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PubMed2003

Solid-phase synthesis of peptide vinyl sulfones as potential inhibitors and activity-based probes of cysteine proteases.

Peptide vinyl sulfones were prepared from 2-chlorotrityl resin-bound phenolic amino vinyl sulfones in high yield and purity. This method enables the convenient synthesis of peptide vinyl sulfones having different amino acids at the P(1) position. It also allows efficient synthesis of vinyl sulfone-containing, activity-based probes of cysteine proteases used in a proteomic experiment.

Amino Acids↗
PubMed2006

A new strategy for the synthesis of taurine derivatives using the 'safety-catch' principle for the protection of sulfonic acids.

The safety-catch principle has been applied for the development of a new method for protecting sulfonic acids. 2,2-Dimethylsuccinic acid was reduced to 2,2-dimethylbutane-1,4-diol, which was selectively silylated to give 4-(tert-butyldiphenylsilanyloxy)-2,2-dimethylbutan-1-ol. Reaction of the latter compound with 2-chloroethanesulfonyl chloride in the presence of triethylamine afforded 4-(tert-butyldiphenylsilyloxy)-2,2-dimethylbutyl ethenesulfonate directly. The ethenesulfonate underwent Michael-type addition with secondary amines to give protected derivatives of taurine (2-aminoethanesulfonic acid). Deprotection was achieved on treatment with tetrabutylammonium fluoride, whereby cleavage of the silicon-oxygen bond led to an intermediate alkoxide that immediately cyclised to 2,2-dimethyltetrahydrofuran with liberation of a sulfonate. Pure sulfonic acids were obtained from the crude product by ion exchange chromatography on a strongly basic resin, which was eluted with aqueous acetic acid. The method developed should be generally applicable to the protection of sulfonic acids and is amenable to a multiparallel format.

Molecular Structure↗
PubMed1979

Clinical effect and metabolism of S-sulfonated immunoglobulin in 7 patients with congenital humoral immunodeficiency.

7 patients with primary humoral immunodeficiency were given an S-sulfonated IgG preparation, 100 mg/kg i.v. at intervals of 3--4 weeks, for treatment of, or prophylaxis against, infection. The clinical effects and metabolism of S-sulfonated IgG were studied. No side reactions attributable to S-sulfonated IgG occurred in any of the patients. The S-sulfonated IgG was completely transformed into intact IgG within 24 h after administration, and had a mean half-life of 21 days, comparable to that of intact IgG. Complete restoration of IgG Fc fragment activity occurred within 24 h following injection, as assessed by reversed passive cutaneous anaphylaxis.

Animals↗
PubMed1994

In vitro and in vivo inhibition of ortho- and paramyxovirus infections by a new class of sulfonic acid polymers interacting with virus-cell binding and/or fusion.

A series of sulfonic acid polymers were shown to be potent and selective inhibitors of respiratory syncytial virus (RSV) and influenza A virus. The compounds inhibit the replication of RSV and influenza A virus in HeLa and MDCK cells, at concentrations of 0.16 and 4.0 micrograms/ml, respectively, and are nontoxic to growing cells at concentrations of > 100 micrograms/ml. The mode of antiviral action of the sulfonic acid polymers can be ascribed to inhibition of virus-cell fusion (for influenza A virus) or inhibition of both virus-cell binding and fusion (for RSV). The sulfonic acid prototype PAMPS [poly(2-acrylamido-2-methyl-1-propanesulfonic acid)], when administered intranasally to mice as a single dose of 10 or 50 mg per kg of body weight at the time of infection, completely inhibited influenza A virus replication (in lungs) and virus-associated lung consolidation in immunocompetent mice and completely protected NMRI and SCID (severe combined immune deficiency) mice against influenza A virus-associated mortality. When administered 1 h before or after virus inoculation, no protective effect was observed at a dose of 10 or 100 mg/kg. Sulfonic acid polymers exert selective inhibitory effects on RSV and influenza A virus replication.

Animals↗
PubMed1996

Antimalarial effects of vinyl sulfone cysteine proteinase inhibitors.

We evaluated the antimalarial effects of vinyl sulfone cysteine proteinase inhibitors. A number of vinyl sulfones strongly inhibited falcipain, a Plasmodium falciparum cysteine proteinase that is a critical hemoglobinase. In studies of cultured parasites, nanomolar concentrations of three vinyl sulfones inhibited parasite hemoglobin degradation, metabolic activity, and development. The antimalarial effects correlated with the inhibition of falcipain. Our results suggest that vinyl sulfones or related cysteine proteinase inhibitors may have promise as antimalarial agents.

