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PubMed1981

Sodium polyanethol sulfonate inactivation of aminoglycosides.

Sodium polyanethol sulfonate and another polyanion (dextran sulfate) both inhibited aminoglycoside activity in vitro. This effect was not produced by an otherwise similar neutral carbohydrate (dextran) or by neutral detergents (Brij-35, Triton X-100) but was antagonized by an anion-exchange resin (Dowex 1X8-50). We conclude that the inactivation of aminoglycosides by sodium polyanethol sulfonate results from its polyanionic nature and is unrelated to its detergent properties.

Aminoglycosides↗
PubMed1976

Use of sodium polyanethol sulfonate to selectively inhibit aminoglycoside and polymyxin antibiotics in a rapid blood level antibiotic assay.

Sodium polyanethol sulfonate inhibits aminoglycoside and polymyxin classes of antibiotics in direct proportion to its concentration. Aminoglycoside and polymyxin class antibiotics are selectively inactivated; penicillin, including the semisynthetic penicillins, cephalothin, chloramphenicol, clindamycin, tetracycline, erythromycin, and vancomycin are not inhibited. By incorporating sodium polyanethol sulfonate directly into the test medium it is possible, in a 4-h antibiotic blood level assay, to selectively obviate the activity of the aminoglycosides and polymyxins to determine the concentration of other antibiotics present in the same serum sample.

Aminoglycosides↗
PubMed1986

Bacterial communities degrading amino- and hydroxynaphthalene-2-sulfonates.

A 6-aminonaphthalene-2-sulfonic acid (6A2NS)-degrading mixed bacterial community was isolated from a sample of river Elbe water. The complete degradation of this xenobiotic compound may be described by a mutualistic interaction of two Pseudomonas strains isolated from this culture. One strain, BN6, could also grow on 6A2NS in monoculture, however, with accumulation of black polymers. This organism effected the initial conversion of 6A2NS into 5-aminosalicylate (5AS) through regioselective attack of the naphthalene skeleton in the 1,2-position. 5AS was totally degraded by another member of the community, strain BN9. After prolonged adaptation of strain BN6 to growth on 6A2NS, this organism readily converted all naphthalene-2-sulfonates with OH- or NH2-substituents in the 5-, 6-, 7-, or 8-position. The corresponding hydroxy- or aminosalicylates were excreted in stoichiometric amounts, with the exception that the metabolite from 5A2NS oxidation was not identical with 6AS.

Aminosalicylic Acids↗
PubMed1988

Mineralization of the dibenzothiophene biodegradation products 3-hydroxy-2-formyl benzothiophene and dibenzothiophene sulfone.

Dibenzothiophene is degraded to 3-hydroxy-2-formyl benzothiophene by various bacteria, including a strain of Pseudomonas putida that also forms dibenzothiophene sulfone via an alternate pathway. By using these end products as substrates, mixed enrichment cultures that could degrade 3-hydroxy-2-formyl benzothiophene and dibenzothiophene sulfone with the formation of CO2 were established.

Biodegradation, Environmental↗
PubMed1992

Complete oxidation of linear alkylbenzene sulfonate by bacterial communities selected from coastal seawater.

Anionic surfactants, especially alkylbenzene sulfonates, are discharged into marine areas in great quantities. Because of their poor biodegradability, linear alkylbenzene sulfonates accumulate in seawater and sediments. Bacterial communities that can degrade surfactants were selected from coastal seawater contaminated by urban sewage. All the isolated strains consisted of gram-negative, strictly aerobic rods or helical bacteria. Some of these, though isolated from coastal seawater, did not need sodium for growth and appeared to be related to the genera Alcaligenes and Pseudomonas. Complete surfactant biodegradation was achieved by three important steps: terminal oxidation of the alkyl chain, desulfonation, and aromatic-ring cleavage. Only a few strains were able to carry out the first two steps. The aromatic ring was then cleaved by other strains that possess very specific enzymatic activities. Finally, a number of strains grew on short acids that were end-of-metabolism products of the others.

