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PubMed2006

Simultaneous quantitative analysis of metabolites using ion-pair liquid chromatography-electrospray ionization mass spectrometry.

We have developed an analytical method, consisting of ion-pair liquid chromatography coupled to electrospray ionization mass spectrometry (IP-LC-ESI-MS), for the simultaneous quantitative analysis of several key classes of polar metabolites, like nucleotides, coenzyme A esters, sugar nucleotides, and sugar bisphosphates. The use of the ion-pair agent hexylamine and optimization of the pH of the mobile phases were critical parameters in obtaining good retention and peak shapes of many of the above-mentioned polar and acidic metabolites that are impossible to analyze using standard reversed-phase LC/MS. Optimum conditions were found when using a gradient from 5 mM hexylamine in water (pH 6.3) to 90% methanol/10% 10 mM ammonium acetate (pH 8.5). The IP-LC-ESI-MS method was extensively validated by determining the linearity (R2 > 0.995), sensitivity (limit of detection 0.1-1 ng), repeatability, and reproducibility (relative standard deviation <10%). The IP-LC-ESI-MS method was shown to be a useful tool for microbial metabolomics, i.e., the comprehensive quantitative analysis of metabolites in extracts of microorganisms, and for the determination of the energy charge, i.e., the cellular energy status, as an overall quality measure for the sample workup and analytical protocols.

Amines↗

PubMed2006

Functionalization of indium tin oxide.

The preparation and functionalization of ITO surfaces has been studied using primarily X-ray photoemission spectroscopy and infrared reflection-absorption spectroscopy (IRRAS) and the reagents n-hexylamine and n-octyltrimethoxysilane (OTMS). Particular attention has been paid to characterization of the surfaces both before and after functionalization. Surfaces cleaned by ultraviolet (UV)/ozone treatment and subsequently exposed to room air have approximately 0.5-0.8 monolayers (ML) of adsorbed impurity C. Most is in the form of aliphatic species, but as much as one-half is partially oxidized and consists of C-OH, C-O-C, and/or >C=O groups. The coverage of these species can be reduced by cleaning in organic solvents prior to UV/ozone treatment. The OH coverage on the ITO surfaces studied here is relatively small (approximately 1.0 OH nm-2), based on the Si coverage after reaction with OTMS. A satellite feature in the O 1s XPS spectrum, often suggested to be a quantitative measure of adsorbed OH, receives a significant contribution from sources not directly related to hydroxylated ITO. n-Hexylamine adsorbs, at a saturation coverage of approximately 0.08 ML, via a Lewis acid-base interaction. The particular acid site has not been conclusively identified, but it is speculated that surface Sn sites may be involved. For OTMS, a saturation coverage of about 0.21 ML is found, and the C/Si atom ratios suggest that some displacement of preadsorbed organic impurities occurs during adsorption. The alkyl chain of adsorbed OTMS is disordered, with no preferred stereoisomer. However, the chain appears to lie mainly parallel to the surface with the plane defined by the terminal CH3-CH2-CH2- segment oriented essentially perpendicular to the surface.

Adsorption↗

PubMed1996

Substituted 2-hydroxy-1,2-dihydropyrrol-3-ones: fluorescent markers pertaining to oxidative stress and aging.

Previous observations that the aging process correlates with occurrence of certain fluorescent biological pigments have led to numerous efforts in elucidating the chemical nature of the fluorophores generated through reactions of primary amines and various products of lipid peroxidation. In this study, model reactions of saturated aldehydes with aliphatic amines in the presence of peroxides were found to generate structurally unusual fluorescent compounds. Substitution of a lysine-containing peptide for simpler amines has also yielded similar fluorescence. The spectral excitation and emission maxima (around 360 and 430 nm, respectively) of these fluorophores match those widely reported in peroxidized biological objects. The fluorescent compounds in our model studies have been chromatographically isolated and their structures determined through mass spectrometry, NMR spectrometry, and Fourier-transform infrared spectroscopy. The spectrometric data indicate the fluorescent products to be alkylated 2-hydroxy-1,2-dihydropyrrol-3-ones, obtained by the action of 1,2,4-triketone intermediates upon the primary amines. Independent syntheses of several 1,2,4-triketones were carried out. One such triketone reacted with hexylamine to form a fluorescent compound spectroscopically identical to the fluorescent reaction product of hexanal, hydrogen peroxide, and hexylamine.

