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Efficacies of albendazole sulfoxide and albendazole sulfone against In vitro-cultivated Echinococcus multilocularis metacestodes.

The metacestode stage of Echinococcus multilocularis is the causative agent of alveolar echinococcosis (AE), a parasitic disease affecting the liver, with occasional metastasis into other organs. Benzimidazole carbamate derivatives such as mebendazole and albendazole are currently used for chemotherapeutic treatment of AE. Albendazole is poorly resorbed and is metabolically converted to its main metabolite albendazole sulfoxide, which is believed to be the active component, and further to albendazole sulfone. Chemotherapy with albendazole has been shown to have a parasitostatic rather than a parasitocidal effect; it is not effective in all cases, and the recurrence rate is rather high once chemotherapy is stopped. Thus, development of new means of chemotherapy of AE is needed. This could include modifications of benzimidazoles and elucidiation of the respective biological pathways. In this study we performed in vitro drug treatment of E. multilocularis metacestodes with albendazole sulfoxide and albendazole sulfone. High-performance liquid chromatography analysis of vesicle fluids showed that the drugs were taken up rapidly by the parasite. Transmission electron microscopic investigation of parasite tissues and nuclear magnetic resonance spectroscopy of vesicle fluids demonstrated that albendazole sulfoxide and albendazole sulfone had similar effects with respect to parasite ultrastructure and changes in metabolites in vesicle fluids. This study shows that the in vitro cultivation model presented here provides an ideal first-round test system for screening of antiparasite drugs.

Albendazole↗

Effect of sodium polyanethol sulfonate in blood cultures.

Fifteen-hundred hospital blood cultures were made in duplicate, with and without 0.05% sodium polyanethol sulfonate in the broth medium. A significantly higher rate and speed of recovery of both gram-positive cocci and gram-negative bacilli was accomplished in sodium polyanethol sulfonate broth. The effect was independent of the content of 0.1% agar in the growth medium. In the cases of Neisseria meningitidis septicemia examined, however, a detrimental result on recoveries was observed. The addition of sodium polyanethol sulfonate also resulted in an increased frequency of recoveries of contaminating organisms.

Bacteria↗

Inhibitory effect in vitro of sodium polyanethol sulfonate on the growth of Neisseria meningitidis.

The influence of 0.05% sodium polyanethol sulfonate on the growth of 24 strains of Neisseria meningitidis in broth medium was examined; several of the strains were markedly inhibited. A paper disk method was evolved for screening the sensitivity of various bacteria to sodium polyanethol sulfonate on solid medium; the highest sensitivity was observed in N. meningitidis and Neisseria gonorrhoeae. Zones of growth inhibition were also observed in a proportion of strains in certain species of gram-positive cocci, whereas all gram-negative bacilli were uniformly resistant. The implications of these observations for the routine use of sodium polyanethol sulfonate in blood culture media are discussed.

Anticoagulants↗

Sodium polystyrene sulfonate used to reduce the potassium content of a high-protein enteral formula: a quantitative analysis.

BACKGROUND: Sodium polystyrene sulfonate (Kayexalate) commonly is used in treating hyperkalemia. As a cation exchange resin, it also can be used to reduce the potassium content of enteral nutrition formulas. This study evaluates the use of Kayexalate to reduce potassium in one high-protein enteral formula and describes the quantitative analysis of the product. METHODS: Sodium polystyrene sulfonate and enteral formula were mixed into a slurry and allowed to settle, and then the supernatant was decanted off and tested as samples. Three sample concentrations were analyzed: a control not subjected to potassium reduction, 0.5 g of Kayexalate per mEq K+ sample, and a 1 g/mEq K+ sample. Of these samples, moisture, lipid, protein, carbohydrate, ash, and mineral content were obtained. RESULTS: Compared with the control, the percentage decrease of potassium ranged from 25% to 36%, depending on the concentration of Kayexalate. A significant increase of 324% in sodium concentration was found in the 1.0 g/mEq K+ sample. Although there was no change in magnesium content, a slight increase in phosphorus, iron, and zinc was evident. CONCLUSIONS: The treatment of an enteral formula with sodium polystyrene sulfonate significantly increases its sodium content, with a modest decrease in potassium content. Clinicians using this method in clinical practice should be aware of the increase in sodium content.

Cation Exchange Resins↗

Detection of phosphoenolpyruvate and ribulose 1,5-bisphosphate carboxylase transcripts in maize leaves by in situ hybridization with sulfonated cDNA probes.

