Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “Benzenesulfonates”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 19 recordsLinked to original sources
PubMed1980

Inhibition of Ehrlich ascites cell anion transport by 1-isothiocyanate-4-benzenesulfonic acid.

The effects of 1-isothiocyanate-4-benzene sulfonic acid on steady state Cl- and SO24(4 transport in Ehrlich mouse ascites tumor cells were investigated. At 10 mM, 1-isothiocyanate-4-benzenesulfonic acid reduced SO24(-) exchange by 94% but Cl- exchange was reduced by only 37%; Cl- exchange was not further inhibited by as much as 60 min of preincubation with 1-isothiocyanate-4-benzenesulfonic acid. Inhibition of Cl- exchange was completely reversible following 30-45 min of contact with 1-isothiocyanate-4-benzenesulfonic acid whereas under the same conditions, inhibition of SO24(-) exchange was irreversible. The effect o 1-isothiocyanate-4-benzenesulfonic acid on SO24(-) transport could be reversed, however, when exposure to 1-isothiocyanate-4-benzene-sulfonic acid lasted for only 2 min. In these respects the action of 1-isothiocyanate-4-benzenesulfonic acid resembles that of 4-acetamido-4'-isothiocyanostilbene-2,2'-disulfonic acid and 4,4'-diisothiocyano-1,2-diphenylethane-2,2'-disulfonic acid; the results are compatible with separate membrane sites for Cl- and SO24(-) transport. The Ki for reversible inhibition of SO24(-) transport, determined from a Dixon plot, was 4.8 mM and the inhibition appeared to be non-competitive.

Animals↗
PubMed2006

The suramin analog 4,4',4'',4'''-(carbonylbis(imino-5,1,3-benzenetriylbis (carbonylimino)))tetra-kis-benzenesulfonic acid (NF110) potently blocks P2X3 receptors: subtype selectivity is determined by location of sulfonic acid groups.

We have previously identified the suramin analog 4,4',4'',4'''-(carbonylbis(imino-5,1,3-benzenetriylbis(carbonylimino)))tetrakis-benzene-1,3-disulfonic acid (NF449) as a low nanomolar potency antagonist of recombinant P2X(1) receptors. Here, we characterize, by two-electrode voltage-clamp electrophysiology, three isomeric suramin analogs designated para-4,4',4'',4''''-(carbonylbis(imino-5,1,3-benzenetriylbis (carbonylimino)))tetrakis-benzenesulfonic acid (NF110), meta-(3,3',3'',3''''-(carbonylbis(imino-5,1,3-benzenetriylbis (carbonylimino)))tetra-kis-benzenesulfonic acid (NF448), and ortho-(2,2',2'',2''''-(carbonylbis(imino-5,1,3-benzenetriylbis (carbonylimino)))tetra-kis-benzenesulfonic acid (MK3) with respect to their potency in antagonizing rat P2X receptor-mediated inward currents in Xenopus laevis oocytes. Meta, para, and ortho refer to the position of the single sulfonic acid group relative to the amide bond linking the four symmetrically oriented benzenesulfonic acid moieties to the central, invariant suramin core. NF448, NF110, and MK3 were >200-fold less potent in blocking P2X(1) receptors than NF449, from which they differ structurally only by having one instead of two sulfonic acid residues per benzene ring. Although the meta- and ortho-isomers retained P2X(1) receptor selectivity, the para-isomer NF110 exhibited a significantly increased activity at P2X(3) receptors (K(i) approximately 36 nM) and displayed the following unique selectivity profile among suramin derivatives: P2X(2+3) = P2X(3) > P2X(1) > P2X(2) >> P2X(4) > P2X(7). The usefulness of NF110 as a P2X(3) receptor antagonist in native tissues could be demonstrated by showing that NF110 blocks alphabeta-methylene-ATP-induced currents in rat dorsal root ganglia neurons with similar potency as recombinant rat P2X(3) receptors. Together, these data highlight the importance of both the number and exact location of negatively charged groups for P2X subtype potency and selectivity.

