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PubMed2001

Lonene-coated sulfonated silica as a packing material in the packed-capillary mode of electrochromatography.

An aliphatic ionene (2-10-ionene) has been selected as a modifier to prepare a novel polymer-coated packing material for capillary electrochromatography. The packing material was produced by dynamical modification of a commercially available sulfonated silica Exsil-100 SCX. Strong ion-exchange interactions in the capillary packed with ionene-modified sulfonated silica have been demonstrated by the example of the retention of p-aminobenzoic acid. The total calculated anion-exchange capacity of the sorbent in the capillary was about 4 x 10(-9) mol. A fast separation (about 15 min) of several aromatic acids was achieved with the packing material. The highest number of theoretical plates obtained was about 120,000. Limits of detection of the aromatic acids were 2-5 microg/ml. The advantages and lacks of the approach are discussed briefly.

Anion Exchange Resins↗
PubMed1975

Chromatographic-fluorometric analysis of antileprotic sulfones.

Modifications to the power supply system of a spectrophotofluorometer are described. These modifications stabilize the output of the xenon are lamp and permit the determination of nanogram quantities of antileprotic sulfones. The sulfones are removed from plasma by a single extraction with ethyl acetate, then separated by high-pressure liquid chromatography on silica, and detected in the effluent by their fluorescence. The method is specific, rapid, and reproducible.

Autoanalysis↗
PubMed2002

The contribution of 2,3,5-trichlorophenyl methyl sulfone, a metabolite of 1,2,4-trichlorobenzene, to the delta-aminolevulinic acid synthetase induction by 1,2,4-trichlorobenzene in rat liver.

In the present study, we investigated the contribution of methylsulfonyl metabolite derived from 1,2,4-trichlorobenzene (1,2,4-TCB) on the delta-aminolevulinic acid (ALA) synthetase induction by the parent compound in rats. The time courses of increasing of hepatic microsomal total cytochrome P450 content after a single i.p. administration of 1,2,4-TCB (1.36 mmol/kg), and 2,3,5- and 2,4,5-trichlorophenyl methyl sulfones (2,3,5- and 2,4,5-TCPSO2Mes) (50 micromol/kg each) were in parallel with those of increasing of the total heme content in liver microsomes. 1,2,4-TCB significantly increased the heme oxygenase activity, but 2,3,5- and 2,4,5-TCPSO2Mes did not. On the other hand, 1,2,4-TCB and 2,3,5-TCPSO2Me markedly enhanced the ALA synthetase activity. No change was observed in this enzyme activity after the administration of 2,4,5-TCPSO2Me. After the administration of 1,2,4-TCB to the rats treated with DL-buthionine-(S,R)-sulfoximine (BSO) and to the non-BSO-treated rats, the concentrations of both 2,3,5- and 2,4,5-TCPSO2Mes were significantly lower in liver of the BSO-treated rats than in liver of the non-BSO-treated rats. Additionally, the 1,2,4-TCB did not elevate the ALA synthetase activity in the BSO-treated rats. On the other hand, the administration of 2,3,5-TCPSO2Me to BSO-treated rats resulted in induction of ALA synthetase. The results strongly suggest that the methyl sulfone derived from 1,2,4-TCB, i.e., 2,3,5-TCPSO2Me, contributes highly to the induction of the ALA synthetase activity by the parent compound.

5-Aminolevulinate Synthetase↗
PubMed1998

Chemical sulfonation and anticoagulant activity of acharan sulfate.

Acharan sulfate is a glycosaminoglycan prepared from the giant African snail, Achatina fulica. This polysaccharide has a repeating disaccharide structure of -->4)-2-deoxy-2-acetamido-alpha-D-glucopyranose (1-->4)-2-sulfo-alpha-L-idopyranosyluronic acid (1-->). Its structure is related to heparin and heparan sulfate but is distinctly different from all known members of these classes of glycosaminoglycans. Because of its structural similarities to heparin, chemically modified acharan sulfate was studied to understand the chemical structure effected its anticoagulant activity. After de-N-acetylation, acharan sulfate was N-sulfonated using either chlorosulfonic acid-pyridine or sulfur trioxide-trimethylamine complex. The sulfate level in these products ranged from 22 to 24%(w/w), significantly less than that of heparin at 36%. The molecular weight of both N-sulfoacharan sulfates were comparable with that of heparin. In vitro anticoagulant activity assays showed that N-sulfoacharan sulfate derivatives were moderately active for the inhibition of thrombin and neither product showed any measurable anti-factor Xa activity. The differences in the activities of N-sulfoacharan sulfates produced by these two methods are probably ascribable to a small level of concomitant O-sulfonation obtained when using chlorosulfonic acid-pyridine.

Animals↗
PubMed1999

Adsorption from plasma and buffer of single- and two-chain high molecular weight kininogen to glass and sulfonated polyurethane surfaces.