Animals↗
PubMed1988

Effects of chlorobenzenes and their methyl sulfone metabolites on microsomal enzymes associated with drug metabolism in rat liver.

The effects of m- and o-dichlorobenzenes (DCBs), 1,2,4-trichlorobenzene (TCB) and their methylsulfonyl metabolites on the activities of hepatic microsomal reduced nicotinamide adenine dinucleotide phosphate (NADPH)-cytochrome c reductase, reduced nicotinamide adenine dinucleotide (NADH)-cytochrome b5 reductase and uridine diphosphate (UDP)-glucuronyltransferase (UDPGT) were studied. The treatment of rats with m-DCB, 1,2,4-TCB, 2,4-, 3,5- or 3,4-dichlorophenyl methyl sulfone (DCPSO2Me) or 2,4,5-trichlorophenyl methyl sulfone (TCPSO2Me) significantly increased NADPH-cytochrome c reductase activity, but o-DCB had no effect on this enzyme activity. All three chlorinated benzenes slightly reduced NADH-cytochrome b5 reductase activity, whereas the methylsulfonyl compounds elicited no change in the enzyme activity. Treatments with m- and o-DCBs, 1,2,4-TCB and 2,4,5-TCPSO2Me enhanced UDPGT activities toward both chloramphenicol (CP) and p-nitrophenol (NP). 2,4-, 3,5- and 3,4-DCPSO2Mes increased the activity of UDPGT toward CP but not toward p-NP. These findings concerning the effects of 2,4-, 3,5- and 3,4-DCPSO2Mes on the activities of NADPH-cytochrome c reductase and UDPGT support our hypothesis that the methylsulfonyl metabolites derived from m- and o-DCBs are phenobarbital-type inducers of the hepatic microsomal drug-metabolizing enzymes. It is concluded that the methyl sulfone derivatives of m- and o-DCBs and 1,2,4-TCB are inducers of phase I reactions in hepatic microsomal drug metabolism, and they have increasing effects on the phase II enzyme activities, such as UDPGT. Thus, the methyl sulfones seem to play an important role in the inducing effects of their parent compounds, m- and o-DCBs and 1,2,4-TCB, on the drug-metabolizing enzyme systems.

Animals↗
PubMedDate not supplied

Dapsone-induced sulfone syndrome.

OBJECTIVE: To report a patient with dapsone-induced sulfone syndrome. CASE SUMMARY: A 42-year-old HIV-infected African American man developed fever, lymphadenopathy, exfoliative dermatitis, hepatitis, and methemoglobinemia 4 weeks after starting dapsone. Complete resolution of symptoms and laboratory abnormalities occurred with cessation of dapsone therapy. DISCUSSION: Sulfone syndrome is not a well-known sequela of dapsone therapy. It is not dose-related, usually occurs in doses of 50-300 mg/d, all cases occur within 2 months of starting dapsone, all patients have fever, and most patients will develop rash and evidence of hepatic injury. The temporal relationship between dapsone therapy and onset of clinical symptoms and objective data led us to believe that dapsone caused sulfone syndrome in our patient. An objective causality assessment revealed that the adverse drug event was probable. CONCLUSIONS: Although sulfone syndrome appears to be relatively uncommon, healthcare practitioners must be aware of the potentially fatal syndrome associated with dapsone use.

Adult↗
PubMed1999

Enhanced amyloidogenicity of sulfonated transthyretin in vitro, a hypothetical etiology of senile amyloidosis.

Genetic variants of transthyretin (TTR) cause systemic amyloidosis and wild-type TTR may also in some situations produce amyloid fibrils. We have analyzed wild-type and variant TTRs by mass spectrometry and found that TTR preparations from all individuals demonstrated free TTR, TTR conjugated with thiol compounds and several minor components. We previously described a component which had a molecular mass 80 Da larger than free TTR and was proved to be TTR conjugated with sulfite. Here, the amyloid fibril formation of the TTR isoforms was monitored by the turbidity at 330 nm, and by a Congo red-binding assay as a function of pH, according to the method of Lai et al. The S-sulfonated TTR showed the highest level of amyloid fibril formation. In contrast, TTR reduced by dithiothreitol, which was free of the S-sulfonated component, showed neither elevation of the turbidity nor the Congo red binding. Commercially purchased TTR without further treatment containing free, S-sulfonated and other species of TTR molecules showed an intermediate elevation. These results suggested that the S-sulfonated wild-type TTR is highly amyloidogenic. Although further experiments are needed to apply the observation to in vivo phenomenon, exogenous sulfite may be a cause of senile systemic amyloidosis.

