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PubMed2004

Development of high-load, soluble oligomeric sulfonate esters via ROM polymerization: application to the benzylation of amines.

The development of high-load, soluble oligomeric sulfonate esters, generated via ROM polymerization, and their utility in the facile benzylation of an array of amines is reported. These polymeric sulfonate esters exist as free-flowing powders, are stable at refrigerated temperatures, and are readily dissolved in CH(2)Cl(2). Following the benzylation event, purification is attained via simple filtration, followed by solvent removal to deliver the desired benzylated product in good to excellent yield and high purity. [structure: see text]

Alkylating Agents↗
PubMedDate not supplied

The in vitro methylation of DNA by a minor groove binding methyl sulfonate ester.

The preparation of sequence and groove specific DNA methylating agents based on N-methylpyrrolecarboxamide subunits appended with an O-methyl sulfonate ester functionality (MeOSO2(CH2)2-Lex) has previously been described [Zhang, Y., Chen, F.-X., Mehta, P., and Gold, B. (1993) Biochemistry 32,7954-7965]. In contrast to simple methyl sulfonate esters, e.g., methyl methanesulfonate (MMS), which predominantly methylate at 7-guanine, MeOSO2-(CH2)2-Lex affords N3-methyladenine (3-MeAde) as its major adduct. Using competitive ELISA determinations, the methylation at major and minor groove sites in calf thymus DNA by MeOSO2(CH2)2-Lex has been precisely quantitated. The yields of N7-methylguanine (7-MeGua), 3-MeAde, and O6-methyldeoxyguanosine (6-Me-dGuo) are 0.424, 3.195, and 0.0027 mmol of adduct/mol of DNA, respectively, using 10 microM MeOSO2(CH2)2-Lex and 100 microM DNA. This compares to 0.773, 0.072, and 0.0033 mmol of adduct/mol of DNA for 7-MeGua, 3-MeAde, and 6-Me-dGuo, respectively, using MMS. The increase in the yield of 3-MeAde due to the minor groove equilibrium binding properties of MeOSO2(CH2)2-Lex is approximately 40-fold relative to MMS.

Adenine↗
PubMed2002

Inhibition of the anaerobic digestion process by linear alkylbenzene sulfonates.

Linear Alkylbenzene Sulfonates (LAS) are the most widely used synthetic anionic surfactants. They are anthropogenic, toxic compounds and are found in the primary sludge generated in municipal wastewater treatment plants. Primary sludge is usually stabilized anaerobically and therefore it is important to investigate the effect of these xenobiotic compounds on an anaerobic environment. The inhibitory effect of Linear Alkylbenzene Sulfonates (LAS) on the acetogenic and methanogenic step of the anaerobic digestion process was studied. LAS inhibit both acetogenesis from propionate and methanogenesis from acetate and hydrogen and it is shown that the propionateutilising bacteria are more sensitive to the presence of LAS than the acetoclastic methanogens. It has been proven that the inhibition intensity depends on the solids concentration and thus the term "biomass specific LAS concentration" has been introduced in order to describe the phenomenon better. Conclusively, it is believed that the inhibitory effect of LAS is the main reason that anaerobic microbial enrichments on LAS have not been succeeded yet. Also, the inhibition caused by LAS on the acetogenic and methanogenic step of the anaerobic digestion process should be seriously taken into consideration when wastewater from a surfactant producing industry is to be treated biologically or enter a municipal wastewater treatment plant that employs anaerobic technology. The upper allowable biomass specific LAS concentration should be 14 mg LAS (gVSS)(-1).

Acetates↗
PubMed2003

Effect of the antioxidant Mesna (2-mercaptoethane sulfonate) on experimental colitis.

