Aminosulfonic Acid Research Articles

Treatment of chronic osteomyelitis with Taurolin-Gel (author's transl)

A study was made to ascertain the effect of Taurolin [Bis-(1-dioxo-perhydro-1, 2, 4-thiadiazinyl-4)-methan]*-Agarose resp. Taurolin -Collagen, using as model a chronic osteomyelitis in a dog's femur. The result was verified by means of X-rays, bone scans, intermittent bacteriological checks and, finally, histology. Taurolin, a chemotherapeuticum derived from the aminosulfonic acid, Taurin, was proven to be compatible. It led to regression of the osteomyelitis.

The Determination of Salbutamol Sulfat Based on a Flow‐Injection Coupling Irreversible Biamperometry at Poly(aminosulfonic acid)‐Modified Glassy Carbon Electrode

The present work describes the development of a simple and efficient method for electrochemical analysis determination of SBS using polymer film coated modified electrode. A glassy carbon electrode (GCE) is successfully modified with electropolymerized film of aminosulfonic acid (ASA) in pH 6.8 phosphate buffer solution (PBS). Cyclic voltammetry (CV) were used to study the electrochemical properties of the polymer film and the appropriate condition for electropolymerization process. The voltammetric behavior of SBS at the PASA GC CMEs has been investigated, the results suggest that the PASA GC CMEs have good effect of electrocatalytic oxidation action to SBS, also propose the mechanism toward SBS. The flow‐injection irreversible biamperometry analysis method was studied under the applied potential difference of 0 V to determinate SBS. In 0.1 mol l−1 (pH 6.80) phosphate buffer solution, a sensitive and irreversible oxidation peak was obtained at the PASA GC CMEs. Under the optimum conditions, SBS can be determined from the range 2.0×10−6 to 1.0×10−3 mol · 1−1 with the sampling frequency of 100 samples per hour. The detection limit for SBS is 6.5×10−7 mol l−1 and the RSD for 20 replicate determinations of 4.0×10−5 mol l−1 SBS is 1.85%. The method is simple, with high selective rapid and sensitive. The method is applied to the determination of SBS in the drug with satisfactory results. Moreover, the physiologically common interferents (i.e., sucrose, lactose, citric acid, and citrate) negligibly affected the response of SBS. The PASA GC CMEs film‐coated electrode exhibited a stable and sensitive response to salbutamol sulfat in the presence of electrocatalysis oxidation.

Synthesis of Aromatic Aminosulfonic Acid Nitroamides.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Quantitative Glycomics of Human Whole Serum Glycoproteins Based on the Standardized Protocol for Liberating N-Glycans

Global glycomics of human whole serum glycoproteins appears to be an innovative and comprehensive approach to identify surrogate non-invasive biomarkers for various diseases. Despite the fact that quantitative glycomics is premised on highly efficient and reproducible oligosaccharide liberation from human serum glycoproteins, it should be noted that there is no validated protocol for which deglycosylation efficiency is proven to be quantitative. To establish a standard procedure to evaluate N-glycan release from whole human serum glycoproteins by peptide-N-glycosidase F (PNGase F) treatment, we determined the efficiencies of major N-glycan liberation from serum glycoproteins in the presence of reducing agents, surfactants, protease treatment, or combinations of pretreatments prior to PNGase F digestion. We show that de-N-glycosylation efficiency differed significantly depending on the condition used, indicative of the importance of a standardized protocol for the accumulation and comparison of glycomics data. Maximal de-N-glycosylation was achieved when serum was subjected to reductive alkylation in the presence of 2-hydroxyl-3-sulfopropyl dodecanoate, a surfactant used for solubilizing proteins, or related analogues, followed by tryptic digestion prior to PNGase F treatment. An optimized de-N-glycosylation protocol permitted relative and absolute quantitation of up to 34 major N-glycans present in serum glycoproteins of normal subjects for the first time. Moreover PNGase F-catalyzed de-N-glycosylation of whole serum glycoproteins was characterized kinetically, allowing accurate simulation of PNGase F-catalyzed de-N-glycosylation required for clinical glycomics using human serum samples. The results of the current study may provide a firm basis to identify new diagnostic markers based on serum glycomics analysis.

Synthesis of Aromatic Aminosulfonic Acid Nitroamides

Nitration of aromatic aminosulfonic acid primary amides to furnish the corresponding sulfononitroamides has been described for the first time. The conditions of nitration applied ensure chemoselective mononitration and prevent decomposition of the product. Synthesis of dabsyl nitroamide sodium salt, as a potential β-amyloid aggregation inhibitor is also reported.