This report outlines an efficient in situ hybridization method for locating specific mRNAs in tissue cryosections using sulfonated cDNA probes. The method involves chemical modification of DNA probes by insertion of a sulfone radical on cytosine residues, which generates a specific epitope. Sulfonated DNA is then detected by using indirect immunochemical procedure. Alternatively, antibodies conjugated to fluorescein or to alkaline phosphatase were used for mRNA detection. In situ hybridization was developed to study aspects of mesophyll and bundle sheath cell differentiation in maize leaves. Our results indicate that phosphoenolpyruvate carboxylase (PEP C) mRNA is restricted to mesophyll cells, and the nucleus-encoded mRNA of the small subunit (SSU) ribulose 1,5-bisphosphate carboxylase (RuBP C) is limited to the cytosol of bundle sheath cells. Thus, using in situ hybridization, we have demonstrated that the differential distribution of PEP C and RuBP C proteins in the two cell types also reflects the location of their mRNAs. These data imply either a tissue-specific transcriptional regulation or a selective mRNA degradation.

Carboxy-Lyases↗

Sulfation and glucuronidation as competing pathways in the metabolism of hydroxamic acids: the role of N,O-sulfonation in chemical carcinogenesis of aromatic amines.

Aromatic amines can be metabolized by N-acetylation and N-hydroxylation to hydroxamic acids; these subsequently are conjugated to form the N,O-sulfonate and N,O-glucuronide conjugates. The N,O-sulfonates are highly labile metabolites that generate reactive intermediates involved in the covalent binding of the parent compound to protein, RNA and DNA, as well as to low molecular compounds like glutathione. This paper discusses methods used to decrease sulfation in vivo, and thereby to enhance the formation of the more stable N,O-glucuronides from N-hydroxy-2-acetylaminofluorene and N-hydroxy-4-acetylamino-4'-fluorobiphenyl. Acetaminophen pretreatment decreases the sulfate availability, but results in many side effects that complicate the analysis of the results. An 8% casein diet reduces the sulfate availability in the rat to approximately 20% of control and thus offers an effective approach to decrease sulfation. The most effective selective inhibition of sulfation is by pentachlorophenol, which very strongly reduces N,O-sulfonation of both hydroxamic acids, and selectively inhibits the formation of DNA adducts that have retained the N-acetyl group. This inhibitor and the related 2,6-dichloro-4-nitrophenol can be employed to study the role of sulfation of hydroxamic acids in initiation and promotion of tumor formation by aromatic amines.

Acetaminophen↗

Chelation with metal is not essential for antitumor photodynamic activity of sulfonated phthalocyanines.

It is generally assumed that a central metal is essential for the efficiency of phthalocyanines in photodynamic therapy (PDT) of cancer. Contrary to the set opinion, the results of the present study indicate that the metal-free sulfonated phthalocyanines (H2PcSn, where n is the number of sulfonate groups per molecule) possess a considerable photoactivity. The relative phototoxicities of H2PcS1.5, H2PcS2.4, H2PcS3.1 and H2PcS3.8 on HEp2 human epidermoid carcinoma cells were 3.3, 20, 3.3 and 1, respectively, thus demonstrating dependence of the activity on the sulfonation degree, known for metallo-PcSn. A significant delay in tumor growth and a decrease in tumor regrowth rate were observed in mice after PDT with H2PcS2.4. The antitumor effect declined in the order H2PcS2.4 > H2PcS3.1 > H2PcS1.5 and vanished for H2PcS3.8. We demonstrate here that the high photodynamic activity of H2PcS2.4 can be explained by its physicochemical properties in living cells and tissues. Thus, H2PcSn (n is about 2) can be considered as a new alternative in PDT of light-accessible neoplasms and further clinic-oriented studies are warranted.

Animals↗

Effects of air cell injection of perfluorooctane sulfonate before incubation on development of the white leghorn chicken (Gallus domesticus) embryo.

Fifty white leghorn chicken (Gallus domesticus) eggs per group were injected with 0.1, 1.0, 10.0, or 20.0 microg perfluorooctane sulfonate (PFOS)/g egg before incubation to investigate the effects of PFOS on the developing embryo. Hatchlings were weighed, examined for gross developmental abnormalities, and transferred to a battery brooder, where they were raised for 7 d. Chicks were then weighed, and 20 birds per treatment were randomly chosen for necropsy. The brain, heart, kidneys, and liver were removed and weighed. Livers were processed further for determination of PFOS concentrations and histological assessment. Hatchability was reduced significantly in all treatment groups in a dose-dependent manner. The calculated median lethal dose was 4.9 microg PFOS/g egg. Perfluorooctane sulfonate did not affect posthatch body or organ weights. Exposure to PFOS caused pathological changes in the liver characterized by bile duct hyperplasia, periportal inflammation, and hepatic cell necrosis at doses as low as 1.0 microg PFOS/g egg. Perfluorooctane sulfonate concentrations in the liver increased in a dose-dependent manner. Based on reduced hatchability, the lowest-observed-adverse-effect level was 0.1 microg PFOS/g egg.