Reactive oxygen species play a key role in intestinal inflammation, although interventional studies using antioxidants have shown only weak beneficial effects both in humans and animals. Hence, our aim was to examine the possible beneficial effect of the antioxidant 2-mercaptoethane sulfonate (Mesna) on experimental colitis. Colitis was induced in rats by intrarectal instillation of trinitrobenzene sulfonic acid (TNB) followed immediately by intrarectal Mesna or saline, administered for 14 days, twice daily. A beneficial effect of Mesna was observed, resulting in a significant reduction in inflammation followed by almost full recovery. iNOS mRNA expression and myeloperoxidase (MPO) activity were significantly increased in the TNB-Mesna group. These results suggest that the induction of iNOS in the presence of Mesna reduced intestinal inflammation. Mesna probably resolved this inflammation by scavenging reactive oxygen species generated by the augmented infiltration of polymorphonuclear leukocytes.

Animals↗
PubMed1998

Changes in plasma and colonic mucosa fatty acid profiles in rats with ulcerative colitis induced by trinitrobenzene sulfonic acid.

Polyunsaturated fatty acids have a key role in the pathogenesis of inflammatory bowel disease since some of the arachidonic acid-derived eicosanoids have been found to be increased in inflamed intestinal mucosa in the acute phase of human disease. The aim of this study was to prospectively assess plasma and colon mucosa fatty acid patterns in rats with experimental ulcerative colitis. Twenty rats were treated with trinitrobenzene sulfonic acid and 20 with NaCl; two groups were killed after one week and two after two weeks to evaluate colon damage. Plasma was obtained by aortic puncture and colonic mucosa was scraped off and the fatty acid pattern was determined by gas-liquid chromatography. Total, saturated, and monounsaturated plasma fatty acids were significantly higher in both periods of ulcerative colitis as compared to controls. Plasma n-6 fatty acids were increased after treatment, but no significant changes were observed concerning to n-3 fatty acids. With regard to colon mucosa, saturated and monounsaturated fatty acids did not change because of the disease; however, n-6 fatty acids decreased in the first week and increased in the second week and n-3 fatty acids were increased. Changes on the fatty acid distribution in plasma did not parallel to those of colonic mucosa except for 22:6(n-3). We have also found that experimental ulcerative colitis induced by trinitrobenzene sulfonic acid reproduces many of the features related to changes in plasma and colon mucosa fatty acids observed in the human disease.

Animals↗
PubMed1998

Dietary monounsaturated n-3 and n-6 long-chain polyunsaturated fatty acids affect cellular antioxidant defense system in rats with experimental ulcerative colitis induced by trinitrobenzene sulfonic acid.

The intrarectal administration of trinitrobenzene sulfonic acid in rats induces ulcerative colitis, which results in histological alterations of colonic mucosa, severe modification of the cellular antioxidant defense system, and enhanced production of inflammatory eicosanoids. This study evaluated the influence of different dietary fatty acids, i.e., monounsaturated, n-3, and n-3 + n-6 polyunsaturated fatty acids, on the recovery of the colonic mucosa histological pattern, the cellular antioxidant defense system of colon, and PGE2 and LTB4 colonic mucosa contents in a model of ulcerative colitis induced by intrarectal administration of trinitrobenzene sulfonic acid. Administration of dietary n-3 polyunsaturated fatty acids led to a minimum stenosis score, a higher histological recovery, lower colon alkaline phosphatase and gamma-glutamyltranspeptidase activities, and lower mucosal levels of PGE2 and LTB4 compared with the other two experimental groups. However, glutathione transferase, glutathione reductase, glutathione peroxidase, and catalase activities were lower in the group treated with n-3 polyunsaturated fatty acids than in the groups fed with either the monounsaturated or the n-6 + n-3 polyunsaturated enriched diet. We conclude that n-3 polyunsaturated fatty acids can be administered to prevent inflammation in ulcerative colitis, but they cause a decrease in the colonic antioxidant defense system, promoting oxidative injury at the site of inflammation.

Animals↗
PubMed2003

Chiral phosphine Lewis base catalyzed asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone and phenyl acrylate.

In the aza-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone (MVK) promoted by chiral phosphine Lewis base: (R)-2'-diphenylphosphanyl-[1,1']binaphthalenyl-2-ol (10 mol%), the aza-Baylis-Hillman adducts 1 were obtained in good yields with high ee (70-94% ee) at -30 degrees C in THF. In CH2Cl2 upon heating at 40 degrees C, the aza-Baylis-Hillman reaction of N-sulfonated imines with phenyl acrylate gave the adducts 2 in high yields (60-97%) with moderate ee (52-77%).

