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PubMed2004

Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts.

The palladium-catalyzed reaction of sulfinic acid salts with a wide variety of aryl and vinyl halides or triflates provides unsymmetrical diaryl sulfones and aryl vinyl sulfones in good to excellent yields. The reaction is strongly influenced by the presence of nBu4NCl, and the use of Xantphos, a rigid bidentate ligand with a wide natural bite angle, was found to be crucial for the success of the reaction. With neutral, electron-rich, and electron-poor aryl iodides best results were obtained by using Pd2(dba)3, Xantphos, Cs2CO3, and nBu4NCl, in toluene at 80 degrees C. Two general procedures were employed with aryl bromides and triflates: sodium p-toluenesulfinate, Pd2(dba)3, Xantphos, Cs2CO3, 120 degrees C, in toluene with nBu4NCl (procedure A: neutral, electron-rich, and slightly electron-poor aryl bromides or triflates) and without nBu4NCl (procedure B: electron-poor aryl bromides or triflates). With vinyl triflates best results were obtained at 60 degrees C omitting nBu4NCl.

Journal Article↗
PubMed1999

Echinosulfonic acids A-C and echinosulfone A: novel bromoindole sulfonic acids and a sulfone from a southern australian marine sponge, echinodictyum

The crude EtOH extract of an Echinodictyum sp. collected during trawling operations in the Great Australian Bight, Australia, displayed antibacterial and antiparasitic properties. Bioassay-directed fractionation yielded three novel sulfonic acids, the echinosulfonic acids A to C (1-3), and a new sulfone, echinosulfone A (4). Structures were assigned to these compounds on the basis of detailed spectroscopic analysis. It was determined that echinosulfonic acids A-C (1-3) and echinosulfone A (4) contributed to the antibacterial but not antiparasitic activity of the crude extract.

Journal Article↗
PubMed2003

Hydrophobic, low-loading and alkylated polystyrene-supported sulfonic acid for several organic reactions in water: remarkable effects of both the polymer structures and loading levels of sulfonic acids.

A hydrophobic, low-loading and alkylated polystyrene-supported sulfonic acid (LL-ALPS-SO3H) has been developed for several organic reactions such as the hydrolysis of thioesters, the deprotection of acetals and an acetonide, and the hydration of an epoxide and an alkyne in pure water on the basis of remarkable effects of both the polymer structures and loading levels of the sulfonic acid catalysts.

Journal Article↗
PubMed1955

Studies on the generalized Shwartzman reaction. VI. Production of the reaction by the synergistic action of endotoxin with three synthetic acidic polymers (sodium polyanethod sulfonate, dextran sulfate, and sodium polyvinyl alcohol sulfonate).

Lesions indistinguishable from those of the generalized Shwartzman reaction occured in rabbits when a single intravenous injection of Gram-negative bacterial endotoxin was accompanied, or followed, by an injection of one of the following synthetic, heparin-like, acidic polymers-sodium polyanethol sulfonate, dextran sulfate, or sodium polyvinyl alcohol sulfonate. These reactions were produced by doses of polymer or of endotoxin which were without demonstrable effect when given singly. Heparin, in those similar to those previously shown to protect rabbits against the lesions of the generalized Shwartzman reaction, prevented the reaction to the combined injection of endotoxin and acidic polymers. Nitrogen mustard, which was previously shown to prevent the lesions of the generalized Shwartzman reaction from occurring after two intravenous injections of endotoxin, had no protective action against the lesions produced by the combined injection of endotoxin and polymer. Cortisone did not affect the reaction to endotoxin and polymer. The role of fibrinogen in the reaction under study is discussed in the paper which follows.

Animals↗
PubMed2001

Influence of aromatic sulfonation on the geometry of [2.2]paracyclophane: crystal structures of one sulfonate, one disulfonic anhydride and five disulfonimides.

The crystal structures of potassium [2.2]paracyclophane-4-sulfonate (1), [2.2]paracyclophane-4,15-disulfonic anhydride (2), [2.2]paracyclophane-4,15-disulfonimide (3), N-n-propyl-[2.2]paracyclophane-4,15-disulfonimide (4), N-isopropyl-[2.2]paracyclophane-4,15-disulfonimide (5), N-cyclopropyl-[2.2]paracyclophane-4,15-disulfonimide (6) and N-phenyl-[2.2]paracyclophane-4,15-disulfonimide (7) were established by single-crystal X-ray diffraction. The structural changes caused by sulfonation are discussed with respect to the parent [2.2]paracyclophane (tricyclo[8.2.2.2(4,7)]hexadeca-4,6,10,12,13,15-hexaene). The main features are a change in the non-bonding distances between the para-phenylene rings and a rotation of these rings with respect to the molecular symmetry plane. The rings are rotated away from each other in the case of monosulfonation (1), but are rotated in the opposite way in the case of the disulfonic anhydride (2) or the disulfonimide compounds (3)-(7). The results are also discussed in terms of the parameters proposed by Keehn [(1983), Organic Chemistry, A Series of Monographs 45, edited by P. H. Keehn & S. M. Rosenfeld, Vol. 1, pp. 69-238. New York: Academic Press] showing that (bonded and non-bonded) angles involving the para-phenylene rings are mainly affected.