Aldehydes↗

PubMed1982

Purification and biochemical properties of tumor-associated transplantation antigens from methylcholanthrene-induced murine sarcomas.

A tumor-associated transplantation antigen with an apparent molecular weight of 75,000 has been isolated from the cytosol of the BALB/c methylcholanthrene-induced sarcoma, Meth A. The antigen was purified either by preparative electrophoresis in the presence of NaDodSO4 or by immunoaffinity chromatography after hexylamine agarose chromatography, gel filtration, and hydroxylapatite chromatography. The 75-kilodalton (kDal) protein prepared by either of these methods effectively primed BALB/c mice to reject the Meth A tumor; such priming provided no protection against challenge by other independently derived sarcomas of BALB/c origin. A second protein, also 75 kDal, was isolated from the cytosol of the recently derived methylcholanthrene-induced sarcoma CI-4 by essentially the same chromatographic scheme. This protein also was immunogenic in the tumor rejection assay and provided protection only against CI-4 challenge. The antigens purified from the Meth A and CI-4 sarcomas appear to be closely related proteins. Both of them can be purified from the cytosol fraction and can be recognized by a rabbit antiserum prepared against the Meth A 75-kDal protein. The two proteins have approximately the same molecular weight, have similar but not identical amino acid compositions, and differ in their chromatographic behavior on hexylamine agarose and hydroxylapatite as well as in their isoelectric points. These results indicate that the individually specific transplantation antigens found in chemically induced sarcomas may be the products of a single multigene family or somatic derivatives of a single gene.

Amino Acids↗

PubMed1982

Interaction of aliphatic amines with glycogen phosphorylase.

A number of aliphatic amines was shown to stimulate AMP-dependent activity of phosphorylase b. The extent of stimulation depends on the molecular structure of amines. For linear amines, the longer the linear chain, the greater the stimulation observed. High concentrations of amines were able to induce a small activation of phosphorylase b in the absence of AMP. Kinetic studies of phosphorylase b indicated that the presence of n-hexylamine (a) results in lowering Km values for AMP and glucose 1-phosphate, (b) increases maximal velocity of the enzyme, and (c) modifies the glucose 6-phosphate, ATP, caffeine, and glucose binding sites of the enzyme by increasing the inhibition constants for these inhibitors. In contrast, the activity of phosphorylase b' is not altered by n-hexylamine. This fact suggests the possibility that amines interact with the N-terminal tail of phosphorylase b chain.

Adenosine Monophosphate↗

PubMed1999

Ammonia blockade of intestinal epithelial K+ conductance.

Ammonia profoundly inhibits cAMP-dependent Cl- secretion in model T84 human intestinal crypt epithelia. Because colonic lumen concentrations of ammonia are high (10-70 mM), ammonia may be a novel regulator of secretory diarrheal responsiveness. We defined the target of ammonia action by structure-function analysis with a series of primary amines (ammonia, methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, heptylamine, and octylamine) that vary principally in size and lipid solubilities. The amine concentrations required for 50% inhibition of Cl- secretion in intact monolayers and 50% inhibition of outward K+ current (IK) in apically permeabilized monolayers vs. the logs of the respective amine partition coefficients give two plots that are strikingly similar in character. Half-maximal inhibition of short-circuit current (Isc) by ammonia was seen at 6 mM and for IK at 4 mM; half-maximal inhibition for octylamine was 0.24 mM and 0.19 mM for Isc and IK, respectively. The preferentially water-soluble hydrophilic amines (ammonia, methylamine, ethylamine) increase in blocking ability with decreasing size and lipophilicity. Conversely, the preferentially lipid-soluble hydrophobic (propylamine, butylamine, pentylamine, hexylamine, heptylamine, octylamine) amines increase in blocking ability with increasing size and lipophilicity. Ammonia does not affect isolated apical Cl- conductance; amine-induced changes in cytosolic and endosomal pH do not correlate with secretory inhibition. We propose that ammonia in its protonated ammonium form (NH4+) inhibits cAMP-dependent Cl- secretion in T84 monolayers by blocking basolateral K+ channels.

