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PubMed2002

Field-amplified sample stacking and nonaqueous capillary electrophoresis determination of complex mixtures of polar aromatic sulfonates.

Nonaqueous CE and field-amplified sample stacking have been used in the determination of complex mixtures of polar aromatic sulfonates (AS; mainly benzene- and naphthalenesulfonates) of environmental concern. The analytical procedure consists of an on-column aqueous sample enrichment, followed by the nonaqueous electrophoretic determination of stacked aromatic sulfonates. Various organic solvents were used as separation medium, acetonitrile and N-methylformamide gave the best results. Optimum capillary electrophoresis separation is obtained with ammonium acetate (25 mM) dissolved in N-methylformamide-methanol (90:10) as background electrolyte. This combined method was applied to the analysis of surface water samples spiked with selected aromatic sulfonates derivatives.

Acetonitriles↗
PubMed2003

Synthetic potential of molluscan sulfatases for the library synthesis of regioselectively O-sulfonated D-galacto-sugars.

The substrate specificities of three molluscan sulfatases (E.C. 3.1.6.1; snail, abalone, and limpet origins) were investigated with assorted p-nitrophenyl (pNP) di-O-sulfonated beta-D-galactopyranosides and beta-lactosides [3,6-SO(3) Gal (1), 3',6'-SO(3) Lac (2), 4, 6SO(3) Gal (3), 2,6-SO(3) Gal (4), 3,4-SO(3) Gal (5), and 3,6-SO(3) GalNAc (6); Ac, acetyl; Gal, galactose; Lac, lactose] together with mono-O-sulfonated beta-D-galactopyranoside [pNP 3SO(3)-Gal (7)] and tri-O-sulfonated alpha-D-galactopyranoside [2,3,6-SO(3)-alpha-Gal (11)]. Some notable differences between the substrate specificity of the three sulfatases were disclosed; snail sulfatase hydrolyzed the 3O- and 2O-sulfo groups of 1 and 4, respectively, to afford 6SO(3) Gal (9) in high yields, while the abalone enzyme did not act on 4. Only the limpet enzyme could cleave the 3O-sulfo groups of 7 to give pNP beta-galactoside. In contrast, every enzyme could utilize 11 as a good substrate to afford a mixture of 6SO(3)-alpha-Gal (13) and 2,6-SO(3) alpha-Gal (12). None of the enzymes could cleave the O-sulfo groups of 5 and 6, which indicates that a primary 6O-sulfo group tends to promote the enzymatic hydrolysis of O-sulfo groups at the secondary positions.

Animals↗
PubMed1991

Interaction of poly(sodium vinyl sulfonate) and its surface graft with antithrombin III.

Poly(sodium vinyl sulfonate) (PVS) was found to be 1/14 times as active as heparin in inducing the conformational change and activation of antithrombin III. The conformational change of antithrombin III was investigated in terms of the intrinsic fluorescence of tryptophan residue, the extrinsic fluorescence using 1,6-diphenyl-1,3,5-hexatriene as fluorescent probe, and Fourier-transform infrared spectroscopy. It was evident in the experiment using 2,4,6-trinitrobenzene sulfonate that PVS elicited the activity of antithrombin III by interacting with amino groups of the protein as does heparin. Sodium vinyl sulfonate was graft-polymerized onto polyetherurethane (PEU) film that was treated with glow discharge in advance. PVS-grafted PEU film adsorbed antithrombin III easily and, like ungrafted PVS, induced conformational change and activation of antithrombin III. However, the mechanism of interaction of the PVS graft with antithrombin III did not seem to be completely the same as that of ungrafted PVS in solution.

Antithrombin III↗
PubMed2003

In vitro biocompatibility assessment of sulfonated polyrotaxane-immobilized polyurethane surfaces.

Sulfonated polyrotaxanes (PRx-SO(3)'s), in which sulfonated alpha-cyclodextrins (alpha-CDs) were threaded onto the poly(ethylene glycol) (PEG) segments in a PEG-b-poly(propylene glycol) (PPG)-b-PEG triblock copolymer (Pluronic) capped with benzyloxycarbonyl (Z)-L-phenylalanine (Z-L-Phe), were prepared as a novel surface-modifying biomaterial. Surface modification of the polyurethane (PU) was carried out by blending the PRx-SO(3)'s with a PU solution, followed by solution casting. The incorporated PRx-SO(3)'s led to the enhanced hydrophilicity by changing the surface properties of the PU matrix. Modified PUs showed the stable entrapment of the PRx-SO(3)'s with little extraction into water and enhanced mechanical properties after exposure to water compared to the PU control. The incorporated PRx-SO(3)'s repelled the proteins and kept them from closely approaching the surface areas, prevented platelet activation by thrombin, and effectively repelled bacteria. These results suggest that both the supramolecular structure of the polyrotaxanes and exposure of the sulfonated groups onto the surfaces contribute to these phenomena. Thus, surface modification with PRx-SO(3)'s is suggested to be useful for the fabrication of biocompatible medical devices.

