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PubMed1975

Bacterial metabolism of arylsulfonates: role of meta cleavage in benzene sulfonate oxidation by Pseudomonas testosteroni.

Pseudomonas testosteroni H-8 oxidizes certain lower alkylbenzene sulfonates at rates inversely related to the length of the alkyl group. Appreciable Q(O)2 values were observed for benzene sulfonate (BS), toluene sulfonate (TS), and ethylbenzene sulfonate (EBS), but not for propylbenzene sulfonate (PS) and higher homologues. Catechol oxidation was catalyzed by a constitutive catechol-2,3-oxygenase (EC 1.99.2.a). Yellow meta cleavage products accumulated when BS-grown cells were exposed to catechol, 4-methylcatechol, 3-methylcatechol, EBS and PS, but not BS or TS. Traces of a yellow metabolite (probably 2-hydroxymuconic semialdehyde) were detectable during growth on BS. PS completely inhibited growth on BS, but not on L-leucine or nutrient broth. Also, PS antagonized respiration on BS and catechol, but not glutamate, the extent of inhibition being directly related to PS concentration. Formation of a meta cleavage product from PS, and inhibition of catechol oxidation by PS, suggested that the actual inhibitor may not be PS itself, but a metabolite.

Arylsulfonates↗
PubMed2000

Inhibition of rat colon tumors by sulindac and sulindac sulfone is independent of K-ras (codon 12) mutation.

Nonsteroidal anti-inflammatory drug (NSAID) use reduces the risk of colorectal cancer by 40-50%. Previous studies suggest that effective inhibition of colorectal cancer by NSAIDs may be dependent on the presence or absence of a K-ras mutation. This study was aimed at determining the relationship between inhibition of colorectal cancer by sulindac and sulindac sulfone and the presence of activating K-ras mutations in the 1,2-dimethylhydrazine dihydrochloride rat model. Sulindac (20 mg x kg(-1) x day(-1)), sulindac sulfone (40 mg x kg(-1) x day(-1)), or vehicle was administered orally to male Sprague-Dawley rats for a 4-wk period beginning 20 wk after tumor induction. Tumor number and volume were measured before treatment by laparotomy and colonoscopy and again after treatment. Sulindac and sulindac sulfone treatment significantly reduced the number and volume of colorectal tumors compared with control rats. For K-ras (codon 12) mutation detection, frozen tumor tissue was collected at the endpoint. We found K-ras codon 12 mutations in 11 of 21 (52%) control tumors. The proportion of tumors with K-ras mutations in the sulindac-treated group [5 of 8 (62%); odds ratio = 1.51 (95% confidence interval = 0.29, 8.33)] and the proportion of sulindac sulfone-treated tumors [9 of 14 (64%); odds ratio = 1.63 (95% confidence interval = 0.41, 6.66)] were not significantly different from controls. Tumor inhibition did not correlate with K-ras (codon 12) mutation status, which suggests that the mechanism of inhibition of rat colorectal cancer by sulindac and sulindac sulfone is independent of K-ras mutation.

1,2-Dimethylhydrazine↗
PubMed1993

Preparation and surface properties of PEO-sulfonate grafted polyurethanes for enhanced blood compatibility.

In order to improve the thromboresistance of the commercial polyurethane(PU), its surface modification was accomplished by three new different methods and their surface characteristics were investigated using ATR-FTIR, ESCA, SEM, and dynamic contact angle measurements. Sulfonations using propane sultone were performed directly onto PU or onto hydrophobic dodecanediol (DDO) grafted PU or onto hydrophilic poly(ethyleneoxide) (PEO) grafted PU. ESCA data coincided well with ATR-IR results, as more 0 at. % for PEO grafted PUs and the presence of S for the sulfonated PUs were revealed. At SEM observation the surfaces of PU-DDO and PU-PEO were relatively smooth, whereas all the sulfonated PU surfaces showed excellent smoothness and homogeneity. The hydrophilicity of the surfaces was considerably increased after PEO grafting or sulfonation. In addition, all the sulfonated PU surfaces, particularly PU-PEO-SO3, which has further hydrophilicity, exhibited complete wetting behavior due to the negatively charged SO3 groups.