Amines↗

PubMed1978

Further study on the effect of mersalyl, an organic mercurial, on relaxing response of a molluscan smooth muscle to monoamines.

The effect of mersalyl on the relaxation of catch by various monoamines was studied in the anterior byssal retractor muscle of Mytilus. As has already been reported, mersalyl blocked the relaxing response to indoleamines but not block that to catecholamines. The relaxations in response to catecholamine-related compounds (dopa, octopamine, tyramine, phenylephrine, beta-phenylethylamine and phenylethanolamine) and hexylamine were, however, antagonized more or less effectively with mersalyl. It was suggested that the catecholamine-related compounds and hexylamine can act on relaxing nerve endings to increase neurotransmitter serotonin in the junctional clefts, and mersalyl antagonizes the relaxation in response to these compounds by blocking the serotonin.

Animals↗

PubMed1988

Evidence for a functional role for histidine in lysyl oxidase catalysis.

The pH-dependent kinetics of lysyl oxidase catalysis was examined for evidence of an ionizable enzyme residue which might function as a general base catalyzing proton abstraction previously shown to be a component of the mechanism of substrate processing by this enzyme. Plots of log Vmax/Km for the oxidation of n-hexylamine versus pH yielded pKa values of 7.0 +/- 0.1 and 10.4 +/- 0.1. The higher pKa varied with different substrates, reflecting ionization of the substrate amino group. A van't Hoff plot of the temperature dependence of the lower pKa yielded a value of 6.1 kcal mol-1 for the enthalpy of ionization. This value as well as the pKa of 7.0 are consistent with those of histidine residues previously implicated as general base catalysts in enzymes. Incubation of lysyl oxidase with low concentrations of diethyl pyrocarbonate, a histidine-selective reagent, at 22 degrees C and pH 7.0 irreversibly inhibited enzyme activity by a pseudo first-order kinetic process. The inactivation of lysyl oxidase correlated with spectral and pH-dependent kinetic evidence for the chemical modification of 1 histidine residue/mol of enzyme, the pKa of which was 6.9 +/- 0.1, within experimental error of that seen in the plot of log Vmax/Km versus pH. Enzyme activity was restored by incubation of the modified enzyme with hydroxylamine, consistent with the ability of this nucleophile to displace the carbethoxy group from N-carbethoxyhistidine. The presence of the n-hexylamine substrate largely protected against enzyme inactivation by diethyl pyrocarbonate. These results thus indicate a functional role for histidine in lysyl oxidase catalysis consistent with that of a general base in proton abstraction.

Algorithms↗

PubMed1984

Relaxation of Mytilus catch muscle by 8-bromo-cyclic GMP and related compounds.

Relaxation of catch tension by 8-bromo-cyclic GMP in the ABRM of Mytilus was blocked in the presence of mersalyl and was markedly reduced after treatment of the muscle with alpha-methyldopa. In the muscle depolarized by 540 mM KCl + 5 mM EGTA solution, 8-bromo-cyclic GMP could not relax Ca-contracture. Hexylamine and phenylethylamine, which are assumed to relax the catch acting on relaxing nerve terminals, could not relax the contracture either. Serotonin and dopamine, which are known to relax the catch acting directly on the muscle fibre membrane, could relax it. In the muscle depolarized by 250 mM KCl + 5 mM EGTA solution, all of the cyclic nucleotides tested (cyclic AMP, cyclic GMP and their analogues), serotonin and dopamine relaxed Ca-contracture, but hexylamine and phenylethylamine did not relax the contracture. The possibilities of the involvement of cyclic GMP in the presynaptic and postsynaptic relaxing mechanisms in the ABRM are discussed.