Journal Article↗
PubMed2003

Smiles-type free radical rearrangement of aromatic sulfonates and sulfonamides: syntheses of arylethanols and arylethylamines.

Smiles-type free radical rearrangements of arenesulfonates and arenesulfonamides are exploited for synthetic purposes. 4-Substituted benzenesulfonates cause Smiles-type rearrangement only when substituted by an electron withdrawing group. Therefore, ipso-attack by an alkyl radical on arenesulfonates takes place in an electrophilic manner. Arenesulfonamides rearrange only when the amide nitrogen is substituted by an alkoxycarbonyl group, due to the electron withdrawing nature of this group. Sulfonates and the N-ethoxycarbonylsulfonamide derivatives of naphthalene, quinoline, and thiophene cause more rearrangement and show synthetic utility. Aromatic amino acid analogues were synthesized by Smiles-type rearrangement with moderate yields. The radical Smiles-type rearrangement of sulfonate and sulfonamide derivatives can be a useful synthetic route when we understand the electronic character of these reactions.

Journal Article↗
PubMed2003

Substitution reactions of 5-nitropyridine-2-sulfonic acid. A new pathway to 2,5-disubstituted pyridines.

We have investigated reactions of 5-nitropyridine-2-sulfonic acid and its potassium salt in which substitution of the sulfonate group by oxygen, nitrogen and halogen nucleophiles has been attempted. By this approach, 2-methoxy- (95% yield), 2-ethoxy- (97%), 2-isopropoxy- (65%), 2-amino- (92%), 2-butylamino- (76%), 2-diethylamino- (62%), 2-ethylamino- (32%), 2-benzylamino- (77%), 2-(R-1-phenylethylamino)- (71%) and 2-chloro-5-nitropyridine (87%) have been obtained. No reactions were observed with phenols or anilines. With t-BuOH, 2-hydroxy-5-nitropyridine was formed together with 2-methylpropene.

Journal Article↗
PubMed1985

The influence of a sequential-type oral contraceptive with ethinylestradiol-sulfonate soft gelatin capsules and norethisterone acetate on carbohydrate metabolism during the first twelve months.

A prospective study was made to investigate the carbohydrate metabolic effects of the sequential-type oral contraceptive in form of a weekly pill with 0.6 mg ethinylestradiol-sulfonate soft gelatin capsules and 10 mg norethisterone acetate. Blood glucose and plasma insulin levels were measured during an intravenous glucose tolerance test in 17 nondiabetic healthy women. Each woman was tested before and after twelve months of drug use. There were no changes neither in average fasting blood glucose nor in glucose assimilation after intake of ethinylestradiol-sulfonate. At twelve months there were significant elevations of basal as well as reactive insulin levels.

Adult↗
PubMed1996

Cecal perforation associated with sodium polystyrene sulfonate-sorbitol enemas in a 650 gram infant with hyperkalemia.

We report a 650 g, 24 week hyperkalemic newborn who developed both cecal impaction and perforation after treatment with sodium polystyrene sulfonate enemas. Flat plate abdominal radiographs revealed impacted resin as a radiodense material outlining the bowel. Pathological examination showed sodium polystyrene sulfonate crystals contained in the cecal abscess. Review of the literature in both adults and children leads us to conclude that the use of this sodium-potassium exchange resin for the treatment of hyperkalemia in this gestational age group is probably not helpful for decreasing serum potassium and may be detrimental to the infant.

Cation Exchange Resins↗
PubMed2005

Resolvin E1, an endogenous lipid mediator derived from omega-3 eicosapentaenoic acid, protects against 2,4,6-trinitrobenzene sulfonic acid-induced colitis.