Efficient Method for Synthesis of the Derivatives of 5‐Arylidene Barbituric Acid Catalyzed by Aminosulfonic Acid with Grinding.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Efficient Method for Synthesis of the Derivatives of 5‐Arylidene Barbituric Acid Catalyzed by Aminosulfonic Acid With Grinding

Aminosulfonic acid is an environmentally friendly catalyst. Grinding a mixture of aromatic aldehydes, barbituric acid, and H2NSO3H at room temperature (without any solvent) gave 5‐arylidene barbituric acid in high yields, providing a simple and efficient route to synthesis of these compounds.

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Tritiated Taurine Handling by Isolated Rat Pancreatic Islets

A gating of volume-sensitive anion channels may participate in the depolarization of the plasma membrane caused by high concentrations of D-glucose in insulin-producing B-cells of the endocrine pancreas. The efflux of tritiated taurine from prelabeled cells is currently used to assess changes in the activity of such channels. The handling of [1,2-3H]taurine by isolated rat pancreatic islets was therefore investigated. The net uptake of [1,2-3H]taurine was found to represent a concentration-, time-, and temperature-dependent process. It was progressively increased in the range of D-glucose concentrations between 2.8 and 8.3 mM, but no further increase was observed at 16.7 mM D-glucose. Over 15 min incubation, the efflux of radioactivity from prelabeled islets was inhibited by MK571 (1.0 mM). It was increased in response to hypoosmolarity both in the presence and absence of extracellular Na+. Whether in salt-balanced or Na+-deprived media, the efflux of radioactivity from prelabeled islets increased in response to a rise in D-glucose concentration from 2.8 to 5.6 or 8.3 mM, but decreased when the concentration of the hexose was further increased from 8.3 to 16.7 mM. In perifused islets, however, the radioactive efflux from prelabeled islets was inhibited, in a concentration- related manner, when islets first deprived of D-glucose for 45 min were then exposed to 2.8, 5.6, or 16.7 mM D-glucose. Likewise, in prelabeled and perifused islets first exposed for 45 min to 4.0 mM D-glucose, a later rise in hexose concentration to 8.3 mM failed to affect significantly effluent radioactivity, while an increase in hexose concentration from 4.0 to 16.7 mM inhibited the radioactive outflow. In these perifusion experiments, the rise in D-glucose concentration provoked the expected changes in insulin output. The findings obtained in islets examined immediately after preincubation in the presence of [1,2-3H]taurine are consistent with the presence of volume-sensitive anion channels in islet cells and with a gating of such channels in response to a rise in D-glucose concentration from 2.8 to 5.6-8.3 mM. However, the radioactive fractional outflow rate from prelabeled islets seems to reach its highest value at about 8.3 mM D-glucose, being unexpectedly decreased at a higher concentration (16.7 mM) of the hexose. In conclusion, the pleiotropic effects of D-glucose upon tritiated taurine outflow from prelabeled rat islets, which could conceivably be ascribed to differences in the handling of this amino sulfonic acid by distinct islet cell types, indicates that the present approach is far from optimal to characterize unambiguously the regulation by the hexose of volume-sensitive anion channel activity in insulin-producing islet cells.

An efficient and practical synthesis of bis(indolyl)methanes catalyzed by aminosulfonic acid under ultrasound

Synthesis of bis(indolyl)methanes via electrophilic substitution reactions of indoles with aromatic aldehydes and ketones catalyzed by aminosulfonic acid was carried out in 23–96% yield at 30–38 °C in EtOH aqueous solution under ultrasound irradiation.

Novel enantioselective strong cation exchangers based on sulfodipeptide selectors: evaluation for enantiomer separation of chiral bases by nonaqueous capillary electrochromatography.

Strong cation exchange (SCX)-type chiral stationary phases (CSPs) based on beta-amino sulfonic acid-terminated dipeptide derivatives as chiral selectors, immobilized on thiol-modified silica particles (3.5 microm), were synthesized and applied to enantiomer separations of chiral bases by nonaqueous capillary electrochromatography (CEC). The effect of structural variations of the sulfodipeptide selectors on the separation factors alpha was investigated. These studies included variation of the acid-terminal amino sulfonic acid residue, variation of the configurations, i.e., comparison of the diastereomeric (S,S)- and (R,S)-configurations of the sulfodipeptides, and finally comparison of sulfodipeptide selectors with corresponding beta-amino sulfonic acid analogs. In general, the capillary columns (100 microm ID) packed with the new SCX-type CSPs showed enantioselectivity for an elaborated set of chiral basic drugs in CEC acting by an enantioselective cation-exchange retention mechanism. N-[N-(4-Allyloxy-3,5-dichlorobenzoyl)-leucyl]-2-amino-3,3-dimethylbutane sulfonic acid, in particular with (R,S)-configuration, turned out to be a more effective SCX-type selector than a more rigid analog based on N-[N-(4-Allyloxy-3,5-dichlorobenzoyl)-leucyl]-2-pyrrolidinemethane sulfonic acid. Both of the former diastereomers were capable to baseline-resolve the enantiomers of ca. 40% of the tested basic chiral solutes including sympathomimetics and beta-blockers, while for the latter SCX-type CSPs only 10-20% of the selected solutes afforded resolutions > 1.5.