Bacteria↗
PubMed1998

Isolation of a bacterial strain with the ability to utilize the sulfonated azo compound 4-carboxy-4'-sulfoazobenzene as the sole source of carbon and energy.

A bacterial strain (strain S5) which grows aerobically with the sulfonated azo compound 4-carboxy-4'-sulfoazobenzene as the sole source of carbon and energy was isolated. This strain was obtained by continuous adaptation of "Hydrogenophaga palleronii" S1, which has the ability to grow aerobically with 4-aminobenzenesulfonate. Strain S5 probably cleaves 4-carboxy-4'-sulfoazobenzene reductively under aerobic conditions to 4-aminobenzoate and 4-aminobenzene-sulfonate, which are mineralized by previously established degradation pathways.

Azo Compounds↗
PubMed1968

Activated-sludge nitrification in the presence of linear and branched-chain alkyl benzene sulfonates.

The effects of biodegradable linear alkyl benzene sulfonate and branched-chain alkyl benzene sulfonate detergents on activated-sludge nitrification were investigated by administering a synthetic waste containing up to 23 mg of each detergent per liter to eight bench-scale, batch, activated-sludge units. It was found that both detergents tended to promote complete oxidation of ammonia to nitrate, whereas control units produced approximately equal amounts of nitrite and nitrate. Various hypotheses are offered to explain the phenomenon.

Ammonia↗
PubMed1974

Conversion of Dexon (p-dimethylaminobenzenediazo sodium sulfonate) to N, N-dimethyl-p-phenylenediamine by Pseudomonas fragi Bk9.

The metabolism of the fungicide Dexon (p-dimethylaminobenzenediazo sodium sulfonate) by a soil bacterium is reported for the first time. The organism which is capable of using Dexon only by a co-metabolic process was obtained by enrichment culture and was identified as Pseudomonas fragi. The first metabolic product of Dexon was identified as N,N-dimethyl-p-phenylenediamine. The presence of an enzyme, p-dimethylaminobenzenediazo sodium sulfonate reductase, capable of reducing Dexon to N,N-dimethyl-p-phenylenediamine has been demonstrated in the cell-free extracts of the organism. The enzyme is found to be in the soluble fraction and requires dithiothreitol as a reductant.

Azo Compounds↗
PubMed1983

A new gene (alkB) of Escherichia coli that controls sensitivity to methyl methane sulfonate.

Seven mutants of Escherichia coli were isolated that are sensitive to methyl methane sulfonate but not to UV light. They exhibited decreased host cell reactivation capacity for methyl methane sulfonate-treated phage lambda. Five of the mutations were mapped in the same region as alkA (previously called alk) and may indeed be identical to known mutations. Another mutation was found near nalA, and the gene responsible was named alkB. Its phenotype was different from that of ada, since the alkB mutant exhibited a normal adaptive response to N-methyl-N'-nitro-N-nitrosoguanidine. A third type of mutation was mapped near polA, but this mutant contained an almost normal level of DNA polymerase I activity.

Drug Resistance, Microbial↗
PubMed1977

Gelatin neutralization of the inhibitory effect of sodium polyanethol sulfonate on Neisseria meningitidis in blood culture media.

The inhibitory effect of sodium polyanethol sulfonate (0.05%) upon growth of Neisseria meningitidis was found to be neutralized by adding gelatin (l.1%) to the growth medium. The neutralizing effect was demonstrated in solid medium, as well as in nutrient broth for blood cultures. The findings parallel those of Wilkins and West (6) regarding gelatin neutralization of the inhibitory effect of sodium polyanethol sulfonate on Peptostreptococcus anaerobius.

Benzenesulfonates↗
PubMed1983

Granulocyte-mediated release of histamine from mast cells. Effect of myeloperoxidase and its inhibition by antiinflammatory sulfone compounds.