Biocompatible Materials↗
PubMed2005

Novel functional biodegradable polymer. III. The construction of poly(gamma-glutamic acid)-sulfonate hydrogel with fibroblast growth factor-2 activity.

Poly(gamma-glutamic acid)-sulfonate (gamma-PGA-S) hydrogel, with fibroblast growth factor (FGF)-2 activity was investigated as a novel, next-generation tissue-engineering material. gamma-PGA-net-gamma-PGA-S72 (S72-netgel) was prepared with gamma-PGA-S and gamma-PGA-S72 (72% sulfonated gamma-PGA) to provide the high mobility of gamma-PGA-S72 for FGF-2 activity. Cell adhesion and proliferation activities were evaluated on gamma-PGA and gamma-PGA-S hydrogels along with S72-netgels. Both cell adhesion and proliferation activities of gamma-PGA and gamma-PGA-S hydrogels were low. In contrast, S72-netgels had high cell adhesion and proliferation activities, because of their low swelling ratios and high sulfonic acid group concentrations. Furthermore, S72-netgels had high FGF-2 activity, because gamma-PGA-S72 retained FGF-2 activity when incorporated into S72-netgels. S72-netgels should be useful as next-generation tissue-engineering material containing FGF-2 activity.

Animals↗
PubMed2006

The biocompatibility of silk fibroin films containing sulfonated silk fibroin.

Sulfonation reaction may be an effective method for preparation of heparin-like materials. However, no sulfonated polymer based on protein backbone was used for improving the blood compatibility of biomaterials. In this study, the biocompatibility of new kind of composite materials films obtained by blending silk fibroin (SF) with sulfonated silk fibroin (SSF) was evaluated. The anticoagulant activity was characterized with prothrombin time (PT), activated partial thromboplastin time (APTT), and thrombin time (TT), which all increased remarkably, the clot times exceeded the measurement limit of clot detection instrument. Its platelet adhesion was also investigated as another parameter of blood compatibility. The cell compatibility of composite films was evaluated through cell morphologies on the films and cell viability by methyl thiazolyl tetrazolium (MTT) assay. Tensile strength and elongation at break of the composite films reached to 44.6 MPa and 50.3%, respectively. All these results indicated that SF/SSF composite film was a potential material for blood-contact materials and tissue engineering matrix.

Animals↗
PubMed1989

Sulfone analogues of taurine as modifiers of calcium uptake and protein phosphorylation in rat retina.

The syntheses of five sulfone analogues of taurine are described: 2-aminoethylmethyl sulfone (AEMS), thiomorpholine-1,1-dioxide (TMS), N-methylthiomorpholine-1,1-dioxide (M-TMS), (+/-)3-aminotetrahydrothiopyran-1,1-dioxide (APS), and (+/-)3-aminotetrahydrothiophene-1,1-dioxide (ATS). When these compounds were evaluated in the rat retina as modulators of ATP-dependent calcium ion uptake at low calcium ion concentrations (10 microM), AEMS, ATS, and APS were found to be more potent stimulators of ATP-dependent calcium ion uptake than taurine. TMS and M-TMS had no effect. At high concentrations of calcium ions (1.44 mM), taurine, AEMS, ATS, APS, and TMS inhibited ATP-independent calcium ion uptake; AEMS, ATS, and APS were more potent inhibitors than taurine. ATS was the only compound tested (including taurine) that inhibited ATP-dependent calcium ion uptake at high calcium ion concentrations. The effects of the sulfone analogues of taurine on the incorporation of phosphate into retinal proteins were also studied. Taurine, AEMS, ATS, APS, and TMS were equipotent inhibitors of phosphate incorporation (30-45%). M-TMS had no effect.

Adenosine Triphosphate↗
PubMed1986

2-Aminoethylmethyl-sulfone (AEMS): a potent stimulator of ATP-dependent calcium uptake.