Separation of anions by ion-interaction chromatography with a novel cationic/zwitterionic eluent

Inorganic and organic anions can be separated on an ordinary silica C18 column using a mobile phase containing tetrabutylammonium hydroxide (TBAH) and an aminosulfonic acid zwitterion reagent (MOPS). The pH of this eluent is close to 7 and the background conductivity is about 50 μS, which is low enough to permit anion analyte detection by direct conductivity. Linear calibration curves were obtained for the six anions studied and detection limits ranged from 0.075 to 0.15 mg/l (ppm) for the five inorganic anions. The method was applied to the determination of water-soluble anions in aerosol samples at concentrations as low as 0.3 mg/l.

Stimulation by surangin B of endogenous amino acid release from synaptosomes

The effect of surangin B, an insecticidal natural product coumarin, on presynaptic release of endogenous amino acids was investigated using a purified synaptosomal fraction isolated from mouse brain. Surangin B stimulated the release of glutamic acid (GLU), γ-aminobutyric acid (GABA), serine, alanine and the aminosulfonic acid taurine from synaptosomes at micromolar concentrations. In all cases, these responses were reduced by removing calcium from the saline and surangin B-evoked release of GLU, GABA, aspartic acid (ASP) and alanine was significantly inhibited by the sodium channel blocker tetrodotoxin. Rotenone (a complex I inhibitor) and carbonyl cyanide chlorophenylhydrazone (CCCP; an uncoupler), were more potent releasers of amino acids from synaptosomes than surangin B, however, carboxin (a complex II-selective inhibitor), was extremely weak to ineffective in this regard. The stimulatory effect of surangin B and complex III-selective inhibitors on release of GLU, GABA, ASP and alanine by synaptosomes was significantly reduced by N,N,N′,N′-tetramethyl- p-phenylenediamine, suggesting that blockade of complex III in intraterminal mitochondria is an important effect of this coumarin. Our results demonstrate that surangin B, in common with CCCP and inhibitors of complex I and III, cause release of both neurotransmitter and non-neurotransmitter amino acids from nerve endings in vitro. However, in contrast to most classical agents which interfere selectively with mitochondrial function, the release of endogenous amino acids from synaptosomes by surangin B also involves a moderate extracellular calcium ion-dependent component and relies partially on sodium ion entry into the nerve ending.

Extraction Behavior of Amino Sulfonic Acid by Tertiary and Quaternary Amines

Based on a systematic investigation of the literature, p-aminobenzenesulfonic acid was selected as a typical solute to be separated from the dilute solution. An aliphatic, straight-chain amine, Alamine 336, and a chlorinated quaternary ammonium salt, Aliquat 336, were used as extractants. The effects of pH value, concentration of the extractant, type of diluents, and salt on the distribution coefficient, D, on extraction equilibrium were studied in the experiments. The results showed that protic, polar diluents were favorable for extracting p-aminobenzenesulfonic acid when Alamine 336 was used as the extractant, while the inert diluent was favorable when Aliquat 336 was used as the extractant. Salt existing in the aqueous phase apparently reduced the D of p-aminobenzenesulfonic acid. Meanwhile, the proton transfer and ion exchange in the extraction process were discussed. The extraction equilibria for both amines were described using the mass action law, and the results showed that the calculating data ag...

Content of taurine in Apulian Cacioricotta goat's cheese

Taurine (Tau) is a sulfonated amino acid which is not incorporated into polypeptide structures and whose importance in the growth of newborns and young children has been well established. It is the most abundant free amino acid in goat's milk, where it occurs in higher amounts than in other kinds of milk. Tau and other free amino acids were analysed by high-performance liquid chromatography in Apulian Cacioricotta goat's cheese. Tau was present in both fresh and ripened cheese, providing a new reason for enhancing the value of this typical local dairy product.

Evaluation of n-substituted aminosulfonic acid pH buffers with a morpholinic ring for cadmium and lead speciation studies by electroanalytical techniques

The electrochemical behavior of cadmium and lead metal ions was investigated in the presence of different pH buffers [3-( N-morpholino)-2-hydroxypropanesulfonic acid (MOPSO), 2-( N-morpholino)ethanesulfonic acid (MES) and 3-( N-morpholino)propanesulfonic acid (MOPS)] by various methods [differential pulse anodic stripping voltammetry (DPASV), differential pulse polarography (DPP) and cyclic voltammetry (CV)]. The complexation and/or adsorption properties of these pH buffers were also examined. Conclusions about the possible influences of these pH buffers on the speciation studies of cadmium and lead metal ions are drawn. MES, MOPSO and MOPS can be suitable pH buffers for determination of both metals by DPP and DPASV as they do not complex these metals and do not modify to a significant extent the reversibility of the electrochemical processes under the experimental conditions used.