Adenosine Triphosphate↗
PubMed2005

Hydrogen-shift isomerism: mass spectrometry of isomeric benzenesulfonate and 2-, 3- and 4-dehydrobenzenesulfonic acid anions in the gas phase.

The isomeric 3- and 4-dehydrobenzenesulfonic acid anions b and c were prepared by collision induced dissociation (CID) of the [M - H](-) ions of isomeric sulfobenzoic acids obtained by negative electrospray ionization (ESI). The CID spectra (MS(3)) of anions b and c are different from each other, and both are different from that of the isomeric benzenesulfonate anion a, obtained from benzenesulfonic acid. The stability of ions b and c shows that 1,2-proton transfer does not take place in this system under the conditions of the CID experiment. Density functional (DFT) calculations at B3LYP/6-31+G(2d,p) level of theory show that benzenesulfonate anion a is the most stable isomer, and the energies of isomers b and c are higher by more than 65 kcal mol(-1). The calculated energies of the transition states involved in the 1,2-hydrogen migration leading to the interconversion of the isomeric anions are very high (>120 kcal mol(-1)relative to ion a, barrier energies >55 kcal mol(-1)), much higher than those of transition structures leading to fragmentation. This situation does not allow isomerization of ions b and c to a, under the conditions of the CID experiments. The isomeric 2-dehydrobenzenesulfonic acid anion isomerizes to the benzenesulfonate anion a by a facile proton transfer from the SO(3)H group to the adjacent position 2. The results of this work indicate that the gas phase deprotonation of meta- and para-sulfobenzoic acids is a kinetically controlled process.

Journal Article↗
PubMed2003

Regioselectivity and the nature of the reaction mechanism in nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted benzenesulfonates with primary amines.

Second-order rate constants have been measured for the reaction of 2,4-dinitrophenyl X-substituted benzenesulfonates with a series of primary amines. The nucleophilic substitution reaction proceeds through competitive S-O and C-O bond fission pathways. The S-O bond fission occurs dominantly for reactions with highly basic amines or with substrates having a strong electron-withdrawing group in the sulfonyl moiety. On the other hand, the C-O bond fission occurs considerably for the reactions with low basic amines or with substrates having a strong electron-donating group in the sulfonyl moiety, emphasizing that the regioselectivity is governed by both the amine basicity and the electronic effect of the sulfonyl substituent X. The apparent second-order rate constants for the S-O bond fission have resulted in a nonlinear Brønsted-type plot for the reaction of 2,4-dinitrophenyl benzenesulfonate with 10 different primary amines, suggesting that a change in the rate-determining step occurs upon changing the amine basicity. The microscopic rate constants (k(1) and k(2)/k(-)(1) ratio) associated with the S-O bond fission pathway support the proposed mechanism. The second-order rate constants for the S-O bond fission result in good linear Yukawa-Tsuno plots for the aminolyses of 2,4-dinitrophenyl X-substituted benzenesulfonates. However, the second-order rate constants for the C-O bond fission show no correlation with the electronic nature of the sulfonyl substituent X, indicating that the C-O bond fission proceeds through an S(N)Ar mechanism in which the leaving group departure occurs rapidly after the rate-determining step.

Journal Article↗
PubMed2004

2,4-Bis(octadecanoylamino)benzenesulfonic acid sodium salt as a novel scavenger receptor inhibitor with low molecular weight.