Alkanesulfonic Acids↗

Spectrophotometric studies of the interaction of noble metals with quercetin and quercetin-5'-sulfonic acid.

Results of some studies on the interaction of noble metals with quercetin (Q) and quercetin-5'-sulfonic acid (QSA), the compounds of flavonoid group, are presented. The reactions of chloride complexes of the metals: RuOHCl5(2-), PdCl4(2-), OsCl6(2-), PtCl6(2-) and AuCl4- with both reagents were examined. The redox reactions of ruthenium and gold with Q and QSA have been identified. The reaction of the metals with both reagents results in the formation of the oxidized form of Q that exhibits maximum absorbance at 291 nm. Ruthenium and gold react with the examined reagents under similar conditions: 0.04 M HCl and 1 x 10(-4) M Q (or QSA). The CH3OH + H2O (1:1) (Q) and pure aqueous (QSA) media can be used. The reaction of gold with Q is slow at room temperature. It can be accelerated by heating the solution being examined. The reaction proceeds significantly faster when the water-soluble sulfonic derivative of quercetin, quercetin-5'-sulfonic acid, is used as a reagent. The new species formed can make the basis of spectrophotometric methods for the determination of ruthenium and gold. The molar absorptivities at 291 nm are equal to 5.0 x 10(3) and 2.2 x 10(4) L mol(-1) cm(-1) for Ru and Au, respectively, independently of the reagent used. Some methods for the determination of the content of gold (0.04%) in a cosmetic cream were developed.

Cosmetics↗

Urinary mercury in twelve cases of cutaneous mercurous chloride (calomel) exposure: effect of sodium 2,3-dimercaptopropane-1-sulfonate (DMPS) therapy.

OBJECTIVE: To evaluate clinical symptoms and urinary mercury before and after chelation therapy in subjects with chronic cutaneous mercurous chloride (HgCl; calomel) exposure. SUBJECTS: Twelve women from 19-45 years who had used a facial cream which contained HgCl (5.9%) for 2 to 10 years. DESIGN: Twenty-four hour urine samples were collected for basal urine mercury. All the subjects received a 5-day cycle of oral sodium 2,3 dimercaptopropane-l-sulfonate (Dimaval capsules 100 mg) 200 mg/d on an outpatient basis. The urine mercury excretion was monitored 24 hours after the first dose and 72 hours after the last dose in eight subjects. RESULT: Exanthem and tremor were detected in two of 12 subjects. The range of urine mercury was 180 to 1876 micrograms/g creatinine. A significant increase in the urinary mercury excretion was observed in the first 24 hours after beginning sodium 2,3-dimercaptopropane-1-sulfonate. CONCLUSION: Chronic topical application of 5.9% HgCl cream was associated with clinical mercurialism in two subjects and with high urinary mercury level in all the cases. Sodium 2,3-dimercaptopropane-1-sulfonate was effective in increasing urine mercury.

Administration, Oral↗

Efficacy of two acidified chlorite postmilking teat disinfectants with sodium dodecylbenzene sulfonic acid on prevention of contagious mastitis using an experimental challenge protocol.

Two acidified sodium chlorite postmilking teat disinfectants were evaluated for efficacy against Staphylococcus aureus and Streptococcus agalactiae by using National Mastitis Council experimental challenge procedures. The effect of these teat dips on teat skin and teat end condition was also determined. Both dips contained 0.32% sodium chlorite, 1.32% lactic, and 2.5% glycerin. Dips differed in the amount of sodium dodecylbenzene sulfonic acid (0.53 or 0.27%) added as a surfactant. Both dips significantly reduced new intramammary infection (IMI) rates compared with undipped controls. The dip containing 0.53% dodecylbenzene sulfonic acid reduced new IMI by Staph. aureus by 72% and Strep. agalactiae by 75%. The dip containing 0.27% dodecylbenzene sulfonic acid reduced new IMI by Staph. aureus by 100% and by Strep. agalactiae by 88%. Changes in teat skin and teat end condition for treatment and control groups varied in parallel over time. Teats treated with either teat dip had higher mean teat skin and teat end scores than control teats at some weeks. However, teat skin and teat end condition did not tend to change from the start to the completion of the trial. Application of the two new postmilking teat dips was effective in reducing new IMI from contagious mastitis pathogens. (Key words: teat dip, contagious mastitis, chlorous acid)

Animals↗

[8-Quinolinol-5-sulfonic acid-loaded resin as a preconcentrating agent in the neutron activation analysis of the chalcophile elements (author's transl)].