Retinal ATP-dependent calcium ion uptake is stimulated by a number of agents, but none are previously reported to be as potent as taurine. We have evaluated the effects of 2-aminoethylmethyl-sulfone (AEMS), thiomorpholine-1,1-dioxide (TMS), and N-methyl-thiomorpholine-1,1-dioxide (M-TMS) on calcium ion uptake. AEMS is twice as potent a stimulator of calcium ion uptake compared to taurine. TMS and M-TMS did not stimulate calcium ion uptake at concentrations up to 20 mM. These data demonstrate that the sulfonic acid moiety can be replaced by a methyl sulfone moiety for stimulation of ATP-dependent calcium ion uptake.

Adenosine Triphosphate↗
PubMed1992

Alkyl phosphonic acids and sulfonic acids in the Murchison meteorite.

Homologous series of alkyl phosphonic acids and alkyl sulfonic acids, along with inorganic orthophosphate and sulfate, have been identified in water extracts of the Murchison meteorite after conversion to their t-butyl dimethylsilyl (tBDMS) derivatives. The methyl, ethyl, propyl, and butyl compounds have been observed in both series. Five of the eight possible alkyl phosphonic acids and seven of the eight possible alkyl sulfonic acids through C4 have been identified. Abundances decrease with increasing carbon number as observed of other homologous series indigenous to Murchison. Concentrations range downward from approximately 380 nmol/gram in alkyl sulfonic acid series, and from 9 nmol/gram in the alkyl phosphonic acid series. Inorganic phosphate is present at about 25 micromoles/gram.

Alkanesulfonic Acids↗
PubMed1995

The syntheses of 3 beta-steroidal diacylglyceryl sulfides, sulfoxides, and sulfones.

The syntheses of the diacylglyceryl-sulfide 4a, sulfoxide 4b, and sulfone 4c of dehydroepiandrosterone (3 beta-hydroxyandrost-5-en-17-one, DHEA, 1a) are described. Nucleophilic substitution of 1,2-dipalmitoyl-3-iodo-rac-3-deoxyglycerol (2) with 3 beta-mercaptoandrost-5-en-17-one (3) afforded the diacylglyceryl-sulfide (4). Selective oxidation of 4 with m-chloroperbenzoic acid gave the diacylglyceryl-sulfoxide 4b and diacylglyceryl-sulfone 4c of DHEA. The sulfide 4a was a very weak inhibitor of glucose-6-phosphate dehydrogenase, whereas the sulfone 4c did not inhibit the enzyme.

Dehydroepiandrosterone↗
PubMed1988

A new sensitive non-isotopic method using sulfonated probes to detect picogram quantities of specific DNA sequences on blot hybridization.

The use of non-radioactive systems to detect target DNA or RNA displays many advantages such as safe manipulation, potential use in non-specialized scientific area and prolonged lifetime of the probes (one year or more). We here describe a method we have improved and optimized using sulfonated DNA probes for hybridization on dot and Southern blots. Sulfonation is an easy chemical modification procedure which does not require enzymatic coctail as does nick-translation. Sensitivity of this method has been particularly improved by using a new blocking solution, containing heparin, which allows easy and fast detection of picogram quantities of DNA. This method allows the use of nitrocellulose as well as nylon membranes with very low background. Equal resolution is obtained in comparative experiments involving both sulfonated and 32P-radiolabelled probes. Single copy gene sequences are readily detected in nuclear DNA. These results allow the use of this procedure for restriction fragment length polymorphism (RFLP) studies.

Base Sequence↗
PubMed1992

Sulfonic acid polymers as a new class of human immunodeficiency virus inhibitors.

Four sulfonic acid polymers [poly(4-styrenesulfonic acid)(PSS), poly(anetholesulfonic acid)(PAS), poly(vinylsulfonic acid)(PVS), poly(2-acrylamido-2-methyl-1-propanesulfonic acid)(PAMPS)] have been found to inhibit the cytopathicity of HIV-1 and HIV-2 in MT-4 cells at concentrations that are not toxic to the host cells. The sulfonic acid polymers also inhibited syncytium formation in co-cultures of MOLT-4 cells with HIV-1- or HIV-2-infected HUT-78 cells. They also inhibited binding of anti-gp120 mAb to HIV-1 gp120 and blocked adsorption of HIV-1 virions to MT-4 cells. PSS and PAS, but not PVS and PAMPS, interfered with the binding of OKT4A/Leu3a to the CD4 receptor. The anti-HIV activity of these polyanionic compounds can be ascribed to inhibition of the gp120-CD4 interaction. Sulfonic acid polymers represent a lead of anti-HIV compounds that warrant further evaluation of their therapeutic potential.

