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PubMed2000

Electron impact induced fragmentation of ( p-substituted phenyl)-(4'-methylphenacyl) sulfones: contribution of sulfinate ester rearrangements

The molecular ions of the title compounds are usually very unstable. The main fragmentation corresponds to the formation of p-MeC(6)H(4)CO(+) as would be expected. Another abundant fragment ion was [M - SO(2)](+) which is formed both from the original sulfone and from the rearranged sulfinate esters. There are, however, three primary ions which can be traced back to each isomeric molecular ion: p-RC(6)H(4)SO(2)(+) to the original sulfone, p-RC(6)H(4)SO(+) to the.CH(2)S(=O)O-. type sulfinate ester and p-RC(6)H(4)OH(+.) to the.CH(2)OS(=O). type sulfinate ester of which the latter seems by far to dominate. Copyright 2000 John Wiley & Sons, Ltd.

Journal Article↗
PubMed2000

Sulfone-linked paracyclophanes via macrocyclic aromatic thioethers: synthetic and structural investigations.

Reaction of 4,4'-sulfonylbis(benzenethiol) with 4,4'-dichlorodiphenylsulfone under pseudo-high-dilution conditions leads to macrocyclic thioethersulfones [-S-Ar-SO2-Ar-]n (Ar = 1,4-phenylene). These include a highly strained [1+1] cyclodimer (n = 2), a cyclotrimer resulting from thioetherexchange reactions, and a [2+2] cyclotetramer which can adopt two entirely different conformations in the crystalline state, one having molecular D2d ("tennis-ball-seam") symmetry. The same type of reaction is successful using 4,4'-thiobis(benzenethiol) instead of 4,4'-sulfonylbis(benzenethiol) and affords macrocycles with a higher ratio of thioether to sulfone linkages. Exhaustive oxidation of macrocyclic thioethersulfones with hydrogen peroxide affords a series of sulfone-linked paracyclophanes, [-Ar-SO2-]4, [-Ar-SO2-]6, [-Ar-SO2-]8 and [-Ar-SO2-]12. Single crystal X-ray analysis reveals [Ar-SO2-]4 to be a near-perfect square box, whilst the cyclic hexamer [-Ar-SO2-]6 adopts a much more irregular conformation. and [-Ar-SO2-]8 displays a "double-box" structure clearly related to that of [Ar-SO2-]4.

Journal Article↗
PubMed2002

Anion exchange in the channels of a robust alkaline earth sulfonate coordination network.

The barium sulfonate network presented herein, [[Ba2(L)(H2O)5]Cl]infinity (1), represents the first metal sulfonate compound to possess a cationic framework. The network is layered with channels between pillaring ligands in which chloride ions reside. Compound 1 contracts slightly upon dehydration but retains its overall structural motif to 420 degrees C. Significantly, the chloride ions of the structure can be exchanged in 80% yield for fluoride ions in a facile manner. This exchange is quantified by elemental analyses, gravimetric determination, and 19F NMR spectroscopy. Confirmation of retention of structure is provided by standardized powder X-ray diffraction experiments. This last point is notable as the F-analogue of the structure is not attainable by a direct synthesis. These results illustrate one of the hallmark features of supramolecular chemistry, that a robust and functional framework can result through cooperative interactions between more weakly interacting units.

Journal Article↗
PubMed2002

Isotachophoretic focusing and mass spectrometry detection as tools for improving the determination of aromatic sulfonates in capillary electrophoresis.

We explored isotachophoresis-capillary zone electrophoresis (ITP-CZE) with diode array detection on a single capillary to find out how to increase the injection volume and decrease the detection limits of aromatic sulfonates in CZE. The ITP was performed by applying a negative voltage in conjunction with hydrodynamic backpressure programming, and the terminating buffer was removed before the CZE separation, which resulted in highly sensitive determinations. The ITP increased the signal response of conventional hydrodynamic injection by a factor of 100, whereas the separation efficiency was unaffected. The limits of detection of the method were between 3 and 5 nugL(-1). The method was successfully used to determine these compounds in water samples. Experimental conditions for capillary electrophoresis-mass spectrometry were optimized and applied to determine aromatic sulfonates in water samples. These techniques enables the 2-naphthalenesulfonate to be determined in water samples.