Amyloid↗
PubMed1994

Synthesis of new sulfonylamido-penicillanic acid sulfones inhibitors of beta-lactamases.

Three new sulfonylamido-penicillanic acid sulfones have been prepared by reaction of 6-aminopenicillanic esters with the monoester or monoamide derivatives obtained in nucleophilic substitution reactions by alcohol or aniline on the carboxyl chloride function of sulfoacetic dichloride followed by oxidation. These penicillin sulfones are converted to beta-lactamases suicide inhibitors by removal of the C3 ester protecting group. This synthetic strategy can give access to sulfonamidopenam sulfones bearing a variety of 6-amino side chain. These inhibitors inactivate the RTEM beta-lactamase rapidly. The kinetics of inactivation are consistent with the partitioning of an acylenzyme intermediate between two main pathways: regeneration of free enzyme and irreversible inactivation, little transient inactivation is observed. A slow inhibition by the product of enzymatic hydrolysis of the sulfones is also observed.

Clavulanic Acid↗
PubMedDate not supplied

Synthesis and tumoricidal activity evaluation of new morin and quercetin sulfonic derivatives.

Flavonoids are a group of naturally occurring compounds with interesting medical properties, such as antiinflammatory, antiallergic, antiviral, antibacterial and antitumor activities. In our experiments we were trying to examine the tumoricidal activity of newly synthesized derivatives of two flavonoids: 3,5,7,2',4'-pentahydroxyflavone (morin) and 3,5,7,3',4'-pentahydroxyflavone (quercetin). These derivatives were: natrium salt of morin-5'-sulfonic acid (NaMSA), natrium salt of quercetin-5'-sulfonic acid (NaQSA), complex of Mg2+ with quercetin-5'-sulfonic acid (QSA), complex of iron(II) with QSA. The antitumor activity of these agents was tested in vitro on two cell lines: L1210--murine lymphocytic leukaemia and P-815--murine mastocytoma. Our experiments showed that sulfonic derivatives of these two flavonoids were less potent than the original agents in their cytostatic and cytotoxic activities. However, their solubility in water was greater than that of the original agents and higher culture medium concentration of these derivatives was obtained. The results indicate that the ability of flavonoids to act tumoricidally is reciprocally correlated with their lipophilicity.

Animals↗
PubMed1988

Combination effects of cis-dichlorodiammineplatinum with selected metahalones, pyrimidine sulfoxides and pyrimidine sulfones on human NHIK 3025 cells in vitro.

Synergistic cell inactivating effects were displayed when human NHIK 3025 cells cultivated in vitro were treated with cis-dichlorodiammineplatinum(II) (cis-DDP) in simultaneous combination with selected metahalones, pyrimidine sulfoxides and sulfones. Cell inactivation was measured as the percentage of single cells surviving and able to give rise to macroscopic colonies following drug treatment. Selection of compounds was made according to the presence and position of certain structural groups. For 5-halo-pyrimidin-2-ones (the metahalones), a propargyl substituent attached to the pyrimidine ring at the 1-position resulted in compounds causing potentiation of cis-DDP-induced cell inactivation. An iodo or trifluoromethyl substituent at the 5-position led to a reduction in cis-DDP + metahalone synergism respective to a 5-chloro substituent. Cell survival following 1 h treatment with the metahalones alone was always near 100%. The cell inactivating effect of pyrimidine sulfoxides and sulfones alone and in simultaneous combination with cis-DDP was also investigated. Treatment of human cells with pyrimidine sulfoxides and sulfones alone resulted in reduced cell survival relative to the metahalones. When tested in combination with cis-DDP, pyrimidine sulfoxides and sulfones containing a propargyl moiety bound at the sulfur atom were found to potentiate the cell inactivating effect of cis-DDP. Other substituents induced only minor effects.

Cell Survival↗
PubMedDate not supplied

Determination of chlorinated methylthiobenzenes and their sulfoxides and sulfones in fish.