The adsorption of high molecular weight kininogen (HK) in its single-chain (SCHK) and two-chain (TCHK) forms from single protein solutions, plasma, and kininogen-deficient plasma, to glass and sulfonated polyurethane surfaces is reported. Using radiolabelling methods, it was found that in a single protein buffered system there was no difference in the adsorbed amounts of SCHK and TCHK over the concentration range 5-100 microg ml(-1) (similar to that in plasma). The adsorption of the two forms from normal plasma was also the same. However, immunoblots using an anti-HK antibody indicated that over the 2 h adsorption time, much of the SCHK present in the plasma was converted to TCHK: the band at 120 kD representative of intact SCHK disappeared, and bands at 56 and 46 kD representative of the heavy and light chains of TCHK were generated. To prevent conversion of SCHK to TCHK, the kallikrein inhibitor aprotinin (or in some cases a protease inhibitor cocktail), was added to the plasma in subsequent experiments. In addition, kininogen-deficient plasma was used (with either labelled SCHK or TCHK added) to avoid ambiguity in the tracer-population relationship. It was again found that there was no difference in the amounts of SCHK and TCHK adsorbed to glass and the sulfonated polyurethanes. The significance of these findings in relation to the reported anti-cell adhesion properties of adsorbed HK is discussed.

Adsorption↗
PubMed2001

Allyl and propargyl substituted penam sulfones as versatile intermediates toward the syntheses of new beta-lactamase inhibitors.

Several alkenyl derivatives were prepared using allyl penam sulfone as the key intermediate. Isomers of these derivatives having beta configuration at C-6 showed potent activity against CcrA enzyme. A new method was developed to prepare propargyl penam sulfone. The majority of the triazoles prepared by this route exhibited good activity against all three representative enzymes used for the inhibition assay.

Alkenes↗
PubMed2000

Antimalarial sulfide, sulfone, and sulfonamide trioxanes.

A series of trioxanes featuring sulfide, sulfone, and sulfonamide substituents in diverse positions has been prepared. Structure-activity relationship (SAR) generalizations highlight two major factors controlling the antimalarial potency of these new chemical entities: (1) the proximity of the sulfur-containing substituent to the crucial peroxide bond and (2) the oxidation state of the sulfur-containing substituent. Generally, sulfones are more antimalarially potent than the corresponding sulfides.

Antimalarials↗
PubMed2002

Synthesis of (bis)sulfonic acid, (bis)benzamides as follicle-stimulating hormone (FSH) antagonists.

Screening efforts identified (bis)sulfonic acid, (bis)benzamides (1-3) as compounds that interact with the follicle stimulating-hormone receptor (FSHR) and inhibit FSH-stimulated cAMP accumulation with IC(50) values in the low micromolar range. Structure-activity relationship studies using novel analogues of 1-3 revealed that two phenylsulfonic acid moieties were necessary for activity and that the carbon-carbon double bond of the stilbene sub-series was the optimum spacer connecting these groups. Selected analogues (2, 14, and 50) were also able to block FSHR-dependent estradiol production in rat primary ovarian granulosa cells and progesterone secretion in a clonal mouse adrenal Y1 cell line. IC(50) values for these compounds in these assays were in the low micromolar range. Optimization of the benzoic acid side chains of 1-3 led to gains in selectivity versus activity at the thyroid stimulating hormone (TSH) receptor (TSHR). For instance, while stilbene (bis)sulfonic acid congener 2 was only 10-fold selective for FSHR over TSHR, analogue 50 with an IC(50) value of 0.9 microM in the FSHR-cAMP assay was essentially inactive at 30 microM in the TSHR-cAMP assay.

Animals↗
PubMed1995

An integrated analytical method for determination of polychlorinated aryl methyl sulfone metabolites and polychlorinated hydrocarbon contaminants in biological matrices.

A simple column chromatography method was developed for separation and cleanup in the determination of chlorinated hydrocarbon contaminants and their methyl sulfone (MeSO2-) metabolites in biological tissues. The method was validated for determination of 11 polychlorinated biphenyls (PCBs), 15 tetra- to heptachloro 3- and 4-MeSO2-PCBs, 3-MeSO2-DDE, and tris(4-chlorophenyl)-methanol spiked to herring gull egg, smelt, and polar bear liver and adipose tissue using gas chromatography with electron-capture detection (GC-ECD). The overall mean recovery relative to the internal standard was 103% +/- 8%, independent of analyte, substrate type, and lipid extract weights up to approximately 0.7 g. Precision of replicate analyses of individual congeners was good. There were no significant residual biogenic or xenobiotic interferences in the aryl methyl sulfone fraction of any substrate. Sensitivity and linearity of molar response of MeSO2-PCBs and MeSO2-DDE was tested for ECD and electron-capture negative ion mass spectrometry monitoring the total ion current (TIC) and the molecular ion (SIM). The mean practical quantitation limit among MeSO2-PCBs and 3-MeSO2-DDE was lowest for SIM (2.1 +/- 0.9 pg) and similar for ECD and TIC (24.2 +/- 4.6 and 44.4 +/- 17.1 pg, respectively). Response factors were linear above the practical quantitation limit to at least the nanogram level for all three techniques. In spite of superior sensitivity, there was more inherent variability in the response factors for SIM (approximately 18%-56% CV) than for ECD (approximately 7%-12% CV) or TIC (approximately 11%-18% CV); therefore, ECD or TIC is recommended for quantitative analysis.

