modified in the presence of D- and of L-tartrate permitted the quantitative estimation of the number of carboxylic acid residues at the active site. The data indicate that two carboxyl groups per (dimeric) enzyme molecule are essential for catalytic activity. It is proposed that one function of the active site carboxyl group may be to protonate the leaving alcohol or phenol portion of the phosphomonoester substrate during the formation of the covalent phosphoenzyme intermediate.

Acid Phosphatase↗
PubMed1989

The role of endosomal traffic in the transendothelial transport of ceruloplasmin in the liver.

Through a process resembling receptor-mediated endocytosis, liver endothelium binds and internalizes the plasma glycoprotein ceruloplasmin (CP) on the luminal side. The protein is then transported via a vesicular system to the albuminal side where it is externalized to the space of Disse. In its path, the glycoprotein is fully desialylated. To determine if the endosomal compartment is involved in this transport, we used endosomal inhibitors NH4Cl, ethylamine as well as monensin to quantitatively measure the magnitude of radiolabeled CP transport across purified liver endothelial cells. All three reagents inhibited the transport of CP and its discharge by endothelium. The magnitude of inhibition was dose-related for all three reagents. We conclude that the endosomal compartment is involved in the transendothelial transport of CP across the liver endothelium.

Ammonium Chloride↗
PubMed1982

Irreversible blockade of responses to a partial agonist acting at the histamine H1-receptor.

N,N-Diethyl-2-(1-pyridyl)-ethylamine (E-2-P) has been shown previously to behave as a simple partial agonist at the histamine H1-receptor of guinea-pig ileum. When isolated longitudinal muscle strips from this preparation were tested with E-2-P before and after blockade with 2-haloalkylamines, it was found that these agents produced an irreversible shift to the right in the dose-response curve without significant depression of the maximum response even at very high antagonist concentrations. Under these circumstances the maximum response to the partial agonist may exceed the maximum response to histamine itself since the latter shows a much diminished maximum response at a very high concentrations of antagonist. These findings are not readily explicable in terms the usual "receptor-reserve' model of the histamine receptor system in ileum. A tentative explanation is provided, involving interaction with the antagonist at more than one site.

Animals↗
PubMed1979

Coupling of acid labile Salmonella specific oligosaccharides to macromolecular carriers.

A coupling method for covalent attachment of acid labile oligosaccharides isolated from S. typhimurium O-polysaccharide to macromolecular carriers is described. Arylamine groups were introduced into the terminal reducing end of oligosaccharides by reacting them with 2-(4-aminophenyl)-ethylamine. After subsequent conversion to the corresponding saccharide-phenylisothiocyanato derivatives saccharides were covalently linked to free epsilon-lysylamine groups of different carrier proteins. The resulting conjugates were highly immunogenic and elicited in rabbits both anti-harptenic and anti-carrier protein specific antibodies. Some of the advantages of this coupling procedure are: (i) it can be used with oligosaccharides containing highly acid or alkali labile structures and/or glycosidic linkages, (ii) it produces conjugates with high degrees of substitution at low saccharide/protein molar input ratios, (iii) it does not grossly affect the immunogenic specificities of the carrier protein, and (iv) it is suitable for preparation of highly substituted affinity columns, e.g., coupling to a polyacrylamide matrix.

Animals↗
PubMed1988

Regulation of macrophage lipoprotein lipase secretion by the scavenger receptor.

The effects of ligand binding to the scavenger receptor on the secretion of lipoprotein lipase by murine macrophages were examined. Inflammatory macrophages exposed to acetylated low-density lipoprotein (AcLDL) exhibited a dose-dependent, 40-80% increase in lipoprotein lipase secretion. This stimulation appeared to be unrelated to intracellular cholesterol and triacylglycerol levels and to phagocytosis in general. Resident and inflammatory macrophages treated with maleylated bovine serum albumin (Mal-BSA) showed a 3-fold increase in lipoprotein lipase secretion in a dose-dependent and time-dependent fashion. In contrast, dextran sulfate, which is another ligand recognized by the scavenger receptor, caused a dose-dependent decrease in lipoprotein lipase secretion. Casein, a ligand recognized by the Mal-BSA receptor, did not affect lipoprotein lipase secretion nor the ability of Mal-BSA to stimulate the enzyme, while dextran sulfate abolished the stimulatory effects of Mal-BSA. Since ethylamine, an inhibitor of receptor-mediated endocytosis, attenuated the increase in lipoprotein lipase secretion induced by AcLDL and Mal-BSA, but did not affect the inhibition induced by dextran sulfate, it is suggested that receptor-mediated endocytosis of ligands via the scavenger receptor might play a key role in the stimulation of lipoprotein lipase secretion in macrophages. This study reveals another mechanism for regulation of macrophage lipoprotein lipase secretion.