In order to investigate the effect of the fixation of the orientations of the two long chains, three types of novel derivatives of scavenger receptor inhibitor 1 were synthesized, and their biological activities were evaluated. Among the novel derivatives, 2,4-bis(octadecanoylamino)benzenesulfonic acid sodium salt (4d) showed the most potent inhibitory activity against the incorporation of 1,1'-dioctadecyl-3,3,3',3'-tetramethylindocarbocyanine perchlorate-labeled acetyl-LDL (DiI-acetyl-LDL) into macrophages. 2,5-Bis(octadecanoylamino)benzenesulfonic acid sodium salt (4c), a regioisomer of 4d, did not exhibit as potent an inhibitory activity as 4d, meaning that the substitution pattern of two long chains on the benzene ring must be important. Compound 4d exhibited 10 times more potent inhibitory activity against the binding of 125I-labeled acetyl-LDL to the surface of macrophages than compound 1.

Animals↗
PubMed2004

Raman spectroscopic study of hydrogen bonding in benzenesulfonic acid/acrylonitrile solutions.

Solutions of benzenesulfonic acid (BSA) in acrylonitrile in the range 1.02-6.53 mol dm(-3) were studied by FT-Raman spectroscopy. Spectra in the region of the acid SOH and benzenesulfonate anion SO3 stretching bands were analysed by band-fitting procedures in order to ascertain the degree of acid dissociation. This parameter changes from 0.42 (1.02 M solution) to 0.185 (6.53 M solution) despite the strong character of the acid. Interaction of acrylonitrile with undissociated BSA produces a new band in the nu(C[triple bond]N) Raman spectral region, displaced +21.4 cm(-1) and assigned to acrylonitrile molecules H-bonded to BSA. This displacement is in accord with the strong H-donor character of the acid. From the concentration of H-bonded acrylonitrile, the mean number of H-bonds in which each solvent molecule participates can be calculated. This number changes from ca. 0.2 in the less concentrated solution up to ca. 2.4 in the most concentrated solution. These results suggest that BSA-acrylonitrile complexes of fixed stoichiometry do not occur in the range of concentrations studied here.

Acids↗
PubMed2005

Influence of pH on the micelle-to-vesicle transition in aqueous mixtures of sodium dodecyl benzenesulfonate with histidine.

Small unilamellar vesicles (approximately 100 nm in diameter) form spontaneously in aqueous mixtures of histidine and sodium dodecyl benzenesulfonate. By manipulating pH, a gradual transition from micelles to vesicles to bilayers to precipitate is observed. The self-assembly of vesicles occurs over a wide range of compositions when the solution pH is lower than 6.0, the pKa of the imidazole moiety on the histidine molecule. This phenomenon is likely the result of attractive interactions between the negatively charged benzenesulfonate headgroups and the positively charged imidazole group in the amino acid. Similar results are obtained when imidazole salt itself is used.

Benzenesulfonates↗
PubMed1977

Degradation of benzenesulfonate to sulfite in bacterial extract.

Sulfite formation from benzenesulfonate was studied in extracts from a bacterium grown on this compound as a main carbon source. The activity of sulfite formation depended on the presence of NADH and oxygen as well as magnesium, suggesting an oxygenation-type reaction. The activity was found in a fraction precipitated by ammonium sulfate at 35-50% saturation; the specific activity was 15 times higher than that of crude extract, probably due to the elimination of inhibitory substances of low molecular weight from the preparation. In a distillate of the reaction mixture, phenol was found. Pyrocatechol as well as benzenesulfonate was oxidized in the crude extract, but phenol was not.

Aerobiosis↗
PubMed1982

Transport of benzenesulfonic acid derivatives through the rat erythrocyte membrane.

Transport of benzenesulfonic acid derivatives through the rat erythrocyte membrane was studied. The transport properties, such as pH-dependence and effects of reagents reacting with amino-groups, were similar to those to anions like Cl- through the human erythrocyte membrane. The rate of transport of anions through rat erythrocyte membranes is higher than through those of other mammals, such as guinea pig and bovine erythrocyte membranes. This relatively high rate of transport makes the rat erythrocyte membrane suitable for use in comparative studies on the transport of slowly penetrating substances, such as organic anions. The transport velocities of benezenesulfonic acid derivatives were compared with their physico-chemical properties. It was shown that the hydrophobicity has no effect on the transport, but the electronic property has a significant effect: the transport rate is mainly dependent on the e- donor capacities. This feature is the inverse to the well-known inhibitory effect of these derivatives on other anion transport: the inhibition is mainly dependent on the e- acceptor capacities. It is suggested that the transport is regulated by the binding capacity of anions to the transport site.