Animals↗
PubMed2001

Inhibition of class C beta-lactamases: structure of a reaction intermediate with a cephem sulfone.

The crystallographic structure of the Enterobacter cloacae GC1 extended-spectrum class C beta-lactamase, inhibited by a new 7-alkylidenecephalosporin sulfone, has been determined by X-ray diffraction at 100 K to a resolution of 1.6 A. The crystal structure was solved by molecular replacement using the unliganded structure [Crichlow et al. (1999) Biochemistry 38, 10256-10261] and refined to a crystallographic R-factor equal to 0.183 (R(free) 0.208). Cryoquenching of the reaction of the sulfone with the enzyme produced an intermediate that is covalently bound via Ser64. After acylation of the beta-lactam ring, the dihydrothiazine dioxide ring opened with departure of the sulfinate. Nucleophilic attack of a side chain pyridine nitrogen atom on the C6 atom of the resultant imine yielded a bicyclic aromatic system which helps to stabilize the acyl enzyme to hydrolysis. A structural assist to this resonance stabilization is the positioning of the anionic sulfinate group between the probable catalytic base (Tyr150) and the acyl ester bond so as to block the approach of a potentially deacylating water molecule. Comparison of the liganded and unliganded protein structures showed that a major movement (up to 7 A) and refolding of part of the Omega-loop (215-224) accompanies the binding of the inhibitor. This conformational flexibility in the Omega-loop may form the basis of an extended-spectrum activity of class C beta-lactamases against modern cephalosporins.

Cephalosporins↗
PubMedDate not supplied

Chitosan-silica complex membranes from sulfonic acid functionalized silica nanoparticles for pervaporation dehydration of ethanol-water solutions.

Nanosized silica particles with sulfonic acid groups (ST-GPE-S) were utilized as a cross-linker for chitosan to form a chitosan-silica complex membranes, which were applied to pervaporation dehydration of ethanol-water solutions. ST-GPE-S was obtained from reacting nanoscale silica particles with glycidyl phenyl ether, and subsequent sulfonation onto the attached phenyl groups. The chemical structure of the functionalized silica was characterized with FTIR, (1)H NMR, and energy-dispersive X-ray. Homogeneous dispersion of the silica particles in chitosan was observed with electronic microscopies, and the membranes obtained were considered as nanocomposites. The silica nanoparticles in the membranes served as spacers for polymer chains to provide extra space for water permeation, so as to bring high permeation rates to the complex membranes. With addition of 5 parts per hundred of functionalized silica into chitosan, the resulting membrane exhibited a separation factor of 919 and permeation flux of 410 g/(m(2) h) in pervaporation dehydration of 90 wt % ethanol aqueous solution at 70 degrees C.

Chitosan↗
PubMed2004

Vinyl sulfones: inhibitors of SrtA, a transpeptidase required for cell wall protein anchoring and virulence in Staphylococcus aureus.

Several small molecule vinyl sulfones were found to exhibit irreversible time-dependent inhibition of the Staphylococcus aureus sortase SrtA in vitro. A representative of these compounds was shown to impair the ability of S. aureus bacteria to bind fibronectin-coated surfaces through in vivo inhibition of SrtA-mediated linkage of fibronectin to the cell surface. These data highlight the potential use of small molecule vinyl sulfones as chemotherapeutics to prevent adhesion to and colonization of host tissues during S. aureus infection.

Aminoacyltransferases↗
PubMed2005

Catalytic enantioselective C-C bond forming conjugate additions with vinyl sulfones.

In this communication, we describe the development of the first highly enantioselective catalytic conjugate addition to vinyl sulfones. Promoted by readily accessible organocatalysts derived from C6'-OH cinchona alkaloid derivatives and under mild, air- and moisture-tolerant conditions, conjugate additions of a wide range of alpha-cyanoacetates bearing either an alpha-aryl or an alpha-alkyl substituent to vinyl sulfones proceeded in excellent enantioselectivity and high yield. Consequently, this efficient and operationally simple enantioselective C-C bond forming conjugate addition provides a new and useful approach for the enantioselective construction of all-carbon quaternary stereocenters.

