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At least 19 recordsLinked to original sources
PubMed1992

Sulfonate analogues of chenodeoxycholic acid: metabolism of sodium 3 alpha, 7 alpha-dihydroxy-25-homo-5 beta-cholane-25-sulfonate and sodium 3 alpha, 7 alpha-dihydroxy-24-nor-5 beta-cholane-23-sulfonate in the hamster.

This report describes the chemical synthesis of a new bile acid analogue, namely, sodium 3 alpha, 7 alpha-dihydroxy-25-homo-5 beta-cholane-25-sulfonate from homochenodeoxycholic acid. The structure of the new compound was assigned by proton magnetic resonance and infrared spectrometry. Its metabolism was studied in the hamster in comparison with sodium 3 alpha, 7 alpha-dihydroxy-24-nor-5 beta-cholane-23-sulfonate and sodium taurochenodeoxycholate. After intraduodenal administration of the 3H-labeled analogues into bile fistula hamsters, both sulfonates were absorbed from the intestine and nearly 80% of the radioactivity was secreted into bile within 8 h. Intra-ileal administration revealed that these compounds resembled taurochenodeoxycholate in that they were much more rapidly absorbed from the ileum than from the proximal small intestine: more than 85% of the radioactivity was recovered in bile within 1 h. After intravenous infusion the sulfonates were efficiently extracted by the liver at rates similar to that of sodium taurochenodeoxycholate. Chromatographic analysis of the bile showed that, regardless of the route of administration, most (> 95%) of the sulfonates were not biotransformed and they became major biliary bile acids. Sodium 3 alpha, 7 alpha-dihydroxy-25-homo-5 beta-cholane-25-sulfonate and, to a lesser extent, sodium 3 alpha, 7 alpha-dihydroxy-24-nor-5 beta-cholane-23-sulfonate induced cholestasis at infusion rates at which sodium taurochenodeoxycholate produced choleresis.

Animals↗
PubMed2001

X-ray investigations of sulfur-containing fungicides. III. Intramolecular forces governing the conformation of a novel orthorhombic polymorph of benzoylmethyl phenyl sulfone, benzoylmethyl 4-chlorophenyl sulfone and benzoylphenylmethyl phenyl sulfone.

The crystal and molecular structures of three beta-ketosulfones: benzoylmethyl phenyl sulfone (I), benzoylmethyl 4-chlorophenyl sulfone (II) and benzoylphenylmethyl phenyl sulfone (III) have been investigated using X-ray analysis and quantum mechanics ab initio calculations. Compound (I) crystallizes in the monoclinic and orthorhombic crystal systems. The crystal structure of the orthorhombic polymorph has not been reported previously. At room temperature and in the presence of daylight the pale yellow orthorhombic crystals undergo transformation to the stable colourless monoclinic polymorph. Hyperconjugative sigma(S-C1) - pi(*)(C2=O3) and sigma(*)(S-C1) - pi(C2=O3) stabilization energies in benzoylmethyl phenyl sulfones are highly dependent on the central dihedral angle alpha: S-C1-C2=O3 and are largest for a gauche arrangement, as found in both crystal forms of (I). The electron density distribution in all compounds (I), (II) and (III) is significantly affected by interactions of oxygen lone pairs with non-bonding orbitals of the adjacent S-C1 and C1-C2 bonds. The latter effect is responsible for back-donation of the electron density from O atoms towards the central part of the molecule.

Journal Article↗
PubMed1997

Sulfones as Radical Progenitors: An Unprecedented Example of Homolytic Sulfone Cleavage Facilitated by o-Stannyl Substitution of Aryl Sulfones(1).

Allylic aryl sulfones bearing an o-allyldialkylstannyl moiety (1b), when converted to stannyl radical 1a, suffer homolytic cleavage via intramolecular attack of the stannyl radical on the sulfone. Allyl radicals generated in this manner can be utilized for further intramolecular radical cyclizations; thus the overall transformation can be viewed as an alkylative desulfonylation reaction. Previously unknown sulfonyl stannane polymer 5 is generated as a byproduct. The o-dibutylstannyl radical derived from nonallylic aryl sulfone 15 does not suffer homolysis but instead forms 9-membered macrocycle 19 via an intramolecular reaction with the phenylacetylene group.