A chelating agent-loaded resin consisting of 8-quinolinol-5-sulfonic acid and an anion-exchange resin (HOx-resin) was prepared in order to concentrate trace chalcophile elements in natural water samples selectively before neutron activation analysis. The exchange capacity of the Diaion SA No. 100 for the reagent (1.8 meq . g-1 resin) corresponds approximately to that for chloride ion (1.83 meq . g-1 resin), indicating that 8-quinolinol-5-sulfonic acid is adsorbed quantitatively on the exchange site of the resin through the sulfonate anion in the reagent. The basic conditions for the adsorption of the metal ions on the resin were investigated by employing the column method. The nitrate concentration and the pH of the sample solution affect the adsorption behavior of metal ions. Several solutions containing metal ions with varying pH or varying nitrate concentration were applied to the resin column (35 mm x 7 mm phi) with a flow rate of 2.0 cm3 . min-1. As a result, the optimum conditions for the quantitative adsorption of copper(II), zinc(II), cadmium(II), cobalt(II), nickel(II) and manganese(II) were as follows: NO3- less than 0.01 mol . dm-3 pH greater than 4.6. Furthermore, the feasibility of the above conditions as well as quantitative adsorption of the chalcophile elements was confirmed through the neutron activation analysis of the synthesized metal solutions.

Activation Analysis↗

Antibacterial effects of N-sulfonated and N-sulfobenzoyl chitosan and application to oyster preservation.

The antibacterial effects of sulfonated and sulfobenzoyl chitosans were evaluated and compared with that of 69% deacetylated chitosan (DD69 chitosan). Minimal inhibitory concentrations of sulfonated chitosan (SC1, 0.63% sulfur content) against Shigella dysenteriae, Aeromonas hydrophila, Salmonella typhimurium, and Bacillus cereus were found to be lower than those of DD69 chitosan. A high sulfur content in sulfonated chitosan adversely influenced its antibacterial effect. Sulfobenzoyl chitosan (SBC) has excellent water solubility and an antibacterial effect comparable to that of SC1. SBC at 1,000 and 2,000 ppm extended the shelf life of oysters at 5 degrees C by 4 days at the former or by 7 days at least at the latter concentration. The growth of coliforms and Pseudomonas, Aeromonas, and Vibrio species on oysters was retarded by the addition of DD69 chitosan or SBC.

Animals↗

Chemopreventive efficacy of sulindac sulfone against colon cancer depends on time of administration during carcinogenic process.

Epidemiological and model studies with laboratory animals have provided evidence that nonsteroidal anti-inflammatory drugs reduce the risk of colon cancer. Sulindac, a nonsteroidal anti-inflammatory drug, has been shown to inhibit azoxymethane (AOM)-induced colon carcinogenesis in rats when administered continuously before, during, and after carcinogen treatment (initiation and postinitiation periods) or when given continuously beginning 14 weeks after carcinogen administration (promotion/ progression stage). The present study was designed to investigate the chemopreventive efficacy of sulindac sulfone (exisulind), the sulfone metabolite of sulindac, when administered during the promotion/progression stage of colon carcinogenesis in comparison to the effect during the initiation and postinitiation periods. We have also studied the modulating effect of exisulind on colonic tumor apoptosis. At 5 weeks of age, groups of male F344 rats were fed diets containing 0%, 0.06%, and 0.12% exisulind. At 7 weeks of age, groups of animals were injected s.c. with AOM (15 mg/kg body weight, once weekly for 2 weeks). Animals intended for the promotion/progression study and receiving 0% exisulind were switched to an experimental diet containing 0.12% exisulind at 14 weeks after the second AOM treatment. All rats remained on their respective dietary regimens until the termination of the study, 50 weeks after the second AOM injection. Colon tumors were evaluated histopathologically for tumor type. Administration of 0.06% and 0.12% exisulind during the initiation and postinitiation periods significantly inhibited the incidence and multiplicity of invasive and/or noninvasive adenocarcinomas of the colon. The inhibition of colon tumorigenesis by exisulind was associated with a significant retardation of body weight gain shortly after sulfone administration and increased apoptosis in the colon tumors. In contrast, administration of the higher dose (0.12%) of exisulind during the promotion/progression stage had only minimal effects on colon tumorigenesis and apoptosis in the colon tumors, suggesting that early administration, but not late administration, may be required for chemopreventive efficacy of this drug.