Antiviral Agents↗
PubMed2004

Sulfone COX-2 inhibitors increase susceptibility of human LDL and plasma to oxidative modification: comparison to sulfonamide COX-2 inhibitors and NSAIDs.

Clinical investigations have demonstrated a link between use of the sulfone cyclooxygenase-2 (COX-2) inhibitor, rofecoxib, and increased risk for atherothrombotic events. This increased risk was not observed for a sulfonamide COX-2 inhibitor (celecoxib), indicating a potential non-enzymatic mechanism for rofexocib. To test this hypothesis, we compared the independent effects of COX-2 inhibitors on human LDL oxidation, an important contributor to atherosclerotic cardiovascular disease. The results showed that rofecoxib (100 nM) significantly decreased (>40%, p<0.001) the lag time for LDL conjugated diene formation and increased levels of thiobarbituric-acid-reactive-substances (TBARS) in vitro. The pro-oxidant activity of rofecoxib was dose-dependent and attenuated by 70% (p<0.001) with the antioxidant, Trolox. Rofecoxib and etoricoxib (100 nM) also caused a marked increase (>35%, p<0.001) in non-enzymatic generation of isoprostanes, as measured by mass spectroscopy. Addition of rofecoxib to fresh human plasma reduced the oxygen radical antioxidant capacity (ORAC) by 34% (p<0.0001). By contrast, other selective (celecoxib, valdecoxib, meloxicam) and non-selective COX inhibitors (ibuprofen, naproxen, diclofenac) had no significant effect on LDL oxidation rates or plasma ORAC values, even at suprapharmacologic levels. X-ray diffraction analysis showed that sulfone COX-2 inhibitors interact differently with membrane phospholipids, suggesting a physico-chemical basis for the pro-oxidant activity. These results demonstrate that sulfone COX-2 inhibitors increase the susceptibility of biological lipids to oxidative modification through a non-enzymatic process. These findings may provide mechanistic insight into reported differences in cardiovascular risk for COX-2 inhibitors.

Animals↗
PubMed2004

Coating of an apatite layer on polyamide films containing sulfonic groups by a biomimetic process.

Coating organic polymers with hydroxyapatite is an attractive method for the development of materials for medical applications, as it allows hydroxyapatite to show its unique biological properties such as its ability for bone bonding and protein adsorption. The biomimetic process focuses attention on fabricating such hydroxyapatite-polymer hybrids, where bone-like apatite is deposited on an organic polymer surface in solutions mimicking physiological conditions. In this process, a bone-like apatite layer can be coated onto organic substrates either by using a simulated body fluid (SBF), which has ion concentrations nearly equal to those of human extracellular fluid, or by using fluids that are supersaturated with respect to apatite at ambient conditions. We previously reported that apatite was deposited on polyamide films containing carboxyl groups in a solution mimicking body fluid, when they were incorporated with calcium salts. In the present study, to find an alternative functional group effective in apatite formation, we examined the apatite-forming ability of polyamide films containing sulfonic groups in the same solution. It was found that the polyamide film containing sulfonic groups could deposit apatite on its surface in the solution when the film was incorporated with calcium salts. These results show that the sulfonic group also acts as a functional group, and is as effective for apatite deposition in the body environment as the carboxyl group.

Biocompatible Materials↗
PubMed2006

Preparation of polyaniline-modified electrodes containing sulfonated polyelectrolytes using layer-by-layer techniques.

Polyaniline (PAni) has been used frequently for the construction of biosensors. However, a prime limitation is its instability at basic or neutral pH because of the loss of its electrochemical activity and conductivity. In this study, three available sulfonated polyanions: Nafion, poly(vinyl sulfonate) (PVS), and poly(styrene sulfonate) (PSS) serving as the counterion and providing an acidic microenvironment to stabilize PAni, are used to fabricate a sensor for ammonium ion detection. Nafion used to be a common ion-sensitive membrane due to its high proton conductivity. However, its high cost and limited solubility has constrained its uses. PVS and PSS are water-soluble polymers, easily incorporating with PAni to form the composites. Surface analysis by electron spectroscopy for chemical analysis (ESCA) and scanning electron microscope (SEM), and the electrochromic property for the PAni composites provided the convenient tools to characterize the electrode fabrication. On the aspect of sensing the ammonium ions, the modified electrodes exhibited electroactivity of PAni in ammonium ion detection and also showed the linear dependence of reduction current on the ammonium ion concentration. The pH effect on the sensing response was also evaluated and found insignificant to the response (ranging from pH 6.9-7.6). For increasing the stability of the electrodes, the diazo-resin (DAR) was introduced to the coat on the outmost layer and then cured by UV irradiation, giving the covalent network between the layers of polyelectrolytes. The PSS-doped PAni electrode was found to perform detection sensitivity in the linear range of 0-100mM of ammonium ion concentration.