During phagocytosis, neutrophilic and eosinophilic granulocytes undergo metabolic activation and degranulation. This leads to accumulation of H2O2 and myeloperoxidase (MPO) or eosinophilic peroxidase (EPO) in the extracellular environment in inflammation. In the present investigation we show that the MPO-H2O2-halide system can degranulate isolated mast cells with release of histamine and 3H-serotonin. This is accomplished both in a system containing purified human MPO and in one containing phagocytosing neutrophils. When using purified MPO and a H2O2-generating system, the release was rapid, with 50% release after less than 20 min. The direct histamine release required less (0.65-2 micrograms/ml) MPO than did the release of 3H-serotonin (1-6 micrograms/ml). The release reaction was inhibited by azide, catalase but not superoxide dismutase. Studying the effect of the antiinflammatory sulfone compounds dapsone and sulfapyridine on the MPO-mediated histamine release, we show effective inhibition of the histamine release at concentrations of 0.025-0.2 mM of sulfone. 5-aminosalicylic acid exhibited some inhibition only in the cell-free system, whereas sulfasalazine was inactive. The antiinflammatory effect of dapsone in dermatitis herpetiformis and sulfasalazine in ulcerative colitis may in part be explained by their inhibitory effects on the granulocyte-mediated histamine release from mast cells in skin and mucosal tissue.

Anti-Inflammatory Agents↗
PubMed2002

Improved blood compatibility and decreased VSMC proliferation of surface-modified metal grafted with sulfonated PEG or heparin.

Although the technique of coronary stenting has remarkably improved long-term results in recent years, (sub)acute thrombosis and late restenosis still remain problems to be solved. Metallic surfaces were regarded as thrombogenic, due to their positive surface charges, and stenosis resulted from the activation and proliferation of vascular smooth muscle cells (VSMCs). In this study, a unique surface modification method for metallic surfaces was studied using a self-assembled monolayer (SAM) technique. The method included the deposition of thin gold layers, the chemisorption of disulfides containing functional groups, and the subsequent coupling of PEG derivatives or heparin utilizing the functional groups of the disulfides. All the reactions were confirmed by ATR-FTIR and XPS. The surface modified with sulfonated PEG (Au-S-PEG-SO3) or heparinized PEG (Au-S-PEG-Hep) exhibited decreased static contact angles and therefore increased hydrophilicity to a great extent, which resulted from the coupling of PEG and the ionic groups attached. In vitro fibrinogen adsorption and platelet adhesion onto the Au-S-PEG-SO3 or Au-S-PEG-Hep surfaces decreased to a great extent, indicating enhanced blood compatibility. This decreased interaction of the modified surfaces should be attributed to the non-adhesive property of PEG and the synergistic effect of sulfonated PEG. The effect of the surface modification on the adhesion and proliferation of VSMCs was also investigated. The modified Au-S-PEG-SO3 or Au-S-PEG-Hep surfaces also exhibited decreased adhesion of VSMCs, while the deposited gold layer itself was effective. The enhanced blood compatibility and the decreased adhesion of VSMCs on the modified metallic surfaces may help to decrease thrombus formation and suppress restenosis. It would therefore be very useful to apply these modified surfaces to stents for improved functions. A long-term in vivo study using animal models is currently under way.

Animals↗
PubMed1998

Sulfonated poly(ethylene oxide)-grafted polyurethane copolymer for biomedical applications.

Sulfonated poly(ethylene oxide) (PEO-SO3)-grafted polyurethane (PU) copolymer (PU-PEO-SO3) was developed for utilization as a material for biomedical applications. Its bulk properties and biocompatibility were investigated and the results were compared to those of PU and PU-PEO (not sulfonated). PU-PEO-SO3 copolymer showed higher water uptake than PU and PU-PEO, indicative of increased hydrophilicity due to the grafting of PEO-SO3. Compared with PU, PU-PEO-SO3 displayed lower glass transition temperature (Tg) and melting endotherm from DSC analysis, suggesting the increase of microphase separation and the suppression of hard-segment packing. PU-PEO-SO3 had practically similar mechanical properties to PU, indicating that the chemical modification of PU was accomplished without reducing its bulk properties. From the results of biocompatibility tests, PU-PEO-SO3 copolymer showed significantly lower adhesion of platelets and S. epidermidis than PU control and PU-PEO. In addition, the platelet factor 4 (PF4) released from platelets was the lowest in PU-PEO-SO3 among the test materials. PU-PEO-SO3 copolymer, which has excellent mechanical properties and biocompatibility, is expected to be useful as coating, molding, and blending materials for artificial organs and medical devices.