Journal Article↗
PubMed1965

Microbial Degradation of the Sulfonate of Dodecyl Benzene Sulfonate.

It has been observed that the sulfonate portion of alkyl benzene sulfonate (ABS) will undergo microbial attack in certain pure and mixed cultures if an energy source, such as glucose, is available. The evidence for this is provided by the stoichiometric relationship between the reduction of ABS concentration and the appearance of inorganic sulfur compounds.

Journal Article↗
PubMed2006

Identification of a novel sulfonated oxysterol, 5-cholesten-3beta,25-diol 3-sulfonate, in hepatocyte nuclei and mitochondria.

This study reports the discovery of a novel sulfonated oxysterol found at high levels in the mitochondria and nuclei of primary rat hepatocytes after overexpression of the gene encoding steroidogenic acute regulatory protein (StarD1). Forty-eight hours after infection of primary rat hepatocytes with recombinant adenovirus encoding StarD1, rates of bile acid synthesis increased by 4-fold. Concurrently, [(14)C]cholesterol metabolites (oxysterols) were increased dramatically in both the mitochondria and nuclei of StarD1-overexpressing cells, but not in culture medium. A water-soluble [(14)C]oxysterol product was isolated and purified by chemical extraction and reverse-phase HPLC. Enzymatic digestion, HPLC, and tandem mass spectrometry analysis identified the water-soluble oxysterol as 5-cholesten-3beta,25-diol 3-sulfonate. Further experiments detected this cholesterol metabolite in the nuclei of normal human liver tissues. Based upon these observations, we hypothesized a new pathway by which cholesterol is metabolized in the mitochondrion.

Animals↗
PubMed1998

Mineral content of infant formula after treatment with sodium polystyrene sulfonate or calcium polystyrene sulfonate.

Options for the management of infants with hyperkalemia secondary to renal insufficiency are limited for infants not maintained on dialysis. Precipitation of potassium (K+) from infant formula with sodium polystyrene sulfonate (KX) prior to feeding has been reported. However, its effect on calcium (Ca2+) and sodium (Na+) has not been quantitatively defined. The purpose of this study was to examine the effects of two K+ exchange resins: KX and calcium polystyrene sulfonate (RC) on Na+, K+, and Ca2+. Infant formula powder (Similac PM 60/40, Ross Laboratories, Columbus, OH, USA) was prepared with deionized water (DW) and KX or RC (1 g/mEq of K+) was added. The formula was decanted after 50 minutes and Na+, K+, and Ca2+ were assayed in the supernatant. Na+ and K+ were also assayed in ready-to-feed PM 60/40 (RTF). KX decreased the K+ concentration by 4.5 fold (P < 0.001) and increased the Na+ content by 3.8 fold (P < 0.001). In RC there was a 1.6-fold increase in Ca2+ content (P < 0.001), and a 13% decrease in K+ concentrations (P < 0.05). Preparation of the formula with DW reduced the K+ concentration by 30% compared to ready-to-feed formula (P < 0.001). We conclude that, although KX significantly reduces the K+ content of formulas, DW may be a more practical and convenient method of preparing formula for the hyperkalemic infant.

Calcium↗
PubMed2003

The polysulfonylamines bis(methylsulfonamido) sulfone and bis(trifluoromethylsulfonamido) sulfone.

Bis(methylsulfonamido) sulfone, C(2)H(8)N(2)O(6)S(3) or SO(2)(NHSO(2)CH(3))(2), was synthesized from imidobis(sulfonyl chloride), HN(SO(2)Cl)(2), and bis(trimethylsilyl)methane, CH(2)[Si(CH(3))(3)](2), in chlorotrimethylsilane solution. In the solid state, there are two independent molecules linked by two N-H...O hydrogen bridges into infinite chains parallel to the b axis. The central S atoms of the independent molecules each lie on a twofold axis. Bis(trifluoromethylsulfonamido) sulfone, C(2)H(2)F(6)N(2)O(6)S(3) or SO(2)(NHSO(2)CF(3))(2), was formed by the reaction of trichlorophosphazosulfuryl trifluoromethane, Cl(3)PNSO(2)CF(3), with fluorosulfonic acid, FSO(3)H. The molecules are connected by bifurcated N-H...O bridges into infinite layers parallel to the [001] plane. The central S atom lies on a twofold axis.