1-Methyl-3-isobutylxanthine↗

PubMed1989

The specific interaction between fibrin(ogen) and hyaluronan: possible consequences in haemostasis, inflammation and wound healing.

We have proposed that fibrin and hyaluronan (HA) are macromolecular regulators during inflammation and wound healing. Here we extend our studies to characterize the specific interaction between fibrin(ogen) and HA. 125I-labelled HA (Mr approximately 32,000) was bound by plastic surfaces coated with human fibrinogen but not bovine serum albumin, ovalbumin, beta-lactoglobin or rabbit immunoglobulin G. 125I-labelled fibrinogen bound to a unique hexylamine derivative of HA coupled to Sepharose and was eluted specifically by HA oligosaccharides in a size-dependent manner. A dot blot assay, in which proteins are adsorbed to nitrocellulose and probed with 125I-HA, also showed specific binding to human fibrinogen. This assay was used to examine fibrinogens from other mammalian species. No specific 125I-HA binding was observed with the protein from horse, rat or cow. Significant binding was detected with human, sheep, rabbit, dog, baboon, goat and pig fibrinogens. Thrombin-induced formation of fibrin clots is also affected by HA, which decreases the lag time before clotting and increases the rate of clot formation. The rate of fibrin polymerization increased over 500% in the presence of 60 microM HA. Furthermore, the structure of the fibrin gel, as assessed by light scattering, was altered by HA or chondroitin sulphate in a concentration-dependent manner. The results support the proposed wound-healing model and indicate that an increase in circulating HA levels could adversely affect haemostasis and increase the risk of thrombosis or bleeding. The interaction between HA and fibrinogen emphasizes the importance of the liver endothelial cell HA receptor in the removal of glycosaminoglycans from the blood. Cultured cells continuously endocytosing 125I-HA for 4 h reutilized their total cellular HA receptors at least once every 50 min even in the presence of cycloheximide. This endocytotic receptor was therefore shown to be part of a recycling system.

Animals↗

PubMed1986

Biochemical characterization and biologic activities of 82- and 86-kDa tumor antigens isolated from a methylcholanthrene-induced sarcoma, CII-7.

Two tumor-specific antigens, with molecular weights of approximately 82 and 86 kDa, have been isolated and purified to apparent homogeneity from the methylcholanthrene-induced sarcoma, CII-7. The method of purification used was essentially that previously employed for the isolation of the 82- and 86-kDa antigens from the Meth A sarcoma and the 86-kDa antigen from mKSA sarcoma. Cytosolic fractions were subjected to hexylamine agarose chromatography, Sepharose S-300 filtration and hydroxylapatite chromatography. A final step, HPLC-DEAE chromatography, was necessary for the purification of the 82-kDa protein. Both isolated antigens retained their specific immunogenicity for CII-7 as determined by in vivo tumor rejection assays, and failed to influence the growth of other syngeneic sarcomas, CI-4, CII-10 and mKSA, which have their own unique TATA. The 82- and 86-kDa antigens appear to be distinct proteins that are well conserved in nature and may represent members of distinct families of TATA.

Animals↗

PubMedDate not supplied

Qualitative determination of false-positive effects in the acetylcholinesterase assay using thin layer chromatography.