Animals↗
PubMed2004

Differentiation and quantification of linear alkyl benzenesulfonate isomers by liquid chromatography-ion-trap mass spectrometry.

Discrimination and quantitation of the 20 positional isomers of C10-C13 linear alkyl benzenesulfonates (LASs), based on the use of reversed-phase liquid chromatography-electrospray ionisation in negative ion mode ion-trap mass spectrometry, was undertaken. Discrimination was achieved by LAS MS-MS analysis into the ion trap, by monitoring specific fragment ions resulting from the benzylic cleavage of the carbon alkyl chain on both side of the LAS phenyl group. Parameters affecting the electrospray ionisation source and the ion-trap operation were optimised. Calibration curves for the different isomers were established and this permitted their quantitation by mass spectrometry for the first time. MS-MS responses were dependent on both the position of the phenyl group on the alkyl chain and the length of this alkyl chain, these responses being higher for the external isomers and the longer alkyl chain homologues. The precision, expressed as relative standard deviation ranged between 9 and 13%. Detection limits for LAS isomers were between 0.03 and 0.07 mg/l and therefore the method is sensitive enough to be applied to environmental samples.

Benzenesulfonates↗
PubMed2005

Low level determination of p-toluenesulfonate and benzenesulfonate esters in drug substance by high performance liquid chromatography/mass spectrometry.

GC/FID and HPLC/MS single ion monitoring methods have been evaluated for the determination of trace levels of methyl, ethyl and isopropyl esters of p-toluenesulfonic acid and methyl, ethyl, isopropyl and n-butyl esters of benzenesulfonic acid in drug substances. These sulfonate esters have been highlighted as potential genotoxins. HPLC/MS was found to be more promising and limits of quantification were between 2.5 and 5 ng/mL, which enabled detection limits in drug substance at 0.01-0.1 ppm for a 50 mg/mL solution. For one drug substance excellent recoveries of 94-95% were obtained at the 1.0 ppm level, however, with a second drug substance, a besylate salt, recoveries ranged from 86% to 100% and were dependant on the sample preparation. Limited stability of the sulfonate esters in various potential sample solutions indicated that samples may need to be prepared immediately before injection.

Benzenesulfonates↗
PubMed2004

Raman spectroscopy of benzenesulfonic and 4-toluenesulfonic acids dissolved in dimethylsulfoxide.

Solutions of benzenesulfonic acid (BSA) and 4-toluenesulfonic acid monohydrate (PTSA) in dimethylsulfoxide (DMSO) were studied by FT-Raman spectroscopy in the concentration range 1.0-3.5 mol dm(-3) (BSA) and 1.0-4.8 mol dm(-3) (PTSA). Spectra in the region of the Raman acid complex band (C-S + C-C + SO3) stretches, at 1124 cm(-1) were analysed by band-fitting procedures in order to ascertain the degree of acid dissociation. In BSA solutions, this parameter changes from 0.78 at 1.02 M to 0.47 at 3.5M, despite the strong character of the acid. Interaction of DMSO with undissociated BSA produces a new band in the solvent nu(C-S) Raman spectral region near 671 cm(-1), displaced >15.0 cm(-1), and assigned to DMSO molecules H-bonded to BSA. In PTSA solutions, hydrogen bonds are formed with the oxonium ion (H3O+) dissociated from the acid. In this case, the displacement observed is only >10.0 cm(-1), indicating a weaker interaction. From the concentration of H-bonded DMSO, the solute/solvent coordination number and its inverse, the mean number of H-bonds participating in bonding with each solvent molecule can be calculated. This coordination number changes in BSA solutions in bimodal way, passing through a maximum and reaching a limit of 2 in the most concentrated solution. This number agrees with that found in the solid solvate BSA.2DMSO. In PTSA solutions, the general trend is similar, but low coordination numbers are obtained, in agreement with the low acidity of the oxonium ion. The bimodal behaviour observed in both acids is explained by the self-associated structure of the solvent.

