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PubMed1995

Increased axonal regrowth of lesioned rat sciatic nerve by veratrylguanidine methane sulfonate.

Neurotrophic factors appear as essential factors for normal development and repair of the nervous tissue. Veratrylguanidine methane sulfonate, has been shown to induce important neurite outgrowth of cultured dorsal root ganglia isolated from newborn rats. Its action was similar to that of NGF and was found to be additive to that of NGF. In order to see if this compound was able to stimulate axonal growth in adult animals, we examined the effect of this substance on the regeneration of the lesioned sciatic nerve. Using histochemical, immunohistochemical and ultrastructural studies, it is shown that a single intraperitoneal injection of veratrylguanidine methane sulfonate significantly increases the axonal growth during repair of the adult rat sciatic nerve. The efficiency of this substance is explained by its good targeting and long life time in the sciatic nerve.

Animals↗

PubMed1989

Evaluation of sulfonated aluminum phthalocyanines for use in photochemotherapy. Cellular uptake studies.

Cellular uptake of aluminum phthalocyanine sulfonated to different degree was studied by means of fluorescence measurements and HPLC chromatography. These results were correlated to the lipophilic property of each drug measured as the distribution of the drug between a lipophilic phase (Triton X-114) and an aqueous phase. All the sulfonated aluminum phthalocyanines were taken up into cells to a higher extent than porphyrins of a similar lipophilicity. The cellular uptake of monosulfonated aluminum phthalocyanine was 10-fold higher than the cellular uptake of tetrasulfonated aluminum phthalocyanine and at least 50% higher than tetra(3-hydroxy-phenyl)porphin which is so far the porphyrin shown to be taken up into cells to the highest extent.

Cells, Cultured↗

PubMed1989

A physico-chemical approach to the study of the binding interaction between S-adenosyl-L-methionine and polyanions: binding constants and nature of the interaction with sodium poly(styrene sulfonate).

The interaction between S-adenosyl-L-methionine (AdoMet) and sodium poly(styrene sulfonate) NaPSS) was studied by means of ultrafiltration and ultraviolet absorption spectroscopy at several pH values and sodium sulfate concentrations. The results obtained are interpreted mainly in terms of electrostatic interactions and permit the evaluation of the binding constants under different experimental conditions. Furthermore, ultraviolet absorption spectroscopy data show a specific short-range interaction between the aromatic electronic system of AdoMet and the NaPSS aromatic ring. The results indicate that the binding strength is greatly affected by the AdoMet positive charge on the adenine ring. The other positive charges on both the sulfonic pole and the amino acidic group of AdoMet contribute only weakly to the binding to the polyanionic matrix, thus assuring some stability of AdoMet even at physiological pH.

Anions↗

PubMed1992

Misoprostol therapy following trinitrobenzene sulfonic acid-induced colitis accelerates healing.

Prostaglandins have been demonstrated to have a mucosal protective effect when administered prior to the experimental induction of colitis in animals. We here determined whether prostaglandins would have a beneficial therapeutic effect when administered after colitis had been established. Diffuse, chronic, trinitrobenzene sulfonic acid-induced colitis was established in rats, and misoprostol was administered daily for up to 10 days following the induction of colitis. The effects of misoprostol therapy were compared to those obtained by treatment with 5-aminosalicylic acid and betamethasone. Misoprostol therapy following trinitrobenzene sulfonic acid-induced colitis accelerated colonic healing, as measured in terms of macroscopic ulceration area and fluid absorption, whereas 5-aminosalicylic acid and betamethasone therapy did not. Ileal fluid absorption impairment was repaired by betamethasone but not by misoprostol or 5-aminosalicylic acid therapy.

Aminosalicylic Acids↗

PubMed2006

Determination of dopamine in the presence of ascorbic acid by poly(styrene sulfonic acid) sodium salt/single-wall carbon nanotube film modified glassy carbon electrode.

In this study, poly(styrene sulfonic acid) sodium salt/single-wall carbon nanotube film was cast onto the surface of glassy carbon electrode and the electrochemical behavior of the modified electrode was investigated. The results show that the anodic peak current is proportional to the concentration of dopamine in the range of 1.6 x 10(-8)-6 x 10(-4) M. The detection limit is 8 x 10(-9) M. The interference of ascorbic acid with the determination of dopamine could be eliminated due to the very distinct attracting interaction between dopamine cations and the negative poly(styrene sulfonic acid) sodium salt film in pH 7.0 phosphate-buffered saline solutions. The proposed method exhibits good sensitivity, selectivity, and reproducibility.

Ascorbic Acid↗

PubMed2006

Bioaccumulation and toxicity of 4-nonylphenol (4-NP) and 4-(2-dodecyl)-benzene sulfonate (LAS) in Lumbriculus variegatus (Oligochaeta) and Chironomus riparius (Insecta).

