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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↗
PubMed2005

Role of the ssu and seu genes of Corynebacterium glutamicum ATCC 13032 in utilization of sulfonates and sulfonate esters as sulfur sources.

Corynebacterium glutamicum ATCC 13032 was found to be able to utilize a broad range of sulfonates and sulfonate esters as sulfur sources. The two gene clusters potentially involved in sulfonate utilization, ssuD1CBA and ssuI-seuABC-ssuD2, were identified in the genome of C. glutamicum ATCC 13032 by similarity searches. While the ssu genes encode proteins resembling Ssu proteins from Escherichia coli or Bacillus subtilis, the seu gene products exhibited similarity to the dibenzothiophene-degrading Dsz monooxygenases of Rhodococcus strain IGTS8. Growth tests with the C. glutamicum wild-type and appropriate mutant strains showed that the clustered genes ssuC, ssuB, and ssuA, putatively encoding the components of an ABC-type transporter system, are required for the utilization of aliphatic sulfonates. In C. glutamicum sulfonates are apparently degraded by sulfonatases encoded by ssuD1 and ssuD2. It was also found that the seu genes seuA, seuB, and seuC can effectively replace ssuD1 and ssuD2 for the degradation of sulfonate esters. The utilization of all sulfonates and sulfonate esters tested is dependent on a novel putative reductase encoded by ssuI. Obviously, all monooxygenases encoded by the ssu and seu genes, including SsuD1, SsuD2, SeuA, SeuB, and SeuC, which are reduced flavin mononucleotide dependent according to sequence similarity, have SsuI as an essential component. Using real-time reverse transcription-PCR, the ssu and seu gene cluster was found to be expressed considerably more strongly during growth on sulfonates and sulfonate esters than during growth on sulfate.

Bacterial Proteins↗
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↗
PubMed2004

Mixed micelles of sodium 4-decyl naphthalene sulfonate with Triton X-100 and sodium dodecyl sulfonate analyzed by 1H NMR.

The characteristics of sodium 4-decyl naphthalene sulfonate (SDNS)/Triton X-100 (TX-100) and sodium dodecyl sulfonate (SDSN)/SDNS mixed micelles with different molar ratios were studied by 1D and 2D 1H NMR. In the mixed micelle of SDNS/TX-100 the phenoxy rings of the TX-100 are embedded in the near vicinity of the alkyl chains of SDNS and its polyoxyethylene segments, but the first oxyethylene group, to which the phenoxy ring is adjacent, are located near the naphthyl rings. In the mixed micelle of the SDNS/SDSN system the sulfonate groups of SDSN are embedded in the naphthyl rings of SDNS; i.e., they are located more internally in the mixed hydrophobic micellar core than those of SDNS. Moreover, the naphthyl rings of SDNS separating these sulfonate groups of SDSN may play an active role in weakening the electrostatic repulsion of the negatively charged sulfonate groups, which favors the mixed micelle aggregation.

Magnetic Resonance Spectroscopy↗
PubMed2006

Preparation and characterization of monovalent cation selective sulfonated poly(ether ether ketone) and poly(ether sulfone) composite membranes.

Highly charged cation permeable composite membranes were prepared by blending of sulfonated poly(ether sulfone) (SPES) with sulfonated poly(ether ether ketone) (SPEEK) in 0 to 90% weight ratio, to adjust the hydrophobic properties and ion selective nature. Extent of sulfonation was confirmed by 1H NMR and ion exchange capacity and degree of sulfonation depending on blending composition. These membranes were characterized as a function of weight fraction of SPEEK by recording ion-exchange capacity, water uptake, thermogravimetric analysis, membrane conductivity and membrane potential in equilibration with different electrolytic solutions. Membrane permselectivity and solute flux were estimated using these data on the basis of non-equilibrium thermodynamic principles and for observing the selectivity of different membranes for mono- or bivalent counter-ions. It was observed that relative selectivity for monovalent in comparison to bivalent counter-ions were increased with the decrease in SPEEK content in the composite membrane matrix. The range of SPEEK content in the blend from 60 to 80% appears the most suitable for the selective separation of monovalent ions from bivalent ions. Furthermore, highly charged nature and stabilities of these membranes extend their applications for the electro-assisted separations of similarly charged ions as well as other electro-membrane processes.

Journal Article↗
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↗