Benzenesulfonates↗
PubMed2006

Evaluation of a newly developed enzyme-linked immunosorbent assay for determination of linear alkyl benzenesulfonates in wastewater treatment plants.

A recently developed enzyme-linked immunosorbent assay (ELISA) for the determination of linear alkyl benzenesulfonates (LAS) and long chain sulfophenyl carboxylates (SPCs) has been evaluated for its application in wastewater control analysis. This ELISA based on the use of polyclonal antibodies in an indirect format shows an IC50 of 28.1 +/- 3.2 microg L(-1) and a limit of detection (LOD) of 1.8 +/- 0.6 microg L(-1) in buffer. The assay uses antibodies raised through a pseudoheterologous immunization strategy using an equimolar mixture of two immunogens, N-(4-alkylphenyl)sulfonyl-3-aminopropanoic acid covalently coupled to keyhole limped hemocyanin (SFA-KLH) and sulfophenyl carboxylate 13C13 coupled to KLH (13C13-SPC-KLH). The immunizing haptens have been designed to address recognition versus two different epitopes of the LAS molecule. To assess the performance of this immunoassay in complex real samples, a cross reactivity study was carried out, and the possible interference of other surfactants commonly detected in wastewater, including nonylphenol ethoxylates (NPEOs), nonylphenol (NP), octylphenol (OP), and coconut fatty acid diethanol amides (CDEA), have been evaluated. Additionally, a study of the matrix effects of different types of wastewater was achieved. This ELISA has been evaluated and validated by measuring the LAS content of 22 samples collected from the influents and the effluents of six wastewater treatment plants (WWTP) located in Catalonia, Spain. A solid-phase extraction followed by liquid chromatography coupled to mass spectrometry detection (SPE-LC-MS) has been used as a validation method of the new ELISA test.

Benzenesulfonates↗
PubMed2001

Large-volume sample stacking for on-capillary sample enrichment in the determination of naphthalene- and benzenesulfonates in real water samples by capillary zone electrophoresis.

We investigated the on-line preconcentration of a test mixture of 15 substituted and unsubstituted naphthalene(NSs) and benzenesulfonates (BZSs) by large-volume sample stacking (LVSS). Analyses were carried out by capillary zone electrophoresis (CZE) with on-column UV detection. In particular, we focused on how experimental variables such as the inside diameter of the capillary, the volume of sample introduced and polarity switching influenced the enrichment procedure. The best results were obtained when 300 nl were injected and stacked using a bubble cell capillary. Under these conditions, LVSS increased the detector response of conventional hydrodynamic injection by a factor of 40. The limits of detection of the method were between 5 and 10 microg l(-1). Determinations were reproducible, in terms of peak area and migration time, under such conditions. The performance of the method was examined by determining NS and BZS in real samples, such as tap, river and surface waters and inflow/outflow waters from a water treatment plant. Real samples were injected directly into the CZE column with little or no preparation.

Benzenesulfonates↗
PubMed1977

Effects of a new rodenticide, benzenesulfonic acid hydrazide, on prenatal mice.