Journal Article↗
PubMed1995

Synthesis and elastase inhibitory activity of 6 alpha-chloro-2,2-dimethyl-3 alpha-(pivaloyloxy)methylpenam sulfone, 6 alpha-chloro-2,2-dimethyl-3-exo-methylenepenam sulfone, benzyl and methyl 6 alpha-substituted penicillanate sulfones.

The triflates and pivalates of 3 alpha-hydroxymethyl-6-substituted-2,2-dimethylpenam sulfones 3, 5; methyl and benzyl 6-substituted penicillanates 6-9 and 3-exo-methylene-6-substituted-2,2-dimethylpenam sulfone 4 were synthesized. These novel compounds were evaluated as elastase inhibitors using porcine pancreatic elastase. The effects that structural modifications of substituents on C-3 and C-6 in the penam nucleus have on elastase activity were examined and several similarities and distinctions were identified when compared to the reported penicillin esters and amides elastase inhibitors.

Animals↗
PubMed1985

Contraluminal sulfate transport in the proximal tubule of the rat kidney. II. Specificity: sulfate-ester, sulfonates and amino sulfonates.

In order to study the specificity for the contraluminal sulfate transport system the inhibitory potency of sulfate esters and sulfonate compounds on the 35SO4(2-) influx from the interstitium into cortical tubular cells in situ has been determined. The following was found: 1. From 10 sulfate monoesters tested 9 inhibited contraluminal sulfate influx with an app. Ki between 0.6 and 6 mmol/l; the two sulfate diesters tested, however, did not. 2. Out of 8 aliphatic sulfonate compounds only three, having a NH- or OH-group in a suitable position, exerted a moderate inhibition (app. Ki ca. 2-6 mmol/l). 3. Amongst 14 benzene sulfonates tested only 2 compounds (5-nitrobenzene-sulfonate and 2-hydroxy-5-nitrobenzenesulfonate) inhibited with a Ki less than 5 mmol/l. 4. Out of 10 naphthalene sulfonates tested 8 inhibited with a Ki less than 5; the highest inhibition was seen with the NH-containing 8-anilinonaphthalene-1-sulfonate (ANS), but no inhibition with 2 compounds containing an amino group. 5. From the polycyclic sulfonates pyrene-3-sulfonate and anthracene-1-sulfonate inhibited with a Ki of approximately 2 mmol/l, while no inhibition was seen with anthracene-2-sulfonate. 6. Out of 4 amino-sulfonates tested benzene-1-amino-sulfonate and a similar benzyl-analog inhibited with a Ki of 1 mmol/l and smaller; cyclohexyl-1-amino-sulfonate (cyclamate), however, inhibited only slightly (app. Ki of 6 mmol/l). The data indicate that sulfate monoesters are well accepted by the contraluminal sulfate transport system. The affinity of sulfonate compounds to this system depends on neighbouring OH-groups --NH-groups, meta-positioned electronegative groups or a hydrophobic moiety in an appropriate position.

Animals↗
PubMedDate not supplied

Novel functional biodegradable polymer: synthesis and anticoagulant activity of poly(gamma-glutamic acid)sulfonate (gamma-PGA-sulfonate).

gamma-Poly(glutamic acid) (gamma-PGA), which is produced by Bacillus subtilis, was sulfonated using 2-aminoethane-1-sulfonic acid (taurine) in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (WSC) to give sulfonated gamma-PGA (gamma-PGA-sulfonate). From (1)H NMR spectroscopy and IR spectroscopy, it was confirmed that taurine was introduced to the side chain of gamma-PGA via an amide linkage. By altering the synthetic conditions, it was possible to control the content of sulfonate in gamma-PGA-sulfonate. Anticoagulant activity was investigated in order to evaluate the biological activity of gamma-PGA-sulfonate by the Lee-White test. The clotting time was prolonged when the concentration of gamma-PGA-sulfonate on the degree of sulfonation was increased. It becomes clear that gamma-PGA-sulfonate is potentially useful for various medical applications, such as drug delivery, tissue engineering, and medical materials.