Adsorption↗
PubMed2005

Mechanically induced self-propagating reactions: analysis of reactive substrates and degradation of aromatic sulfonic pollutants.

Mechanochemical reactions have been identified as a valuable alternative to conventional methodologies for the degradation of toxic pollutants as well as for their abatement in contaminated matrices. This paper discusses the application of the mechanochemical technique to the degradation of sulfonic acids in a contaminated matrix. The degradation of the pollutant compound was carried out by taking advantage of combustive reactions on a suitable reactive system ignited under mechanical treatment conditions. Two systems have been investigated as possible reactive substrates. The first one was a Mg-SiO2 powder mixture while the second system was a Ca-SiO2 powder mixture. Milling trials performed under different mechanical processing conditions allowed one to characterise the reactivity of these chemical systems, which basically undergo a reduction/oxidation reaction involving the formation of MgO and Si phases when the Mg-SiO2 system is considered and CaO and Si phases when the Ca-SiO2 system is employed, respectively. The systematic change of the stoichiometric ratios Mg:SiO2 and Ca:SiO2 permitted to identify the minimum Mg or Ca content necessary for the ignition of the combustive reactions. The experimental runs performed with such systems have shown a greater effectiveness of the Mg-SiO2 because of less energy inputs required to ignite a combustion. For this reason the Mg-SiO2 has been considered as a reactive substrate in the following trials. Since the SiO2 amount in stoichiometric excess may be regarded as inert phase, it was substituted with a different phase consisting of the matrix contaminated by sulfonic acids. This aspect permitted to ignite a combustive reaction with the minimum possible content of Mg-SiO2 reacting mixture. The chemical analyses performed after the combustive reaction proved the complete removal of the sulfonic acid from the contaminated matrix.

Calcium↗
PubMed2006

Pseudo-homogeneous micelle extraction of ion-associates formed between tetrabutylammonium ion and some aromatic sulfonate ions into nonionic surfactant micelle studied through the mobility measurements in capillary zone electrophoresis.

Ion-association extraction of some aromatic sulfonate ions including alkylbenzene sulfonates with tetrabutylammonium ion (TBA+) into nonionic surfactant micelle has been investigated through the changes in the electrophoretic mobility. Nonionic surfactants of Brij 35 and Brij 58 were used as micelle substrates to which the ion-associates formed could distribute. The electrophoretic mobility of the aromatic sulfonate ions was measured by capillary zone electrophoresis in the presence of TBA+ and/or the nonionic surfactant to determine ion-association constants (K(ass)), binding constants of the anions to the nonionic surfactant micelle (K(B)), and binding constants of the ion-associates to the nonionic surfactant micelle (K(B,IA)). Nonlinear phenomena induced with the alkyl chain moiety were observed on K(ass) and K(B) by its linear structure and the mixed micelle formation, respectively. Larger K(B) values were obtained with Brij 58 as micelle matrix than with Brij 35, while the differences in K(B,IA) were small between Brij 58 and Brij 35.

Electrophoresis, Capillary↗
PubMed2005

Process intensification using cavitation: optimization of oxidation conditions for synthesis of sulfone.

Cavitation can be effectively used for intensification of chemical reactions due to the production of free radicals and conditions of high temperatures and pressures locally. In the present work, use of cavitation for the intensification of the synthesis of sulfone has been explored. The oxidation of thioether or sulfide to synthesize corresponding sulfone with 30% H(2)O(2) as an oxidant was studied under acoustic cavitation and the results have been compared with the conventional approach based on the use of mechanical agitation. The aim has been also to optimize the different operating conditions viz. molar ratio of reactants to the oxidizing agent, type of the catalyst as well as its concentration, type of the solvent and the reactant concentration, so as to maximize the degree of intensification. It was observed that under the optimized conditions of sonication, the yield of sulfone was about five to six times higher as compared to the conventional approach of using mechanical agitation only.

Catalysis↗