Arylsulfonates↗
PubMed2007

Silica gel triggered transformations of 3-methylenecyclopropylmethyl sulfonates to 3-methylenecyclobutyl analogues: experimental and computational studies.

Methylenecyclopropylcarbinols treated with sulfonyl chloride and Et(3)N form the sulfonated products in almost quantitative yields, which can be transformed to the corresponding 3-methylenecyclobutyl sulfonates with silica gel chromatography work-up. The rational explanation was proposed on the basis of computational studies.

Journal Article↗
PubMed2006

The sulfone syndrome secondary to dapsone prophylaxis in a patient undergoing unrelated hematopoietic stem cell transplantation.

Dapsone is commonly used for pneumocystis carinii pneumonia (PCP) prophylaxis in immunocompromised patients. It has been used as an alternative therapy in the hematopoietic stem cell transplant (HSCT) setting in patients who can't tolerate trimethoprim-sulfamethoxazole. The Sulfone syndrome is not a well-known sequela of dapsone therapy and occurs at various doses, ranging from 50-300 mg/d. In all cases the syndrome occurs within 2 months of initiating therapy. Its clinical manifestations include: fever, methemoglobinemia, hemolytic anemia, exfoliative dermatitis and transaminits. A 51-year old female underwent a matched unrelated hematopoiectic stem cell transplant for acute mylogenous leukemia. Dapsone therapy was initiated on day +28 at a dose of 100 mg/day for PCP prophylaxis secondary to the patient's history of a sulfonamide allergy. On day +59, one month after initiation of therapy she developed hepatitis, hemolytic anemia, fever and methemoglobinemia of 8%. She was transferred to the intensive care unit and subsequently developed an exfoliative dermatitis. We conclude that the clinical presentation of this patient after HSCT on dapsone therapy coincide with the sulfone syndrome not previously described in a patients after HSCT.

Anemia, Hemolytic↗
PubMed1991

The three-dimensional structure of class pi glutathione S-transferase in complex with glutathione sulfonate at 2.3 A resolution.

The three-dimensional structure of class pi glutathione S-transferase from pig lung, a homodimeric enzyme, has been solved by multiple isomorphous replacement at 3 A resolution and preliminarily refined at 2.3 A resolution (R = 0.24). Each subunit (207 residues) is folded into two domains of different structure. Domain I (residues 1-74) consists of a central four-stranded beta-sheet flanked on one side by two alpha-helices and on the other side, facing the solvent, by a bent, irregular helix structure. The topological pattern resembles the bacteriophage T4 thioredoxin fold, in spite of their dissimilar sequences. Domain II (residues 81-207) contains five alpha-helices. The dimeric molecule is globular with dimensions of about 55 A x 52 A x 45 A. Between the subunits and along the local diad, is a large cavity which could possibly be involved in the transport of nonsubstrate ligands. The binding site of the competitive inhibitor, glutathione sulfonate, is located on domain I, and is part of a cleft formed between intrasubunit domains. Glutathione sulfonate is bound in an extended conformation through multiple interactions. Only three contact residues, namely Tyr7, Gln62 and Asp96 are conserved within the family of cytosolic glutathione S-transferases. The exact location of the binding site(s) of the electrophilic substrate is not clear. Catalytic models are discussed on the basis of the molecular structure.

Amino Acid Sequence↗
PubMed1984

Lack of synergistic effect between arsenic, mercury and ethyl methane sulfonate on the frequency of chromosomal aberrations in mice.

The influence of arsenic and mercury on the frequency of chromosome aberrations induced by ethylmethane sulfonate was studied in mice. No synergistic effects could be demonstrated in somatic and germ cells of mice given a combined treatment of arsenic trioxide solution (As2O3, 12 mg per kg body weight) or of mercuric chloride solution (HgCl2, 6 mg per kg body weight) with ethylmethane sulfonate (EMS, 200 mg per kg body weight).