Alkanesulfonates↗
PubMed1986

Delayed inactivation of Citrobacter freundii cephalosporinase by 6 beta-[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]penicillin sulfone.

When Citrobacter freundii cephalosporinase was incubated with 6 beta-[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]penicillin sulfone (cloxacillin sulfone) in phosphate buffer, the enzyme was suddenly inactivated just after the completion of enzymatic degradation of the cloxacillin sulfone. Such delayed inactivation was due to a secondary inhibitor formed from cloxacillin sulfone during the incubation period. The inactivation was delayed due to the protection of the enzyme by cloxacillin sulfone from the attack of the secondary inhibitor. Phosphate anions were essential for the formation of the secondary inhibitor. However, once the secondary inhibitor was formed, the inactivation occurred in the absence of phosphate anions although the degree of the inactivation depended on the length of the preincubation period with phosphate anions. The main species (more than 80%) of the inactivated enzyme was detected as a single protein band with a slightly lower pI value than that of the native enzyme on isoelectric focusing on a plate.

Buffers↗
PubMed1996

Sodium polystyrene sulfonate (kayexalate) aspiration: histologic appearance and infrared microspectrophotometric analysis of two cases.

OBJECTIVE: Sodium polystyrene sulfonate (kayexalate) is a cation-exchange resin given enterally for the treatment of hyperkalemia. Aspiration of this material is a rare occurrence, but when visualized in the alveolus, it has a characteristic microscopic appearance that is virtually diagnostic. In two cases, recognition of the characteristic morphology of the foreign material raised the question of sodium polystyrene sulfonate. DESIGN: We used infrared spectroscopy to demonstrate the presence of this material in lung biopsies of two patients by identifying foreign body particles. Histories of the patients were reviewed for exposure to sodium polystyrene sulfonate. SETTING: Two lung specimens were referred to the Armed Forces Institute of Pathology with an unknown foreign material identified within the air spaces. PATIENTS: The lung biopsies were from two children, one postterm female infant who died at 3 days of life and a 4-year-old girl who underwent lung biopsy during surgical repair for tetralogy of Fallot. Both patients had received sodium polystyrene sulfonate previously for control of hyperkalemia. RESULTS: The lung specimens showed characteristic basophilic, amorphous foreign material in airspaces on histologic sections. The identity of this material was confirmed by Fourier transform infrared microspectrophotometry. CONCLUSIONS: To our knowledge, we report the first two cases of sodium polystyrene sulfonate aspiration in children. This material has a distinctive morphologic appearance on histologic sections, and its identity can be confirmed by Fourier transform infrared microspectrophotometry.

Cation Exchange Resins↗
PubMed2000

[Synthesis and application of sulfonated beta-cyclodextrins as chiral additives in capillary electrophoresis].

Three new kinds of the sodium salt of sulfonated beta-cyclodextrins with different degrees of substitution were synthesized and characterized. A simple synthesis method was employed by direct sulfonating reaction with concentrated sulfuric acid. Sulfonated beta-cyclodextrins were used as chiral resolving agents for the capillary electrophoretic separation of enantiomers in high pH and low pH background electrolytes. In different electrophoretic polarity mode, the effects of the type and concentration of sulfonated beta-cyclodextrin were investigated. Sulfonated beta-cyclodextrins were proved to be strong complexing agents for basic and neutral analytes.

Cyclodextrins↗
PubMed1999

[FTIR and fluorescence emission spectra of sulfonated PS and its ionomers].

The FTIR spectra of sulfonated polystyrene and Zn and La ionomers change with sulfonation degree and the kind of metal ion. With increasing the sulfonation degree, the stretching vibrational strength of -SO3H and -SO3 increases. Because of the interaction of polar group, the FTIR spectra around 1200 cm(-1) or so split. On the other hand, the degree of sulfonation influences somewhat on the intensity and position of fluorescence spectra of sulfonation polystyrene and its ionomers.

English Abstract↗
PubMed1985

Reduced taurine contents and modification of anticonvulsive effects of phenobarbital and phenytoin by guanidinoethane sulfonate in mice.