Resolvin E1 (RvE1; 5S,12R,18R-trihydroxyeicosapentaenoic acid) is an antiinflammatory lipid mediator derived from omega-3 fatty acid eicosapentaenoic acid (EPA). At the local site of inflammation, aspirin treatment enhances EPA conversion to 18R-oxygenated products, including RvE1, which carry potent antiinflammatory signals. Here, we obtained evidence for reduced leukocyte infiltration in a mouse peritonitis model, where the administration of EPA and aspirin initiated the generation of RvE1 in the exudates. Similar results were obtained with the administration of synthetic RvE1, which blocked leukocyte infiltration. RvE1 also protected against the development of 2,4,6-trinitrobenzene sulfonic acid-induced colitis. The beneficial effect was reflected by increased survival rates, sustained body weight, improvement of histologic scores, reduced serum anti-2,4,6-trinitrobenzene sulfonic acid IgG, decreased leukocyte infiltration, and proinflammatory gene expression, including IL-12 p40, TNF-alpha, and inducible nitric oxide synthase. Thus, the endogenous lipid mediator RvE1 counter-regulates leukocyte-mediated tissue injury and proinflammatory gene expression. These findings show an endogenous mechanism that may underlie the beneficial actions of omega-3 EPA and provide targeted approaches for the treatment of intestinal inflammation.

Animals↗
PubMed2003

Modulation of prion protein oligomerization, aggregation, and beta-sheet conversion by 4,4'-dianilino-1,1'-binaphthyl-5,5'-sulfonate (bis-ANS).

The prion protein (PrP) is the major agent implicated in the diseases known as transmissible spongiform encephalopathies. The onset of transmissible spongiform encephalopathy is related to a change in conformation of the PrP(C), which loses most of its alpha-helical content, becoming a beta-sheet-rich protein, known as PrP(Sc). Here we have used two Syrian hamster prion domains (PrP 109-141 and PrP 109-149) and the murine recombinant PrP (rPrP 23-231) to investigate the effects of anilino-naphtalene compounds on prion oligomerization and aggregation. Aggregation in the presence of bis-ANS (4,4'-dianilino-1,1'-binaphthyl-5,5'-sulfonate), ANS (1-anilinonaphthalene-8-sulfonate), and AmNS (1-amino-5-naphtalenesulfonate) was monitored. Bis-ANS was the most effective inhibitor of prion peptide aggregation. Bis-ANS binds strongly to rPrP 23-231 leading to a substantial increase in beta-sheet content and to limited oligomerization. More strikingly, the binding of bis-ANS to full-length rPrP is diminished by the addition of nanomolar concentrations of oligonucleotides, demonstrating that they compete for the same binding site. Thus, bis-ANS displays properties similar to those of nucleic acids, causing oligomerization and conversion to beta-sheet (Cordeiro, Y., Machado, F., Juliano, L., Juliano, M. A., Brentani, R. R., Foguel, D., and Silva, J. L. (2001) J. Biol. Chem. 276, 49400-49409). This dual effect of bis-ANS on prion protein makes this compound highly important to sequester crucial conformations of the protein, which may be useful to the understanding of the disease and to serve as a lead for the development of new therapeutic strategies.

Anilino Naphthalenesulfonates↗
PubMed2004

O-sulfonation of serine and threonine: mass spectrometric detection and characterization of a new posttranslational modification in diverse proteins throughout the eukaryotes.

Protein sulfonation on serine and threonine residues is described for the first time. This post-translational modification is shown to occur in proteins isolated from organisms representing a broad span of eukaryote evolution, including the invertebrate mollusk Lymnaea stagnalis, the unicellular malaria parasite Plasmodium falciparum, and humans. Detection and structural characterization of this novel post-translational modification was carried out using liquid chromatography coupled to electrospray tandem mass spectrometry on proteins including a neuronal intermediate filament and a myosin light chain from the snail, a cathepsin-C-like enzyme from the parasite, and the cytoplasmic domain of the human orphan receptor tyrosine kinase Ror-2. These findings suggest that sulfonation of serine and threonine may be involved in multiple functions including protein assembly and signal transduction.

Animals↗
PubMed2002

The role of mast cells in the development of 2, 4, 6-trinitrobenzene sulfonic acid-induced colitis in rats.