Animals↗
PubMed1991

Inclusion complex of 8-anilinonaphthalene-1-sulfonate with beta-cyclodextrin.

The interaction of 8-anilinonaphthalene-1-sulfonate with beta-cyclodextrin was investigated in 0.1 M phosphate buffer at pH 7.4 by fluorescence spectrophotometry. Utilizing the fact that the fluorescence intensity of 8-anilinonaphthalene-1-sulfonate increases in the presence of beta-cyclodextrin, the thermodynamic parameters for the inclusion complex formation were determined as follows: delta G degrees = -2.52 kcal/mol at 25 degrees C, delta H degree = -1.92 kcal/mol, and delta S degree = 2.1 eu. The driving forces for the inclusion complex formation were considered to be van der Waals-London dispersion force and hydrophobic interaction. Also, from the measurements of 1H NMR spectra and from studying the Corey-Pauling-Koltun (CPK) model, the structure of the inclusion complex was discussed.

Anilino Naphthalenesulfonates↗
PubMed2004

Highly informative proteome analysis by combining improved N-terminal sulfonation for de novo peptide sequencing and online capillary reverse-phase liquid chromatography/tandem mass spectrometry.

Recently, various chemical modifications of peptides have been incorporated into mass spectrometric analyses of proteome samples, predominantly in conjunction with matrix-assisted laser desorption/ionization mass spectrometry (MALDI MS), to facilitate de novo sequencing of peptides. In this work, we investigate systematically the utility of N-terminal sulfonation of tryptic peptides by 4-sulfophenyl isothiocyanate (SPITC) for proteome analysis by capillary reverse-phase liquid chromatography/tandem mass spectrometry (cRPLC/MS/MS). The experimental conditions for the sulfonation were carefully adjusted so that SPITC reacts selectively with the N-terminal amino groups, even in the presence of the epsilon-amino groups of lysine residues. Mass spectrometric analyses of the modified peptides by cRPLC/MS/MS indicated that SPITC derivatization proceeded toward near completion under the experimental conditions employed here. The SPITC-derivatized peptides underwent facile fragmentation, predominantly resulting in y-series ions in the MS/MS spectra. Combining SPITC derivatization and cRPLC/MS/MS analyses facilitated the acquisition of sequence information for lysine-terminated tryptic peptides as well as arginine-terminated peptides without the need for additional peptide pretreatment, such as guanidination of lysine amino group. This process alleviated the biased detection of arginine-terminated peptides that is often observed in MALDI MS experiments. We will discuss the utility of the technique as a viable method for proteome analyses and present examples of its application in analyzing samples having different levels of complexity.

Amino Acid Sequence↗
PubMed2004

De novo sequencing of tryptic peptides sulfonated by 4-sulfophenyl isothiocyanate for unambiguous protein identification using post-source decay matrix-assisted laser desorption/ionization mass spectrometry.

A simple method of solid-phase derivatization and sequencing of tryptic peptides has been developed for rapid and unambiguous identification of spots on two-dimensional gels using post-source decay (PSD) matrix-assisted laser desorption/ionization (MALDI) mass spectrometry. The proteolytic digests of proteins are chemically modified by 4-sulfophenyl isothiocyanate. The derivatization reaction introduces a negative sulfonic acid group at the N-terminus of a peptide, which can increase the efficiency of PSD fragmentation and enable the selective detection of only a single series of fragment ions (y-ions). This chemically assisted method avoids the limitation of high background normally observed in MALDI-PSD spectra, and makes the spectra easier to interpret and facilitates de novo sequencing of internal fragment. The modification reaction is conducted in C(18) microZipTips to decrease the background and to enhance the signal/noise. Derivatization procedures were optimized for MALDI-PSD to increase the structural information and to obtain a complete peptide sequence even in critical cases. The MALDI-PSD mass spectra of two model peptides and their sulfonated derivatives are compared. For some proteins unambiguous identification could be achieved by MALDI-PSD sequencing of derivatized peptides obtained from in-gel digests of phosphorylase B and proteins of hepatic satellite cells (HSC).