A procedure was developed to determine chlorinated methylthiobenzenes and their respective sulfur oxidation products in fish. Perch samples fortified at the 0.1 ppm level with 2,4,5-trichloromethylthiobenzene, pentachloromethylthiobenzene, and their sulfoxides and sulfones were extracted and cleaned up using an adaptation of the official AOAC method for multiple residues of organochlorine pesticides. The Florisil column cleanup was modified; 200 mL 6% petroleum etherethyl ether eluted the methylthiobenzenes, 200 mL 50% PE-EE eluted the sulfones, and 200 mL EE eluted the sulfoxides. Recoveries determined by electron capture (ECD) gas chromatography (GC) were 75-101% for the methylthiobenzenes and their sulfones and 63-93% for the sulfoxides. Co-extracted materials in the Florisil eluates that interfered with the ECD/GC quantitation were removed by partitioning the sulfoxides and sulfones into sulfuric acid and by thin layer chromatography on silica gel, using methylene chloride-hexane (50 + 50) as the developing solvent. Seven fish samples containing residues of chlorinated benzenes or polychlorinated biphenyls (PCBs) were examined for chlorinated methylthiobenzenes, methylthio-PCBs, and their oxidation products by matching GC retention times obtained with the EC detector and a flame photometric detector operated in the sulfur mode. These analytes were not found in the fish samples above a detection level equivalent to 0.02 ppm 2,4,5-trichloromethylthiobenzene.

Animals↗
PubMed1976

[Chemotherapeutically active nitro compounds. 2nd communication: Nitrodiphenyl sulfones (author's transl)].

A number of new 4-nitro-4'-amino-diphenyl sulfones and related compounds were prepared and investigated as to their therapeutic activity. They showed a good systemic activity against tubercle bacilli (M. bovis, NMRI mouse) and plasmodia (P. berghei, NMRI mouse). The test results reveal that the 4-nitro-4'-amino-diphenyl sulfones possess a spectrum of activity similar to that of diamino-diphenyl sulfone (DDS). It is assumed that 4-nitro-4'-amino-diphenyl sulfones in vivo are converted into DDS derivatives by reduction. The advantages of the new compounds, however, were too insignificant as compared to DDS to justify further extensive trials.

Animals↗
PubMed1997

The sulfonic acid polymers PAMPS [poly(2-acrylamido-2-methyl-1-propanesulfonic acid)] and related analogues are highly potent inhibitors of angiogenesis.

The sulfonic acid polymers poly(2-acrylamido-2-methyl-1-propanesulfonic acid) (PAMPS), poly(4-styrenesulfonic acid) (PSS), and poly(anetholesulfonic acid) (PAS) proved to be highly potent inhibitors of angiogenesis in the chick chorioallantoic membrane (CAM) assay. PAMPS was found to achieve a dose-dependent inhibition of microvessel formation in the CAM assay ranging from 57 +/- 16% inhibition at 10 micrograms/disc to 72 +/- 15% at 150 micrograms/ disc. Also, PSS and PAS caused a strong inhibition of angiogenesis (55 +/- 19% and 48 +/- 16%, respectively, at 50 micrograms/disc), whereas poly(vinylsulfonic acid) (PVS) was found to be inactive at this dose. The compounds proved to be nontoxic for the developing chick embryo at these doses. Suramin, which was included as a reference compound, caused only a slight inhibition of vascular density, at a dose of 150 micrograms/disc, whereas pentosan polysulfate (PPS) was found to be toxic. PAMPS, PAS, and PSS, but not PVS, inhibited microvessel formation in the rat aorta-ring assay. In addition, the increased [3H-methyl]dThd uptake in endothelial cells in vitro upon stimulation with basic fibroblast growth factor (bFGF) was inhibited by PAMPS, PAS, and PSS at 20 micrograms/ml. A strong correlation (r = 0.95) was found between the antiangiogenic effect of the sulfonic acid polymers in the CAM assay and their inhibition of the bFGF-induced mitogenic response, indicating that bFGF is the target for these sulfonic acid polymers. These results suggest that sulfonic acid polymers, and in particular PAMPS, may be considered as specific, nontoxic angiogenesis inhibitors.

Animals↗
PubMed1990

Photodynamic therapy with chloroaluminum-sulfonated phthalocyanine.