Journal Article↗
PubMed1988

Arginine 2-mercaptoethane sulfonate and sodium 2-mercaptoethane sulfonate: a comparative study of their effects upon tumour cells.

The action of arginine 2-mercaptoethane sulfonate in comparison with sodium 2-mercaptoethane sulfonate on cell growth and cell adhesion of a metastatic sub-line of murine melanoma (F10/B16) was investigated. The capability of the two compounds to interfere with the cytotoxicity of 4-hydroperoxycyclophosphamide and of cis-dichlorodiammineplatinum(II) in F10 cells was studied. The in vivo studies included the determination of acute and sub-acute toxicity of the two salts on mice. Very low toxicity and no significant differences between the two compounds were detected.

Animals↗
PubMed1994

[The repair of UV-induced postreplication DNA gaps in Escherichia coli cells adapted to methylmethane sulfonate and ethylmethane sulfonate].

The survival (only after the adaptation to methylmethane sulfonate, MMS) and repair of DNA postreplication gaps in UV-irradiated Escherichia coli, adapted to MMS (20 mkg/ml for 3 h) and ethylmethane sulfonate (EMS, 100 mkg/ml for 3 h), have been investigated. The survival of MMS-adapted bacteria of wild strains B/r and K12 AB1157 somewhat increased, whereas the survival of AB1886 uvrA mutant, which unlike the wild type bacteria is unable to excise cyclobutane pyrimidine dimers, was seen to decrease. The repair of postreplicative gaps in MMS-adapted bacteria correlates qualitatively with changes in survival: in B/r and AB1157 strains the repair is somewhat more effective (10-15%), while in AB1886 uvrA mutant significantly slower (near 30%) than in non-adapted bacteria. Similar changes of postreplicative repair (PRR) of DNA are observed in AB1157 and AB1886 uvrA strains adapted to EMS. It is suggested that the decreased efficiency of PRR in bacteria AB1886 uvrA, adapted to alkylating agent, may be due to the interference between the two inducible repair processes: adaptive response and SOS response. The latter process is involved in the repair of some part of postreplicative gaps of DNA. Different results of PRR of DNA in bacteria of wild types, adapted to MMS and EMS, may be associated with the intrinsic PRR in uvr+ strains. Due to this process in uvr+ bacteria SOS component of PRR of DNA is not formed. It is suggested that PRR in uvr+ bacteria adapted to alkylating agents is accelerated by enzymes of adaptive response in the absence of antagonism between the SOS response and the adaptive response.

Adaptation, Physiological↗
PubMed1990

Aluminum phthalocyanines with asymmetrical lower sulfonation and with symmetrical higher sulfonation: a comparison of localizing and photosensitizing mechanism in human tumor LOX xenografts.

A comparison of time-dependent localization patterns between lower, asymmetrical (AIPCS2a) and higher, symmetrical (AIPCS4) sulfonates of aluminum phthalocyanines in human malignant melanoma LOX transplanted to athymic nude mice from 1 to 120 hr after i.v. administration was made by means of laser scanning fluorescence microscopy. The lipophilic AIPCS2a was distributed mainly in tumor cells, while the hydrophilic AIPCS4 localized only in the vascular stroma of the tumor tissue. Concomitantly, comparative observations on the killing mechanism of photodynamic effects after treatment with a much lower i.v. dose of AIPCS2a and AIPCS4 plus laser light on the human tumor LOX were also made by morphological studies. Light and electron microscopy showed that there was a direct, extensive, photo-damaging action on all organelles and nuclear structure in the tumor cells after PDT with AIPCS2a; whereas the photo-induced injury to the tumor tissue after treatment with AIPCS4 and light was largely the consequence of initial functional vasogenic response and ultimate damage to vascular structure. These findings correlate well with the different localization patterns of the 2 dyes observed in human tumor tissues.

Animals↗
PubMed2003

Relative rates of Michael reactions of 2'-(phenethyl)thiol with vinyl sulfones, vinyl sulfonate esters, and vinyl sulfonamides relevant to vinyl sulfonyl cysteine protease inhibitors.

[reaction: see text] The relative rates of Michael additions of 2'-(phenethyl)thiol to representative vinyl sulfonyl Michael acceptors were measured. The dependence of the reactivity of the Michael acceptor on the nature of the sulfonyl R substituent was determined in order to evaluate the effect of these substituents on the inactivation kinetics of comparably substituted vinyl sulfonyl cysteine protease inhibitors. The rates of these Michael additions vary over 3 orders of magnitude, with phenyl vinyl sulfonate esters (R = OPh) being ca. 3000-fold more reactive than N-benzyl vinyl sulfonamides (R = NHBn).