Amino Acid Sequence↗
PubMed2000

Virus inactivation by anilinonaphthalene sulfonate compounds and comparison with other ligands.

Bis-(8-anilinonaphthalene-1-sulfonate) (bis-ANS) causes inactivation of vesicular stomatitis virus (VSV) at micromolar concentrations while butyl-ANS and ANS are effective at concentrations one and two orders of magnitude higher, respectively. VSV fully inactivated by the combined effects of 10 microM bis-ANS and 2.5 kbar hydrostatic pressure elicited a high titer of neutralizing antibodies. Incubation of VSV with >/=2 M urea at atmospheric pressure caused very little virus inactivation, whereas at a pressure of 2.5 kbar, 1 M urea caused inactivation that exceeded by more than two orders of magnitude the sum of the inactivating effects produced by urea and pressure separately. Measurements of bis-ANS fluorescence showed that increasing the urea concentration reduces the pressure required to disrupt the structure. We conclude that anilinonaphthalene sulfonate compounds inactivate VSV by a mechanism similar to that produced by pressure. The most effective antiviral compound was bis-ANS which can be used for the preparation of safe viral vaccines or as an antiviral drug eventually.

Anilino Naphthalenesulfonates↗
PubMed2001

Micellar Effects on S(N)2 Reactions of Alkyl Naphthalene-2-sulfonates:The Role of Hydrophobic Substituents.

Reactivities of methyl naphthalene-2-sulfonate, MeONs, and its 6-alkyl derivatives, alkyl=Me, n-C(6)H(13) and n-C(12)H(25), 6-Me-MeONs, 6-Hex-MeONs, and 6-Do-MeONs, respectively, are compared for reactions in cetyl trialkylammonium bromide micelles, n-C(16)H(33)NR(3)Br, R=Me, Et, n-Pr, n-Bu, CTABr, CTEABr, CTPABr, CTBABr, respectively. Similar experiments were made on reactions of Br(-) with n-butyl and n-decyl naphthalene-2-sulfonates, BuONs, and DeONs, respectively. Reactions with OH(-) were followed in cetyl trialkylammonium hydroxide, alkyl=Me, Et, n-Pr, CTAOH, CTEAOH, and CTPAOH, solubility permitting. Some reactions with OH(-) or Br(-) were also followed in mixed-ion systems of CTAOMs or CTPAOMs (OMs=MeSO(3)). Micellar rate effects were analyzed by using pseudophase treatments including interionic competition in mixed-ion systems. Second-order rate constants in the micellar pseudophase increase systematically with increases in substrate hydrophobicity and for reactions with Br(-), but not OH(-), they also increase with bulk of the cationic head group. Copyright 2001 Academic Press.

Journal Article↗
PubMed2002

Chemical, structural, and thermal properties of Zn(II)-Cr(III) layered double hydroxides intercalated with sulfated and sulfonated surfactants.

Zn(II)-Cr(III)-LDHs (layered double hydroxides) containing sulfated or sulfonated surfactants as the interlamellar anion were synthesized by the coprecipitation method. The syntheses were conducted under various different experimental conditions, such as the Zn : Cr ratio, pH, and aging time. In each of the prepared materials, unlike previously reported data, the interlayer anion arrangement did not change, being consistent with a perpendicular monolayer. The thermal decomposition process of the prepared materials was studied by a set of analysis methods, such as TG/DTA, TG/MS, PXRD, and FT-IR. From the results obtained it was possible to conclude that, in an air atmosphere, the anions decomposed by a partial combustion, leading to the formation of sulfide. The results also showed that sulfonated surfactants containing LDHs are much more stable than those containing sulfated surfactants. A mechanism was proposed for the thermal decomposition of such LDHs based on the experimental results.

Benzenesulfonates↗
PubMed2002

Perfluorooctane sulfonate in oysters, Crassostrea virginica, from the Gulf of Mexico and the Chesapeake Bay, USA.