To study the vascular effects of a new photosensitizing agent independent of the influence of tumor growth, a cutaneous wound model was used. Six-week-old Harlan-Sprague-Dawley "Fuzzy" rats were surgically wounded in a standard fashion. The animals were then divided into three groups: the first group received chloroaluminum-sulfonated phthalocyanine only, the second group was treated with light only, and a third group was treated with both chloroaluminum-sulfonated phthalocyanine and light. Photodynamic therapy with chloroaluminum-sulfonated phthalocyanine had a direct effect on the neovasculature of a healing wound. The vasodilatation that was seen in the wound neovasculature that occurred 12 hours after the completion of chloroaluminum-sulfonated phthalocyanine-photodynamic therapy may have indicated a therapeutic "window" at which other therapies can be employed to improve clinical efficacy.

Animals↗
PubMed2000

Synthesis, surface characterization, and platelet reactivity evaluation for the self-assembled monolayer of alkanethiol with sulfonic acid functionality.

Owing to the capability of fabricating a well-defined chemical structure on the surface, self-assembled alkanethiols with a variety of terminal functionalities were prepared on the gold substrate for investigating the interactions between the biological environment and synthetic surface. In this study, we report the synthesis of the sulfonic acid terminated long-chain alkanethiol, 10-mercaptodecane-sulfonic acid, for direct preparation of a self-assembled monolayer (SAM) with -SO(3)H functionality. Nuclear magnetic resonance (NMR) and elemental analysis studies indicated that a high purity of sulfonic acid terminated alkanethiol was obtained. Surface characterization results showed that the -SO(3)H terminated SAM is hydrophilic and has a slightly higher hysteresis value, possibly because of the slower chain mobility of the bound sulfonic acid alkanethiol. Electron spectroscopy for chemical analysis (ESCA) analysis demonstrated that the -SO(3)H terminal group is situated in the outermost layer of the monolayer, as previous alkanethiol SAM structure models proposed. The platelet reactivity of the -SO(3)H SAM was higher than that of -OH SAM but less than the -CH(3) terminated one in vitro, whereas similar platelet reactivity was noticed between the -SO(3)H and -COOH SAMs. The higher platelet reactivity found on the -SO(3)H SAM could be caused by the higher surface functional group density inherent in the SAM structure and/or the composition and conformation state of the adsorbed protein layer.

Alkanesulfonic Acids↗
PubMed2002

Anticoagulant activity of sulfonated polyrotaxanes as blood-compatible materials.

Polyrotaxanes, in which alpha-cyclodextrins (alpha-CDs) are threaded onto poly(ethylene glycol)-b-poly(propylene glycol)-b-poly(ethylene glycol) triblock copolymers (Pluronic) capped with benzyloxycarbonyl(Z)-L-phenylalanine (Z-L-Phe), were prepared, and sulfopropyl groups were introduced to hydroxyl groups of alpha-CDs in the polyrotaxanes. The supramolecular structure and the chemical composition of the polyrotaxanes after the sulfonation were confirmed by 1H-NMR, 13C-NMR, and elemental analysis. Anticoagulant activity of the polyrotaxanes and sulfonated polyrotaxanes was measured by activated partial thromboplastin time (APTT). It was found that the polyrotaxanes and the sulfonated polyrotaxanes showed greater anticoagulant activity than Pluronic itself, suggesting that both the supramolecular structure of the polyrotaxanes and the sulfonated groups contribute to the inhibition of intrinsic coagulation factors. Finally, our designed polyrotaxanes are suggested to be a promising candidate when fabricating blood-compatible medical devices by blending with or coating on clinically used polymers.

Anticoagulants↗
PubMed1989

Properties and biological interactions of polyurethane anionomers: effect of sulfonate incorporation.

In order to investigate the factors affecting the interaction of polyurethanes and blood, a series of poly(tetramethylene oxide)-based polyurethane block copolymers was synthesized with systematically varying levels of ion incorporation in the hard segment block. A bimolecular nucleophilic substitution reaction was used to replace up to 20% of the urethane hydrogens with propyl sulfonate groups. Bulk and surface characterization was performed, and a canine ex vivo arteriovenous shunt was used to monitor initial platelet and fibrinogen deposition on these surfaces. The microphase separation and bulk physical properties were found to vary with ionic content. Surface analysis using both in vacuo (ESCA) and water-equilibrated (contact angle) methods indicated that these polymers, and especially the highly sulfonated materials, could rearrange to minimize their interfacial tension, depending on the contacting environment. Platelet deposition onto these materials decreased as the level of sulfonation increased, with the highly sulfonated polymer showing substantially less platelet spreading and activation than previously seen in the same experiment with other polymers.

Anions↗