Carbon↗
PubMed2006

Rational design of a beta-lactamase inhibitor achieved via stabilization of the trans-enamine intermediate: 1.28 A crystal structure of wt SHV-1 complex with a penam sulfone.

beta-Lactamases are one of the major causes of antibiotic resistance in Gram negative bacteria. The continuing evolution of beta-lactamases that are capable of hydrolyzing our most potent beta-lactams presents a vexing clinical problem, in particular since a number of them are resistant to inhibitors. The efficient inhibition of these enzymes is therefore of great clinical importance. Building upon our previous structural studies that examined tazobactam trapped as a trans-enamine intermediate in a deacylation deficient SHV variant, we designed a novel penam sulfone derivative that forms a more stable trans-enamine intermediate. We report here the 1.28 A resolution crystal structure of wt SHV-1 in complex with a rationally designed penam sulfone, SA2-13. The compound is covalently bound to the active site of wt SHV-1 similar to tazobactam yet forms an additional salt-bridge with K234 and hydrogen bonds with S130 and T235 to stabilize the trans-enamine intermediate. Kinetic measurements show that SA2-13, once reacted with SHV-1 beta-lactamase, is about 10-fold slower at being released from the enzyme compared to tazobactam. Stabilizing the trans-enamine intermediate represents a novel strategy for the rational design of mechanism-based class A beta-lactamase inhibitors.

Amines↗
PubMed2003

Influence of some technological parameters on the formation of dimethyl sulfide, 2-mercaptoethanol, methionol, and dimethyl sulfone in port wines.

Volatile sulfur compounds of 15 young port wines and 12 old port wines were determined. As there is a great difference in the pool of sulfur compounds between the two groups of wines, an experimental protocol was performed to determine which technological parameter (dissolved O(2), free SO(2) levels, pH, and time/temperature) was related with the formation/consumption of these compounds. Four sulfur compounds were selected for this purpose: dimethyl sulfide, 2-mercaptoethanol, dimethyl sulfone, and methionol. The synergistic effects of increasing temperature and O(2) at lower pH had the largest impact. Dimethyl sulfide was formed during the experimental period in the presence of O(2). Dimethyl sulfone had the same behavior. Methionol decreased significantly in the presence of O(2), but no methional was formed. 2-Mercaptoethanol, considered to be an important "off-flavor" in dry wines, also decreased during the experimental period (54 days) in the presence of O(2), and the respective disulfide was formed. These results corroborate the fact that old port wine (barrel aged) never develops "off-flavors" associated with the presence of methionol (cauliflower), 2-mercaptoethanol (rubber/burnt), or methional (cooked potato). In fact, temperature and oxygen are the major factors in the consumption of these molecules. However, some notes of "quince" and "metallic" can appear during port wine aging, and these can be associated with the presence of dimethyl sulfide.

Aldehydes↗
PubMed1999

Metabolism of 7-fluoro-6-(3,4,5,6-tetrahydrophthalimido)-4- (2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (S-53482) in rat. 1. Identification of a sulfonic acid type conjugate.

To examine the metabolic fate of 7-fluoro-6-(3,4,5, 6-tetrahydrophthalimido)-4-(2-propynyl)-2H-1,4-benzoxazin-3( 4H)-one (S-53482), rats were given a single oral dose of [phenyl-(14)C]-S-53482 at 1 (low) or 100 (high) mg/kg. The radiocarbon was almost completely eliminated within 7 days after administration in both groups. (14)C recoveries (expressed as percentages relative to the dosed (14)C) in feces and urine were 56-72 and 31-43%, respectively, for the low dose and 78-85 and 13-23%, respectively, for the high dose. S-53482 and seven metabolites were identified in urine and feces. Six of them were purified by several chromatographic techniques and identified by spectroanalyses (NMR and MS). Alcohol derivatives and an acetoanilide derivative were isolated from urine. Three sulfonic acid conjugates having a sulfonic acid group incorporated into the double bond of the 3,4,5,6-tetrahydrophthalimide moiety were isolated from feces. On the basis of the metabolites identified in this study, the metabolic pathways of S-53482 in rats are proposed.

Animals↗
PubMed1989

Quantitative structure-activity relationships in dihydropteroate synthase inhibition by multisubstituted sulfones. Design and synthesis of some new derivatives with improved potency.

On the bases of the linear correlation existing for a training set of homomultisubstituted 4-aminodiphenyl sulfones between the computed (INDO) electronic net charges of the SO2 group and the enzymic inhibition data on dihydropteroate synthase from Escherichia coli, seven new heteromultisubstituted derivatives were designed, synthesized, and tested for their inhibition potencies. These compounds were found to be from 5-11 times more effective than 4,4'-diaminodiphenyl sulfone. The implications of the results in the drug design and in the model for the enzyme-inhibitors interaction are discussed.

Dihydropteroate Synthase↗