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PubMedDate not supplied

In vitro studies of immobilized heparin and sulfonated polyurethane using epifluorescent video microscopy.

In situ surface modification techniques to improve the blood compatibility of blood contacting surfaces of medical devices have been developed by the authors. The techniques include heparin immobilization and sulfonated polymer grafting onto a polyurethane (PU) surface by using either ozone oxidation or photo reaction. These modified PUs were evaluated using an epifluorescent video microscope combined with a parallel plate flow cell. The epifluorescent video microscope system measured the amount of platelet coverage on the PU surfaces using whole human blood containing mepacrine labeled platelets perfused at a wall shear rate of 100 sec-1 for 20 min. Platelet activation and complement activation were also measured. Both immobilized heparin and sulfonated PUs showed significantly lower levels of platelet adhesion than the control PU. The platelet activation levels of these modified PUs also correspond to the results of the platelet adhesion. As for complement activation, heparin the immobilized surface showed the least complement activation, while sulfonated PU and the control PU showed higher levels of complement activation. In situ surface modification techniques, which use either ozone oxidation or photo reaction, are useful in a variety of medical devices even of a complex design, such as membrane oxygenators or artificial hearts.

Allylamine↗
PubMed1998

Bacillus subtilis genes for the utilization of sulfur from aliphatic sulfonates.

A 5 kb region upstream of katA at 82 degrees on the Bacillus subtilis chromosome contains five ORFs organized in an operon-like structure. Based on sequence similarity, three of the ORFs are likely to encode an ABC transport system (ssuBAC) and another to encode a monooxygenase (ssuD). The deduced amino acid sequence of the last ORF (ygaN) shows no similarity to any known protein. B. subtilis can utilize a range of aliphatic sulfonates such as alkanesulfonates, taurine, isethionate and sulfoacetate as a source of sulfur, but not when ssuA and ssuC are disrupted by insertion of a neomycin-resistance gene. Utilization of aliphatic sulfonates was not affected in a strain lacking 3'-phosphoadenosine 5'-phosphosulfate (PAPS) sulfotransferase, indicating that sulfate is not an intermediate in the assimilation of sulfonate-sulfur. Sulfate or cysteine prevented expression of beta-galactosidase from a transcriptional ssuD::lacZ fusion. It is proposed that ssuBACD encode a system for ATP-dependent transport of alkanesulfonates and an oxygenase required for their desulfonation.

ATP-Binding Cassette Transporters↗
PubMed1991

Sulfonation of arginine residues as side reaction in Fmoc-peptide synthesis.

Several arginine-rich peptides containing the C-terminus of neuropeptide Y (NPY) were prepared by solid phase peptide synthesis using Fmoc chemistry and cleaved from the resin with trifluoroacetic acid (TFA). The products were characterized by fast atom bombardment-MS, LC-thermospray-MS, ion spray-MS/MS, and Edman degradation. The side products could be identified as peptides with sulfonated arginine residues resulting from an unexpected cleavage of Mtr or Pmc protecting groups. The degree of sulfonation depended on the choice and composition of the cleavage solution. Several scavenger mixtures were used and a mixture of thioanisole/thiocresol was found to be the most efficient for suppressing sulfonation. Furthermore treatment with the enzyme arylsulfate-sulfohydrolase desulfonated the peptides yielding the correct sequence.

Amino Acid Sequence↗
PubMed1995

Inhibition of 3-hydroxy-3-methylglutaryl-CoA reductase and citrate synthase by sulfoxides and sulfones of substrate-analogue CoA-thioether derivatives.

Sulfoxides and sulfones were prepared by specific oxidation of 3-hydroxy-3-methylglutaryl-CoA-analogue CoA-thioether derivatives and their kinetic properties were determined with 3-hydroxy-3-methylglutaryl-CoA reductase. The oxidized CoA-thioether derivatives with a hydroxyl group at C3 were powerful competitive inhibitors, their Ki values being much smaller than the Km for 3-hydroxy-3-methylglutaryl-CoA. Sulfoxides and sulfones of substrate analogues of citrate synthase were also prepared. When tested in the appropriate reaction with citrate synthase, the sulfoxide and sulfone derivatives were competitive inhibitors, but their Ki values were greater than the Km values of the corresponding unmodified substrates.

Citrate (si)-Synthase↗
PubMed2005

Formation of tamoxifen-DNA adducts via O-sulfonation, not O-acetylation, of alpha-hydroxytamoxifen in rat and human livers.