Concentrations of perfluorooctane sulfonate (PFOS), a metabolite of several sulfonated perfluoroorganic compounds, were measured in oysters collected from 77 locations in the Gulf of Mexico and Chesapeake Bay of the United States. PFOS was detected in oysters collected from 51 of the 77 locations at concentrations ranging from < 42 to 1,225 ng/g on a dry weight basis. This study provides baseline data for future monitoring programs to examine long-term trends in concentrations of PFOS.

Alkanesulfonic Acids↗
PubMed2005

Protective effect of MESNA (2-mercaptoethane sulfonate) against hepatic ischemia/reperfusion injury in rats.

PURPOSE: Reoxygenation of ischemic tissue generates various reactive oxygen metabolites (ROMs), which have a deleterious effect on various cellular functions. We evaluated the possible protective effect of 2-mercaptoethane sulfonate (MESNA) on hepatic ischemia/reperfusion (I/R) injury. METHODS: Wistar albino rats were subjected to 45-min hepatic ischemia, followed by 60-min reperfusion. 2-Mercaptoethane sulfonate, 150 mg/kg, or saline was given intraperitoneally (i.p.) twice, 15 min before ischemia and immediately before reperfusioin. We measured serum aspartate aminotransferase (AST) and alanine aminotransferase (ALT) levels to assess liver function. Liver tissue samples were taken to measure the levels of malondialdehyde (MDA), an end-product of lipid peroxidation; glutathione (GSH), a key antioxidant; and myeloperoxidase (MPO) activity, as an indirect index of neutrophil infiltration. We also measured hepatic collagen content, as a fibrosis marker. RESULTS: Plasma ALT and AST levels were higher in the I/R group than in the control group, but this increase was significantly decreased by MESNA treatment. Hepatic GSH levels, which were significantly depressed by I/R, increased back to the control levels in the MESNA-treated I/R group. Increases in tissue MDA levels and MPO activity caused by I/R injury decreased back to the control levels after MESNA treatment. Similarly, the increased hepatic collagen content in the I/R group decreased to the level of the control group after MESNA treatment. CONCLUSION: The fact that MESNA alleviated I/R-induced injury of the liver and improved hepatic structure and function suggests that its antioxidant and oxidant scavenging properties may be of therapeutic value in protecting the liver against oxidative injury caused by I/R.

Animals↗
PubMed2005

QSAR for anti-malarial activity of 2-aziridinyl and 2,3-bis(aziridinyl)-1,4-naphthoquinonyl sulfonate and acylate derivatives.

Quantitative structure-activity antimalarial relationships have been studied for 63 analogues of 2-aziridinyl and 2,3-bis(aziridinyl)-1,4-naphthoquinonyl sulfonate and acylate derivatives by means of multiple linear regression (MLR) and artificial neural networks (ANN). The antimalarial activity [-log(IC50x10(6))] of the compounds studied were well correlated with descriptors encoding the chemical structure. Using the pertinent descriptors revealed by a stepwise procedure in the multiple linear regression technique, a correlation coefficient of 0.9394 (s=0.2121) for the training set was obtained for the ANN model in a [3-5-1] configuration. The results show that the antimalarial activity of 2-aziridinyl and 2,3-bis(aziridinyl)-1,4-naphthoquinonyl sulfonate and acylate derivatives is strongly dependent on hydrophobic character, hydrogen-bond acceptors and also steric factors of the substituents.

Acylation↗
PubMed1985

Fluorescent properties of histone-1-anilinonaphthalene 8-sulfonate complexes in the presence of denaturant agents: application to the rapid staining of histones in urea and Triton-urea-polyacrylamide gels.

In the present report it is shown that histone bands in urea-acetic acid or Triton-urea-acetic acid-polyacrylamide gels can be stained with the fluorescent dye 1-anilinonaphthalene 8-sulfonate and visualized by transillumination of the gel with an uv-light source. The 1-anilinonaphthalene 8-sulfonate staining method described here for urea and Triton-urea gels is rapid (it can be completed in 90 min) and allows the detection of less than 1 micrograms of histone per band.

Anilino Naphthalenesulfonates↗