Alkanesulfonates↗
PubMed2005

Gargling with sodium azulene sulfonate reduces the postoperative sore throat after intubation of the trachea.

Postoperative sore throat (POST) is a complication that remains to be resolved in patients undergoing endotracheal intubation. In this study, we investigated whether preoperative gargling with sodium 1,4-dimethyl-7-isopropylazulene-3-sulfonate monohydrate (sodium azulene sulfonate, Azunol) reduces POST after endotracheal intubation. Forty patients scheduled for elective surgery under general anesthesia were randomized into Azunol and control groups. In the Azunol group, patients gargled with 4 mg Azunol diluted with 100 mL tap water (40 microg/mL). In the control group, patients gargled with 100 mL of tap water. After emergence from general anesthesia, the patients with POST were counted and POST was evaluated using a verbal analog pain scale. There were no significant differences between the two groups by age, height, body weight, gender distribution, or duration of anesthesia and surgery. In the control group, 13 patients (65%) complained of POST, which remained 24 h later in nine patients (45%). In the Azunol group, five patients (25%) also complained of POST, which completely disappeared by 24 h later. The incidence of POST and verbal analog pain scale scores in the Azunol group decreased significantly compared with the control group. We demonstrated that gargling with Azunol effectively attenuated POST with no adverse reactions.

Administration, Oral↗
PubMed2000

Purification and characterization of dibenzothiophene sulfone monooxygenase and FMN-dependent NADH oxidoreductase from the thermophilic bacterium Paenibacillus sp. strain A11-2.

A dibenzothiophene (DBT) sulfone monooxygenase (TdsA), which catalyses the oxidative CS bond cleavage of DBT sulfone to produce 2-(2-hydroxyphenyl)benzenesulfinate (HPBS) was purified from the thermophilic DBT desulfurizing bacterium Paenibacillus sp. strain A11-2 by multistep chromatography. The molecular mass of the purified enzyme was determined to be 120 kDa by gel filtration and the subunit molecular mass was calculated to be 48 kDa by SDS-polyacrylamide gel electrophoresis (SDS-PAGE) indicating a dimeric structure. The N-terminal amino acid sequence of the purified TdsA was determined to be MRQMHLAGFFAAGNTHH, which revealed no significant similarity to any other known amino acid sequences. The purified TdsA absolutely required an oxidoreductase for its activity. This oxidoreductase (TdsD) was also purified to homogeneity, and its molecular size was calculated to be 50 kDa and 25 kDa by gel filtration and SDS-PAGE, respectively. TdsD was completely FMN-dependent, and FAD could not act as a cofactor. The N-terminal amino acid sequence of the purified TdsD was determined to be TSQTAEQSIAPIVAQYRHPEQPISALFVNR, which showed significant similarity to kinesin-like protein (44% identity). The optimal temperatures for the activity of TdsA and TdsD were 45 degrees C and 55 degrees C, respectively. Both enzymes showed optimal activity at pH 5.5. TdsA was slightly inhibited by sulfate, but not by 2-hydroxybiphenyl (2-HBP), which is another end product of DBT. TdsA showed higher activity toward bulkier substrates than its mesophilic counterpart, DszA. These properties suggest the applicability of biodesulfurization to the processing of actual petroleum fractions.

Journal Article↗
PubMed2002

Anaerobic reduction of a sulfonated azo dye, Congo Red, by sulfate-reducing bacteria.

The capacity for anaerobic decolorization of a sulfonated azo dye, Congo Red, by a strain of a sulfate-reducing bacterium was evaluated. After optimizing the growth rate of the bacteria on a simple carbon source and terminal electron acceptor pair, lactate and sulfate, respectively, the effect of the dye concentration on their growth rate was analyzed. The decolorization rate was affected by the dye concentration in the growth medium. The azo-bond cleavage mechanism of reductive decolorization with the formation of benzidine was consistent with the results, as this metabolite was identified by high-performance liquid chromatography. Several fractions of the culture medium, including lysed cell extracts, were examined for the capacity to reduce the azo dye. This reduction capacity was found in the culture medium in which the cells had previously grown. The results showed that the mechanism of reductive decolorization of this sulfonated azo dye was extracellular and nonenzymatic, consistent with the production of sulfide anion by the microorganisms while growing on lactate and sulfate. The sulfide anions were the cause of the reduction leading to the disappearance of color in the medium. To increase the rate of decolorization, the presence of ferrous ion was also necessary together with the lactate and sulfate substrates.