Tamoxifen (TAM) is used as the standard endocrine therapy for breast cancer patients and as a chemopreventive agent for women at high risk for this disease. Unfortunately, treatment of TAM increases the incidence of endometrial cancer; this may be due to the genotoxic damage induced by TAM metabolites. Formation of TAM-DNA adducts in rat liver correlates with the development of hepatocarcinoma. TAM-DNA adducts are proposed to be formed through O-sulfonation and/or O-acetylation of alpha-hydroxylated TAM and its metabolites. However, the role of O-sulfonation and O-acetylation in the formation of TAM-DNA adducts has not been extensively investigated. Rat or human hydroxysteroid sulfotransferases (HST), acetyltransferases, and liver cytosol were incubated with calf thymus DNA, alpha-OHTAM, and either 3'-phosphoadenosine 5'-phosphosulfate (PAPS) or acetyl coenzyme A (acetyl-CoA) as a cofactor and analyzed for TAM-DNA adduct formation, using 32P postlableling/polyacrylamide gel electrophoresis analysis. TAM-DNA adduct was formed when PAPS, not acetyl-CoA, was used. No TAM-DNA adducts were produced using human N-acetyltransferase I and II. HST antibody inhibited approximately 90% of TAM-DNA adduct formation generated by the cytosol or HST, suggesting that HST is primarily involved in the formation of TAM-DNA adducts. The formation of TAM-DNA adducts with rat liver cytosol and HST was much higher than that of human liver cytosol and HST. Our results indicate that TAM-DNA adducts are formed via O-sulfonation, not O-acetylation, of alpha-hydroxylated TAM and its metabolites.

Acetylation↗
PubMed2003

Identification of a rare sulfonic acid metabolite of andrographolide in rats.

Andrographolide is widely used in clinic as an anti-inflammatory and antibiotic drug. In this paper, the metabolites of andrographolide in rats after single oral doses of 120 mg/kg were investigated. The structures of the metabolites were elucidated by high-resolution mass spectra, NMR spectroscopy including 1H NMR, 13C NMR, and two-dimensional NMR, through comparison to a synthetic standard. The main metabolite of andrographolide in rats was 14-deoxy-12(R)-sulfo andrographolide. In the proposed mechanism, the beta-carbon of alpha, beta-unsaturated carbonyl was attacked by sulfonic acid, to form the sulfonate compound. This was a rare metabolic reaction. It may be the main metabolic pathway of andrographolide in rats. The polarity of the sulfonate metabolite increased greatly and could be easily eliminated from body.

Administration, Oral↗
PubMed1999

Low-molecular-weight sulfonates, a major substrate for sulfate reducers in marine microbial mats.

Several low-molecular-weight sulfonates were added to microbial mat slurries to investigate their effects on sulfate reduction. Instantaneous production of sulfide occurred after taurine and cysteate were added to all of the microbial mats tested. The rates of production in the presence of taurine and cysteate were 35 and 24 microM HS(-) h(-1) in a stromatolite mat, 38 and 36 microM HS(-) h(-1) in a salt pond mat, and 27 and 18 microM HS(-) h(-1) in a salt marsh mat, respectively. The traditionally used substrates lactate and acetate stimulated the rate of sulfide production 3 to 10 times more than taurine and cysteate stimulated the rate of sulfide production in all mats, but when ethanol, glycolate, and glutamate were added to stromatolite mat slurries, the resulting increases were similar to the increases observed with taurine and cysteate. Isethionate, sulfosuccinate, and sulfobenzoate were tested only with the stromatolite mat slurry, and these compounds had much smaller effects on sulfide production. Addition of molybdate resulted in a greater inhibitory effect on acetate and lactate utilization than on sulfonate use, suggesting that different metabolic pathways were involved. In all of the mats tested taurine and cysteate were present in the pore water at nanomolar to micromolar concentrations. An enrichment culture from the stromatolite mat was obtained on cysteate in a medium lacking sulfate and incubated anaerobically. The rate of cysteate consumption by this enrichment culture was 1.6 pmol cell(-1) h(-1). Compared to the results of slurry studies, this rate suggests that organisms with properties similar to the properties of this enrichment culture are a major constituent of the sulfidogenic population. In addition, taurine was consumed at some of highest dilutions obtained from most-probable-number enrichment cultures obtained from stromatolite samples. Based on our comparison of the sulfide production rates found in various mats, low-molecular-weight sulfonates are important sources of C and S in these ecosystems.