In the present study, we investigated whether administration of guanidinoethane sulfonate, and inhibitor of taurine uptake, worsens electroshock-induced convulsions or modifies the antiepileptic actions of phenobarbital or phenytoin against maximal electroshock seizures in mice. Treatment with 1% guanidinoethane sulfonate in drinking water for 9 days decreased taurine concentration in the brain to 76% of control value. Under these conditions, neither the severity of tonic convulsions of maximal electroshock seizures nor the threshold for tonic extension caused by electroshock was altered. On the other hand, the antiepileptic potency of phenobarbital and phenytoin against tonic convulsions of maximal electroshock seizures in mice was significantly lessened by chronic administration of guanidinoethane sulfonate. This decrease in potency was not due to an alteration in pharmacokinetics, as the brain levels of these drugs were unchanged. Furthermore, administration of the anticonvulsive drugs did not change brain concentrations of guanidinoethane sulfonate and total guanidino compounds. It is suggested that the observed loss of anticonvulsive potency of phenobarbital and phenytoin may be related to the decreased concentration of taurine produced by administration of guanidinoethane sulfonate.

Amino Acids↗
PubMed2000

Negative fast atom bombardment ionization of aromatic sulfonic acids: unusual sample-matrix interaction.

The most intense ion(s) in negative ion fast atom bombardment (FAB) mass spectra of 2- and 4-benzaldehyde sulfonic acid (BSA) in glycerol or 3-nitrobenzyl alcohol matrix corresponds to a covalent association of the analyte with one or two matrix molecules accompanied by the elimination of a molecule of water. The molecular ion [M - H](-), however, is of low abundance. The identity of the resulting ions [M + nA - H(2)O - H](-) (where M is the analyte and A is the matrix) was confirmed by exact mass measurement using the peak matching technique. These covalent matrix-analyte complexes were not observed when the sulfonic acid functionality in BSA was substituted with COOH, NO(2), and OH or when the sulfonic acid was in salt form. These observations indicate that the free sulfonic acid group in BSA is responsible for the covalent adduct formation. To our knowledge, analyte-matrix covalent association in negative ion FAB spectra of BSA has not been reported previously.

Benzaldehydes↗
PubMedDate not supplied

Continuous separation of serum proteins using a stirred cell charged with carboxylated and sulfonated microspheres.

We contrived a new separation system using a stirred cell charged with uncoupled microsphere similar to the chromatographic separation. Microspheres, carboxylated PS/PMAA and sulfonated PS/PNaSS, were prepared by emulsifier-free emulsion polymerization. To complement the submicron size weakness and the absence of ligands, we employed the latex form, the dispersion of microsphere, and took advantage of interaction relationships between proteins and microspheres. Adsorption isotherm is contemplated to investigate continuous separation behaviours of serum proteins. Selectivity of separation is in the following order: PS/PNaSS-2.0 (high sulfonated) < PS/PNaSS-0.3 (low sulfonated) < PS/PMAA-0.5 (low carboxylated). Unlike previous works on batch separation, not only the adsorbed amount in equilibrium (Cm), but also adsorption coefficient (K), played an important role in continuous separation. Functional groups (carboxyl and sulfonate), induced from the co-monomer, also affected the adsorption behaviours.

Adsorption↗
PubMed2001

Capillary electrochromatography with polyacrylamide monolithic stationary phases having bonded dodecyl ligands and sulfonic acid groups: evaluation of column performance with alkyl phenyl ketones and neutral moderately polar pesticides.

In this report, we describe the preparation of porous polyacrylamide-based monolithic columns via vinyl polymerization. These monoliths possess in their structures bonded dodecyl ligands and sulfonic acid groups. While the sulfonic acid groups are meant to support the electroosmotic flow (EOF) necessary for moving the mobile phase through the monolithic capillary, the dodecyl ligands are introduced to provide the nonpolar sites for chromatographic retention. However, incorporating the sulfonic acid groups in the monoliths does not only support the EOF but also exhibit hydrophilic interaction with moderately polar compounds such as urea herbicides and carbamates insecticides. Consequently, mixed-mode (reversed-phase/normal phase) retention behavior is observed with neutral and moderately polar pesticides. The amount of sulfonic acid group in the monolith can be conveniently adjusted by changing the amount of vinylsulfonic acid added to the polymerization reaction. Optimum EOF velocity and adequate chromatographic retention are obtained when 15% vinylsulfonic acid is added to the reaction mixture. Under these conditions, rapid separation and high plate counts reaching greater than 400000 plates/m are readily obtained.