Adenocarcinoma↗

Assessing the toxicity of dodecylbenzene sulfonate to the midge Chironomus riparius using body residues as the dose metric.

Dodecylbenzene sulfonate (DBS) is a component of linear alkylbenzene sulfonate (LAS), an anionic surfactant, mainly used in household detergents. Due to the large quantity of DBS in use, there is concern over adverse environmental effects. This work examined the toxicokinetics and toxicity of the 2-phenyl isomer of dodecylbenzene sulfonate in 4-d, 10-d, and partial life-cycle tests on the midge, Chironomus riparius, exposed to aqueous solutions. Toxicokinetics were determined in 10-d uptake and 5-d elimination tests. The toxicokinetics were based on parent compound concentration in water and yielded an uptake coefficient (ku) of 17.5 (14.87-20.20) ml/g/h, an elimination rate constant (ke) of 0.073 (0.062-0.085) per h, a bioconcentration factor (BCF) of 56 to 240, and a half-life (t 1/2) of 9.5 (8.0-11.0) h. Biotransformation measurements did not reveal evidence for DBS metabolism. Thus, body residues, determined in the toxicity study, represent parent compound. In toxicity tests, 4- and 10-d LR50s (the body residue required to cause 50% mortality) in live midges were 0.72 (0.65-0.79) and 0.18 (0.08-0.42) mmol/kg, respectively. Thirty-day LR50s were 0.18 (0.09-1.64) and 0.21 (0.15-0.39) mmol/kg in duplicate studies. Of the sublethal endpoints, only developmental time increase was significant, with the lowest-observed-effect residues of 0.085 (0.067-0.105) and 0.100 (0.087-0.114) mmol/kg for male and female midges, respectively. Deformities in surviving larvae were also observed as chronic responses for body residues exceeding the 30-d LR50. The body residues required for mortality suggest that DBS acts like a polar narcotic in the midge.

Animals↗

[Experiment on extraction, sulfonate of paeonol and its antibiotic effect on plant pathogen].

Paeonol contents in root barks, cores, stems and leaves of Paeonia suffruticosa Andr. from Nanling county, Anhui province were determined and paeonol was extracted with alcohol, acid alcohol and alkali alcohol. Sodium paeonol sulfonate was synthesized by treating paeonol with concentrated sulfuric acid and oleums, and its physicochemical properties were surveyed by HPLC, TLC, FTIR and UV. Antibiotic experiment on plant pathogenic fungi and bacteria showed that paeonol and sodium paeonol sulfonate had remarkably inhibitive effects on Xanthmonas oryzae pv. oryzicola, Pseudomonas solanacearum, Phyllosticta mali and Rhizoctonia solani. Paeonol and sodium paeonol sulfonate had antibiotic effect on maize sheath blight.

Acetophenones↗

The shape of cells adhering to sulfonated copolymer surfaces.

We studied the shape of L1210 leukaemia cells adhering in a protein-free medium to sulfonated (styrene/methyl methacrylate) copolymer surfaces of two sulfonic group densities, and thus of differing wettability. The use of our image analysis method and the mathematical procedure [Kowalczynska, H.M. et al, Colloids Surfaces B: Biointerfaces, 30 (2003) 193-206.] allowed us to calculate the values of the so-called shape parameter, which quantitatively determines the three-dimensional cell shape. Here, we show that the values of the shape parameter of the adhering cells and the F-actin concentration, in the region near the cell-substratum interface, depend on the density of sulfonic groups present on the substratum surface.

Actins↗

Large-scale synthesis of single crystal silver nanowires by a sodium diphenylamine sulfonate reduction process.

Silver nanowires with high aspect ratios of up to more than 60 were synthesized on a large scale by the redox reaction between silver nitrate and sodium diphenylamine sulfonate at room temperature and in the absence of surfactant and hard-template and seed. When the molar ratio of reductant sodium diphenylamine sulfonate and silver nitrate < or =1, most products were all the nanowires. When the molar ratio increases to 2:1, silver nanowires and nanobelts were concomitantly formed. The redox product N, N'-diphenylbenzidinedisulfonate and sodium diphenylamine sulfonate all play an important role in the formation of silver nanostructures. The structure, morphology, and composition of the silver nanowires were characterized by the X-ray powder diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray energy dispersive microanalysis (EDX), and UV-Vis spectroscopy respectively. High-resolution transmission microscopy (HRTEM) and selected area electron diffraction (SAED) reveal the single-crystal nature of the silver nanowires.

Benzenesulfonates↗