Cysteic Acid↗
PubMed1971

Bacterial metabolism of arylsulfonates. I. Benzene sulfonate as growth substrate for Pseudomonas testosteroni H-8.

Pseudomonas testosteroni H-8 utilizes as sole carbon source benzene sulfonate (BS), p-toluene sulfonate (pTS), and ethylbenzene sulfonate (EBS) but not higher homologs. Growth on BS was rapid (generation time, 3 hr) and efficient (Y = 57), and resulted in accumulation of sulfate. As the culture is acid-sensitive, the medium must be heavily buffered to permit extensive growth. The BS oxidase system is inducible. Cells grown on BS, but not glutamate, oxidized BS, pTS, or EBS without lag (QO(2) = 50 to 100). Oxygen uptake on BS is temperature-dependent and sensitive to cyanide. Complete oxidation of 1 mumole of BS consumed approximately 5.7 mumoles of oxygen.

Barium↗
PubMed1973

Effect of methionine sulfoximine and methionine sulfone on glutamate synthesis in Klebsiella aerogenes.

At least two pathways exist in Klebsiella aerogenes for glutamate synthesis. A mutant blocked in one pathway due to the loss of glutamate dehydrogenase (gltD) does not require glutamate and has the same growth characteristics as the parent strain in most media; however, its growth is inhibited by the analogues methionine sulfoximine and methionine sulfone. Wild-type Klebsiella is resistant to 0.1 M methionine sulfoximine or methionine sulfone, whereas the gltD mutant is sensitive to 1 mM concentrations. Either glutamate or glutamine is effective in overcoming this inhibition. Activities of both glutamine synthetase and glutamate synthetase, two enzymes involved in the second pathway of glutamate synthesis, are inhibited by methionine sulfoximine and methionine sulfone. The primary effect of methionine sulfoximine appears to be the prevention of glutamine production necessary for subsequent glutamate synthesis via glutamate synthetase enzyme.

Cell-Free System↗
PubMed1995

Coadsorption of IgG and BSA onto sulfonated polystyrene latex: II. Colloidal stability and immunoreactivity.

The present work deals with the study of the colloidal stability and immunoreactivity of sulfonated polystyrene latex particles covered by different amounts of m-BSA and IgG/a-CRP. These proteins have been previously adsorbed onto a sulfonated latex by sequential and competitive coadsorption experiments and it was possible to obtain latex-protein particles with different degrees of coverage by each protein. The latex particles, fully or partially covered by each protein (termed latex-protein complexes), were resuspended under several conditions (different pH and ionic strength values) and their colloidal stability, vs the addition of the electrolyte was studied using turbidity measurements. This stability appeared at a high degree of coverage by BSA and at a pH in which the BSA was negatively charged. At a high degree of coverage by IgG, the latex particles were unstable at all pHs. As a final part of this work, the immunoreactivity of several complexes was studied following the changes in the turbidity after the addition of CRP antigen. Only the complexes which were colloidally stable gave detectable reactivity. However, the complexes with a relatively low degree of coverage by IgG/a-CRP gave good immunoreactivity. Therefore, the latex-protein complex properties depended on the percentage of BSA or IgG adsorbed and on the electric state of the proteins at the redispersion pH. Under specific incubation conditions, sulfonated latex covered by significant IgG/BSA percentages was obtained, which showed a high colloidal stability and good immunoreactivity.

Adsorption↗
PubMed1994

Formation of pi, tau-dimethylhistidine on alkylation of trypsin with active-site-directed sulfonic acid methyl esters.

The possibility of synthesizing stable alkyl analogues of acyl trypsins by introducing the alkyl residue by means of active-site-directed sulfonic acid esters was studied. Nine amidino- or guanidino-substituted sulfonic acids of different geometries and their methyl esters were prepared. The time-dependent inhibition of bovine trypsin by these esters, indicating modification at the active site of the enzyme, was followed. With the exception of p-guanidinobenzenesulfonic acid methyl ester, all the esters acted as irreversible inhibitors. The site of methylation, Ser-195 or His-57 (chymotrypsinogen numbering), was determine by analyzing for O-methylserine and methylhistidines. With four of the esters indications of a possible formation of, at most, 0.1 residue of O-methylserine per inactivated trypsin molecule were obtained. tau-Methylhistidine (but no pi-methylhistidine) was, however, always observed as the main product of the modification reaction. A further product, hitherto not yet described in active site methylations of serine proteinases, was pi, tau-dimethylhistidine (1,3-dimethylhistidine). The failure of an attempted synthesis of the N-acetyl-ethanolamine ester of p-toluene-sulfonic acid reported in the literature is shown to be due to the high instability of this ester.