Catalysis↗
PubMed2006

Halichondria sulfonic acid, a new HIV-1 inhibitory guanidino-sulfonic acid, and halistanol sulfate isolated from the marine sponge Halichondria rugosa Ridley & Dendy.

A new sulfur-containing guanidino derivative, halichondria sulfonic acid (1) showing anti-HIV-1 activity, and halistanol trisulfate (2) with anti-tumor activity have been isolated from the marine sponge Halichondria rugosa Ridley & Dendy collected in the Chinese Southern Sea. The structure of 1 was elucidated by analysis of spectroscopic and crystal data.

Animals↗
PubMed1978

Derivatives of methyl vinyl sulfone. Distribution and elimination of methyl (2,2-diphenyl)-vinyl sulfone labelled with 14carbon in mice.

The investigation of methyl (2,2-diphenyl)-vinyl sulfone (14C-MDVS) administered i.p. in mice shows that this product appears rapidly in the general circularoty system. The blood concentration of MDVS reaches a maximum 1 h after injection. Part of the MDVS is bound to the plasma proteins. Infrared spectrometry analysis of radioactive products eliminated by the urine confirms that the product is not split, but also reveals the presence of hydroxyl and carbonyl groups in the metabolic conversion products.

Animals↗
PubMed2007

Titanocene(II)-promoted multicomponent reactions utilizing alkynyl sulfones, alkenyl sulfones, and carbonyl compounds: a novel method for the synthesis of vinylallenes.

Titanocene(II)-promoted cross coupling of alkynyl- and (Z)-alkenyl sulfones affords alpha-(phenylsulfonyl)alkenyltitanium species. Further treatment of these species with the titanocene(II) reagent generates titanium vinylvinylidene complexes, which react with carbonyl compounds in one pot to produce substituted vinylallenes with complete stereoselectivity. By using alpha,beta-unsaturated ketones, 1,3,4,6-tetraenes are also obtained stereoselectively.

Journal Article↗
PubMed1983

S-sulfonation: a reversible chemical modification of human immunoglobulins permitting intravenous application. I. Physicochemical and binding properties of S-sulfonated and reconstituted IgG.

S-sulfonation represents a reversible chemical modification of disulfide bonds by which under the special conditions chosen only about 2.2 cystine units per IgG molecule are cleaved. Physicochemical and functional evidence for reconstitution is presented. Molecules reconstituted in vitro or in vivo regain, within a few hours, a reactivity (antigen binding, immunoprecipitation, Clq-mediated cross-linking of immune complexes) comparable to equimolar control preparations.

Animals↗
PubMed2001

Effects and risk assessment of linear alkylbenzene sulfonates in agricultural soil. 5. Probabilistic risk assessment of linear alkylbenzene sulfonates in sludge-amended soils.

Linear alkylbenzene sulfonates (LAS) can be found in high concentrations in sewage sludge and, hence, may enter the soil compartment as a result of sludge application. Here, LAS may pose a risk for soil-dwelling organisms. In the present probabilistic risk assessment, statistical extrapolation has been used to assess the risk of LAS to soil ecosystems. By use of a log-normal distribution model, the predicted no-effect concentration (PNEC) was estimated for soil fauna, plants, and a combination of these. Due to the heterogeneous endpoints for microorganisms, including functional as well as structural parameters, the use of sensitivity distributions is not considered to be applicable to this group of organisms, and a direct, expert evaluation of toxicity data was used instead. The soil concentration after sludge application was predicted for a number of scenarios and used as the predicted environmental concentration (PEC) in the risk characterization and calculation of risk quotients (RQ = PEC/PNEC). A LAS concentration of 4.6 mg/kg was used as the current best estimate of PNEC in all RQ calculations. Three levels of LAS contamination (530, 2,600, and 16,100 mg/kg), three half-lives (10, 25, and 40 d), and five different sludge loads (2, 4, 6, 8, and 10 t/ha) were included in the risk scenarios. In Denmark, the initial risk ratio would reach 1.5 in a realistic worst-case consideration. For countries not having similar sludge regulations, the estimated risk ratio may initially be considerably higher. However, even in the most extreme scenarios, the level of LAS is expected to be well beyond the estimated PNEC one year after application. The present risk assessment, therefore, concludes that LAS does not pose a significant risk to fauna, plants, and essential functions of agricultural soils as a result of normal sewage sludge amendment. However, risks have been identified in worst-case scenarios.

Agriculture↗