Acrylic Resins↗
PubMed1995

Synthesis of pyrryl aryl sulfones targeted at the HIV-1 reverse transcriptase.

Various aryl 1-pyrryl sulfones were synthesized and tested as inhibitors of HIV-1. 2-Nitrophenyl-2-ethoxycarbonyl-1-pyrryl sulfone, the most active among test derivatives, was selected as lead compound of the aryl pyrryl sulfone series. The in vitro anti-HIV-1 activity and cytotoxicity of 41 compounds is reported. Some structure-activity relationships are discussed also in comparison with the known NPPS (2-nitrophenyl phenyl sulfone).

Cell Survival↗
PubMed2004

Wedge-shaped molecules with a sulfonate group at the tip--a new class of self-assembling amphiphiles.

The synthesis of 4-N-[3',4',5'-tris(dodecyloxy)benzamido]benzene-4-sulfonic acid (1) and 4'-[3",4",5"-tris(dodecyloxy)benzoyloxy]azobenzene-4-sulfonic acid (2) is described. Pure acid 1 is stable, while 2 can be stored only in solution. Both acids were obtained from their sodium salts and were quantitatively transformed into the pyridinium salts. The phase behavior of these acids, as well as the sulfonates was investigated by differential scanning calorimetry and polarizing optical microscopy. The investigated compounds exhibit columnar mesophases. The formation of columnar superstructures was demonstrated for the sodium sulfonates by scanning force microscopy, gelation experiments, and proton magnetic resonance spectroscopy.

Azo Compounds↗
PubMed1991

Negative cilia concept for thromboresistance: synergistic effect of PEO and sulfonate groups grafted onto polyurethanes.

In order to investigate the interaction between various sulfonated polyurethanes (PUs) and blood, a commercial PU surface was chemically modified by poly(ethylene oxide) (PEO), dodecanediol(DDO), and propane sultone to give hydrophilic, hydrophobic, and negative sulfonated surfaces, respectively. The blood compatibility of modified PUs was evaluated by an in vitro platelet adhesion test, activated partial thromboplastin time (APTT), and prothrombin time (PT) measurements as well as an ex vivo rabbit A-A shunt method. In the platelet adhesion test, the hydrophilic PEO grafted PUs showed less platelet adhesion than untreated PU and hydrophobic DDO grafted PU. Sulfonated PU-PEO exhibited a lower degree of adhesion and shape change of platelet. The APTT and PT, especially APTT, of the sulfonated PUs were extended, whereas those of PU-PEO and PU-DDO did not show any significant change compared with untreated PU. Meanwhile, in the ex vivo experiment, hydrophilic PEO grafted PUs showed longer occlusion times than untreated PU or hydrophobic DDO grafted PU. In addition, the incorporation of SO3 groups at the end of PU-DDO and PU-PEO, particularly PU-PEO-SO3, exhibited an enormous prolongation in occlusion time, indicating a synergistic effect of the hydrophilic PEO and the negative SO3 groups on thromboresistance. These occlusion times corresponded well to in vitro evaluation results: the less adhesion and shape change of platelet and the longer APTT and PT, the more extended the ex vivo occlusion time.

Animals↗
PubMed2006

Novel sulfonated hydrogel composite with the ability to inhibit proteases and bacterial growth.