Amino Acids↗
PubMedDate not supplied

[Divinyl sulfone as a cross-linking reagent for oligomeric proteins].

The kinetics of the nucleophilic addition reactions of divinyl sulfone to amino groups of glycine and model proteins was studied in aqueous solution at 30 degrees C. The rate constants for glycine, bovine serum albumin, and alpha 1-casein were (4.84 +/- 0.58) x 10(-1), (2.97 +/- 0.31) x 10(-2), and (2.38 +/- 0.49) x 10(-2) M-1s-1, respectively. Divinyl sulfone was proposed as a cross-linking reagent for the qualitative detection of protein association in solution. The cross-linking capacity of divinyl sulfone was compared to that of 1,3,5-triacryloylhexahydro-s-triazine.

Biochemistry↗
PubMed1992

Sulfonic acid dyes: inhibition of the human immunodeficiency virus and mechanism of action.

Over 50 different commercially available sulfonic acid-containing dyes were analyzed for their ability to prevent HIV-1-induced cell killing and in inhibiting HIV-1 replication. Compounds of remarkably similar structure, but with differing patterns of sulfonic acid group substitutions, had a wide range of potency in inhibiting HIV-1. Chicago sky blue (CSB) was highly effective in the inhibition of HIV-1 with less toxicity to CEM-SS cells than most of the other sulfonated dyes tested. Synthesis of CSB was undertaken to produce a product greater than 98% pure and this compound was used to elucidate the possible mechanisms by which this class of structurally related compounds inhibits HIV-1. Addition of CSB to cells infected at high multiplicity at any time up to 24 h after infection, unlike dideoxycytidine (ddC) or oxathiin carboxanilide (OC), inhibited HIV-1-induced cell killing. Other postinfection time course studies revealed that CSB had to be present for 24 h or longer immediately after infection to be protective. Virus binding to cells occurred in the presence of CSB, but the requirement for virion envelope-cell membrane fusion was delayed. CSB was a potent inhibitor of the reverse transcriptase (RT) of both HIV-1 and HIV-2, although it was less active against HIV-2 in a cell killing-based assay. CSB also inhibited Rauscher and LP-BM5 murine leukemia viruses. CSB appears to disrupt the interaction between viral proteins and cell membranes, both in the fusion step early in the infection cycle and in the development of syncytia in the late stages of virus infection.

Antiviral Agents↗
PubMed2005

[Effect of sulfonation of polyethersulfone sheets on the adsorption of beta2-microglobulin].

This study was performed to evaluate the adsorption of beta2-microglobulin(beta2 M) by blood dialysis membrane materials which are polyethersulfone (PES), sulfonated polyethersulfones, (PES-SO3Na-I and PES-SO3Na-I ) in vitro incubated in human serum and radiolabeled beta2M (125I-beta2 M) solution respectively. In these experiments, the materials were incubated in 125I-beta2 M solution and human serum at the appointed time ranging from 15 minutes to four hours at 37 degrees C, and then the amounts of 125I-beta2M and serum beta2M adsorbed by materials were measured by radioimmunoassay (RIA). In the 125I-beta2 M system, amounts of 125I-beta2M adsorbed by the materials decreased in sequence of PES-SO3 Na-II > PES-SO3Na-I >> PES. In the serum system, amounts of beta2M adsorbed reached maximums at 30 minutes and the final adsorptions decreased in sequence of PES-SO3Na-II > PES-SO3Na-I > PES. Sulfonated PES removes beta2M more than PES does and the adsorption of beta2M increases with the increase in the degree of sulfonation. Its ability to remove significant amount of beta2M may result in less beta2M available for incorporation into amyloid. The use of PES-SO3Na membranes lessens the likelihood of dialysis-related amyloidosis (DRA) development, which remains a major source of morbidity for patients treated with long-term hemodialysis.

Adsorption↗
PubMedDate not supplied

Formation of sulfone metabolites from chlorpromazine and perazine in man.