Anticoagulants↗
PubMed2000

Effect of 6-O-sulfonate hexosamine residue on anticoagulant activity of fully O-sulfonated glycosaminoglycans.

Intact and fully O-sulfonated glycosaminoglycans (GAGs) including chondroitin sulfate, dermatan sulfate, hyaluronan, heparan sulfate and heparin were chemically de-O-sulfonated on their hexosamine C-6 position (6-O-desulfonation) using N,O-bis(trimethylsilyl) acetamide. 1H NMR spectroscopy and chemical compositional analysis showed that the chemical de-O-sulfonation at C-6 position of hexosamine residues in both intact and fully O-sulfonated GAGs was completely achieved. Since GAGs and their derivatives are often used as anticoagulant agents, their anti-amidolytic activities were determined. While most of anticoagulant activity of fully O-sulfonated GAGs (FGAGs) and heparin disappeared following chemical 6-O-desulfonation, the activity of 6-O-desulfonated fully O-sulfonated dermatan sulfate (De6FDS) remained. This observation suggests the importance of the position of O-sulfonate groups for anti-coagulant activity.

Anticoagulants↗
PubMed1990

Initial steps in the degradation of benzene sulfonic acid, 4-toluene sulfonic acids, and orthanilic acid in Alcaligenes sp. strain O-1.

Alcaligenes sp. strain O-1 grew with benzene sulfonate (BS) as sole carbon source for growth with either NH4+ or NH4+ plus orthanilate (2-aminobenzene sulfonate, OS) as the source(s) of nitrogen. The intracellular desulfonative enzyme did not degrade 3- or 4-aminobenzene sulfonates in the medium, although the enzyme in cell extracts degraded these compounds. We deduce the presence of a selective permeability barrier to sulfonates and conclude that the first step in sulfonate metabolism is transport into the cell. Cell-free desulfonation of BS in standard reaction mixtures required 2 mol of O2 per mol. One mol of O2 was required for a catechol 2,3-dioxygenase. When meta ring cleavage was inhibited with 3-chlorocatechol in desalted extracts, about 1 mol each of O2 and of NAD(P)H per mol of BS were required for the reaction, and SO3(2-) and catechol were recovered in high yield. Catechol was shown to be formed by dioxygenation in an experiment involving 18O2. 4-Toluene sulfonate was subject to NAD(P)H-dependent dioxygenation to yield SO3(2-) and 4-methylcatechol, which was subject to meta cleavage. OS also required 2 mol of O2 per mol and NAD(P)H for degradation, and SO3(2-) and NH4+ were recovered quantitatively. Inhibition of ring cleavage with 3-chlorocatechol reduced the oxygen requirement to 1 mol per mol of OS SO3(2-) (1 mol) and an unidentified organic intermediate, but no NH4+, were observed.

Alcaligenes↗
PubMed2003

Studies on hydrozirconation of 1-alkynyl sulfoxides or sulfones and the application for the synthesis of stereodefined vinyl sulfoxides or sulfones.

The hydrozirconation reaction of 1-alkynyl sulfoxides or sulfones with Cp2Zr(H)Cl in THF at room temperature predominantly gave Z-beta-zirconated vinyl sulfoxides or sulfones with excellent regioselectivity. Compared with 1-alkynyl sulfoxides, the hydrozirconation reaction of 1-alkynyl sulfones exhibits great synthetic potential, leading to the efficient preparation of Z-beta-halovinyl sulfones, Z-beta-sulfonyl alpha,beta-unsaturated ketones, and Z-beta-alkynyl vinyl sulfones. Although the reaction mechanisms are still not clear, the neighboring group participation of the sulfinyl or sulfonyl group may be playing an important role in this unique hydrozirconation reaction.

Journal Article↗
PubMed1991

Mineralization of the sulfonated azo dye Mordant Yellow 3 by a 6-aminonaphthalene-2-sulfonate-degrading bacterial consortium.