BACKGROUND: The role of mast cells in Crohn disease (CD) remains to be established. The aim of this study was to elucidate this in the development of CD-like colitis in rats by the use of mast-cell-deficient Ws/Ws and their control W+/W+ rats. METHODS: CD-like colitis was induced in both groups by an enema of 10 mg of 2,4, 6-trinitrobenzene sulfonic acid (TNBS) in 50% ethanol. Colonic damage, adhesion and colonic weight were measured at 7 and 14 days after the TNBS/ethanol enema. Rat mast cell protease-2 (RMCP-2) in the colonic tissue was also measured at 7 days after the enema. RESULTS: There was no significant difference between W+/W+ and Ws/Ws rats in terms of colonic damage, adhesion or colonic weight. The tissue content of RMCP-2 in Ws/Ws rats treated with either saline or TNBS/ethanol was only maintained at a much lower level than that in W+/W+ rats with the corresponding treatment. CONCLUSIONS: These results demonstrate that mast cells are not essential in the development of 2, 4, 6-trinitrobenzene sulfonic acid-induced colitis in rats.

Animals↗
PubMed1977

A rapid GC method of monitoring Mesurol (4-(methylthio)-3,5-xylyl-N-methyl carbamate) and its sulfoxide and sulfone metabolites and their persistence in lowbush blueberries.

A facile analytical procedure was developed for determining Mesurol (4-(methylthio)-3,5-xylyl-N-methyl carbamate) and its oxidation products in blueberries. It involved blending with acetone, partition with chloroform and derivatization with trifluoroacetic anhydride and quantitation by gas chromatography/flame photometric detector (GC/FPD). The method showed good recoveries for Mesurol and its sulfoxide at the 0.1 ppm level and Mesurol sulfone at the 0.3 ppm level with a 25 g sample. It was applied to monitor levels of the insecticide and its oxidation products on field-treated blueberries. The sensitivity of the method may be increased 5-fold by the inclusion of a clean-up step. The optimal conditions for the detection of Mesurol TFA by the modified Bendix sulphur/phosphorus emission detector operating in the sulphur mode required an oxygen/hydrogen ratio of 0.38, for a column flow of 60 ml/min. The minimum detectable amounts of the TFA derivatives of Mesurol, its sulfoxide and sulfone were calculated as 1.3, 2.3 and 5.8 X 10(-11) g/sec, respectively.

Chromatography, Gas↗
PubMed2005

Photocatalytic treatment of linear alkylbenzene sulfonate (LAS) in water.

The photocatalytic degradation of aqueous linear alkylbenzene sulfonate (LAS) was studied. Two different photocatalysts, Degussa P25 TiO2 and Hombikat UV 100 TiO2, were used to degrade aqueous linear alkylbenzene sulfonate in slurry batch photoreactors. For a 100 mg/L LAS solution based on first-order rate constants, the optimum photocatalyst loading for Degussa P25 TiO2 was 4.0 g/L, while for Hombikat UV 100 TiO2 it was 2.0 g/L. The photoactivity of Degussa P25 TiO2 it was higher than that of Hombikat UV 100 TiO2 for the treatment of LAS. A mixture of both photocatalysts did not improve the LAS degradation rates in batch experiments. Combination of Degussa P25 TiO2 and 600 mg/L H2O2 along with irradiation with UV light at either 254 or 365 nm did not improve the LAS degradation rates over the photocatalytic or photolytic processes individually.

Alkanesulfonic Acids↗
PubMed2005

Photolytic treatment of aqueous linear alkylbenzene sulfonate.

Treatment of a model detergent compound, linear alkylbenzene sulfonate (LAS), using photolytic processes was studied. In the photolytic degradation of LAS, both ultraviolet (UV) light at 254 nm wavelength and its combination with hydrogen peroxide (H2O2) were investigated. Based on first-order rate constants, it was shown that 5000 mg/L of H2O2 for degradation of a 100-mg/L solution of linear alkylbenzene sulfonate was optimum. Addition of H2O2 at different illumination times with UV light at 254 nm did not improve first-order rate constants compared with the addition of H2O2 at the start of illumination. Degradation rates of the model compound (LAS) with three detergents were compared.

Alkanesulfonic Acids↗