Acamprosate Decreases the Hypermotility During Repeated Ethanol Withdrawal

One of the known behavioral actions of acamprosate is to prevent relapse in weaned alcoholics. However, the mechanism underlying this effect remains unclear. In this study, the motility of Wistar male rats, which were either alcoholized by ethanol inhalation or simultaneously alcoholized and treated orally by acamprosate (400 mg/kg/day) for 4 weeks, was measured during four episodes of the ethanol withdrawal. The concentrations of excitatory and inhibitory amino acids were also assayed by the microdialysis technique with OPA/BME precolumn derivatisation and electrochemical detection in the nucleus accumbens. Acamprosate reduces both the motility and the glutamate microdialysate content during the first 12 h of ethanol withdrawal in comparison to the alcoholized untreated group. The basal concentration of the sulfonated amino acid taurine increased significantly in alcoholized acamprosate-treated rats compared to alcoholized untreated rats. These results suggest that acamprosate is able to reduce the hypermotility during ethanol withdrawal syndrome directly by reducing the nucleus accumbens glutamate concentration or indirectly by increasing the taurine and GABA brain level.

Regulation of Connexin Channels by pH: DIRECT ACTION OF THE PROTONATED FORM OF TAURINE AND OTHER AMINOSULFONATES

Protonated aminosulfonate compounds directly inhibit connexin channel activity. This was demonstrated by pH-dependent connexin channel activity in Good's pH buffers (MES (4-morpholineethanesulfonic acid)), HEPES, and TAPS (3-({[2-hydroxy-1, 1-bis(hydroxymethyl)ethyl]amino]-1-propanesulfonic acid)) that have an aminosulfonate moiety in common and by the absence of pH-dependent channel activity in pH buffers without an aminosulfonate moiety (maleate, Tris, and bicarbonate). The pH-activity relation was shifted according to the pKa of each aminosulfonate pH buffer. At constant pH, increased aminosulfonate concentration inhibited channel activity. Taurine, a ubiquitous cytoplasmic aminosulfonic acid, had the same effect at physiological concentrations. These data raise the possibility that effects on connexin channel activity previously attributed to protonation of connexin may be mediated instead by protonation of cytoplasmic regulators, such as taurine. Modulation by aminosulfonates is specific for heteromeric connexin channels containing connexin-26; it does not occur significantly for homomeric connexin-32 channels. The identification of taurine as a cytoplasmic compound that directly interacts with and modulates connexin channel activity is likely to facilitate understanding of cellular modulation of connexin channels and lead to the development of reagents for use in structure-function studies of connexin protein.

Blends of polyester having amino sulfonic acid moieties with poly(vinyl alcohol) and their metal complex formation

Polyester having amino sulfonic acid moieties (TBES) was prepared by a liquid/solid biphase polycondensation of terephthaloyl chloride (TPC) and N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid (BES) in trimethyl phosphate (TMP) using triethylamine (TEA) as an acid acceptor. Blends of TBES with PVA and their metal complexes with Ni2+ and Co2+ ions were prepared. A strong interaction was observed between TBES and PVA. An electric conductivity of 10−6 S cm−1 was attained for the blend films containing about 5 wt % water. A coordination structure with two chelate rings is proposed for the metal complex with Ni2+ and Co2+ ions when the molar ratio of amino sulfonic acid groups in TBES to metal ions is larger than 2. Polymer blends complexed with Ni2+ or Co2+ ions result in semi-interpenetrating polymer networks from chelate formation. © 1997 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 35: 3561–3569, 1997

Blends of polyester having amino sulfonic acid moieties with poly(vinyl alcohol) and their metal complex formation

Polyester having amino sulfonic acid moieties (TBES) was prepared by a liquid/solid biphase polycondensation of terephthaloyl chloride (TPC) and N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid (BES) in trimethyl phosphate (TMP) using triethylamine (TEA) as an acid acceptor. Blends of TBES with PVA and their metal complexes with Ni2+ and Co2+ ions were prepared. A strong interaction was observed between TBES and PVA. An electric conductivity of 10−6 S cm−1 was attained for the blend films containing about 5 wt % water. A coordination structure with two chelate rings is proposed for the metal complex with Ni2+ and Co2+ ions when the molar ratio of amino sulfonic acid groups in TBES to metal ions is larger than 2. Polymer blends complexed with Ni2+ or Co2+ ions result in semi-interpenetrating polymer networks from chelate formation. © 1997 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 35: 3561–3569, 1997