Didesmethylchlorpromazine sulfone [gamma-(2-chlorophenothiazinyl-10)-propylamine sulfone] has been isolated from the urine of a patient under continuous chlorpromazine therapy and identified by mass spectrometry. The same compound was present in organs of rats after injection of the corresponding sulfide. The Cl-free analogue, gamma-(phenothiazinyl-10)-propylamine sulfone, was excreted by patients receiving perazine and by a volunteer after ingestion of the primary amine sulfoxide.

Adult↗
PubMedDate not supplied

Formation of the sulfone metabolite of didesmethylchlorpromazine in the rat in vivo and in vitro.

In peripheral tissues of male rats given 25 mg of didesmethylchlorpromazine [gamma-(2-chlorophenothiazinyl-10)-propylamine, Cl-PPA] per kg ip, high levels of the corresponding sulfoxide (Cl-PPA-SO) and the sulfone (Cl-PPA-SO2) were measured during the following 2-24 hr. Small quantities of these metabolites were excreted in bile, whereas 7-hydroxy-Cl-PPA could not be detected. By comparison of the areas under the tissue concentration-time curves with those measured after injection of Cl-PPA-SO2, it could be shown that at least 50% of the Cl-PPA dose was converted to the sulfone. Following administration of Cl-PPA-SO, the sulfone was present in tissues and in urine. An NADPH-dependent oxygenase catalyzing the conversion of Cl-PPA-SO to Cl-PPA-SO2 was localized in liver microsomes. Attempts to characterize the enzyme by means of induction and inhbition experiments did not lead to unequivocal conclusions concerning its nature.

Animals↗
PubMed1981

Pulmonary adenoma response of strain A mice to sulfonic acid derivatives of 1- and 2-naphthylamines.

Various sulfonic acid derivatives of 1-naphthylamine and 2-naphthylamine were tested in inbred A/St (male and female) mice by the pulmonary adenoma bioassay to determine if this class of compounds, used as intermediates in the dye-stuff industry, possesses tumorigenic activity. Neither 1-naphthylamine nor the four sulfonic acid derivatives of 1-naphthylamine tested were tumorigenic. However, 2-naphthylamine and two of the three sulfonic acid derivatives of 2-naphthylamine tested produced statistically significant lung tumor responses at comparable doses. These results indicated that this class of compounds should be examined more extensively for carcinogenic activity.

1-Naphthylamine↗
PubMed1996

3 alpha, 7 alpha, 12 alpha-trihydroxy-24-nor-5 beta-cholan-23-sulfonate: synthesis and suitability for the study of cholate transport.

In order to facilitate the study of transport processes of unconjugated C-24 bile salts, simple syntheses of 3 alpha, 7 alpha, 12 alpha-trihydroxy-24-nor-5 beta-cholan-23-sulfonate (norcholansulfonate) and 3 alpha, 7 alpha, 12 alpha-trihydroxy-24-nor-5 beta-[7 beta 5H] cholan-23-sulfonate were devised. The hydrophilic-hydrophobic properties of norcholansulfonate, as determined by its chromatographic behavior as well as by its partition between l-octanol and water, are more similar to those of cholyltaurine than to those of cholate. Self-association of norcholansulfonate in phosphate buffer, pH 7.4, with an ionic strength of 150 mM begins at a concentration of about 1 mM, comparable to that of cholyltaurine and cholate, as determined by spectral changes in fluorescence emissions of {N-[7-(4-nitrobenzo-2-oxa-1, 3-diazol)]-7b-amino-3a, 12a-dihydroxy-5b-cholan-24 - oyl}-2'-aminoethanesulfonate (7 beta-NBD-NCT). The apparent CMC value obtained from solubilization of the dye Orange OT, 8.5 mM, is comparable to that of cholytaurine. 7.5 mM, and lower than that of cholate, 9.5 mM. Norcholansulfonate is readily taken up by rat liver and completely excreted unmetabolized into bile with about the same secretion maximum (Tm) as cholyltaurine. Biliary excretion of norcholansulfonate is inhibited by cholyltaurine, and, vice versa, norcholansulfonate inhibits cholyltaurine secretion. Concerning metabolism and excretion, norcholansulfonate with the sulfonate group in the position where cholate has the carboxylate group should behave as an appropriate cholate analogue in mediated transport processes.

Animals↗