Under anaerobic conditions the sulfonated azo dye Mordant Yellow 3 was reduced by the biomass of a bacterial consortium grown aerobically with 6-aminonaphthalene-2-sulfonic acid. Stoichiometric amounts of the aromatic amines 6-aminonaphthalene-2-sulfonate and 5-aminosalicylate were generated and excreted into the medium. After re-aeration of the culture, these amines were mineralized by different members of the bacterial culture. Thus, total degradation of a sulfonated azo dye was achieved by using an alternating anaerobic-aerobic treatment. The ability of the mixed bacterial culture to reduce the azo dye was correlated with the presence of strain BN6, which possessed the ability to oxidize various naphthalenesulfonic acids. It is suggested that strain BN6 has a transport system for naphthalenesulfonic acids which also catalyzes uptake of sulfonated azo dyes. These dyes are then gratuitously reduced in the cytoplasm by unspecific reductases.

Aerobiosis↗
PubMed1997

Molecular Modeling Studies on Aromatic Sulfonation. 1. Intermediates Formed in the Sulfonation of Toluene.

Molecular modeling studies suggest that the mechanism of the sulfonation of toluene with sulfur trioxide proceeds via the formation of a pi-complex (4b) which rearranges to form a Wheland intermediate (5). This structure is unable to form toluenesulfonic acid (8) directly and prefers to react with a further molecule of sulfur trioxide to form a pyrosulfonate intermediate (6a) which undergoes a facile prototropic rearrangement involving the transfer of the ring hydrogen at the sp(3) carbon of 6a to the sulfonate oxygen atom to form the corresponding acid (7). The formation of toluenesulfonic acid (8) appears to arise from an exothermic reaction of between the pyrosulfonic acid (7) and toluene. The overall calculated thermodynamic change in moving from the reaction of one molecule of sulfur trioxide with toluene to the sulfonic acid (8b) is fully consistent with an estimated experimental value of -33.5 kcal mol(-1) for the same reaction using simple alkylbenzenes.

Journal Article↗
PubMed2003

Residue 345 of dibenzothiophene (DBT) sulfone monooxygenase is involved in C-S bond cleavage specificity of alkylated DBT sulfones.

Rhodococcus erythropolis IGTS8 that possesses dibenzothiophene sulfone monooxygenase mutated at residue 345 (Q345A), can degrade octyl sulfide on which the wild strain cannot grow. Residue 345 and the neighbouring residues were changed by site-directed mutagenesis. Only DszA changed at residue 345 gave an altered C-S bond cleavage pattern of 3-methyl DBT sulfone. This residue is therefore involved in C-S bond cleavage specifically for alkylated DBT sulfone.

Amino Acid Sequence↗
PubMed1990

Synthesis of new bile salt analogues, sodium 3 alpha, 7 alpha-dihydroxy-5 beta-cholane-24-sulfonate and sodium 3 alpha, 7 beta-dihydroxy-5 beta-cholane-24-sulfonate.

This report describes the chemical synthesis of two new bile salt analogues, namely sodium 3 alpha,7 alpha-dihydroxy-5 beta-cholane-24-sulfonate and sodium 3 alpha,7 beta-dihydroxy-5 beta-cholane-24-sulfonate from chenodeoxycholic acid and ursodeoxycholic acid, respectively. Each common bile acid was converted into the corresponding 5 beta-cholane-3,7,24-triol by treatment with ethyl chloroformate in the presence of triethylamine followed by sodium borohydride reduction. Reaction of the cholanetriol with p-toluenesulfonyl chloride at 4 degrees C afforded the partially tosylated product, 24-p-toluenesulfoxy-5 beta-cholane-3,7-diol, which was then treated with sodium iodide to produce 24-iodo-5 beta-cholane-3,7-diol. The 24-iodide was refluxed with sodium sulfite in aqueous ethanol to give the desired sulfonate analogue of the naturally occurring bile acid, chenodeoxycholic acid or ursodeoxycholic acid.

Bile Acids and Salts↗