Animals↗
PubMed1989

Stabilization and quantitative analysis of fecapentaenes in human feces, using synthetic fecapentaene-12.

Naturally occurring fecal mutagens, called fecapentaenes, are hypothesized to contribute to large bowel carcinogenesis. To understand health risks it is necessary to relate fecal mutagen concentrations to intestinal pathologies, i.e. colon cancer. However, fast and reliable methods for analysis of stool for fecapentaene levels are not available. This study presents an evaluation of stabilizing effects on synthetic fecapentaene-12 of various antioxidants, indicating tri-ethylamine to give the best results. Furthermore, it describes a fast extraction procedure for human stool and a subsequent HPLC-analysis which produces quantitative data on fecapentaene-12 concentrations within 30 min.

Butylated Hydroxytoluene↗
PubMed1982

Inhibition of platelet aggregation by primary amines. Evidence for a possible role of membrane-associated calcium.

The aggregation of human blood platelets by thrombin, adenosine diphosphate, wheat germ agglutinin or ristocetin was inhibited by primary amines. In general, thrombin-induced platelet aggregation was strongly affected by the amines while the effect was weak on cell aggregation by ristocetin. Usually, the diamines were stronger inhibitors of aggregation than the monoamines with cadaverine as the strongest and ethylamine as the weakest inhibitor. At concentration where platelet aggregation was inhibited, the amines neither displaced serotonin from serotonin-loaded platelets nor caused lysis of human red cells. The lectin activity of wheat germ agglutinin on human red cells was not affected by the amines indicating that the amines probably acted on platelets and not on the agglutinin. The clotting activity of thrombin on fibrinogen was partially inhibited by the amines while its esterolytic activity remained unaltered. The inhibitory action of the amines on platelet aggregation could be overcome with small amounts of calcium while other divalent cations tested had little effect. It is suggested that the amines affect platelet aggregation by interfering with the actions of membrane-associated calcium.

Adenosine Diphosphate↗
PubMed2005

Studies towards the next generation of antidepressants. Part 4: derivatives of 4-(5-fluoro-1H-indol-3-yl)cyclohexylamine with affinity for the serotonin transporter and the 5-HT1A receptor.

Derivatives of the serotonin reuptake inhibitor 4-(5-fluoro-1H-indol-3-yl)cyclohexylamine, in which serotonin 1A (5-HT(1A)) receptor pharmacophoric elements are incorporated, are reported. Analogs exhibiting affinity for both the serotonin transporter and the 5-HT(1A) receptor are described. Compounds containing 1-(4-indolyl)piperazine and 2-(1H-indol-4-yloxy)ethylamine are promising leads for further SAR studies.

Antidepressive Agents↗
PubMed2004

Cytotoxicity of enantiomers of gossypol Schiff's bases and optical stability of gossypolone.

Optical Schiff's bases of gossypol were prepared with chiral gossypol and ethylamine. As has been similarly observed among the gossypol enantiomers, the (-)-gossypol ethylimine was more active than either the (+)-gossypol ethylimine or the racemic gossypol ethylimine against KB and MCF7 cells. Gossypolone was also observed to be more toxic than gossypol against both cell lines. All of the gossypol products tested showed comparable toxicity toward MCF7/ADR (adriblastine-resistant) cells. Attempts at producing chiral gossypolone from chiral gossypol failed because of rapid racemization. In addition, the Schiff's base derivatives of gossypolone formed with R-(+)-2-amino-3-phenyl-1-propanol could only be separated at reduced temperature, indicating that gossypolone Schiff's bases are less optical stable than gossypol Schiff's bases.

Antineoplastic Agents↗