A method has been developed to determine the false-positive effects on acetylcholinesterase inhibition in the TLC assay based on Ellman's method. Various aldehydes and amines have been tested in order to determine whether the observed inhibition is due to a true enzyme inhibition or due to the inhibition of the reaction between thiocholine and 5,5'-dithiobis-(2-nitrobenzoic acid). 4-Dimethylaminobenzaldehyde, 3-ethoxy-4-hydroxybenzaldehyde, diethylamine, triethylamine, triethanolamine and tyramine showed real enzyme inhibition, although their activity was about 10(3) times lower than that shown by galanthamine. Heptanal, decanal, cinnamaldehyde, anisaldehyde, benzaldehyde, hexylamine and tryptamine appeared to show a non-specific chemical inhibition. By checking this chemical inhibition on the TLC assay, the true enzyme inhibition could be distinguished from the false-positive chemical inhibition observed in the toluene extract of Nerine bowdenii in the course of isolation of active compounds.

Acetylcholinesterase↗

PubMed2001

A fluorescence-based homogeneous assay for measuring activity of UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase.

UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase (LpxC) is one of the key enzymes of bacterial lipid A biosynthesis, catalyzing the removal of the N-acetyl group of UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine. The lpxC gene is essential in Gram-negative bacteria but absent from mammalian genomes, making it an attractive target for antibacterial drug discovery. Current assay methods for LpxC are not suitable for high throughput screening, since they require multiple product separation steps and the use of radioactively labeled material that is difficult to prepare. A homogeneous fluorescence-based assay was developed that uses UDP-3-O-(N-hexyl-propionamide)-N-acetylglucosamine as a surrogate substrate. This surrogate can be prepared from commercially available UDP-GlcNAc by enzymatic conversion to UDP-MurNAc, which is then chemically coupled to n-hexylamine. Following the LpxC reaction, the free amine of the deacetylation product can be derivatized by fluorescamine, thus generating a fluorescent signal. This surrogate substrate has a K(m) of 367 microM and k(cat) of 0.36 s(-1), compared to 2 microM and 1.5 s(-1) for the natural substrate. Since no separation is needed, the assay is easily adaptable to high throughput screening. IC(50)s of LpxC inhibitors determined using this assay method is similar to those measured by traditional method with the natural substrate.

Amidohydrolases↗

PubMed1984

Trichosporon adeninovorans sp. nov., a yeast species utilizing adenine, xanthine, uric acid, putrescine and primary n-alkylamines as the sole source of carbon, nitrogen and energy.

A new yeast species, Trichosporon adeninovorans, was isolated from soil by the enrichment culture method. Apart from adenine, the strain utilized uric acid, guanine, xanthine, hypoxanthine, 6,8-dihydroxypurine, putrescine, propylamine, butylamine, pentylamine, hexylamine and octylamine as sole source of carbon, nitrogen and energy. The structure of the cell wall of Tr. adeninovorans was ascomycetous. On the subcellular level growth on adenine or uric acid was accompanied with the development of microbodies in the cell. These cell organelles probably were the site of urate oxidase, an enzyme that, after growth on purine substrates, together with allantoinase was present at high activities. Low activities of adenine amidohydrolase and xanthine dehydrogenase were also demonstrated.

Adenine↗

PubMed1983

Induction of tumors of the esophagus in rats by nitrosomethylalkylamines.

The carcinogenic effectiveness of nitrosomethyl-n-butylamine,-n-hexylamine and -n-heptylamine was compared by administration to F344 rats at various concentrations in drinking water and by gavage in oil. Nitrosomethylbutylamine induced only tumors of the upper gastrointestinal tract, and was very toxic. Nitrosomethylhexylamine was less toxic and induced tumors of the liver and lung, as well as those the upper GI tract, when given by gavage, but only tumors of the GI tract when given in drinking water. In contrast, nitrosomethylheptylamine induced tumors of the liver and lung when given in drinking water or by gavage, but there were tumors of the esophagus only in those rats treated via the drinking water. As measured by the dose needed to produce a given carcinogenic effect, nitrosomethylheptylamine was a weaker carcinogen than the other two nitrosamines, but was not inactive as has been reported previously.