Benzenesulfonic acid [(3-amino-2,4,6-trichlorophenyl)methylene] hydrazide, a candidate rodenticide coded as DRC-4575, was administered by gavage to pregnant female BALB/c mice. Each dose (5.5, 28.0, 42.0, 62.0 and 94.0 mg/kg) was given to one of five groups of ten mice on day 8 of gestation, making a total of five different dose groups on day 8. This same procedure was followed for days 9, 10, 11, 12, and 13. This made a total of 30 dose-day treatment groups. Six control females were dosed each day. Dam survival to day 18 declined as the dose increased; only 2% of the dams survived at 94 mg/kg. When the surviving females were killed at day 18, no significant differences were found between treatment and control animals in the number or weight of live fetuses, or in the ratio of male to female fetuses. However, the percentage of live fetuses was significantly lower and the number of resorptions was significantly higher for the treated dams at the 62 mg/kg dose level than for the control dams. Skeletal anomalies were limited primarily to unossified phalanges, which were probably related to the lower weights of those fetuses. Slight hydrocephalus occurred infrequently at all dose levels and in the controls, and was not dose-related. These data indicate that DRC-4575 would be embryotoxic only at doses of 62 mg/kg or higher and would not be teratogenic.

Animals↗
PubMed1987

Microbial desulfonation of substituted naphthalenesulfonic acids and benzenesulfonic acids.

Sulfur-limited batch enrichment cultures containing one of nine multisubstituted naphthalenesulfonates and an inoculum from sewage yielded several taxa of bacteria which could quantitatively utilize 19 sulfonated aromatic compounds as the sole sulfur source for growth. Growth yields were about 4 kg of protein per mol of sulfur. Specific degradation rates were about 4 to 14 mu kat/kg of protein. A Pseudomonas sp., an Arthrobacter sp., and an unidentified bacterium were examined. Each desulfonated at least 16 aromatic compounds, none of which served as a carbon source. Pseudomonas sp. strain S-313 converted 1-naphthalenesulfonic acid, 2-naphthalenesulfonic acid, 5-amino-1-naphthalenesulfonic acid, benzenesulfonic acid, and 3-aminobenzenesulfonic acid to 1-naphthol, 2-naphthol, 5-amino-1-naphthol, phenol, and 3-aminophenol, respectively. Experiments with 18O2 showed that the hydroxyl group was derived from molecular oxygen.

Arthrobacter↗
PubMedDate not supplied

Correlation of the photosynthetic reduction of p-(diazonium-) benzenesulfonic acid with the increased binding of the probe to the thylakoid membrane.

The reactions of chloroplast thylakoid lamellae with the chemical probe p-(diazonium-) benzenesulfonic acid (DABS) in the light have been reinvestigated. In contrast to a previous report, electron transport from a photosystem I electron donor to methylviologen was found to be inhibited by this treatment. During the incubation of chloroplasts with DABS in the light, the probe is altered with high rates. Under aerobic conditions, a concomitant oxygen uptake is observed, which is stoichiometric to the amount of DABS altered. Under anaerobic conditions, the binding of the 35S-labeled probe to the membranes in the light is stimulated 2-3 fold as compared to the binding under aerobic conditions. The data are taken as evidence that the photoreduction of the probe rather than a conformational change of the membrane may be at least partially responsible for the increased reagent binding observed in the light.

Benzenesulfonates↗
PubMed1997

Spectrophotometric assay for superoxide dismutase based on tetrazolium salt 3'--1--(phenylamino)-carbonyl--3, 4-tetrazolium]-bis(4-methoxy-6-nitro)benzenesulfonic acid hydrate reduction by xanthine-xanthine oxidase.

XTT (3'-{1-[(phenylamino)-carbonyl]-3, 4-tetrazolium}bis(4-methoxy-6-nitro)benzenesulfonic acid hydrate) was reduced to a water-soluble product with an absorbance maximum at about 470 nm by superoxide anion generated by xanthine-xanthine oxidase (XO). The rate of XTT reduction was linearly related to XO activity and the reduction was inhibited by superoxide dismutase (SOD). A perfect inhibition of the reduction of XTT by SOD was achieved, suggesting that XTT does not interact with XO. The present XTT-based assay had a higher sensitivity than a conventional nitroblue tetrazolium-based assay by a factor of 2.5 at pH 10.2. This method was applicable to the SOD assay in the pH range 8.0-10.2.

Animals↗