Azo Compounds↗
PubMed2001

Effect of fluoride anions on gramicidin photoinactivation sensitized by sulfonated aluminum phthalocyanines.

Interaction of potent photodynamic agents, sulfonated aluminum phthalocyanines (AlPcSn where n is a number of sulfonic groups), with biological membranes was studied here using model systems: sensitized photoinactivation of gramicidin channels in planar lipid bilayers and adsorption on lipid monolayers. Fluoride anions known to form complexes with aluminum were found to inhibit both the adsorption of aluminum phthalocyanines on lipid monolayers, as measured with a Langmuir trough by surface pressure and surface potential changes, and photodynamic efficacy of the dyes, as studied by gramicidin channel photoinactivation. The similar effects were caused by the alkalinization of the medium. Fluoride anions appeared to be much more effective in the case of AlPcS4 as compared to AlPcS3. The suppression of the photodynamic potency of aluminum phthalocyanines was attributed to desorption of the dyes from lipid bilayers induced by fluoride or hydroxyl ions. With AlPcS4 an enhancement of the dye aggregation leading to a decrease in the sensitizing activity was probably involved in the fluoride effect as revealed by absorption and fluorescence spectral measurements. Capillary electrophoresis was employed to understand the mechanism of the dye desorption. The results of these experiments indicated that the reduction in the membrane affinity was associated with an increase in the negative charge of the dye molecules due to the binding of fluoride or hydroxyl ions.

Fluorides↗
PubMedDate not supplied

Evaluation of genotoxic activity of maleic hydrazide, ethyl methane sulfonate, and N-nitroso diethylamine in Tradescantia.

OBJECTIVE: To assess the genotoxic activity of N-nitroso diethylamine (NDEA), maleic hydrazide (MH), and ethyl methane sulfonate (EMS) using two systems: the comet assay on nuclei from Tradescantia, and the pink mutation test on Tradescantia staminal hairs (clone 4430). MATERIAL AND METHODS: Tradescantia cups was obtained from Laboratorio de Citogenética y Mutagénesis del Centro de Ciencias de la Atmósfera de la Universidad Nacional Autónoma de México and treated with: N-nitroso diethylamine (NDEA) at 1, 5, 10 mM, maleic hydrazide (MH) at 1, 5, 10 mM and ethyl methane sulfonate (EMS) at 15, 30 and 45 mM; and used in both pink mutation assay and comet assay using cellular nuclei from Tradescantia staminal hairs. The observation of staminal hair was realized along eight days (6-14) after treatment), flowers produced day 14 after treatment were utilized done according to Underbrink. In previous reports on plants, were comet assay was used, breaking cellular wall and separating by centrifugation gradient are necessary. Here, nuclei from staminal hairs were obtained by squashing the cells (is not necessary to utilize to break special procedure cellular wall), collected using a nylon mesh of 80 Mm and next the comet assay was applied. Student's T test was the statistical test used for analyzing the comet assay data. RESULTS: Both assays showed a great sensitivity to the studied mutagens. A relationship between the dose-pink event and the dose-tail length was evident. Even though the Tradescantia mutation assay is a sensitive test with MH and EMS, low doses of NDEA were not able to induce a significant increase in the pink event frequencies; however, the comet assay was able to detect the mutagenic effect of NDEA at the same dose. Thus, it is clear that the comet assay is highly sensitive to the lowest dose of chemical mutagens. CONCLUSIONS: The comet assay on nuclei from Tradescantia staminal hairs is a useful tool to monitor genotoxic agents; it is simple, highly sensitive, and faster than the pink mutation test.

Comet Assay↗