Animals↗

PubMed1995

A phase I and pharmacology study of an oral platinum complex, JM216: dose-dependent pharmacokinetics with single-dose administration.

JM216 [bis-acetato-ammine-dichloro-cyclo-hexylamine-platinum (IV)] is an oral platinum complex with in vivo activity against murine and human tumor models and a lack of nephro- and neurotoxicity in rodents. During a phase I study of a single-dose schedule, JM216 was given in dry-filled hard gelatin capsules by mouth without hydration or diuresis. In all, 37 patients were given a total of 88 courses at doses ranging from 60 to 700 mg/m2. The study was stopped before the MTD was reached because of nonlinear pharmacokinetics. Myelosuppression was manifest by leucopenia or thrombocytopenia and showed marked variability at 420-700 mg/m2. Vomiting was mild and controllable by antiemetics in approximately 50% of courses. The onset of vomiting was delayed to 4 h after during ingestion. There was no nephro-, oto- or neuro-toxicity. A partial response was recorded in a patient with recurrent ovarian cancer, and significant falls in plasma tumour markers (CA125) were seen in two further cases. Plasma pharmacokinetics were linear and showed moderate interpatient variability at dose levels of < or = 120 mg/m2. At dose levels of > or = 200 mg/m2, Cmax and AUC increased less than proportionally to dose. This was associated with greater interpatient pharmacokinetic variability and reduced urinary platinum recovery. A significant sigmoidal relationship existed between ultrafilterable plasma AUC and the percentage of reduction in platelet count (r2 = 0.78). Nonlinear absorption was a limitation to this single-dose schedule of oral NM216; however, little non-haematological toxicity was seen at doses associated with myelosuppression and antitumour activity. Clinical studies of divided dose schedules using doses within the range of pharmacokinetic linearity (< or = 120 mg/m2) are now being investigated.

Administration, Oral↗

PubMed1996

Determination of aliphatic and alicyclic amines in water by gas and liquid chromatography after derivatization by chloroformates.

Two new methods were developed for the analysis of aliphatic (n-propylamine, pentylamine, hexylamine, heptylamine, octylamine) and alicyclic (pyrrolidine, morpholine, piperidine, piperazine) amines in water samples after derivatization and liquid-liquid-extraction. The carbamate-derivatives formed were determined by GC/MS (trichloroethyl carbamates) as well as by HPLC/fluorescence detection (9-fluorenylmethyl carbamates) in a concentration range between 0.05 and 1.0 microg/l suitable for drinking water analysis. Applications to German rivers and sewage plants show that both new methods produce corresponding results in analysing aliphatic and alicyclic amines in surface waters as well as in waste water samples.

Journal Article↗

PubMed2004

Synthesis of Nepsilon-protected-L-lysine and gamma-benzyl-L-glutamate N-carboxyanhydrides (NCA) by carbamoylation and nitrosation.

This paper reports on an original process to synthesize N-carboxyanhydrides, which consists of nitrosating N-carbamoylamino acids with a NO/O(2) gas mixture in acetonitrile. The synthesis of several N-carbamoylamino acids of L-lysine was described using potassium cyanate in water. The latter were then nitrosated to yield the corresponding NCA with more or less efficiency. Indeed, the NCA carrying an acid-sensitive protecting group led to a partial deprotection to give the L-lysine NCA salt. The NCA of N(epsilon)-trifluoroacetyl-L-lysine, N(epsilon)-benzyloxycarbonyl-L-lysine and gamma-benzyl-L-glutamate were successfully synthesized with satisfactory yields. Their polymerizability was compared to that of the N(epsilon)-trifluoroacetyl-L-lysine NCA initiated by n-hexylamine in N,N-dimethylformamide. It also showed that this new process of NCA synthesis could be applied to the synthesis of polypeptides and more generally to the protein chemistry.

Anhydrides↗