There is a growing interest in the development of wound dressings that possess functionality beyond providing physical protection and an optimal moisture environment for the wound. To this end, a novel dressing material based on a sulfonated triblock polymer has been developed. This versatile polymer possesses an ion-exchange capability that is amenable to binding and controlled release of a variety of therapeutic agents. This sulfonated polymer offers several advantages over existing commercial hydrogels used as wound dressings. These include (1) hydrophilicity that is proportional to sulfonation level, (2) easy preparation of fabric supported dressings (e.g., polyester, cotton, nylon), (3) excellent mechanical integrity of the materials when hydrated, (4) stability to a variety of chemistries, and (5) stability to a variety of sterilization methodologies. In this study, polymer was coated onto a polyester fabric and then modified by ion exchange to prepare the sodium, silver, or doxycycline salts. These sulfonated triblock polymer formulations were then evaluated for their capacity to sequester the neutrophil proteases, elastase, and collagenase-2 (MMP-8). Several of the formulations were found to sequester significant amounts of either elastase or collagenase. These formulations were demonstrated to be tested against a commercially available dressing that is currently marketed for its protease-inhibiting capability. The experimental dressing was statistically superior to the commercial dressing at inhibiting MMP-8 and elastase under the same conditions.

Anti-Bacterial Agents↗
PubMed1993

Pharmacokinetics and metabolic interconversion of intravenous 4-amino-5-chloro-2-[(methylsulfinyl)ethoxy]-N-[2-(diethylamino)ethyl] benzamide and its sulfide and sulfone metabolites in rats.

The pharmacokinetics of a new 5-hydroxytryptamine (5HT3) receptor antagonist, 4-amino-5-chloro-2-[(methylsulfinyl)ethoxy]-N-[2-(diethylamino)ethyl] benzamide (ML-1035, 1), and its sulfone and sulfide metabolites were examined in 12 rats. Each of these compounds (25.4 mumol/kg) was administered to rats intravenously. Their plasma concentrations were measured by high-performance liquid chromatography. These plasma data revealed that 1, a sulfoxide, underwent interconversion with its sulfide metabolite. However, no interconversion was observed between 1 and its sulfone metabolite. Examination of mean times and additional properties of the 1/sulfide metabolite system revealed that total exposure times of 1 and the sulfide metabolite were moderately and weakly, respectively, influenced by the metabolic interconversion process. However, the tissue distribution process strongly influenced the total exposure times of both compounds. The disposition of the sulfone metabolite of 1 was also strongly influenced by the tissue distribution process. In addition, < 3% of the intravenous dose of 1 or the sulfide was available to the general circulation as the sulfone metabolite.

Animals↗
PubMed2006

Vinyl sulfones: synthetic preparations and medicinal chemistry applications.

Vinyl sulfones have long been known for their synthetic utility in organic chemistry, easily participating in 1,4-addition reactions and cycloaddition reactions. This functional group has also recently been shown to potently inhibit a variety of enzymatic processes providing unique properties for drug design and medicinal chemistry. This review includes traditional methods used for the synthesis of vinyl sulfones, but focuses mainly on newer reactions applied to vinyl sulfones, including olefin metathesis, conjugate reduction, asymmetric dihydroxylation (AD), and the use of vinyl sulfones to arrive at highly functionalized targets, all illustrating the rich and versatile chemistry this group can efficiently perform. In addition, geminal disulfones are discussed with respect to their formation, reactions, and medicinal applications of this underutilized functional group.

Chemistry, Pharmaceutical↗
PubMed1999

Inhibition of hyaluronidase by fully O-sulfonated glycosaminoglycans.

We report a new flow injection assay (FIA) method for determining hyaluronidase activity and the inhibitory effects of chemical fully O-sulfonated glycosaminoglycans on this enzyme. The products of enzymatic action on hyaluronidase can be detected by FIA using fluorometric detection with the fluorogenic reagent 2-cyanoacetamide. The major products derived from hyaluronan by the action of mammalian testicular hyaluronidase (a hydrolyase) were confirmed by (1)H NMR spectroscopy and capillary electrophoresis. The FIA method was next applied to the assay of hyman urinary hyaluronidase activity and the screening of hyaluronidase inhibitors. The human urinary hyaluronidase activity measured ranged from 46 to 59 turbidity reducing units/mg protein. Among the glycosaminoglycans only heparin showed hyaluronidase inhibition. Chemically O-sulfonated glycosaminoglycans showed IC(50) values of hyaluronidase inhibition that correlated with the degree of O-sulfonation. Heparin was found to inhibit hyaluronidase activity noncompetitively, while chemically O-sulfonated HA strongly inhibited hyaluronidase through both competitive and noncompetitive effects.

Enzyme Inhibitors↗