The discharge of surfactants, such as 4-nonylphenol (4-NP) and linear alkylbenzene sulfonates (LAS), into water bodies leads to accumulation of the chemicals in the sediments and may thus pose a problem to benthic organisms. To study the bioaccumulation of surfactants, Oligochaeta worm Lumbriculus variegatus was exposed to sediment-spiked, [14C]-labeled 4-NP and 4-(2-dodecyl)-benzene sulfonate (C12-LAS) in three different sediments (S1-S3). The sediments were characterized for organic carbon (OC) content and particle size distribution. The acute toxicity was examined by exposing L. variegatus and three to four instar Chironomus riparius (Insecta) larvae in water-only exposure to 4-NP and LAS at different concentrations. After 48-h exposure, lethal water concentrations (LC50) and lethal body residues (LBR50) were estimated using liquid scintillation counting. Chronic toxicity was evaluated in two different sediments by exposing first instar C. riparius larvae to sediment-spiked chemicals at different concentrations. After 10 days, the sublethal effects of surfactants were observed by measuring wet weight and head capsule length. Finally, another 10-day test was set up in order to measure the LAS body residues associated with sublethal effects in C. riparius in S2 sediment. The bioaccumulation test revealed that the bioaccumulation of both 4-NP and LAS increased as the sediment organic matter content decreased. It is assumed that the chemical binding to organic material decreased chemical bioavailability. The acute toxicity tests showed that L. variegatus was more tolerant of 4-NP, and C. riparius was more tolerant of LAS when based on water exposure concentration. The LBR-estimates revealed, however, that L. variegatus tolerated clearly higher tissue residues of both chemicals compared with C. riparius. Both chemicals had sublethal effects on C. riparius growth in sediment exposure, reducing larvae wet weight and head capsule size. 4-NP, however, showed an irregular dose-response pattern. The characteristics of the exposure media affected the bioaccumulation potential of both chemicals. Thus, exposure concentrations offered no prediction of body residue, and therefore it is proposed that organism body residue offered a more accurate dose-metric for chemical exposure than the chemical concentration of the environment.

Alkanesulfonic Acids↗

PubMed2005

4,4'-Dianilino-1,1'-binaphthyl-5,5'-sulfonate, a novel molecule having chaperone-like activity.

4,4'-Dianilino-1,1'-binaphthyl-5,5'-sulfonate (bis-ANS) and 1-anilinonaphthalene-8-sulfonate (ANS) are hydrophobic probes that are widely used in protein folding studies, using their capacity to bind to hydrophobic regions of partially unfolded proteins and in turn leading to an increase in fluorescence. Here we reveal a novel chaperone-like activity for bis-ANS, which acted as a highly effective inhibitor for the thermal- or chemical-induced aggregation of alcohol dehydrogenase, insulin or the whole cell extract of Escherichia coli, with ANS showing a much weaker effect. The studies to elucidate the mechanism underlying this activity show that bis-ANS is able to form stable soluble aggregates with the denaturing proteins and dramatically increase its fluorescence intensity upon incubation with aggregation-prone proteins. Moreover, we found that bis-ANS is able to prevent the heat inactivation of citrate synthase. These observations suggest that bis-ANS is able to block the exposed hydrophobic surfaces to suppress protein aggregation, acting in a way similar to what small heat shock proteins (one sub-class of molecular chaperones) do. The data presented here, together with the report that bis-ANS was able to suppress the amyloid formation of the prion peptide [J. Biol. Chem. 279 (2004) 5346], suggest that this molecule may be used as a potential protein stabilizer in addition to its current application as a hydrophobic probe.

Anilino Naphthalenesulfonates↗

PubMed2006

Syntheses of fully sulfonated polyaniline nano-networks and its application to the direct electrochemistry of cytochrome c.

Fully sulfonated polyaniline nano-particles, nano-fibrils and nano-networks have been achieved for the first time by electrochemical homopolymerization of orthanilic acid using a three-step electrochemical deposition procedure in a mixed solvent of acetonitrile (ACN) and water. The diameter of the uniform nano-particles is about 60 nm, and the nano-fibrils can be organized in two-dimensional (2D) or three-dimensional (3D) non-periodic networks with good electrical contact. Average distance between contacts is about 850 and 600nm for a 2D and 3D system, respectively. The details of the poly(orthanilic acid) (POA) nano-structure were examined with a field emission scanning electron microscope (SEM). The structure and properties of POA were characterized with FTIR, UV-vis and electrochemical methods. The 3D POA nano-networks coated platinum electrode gave a direct electrochemical behavior of horse heart cytochrome c (Cyt c) immobilized on this electrode surface, a pair of well-defined redox waves with formal potential (E( degrees ')) of -0.032 V (versus Ag/AgCl) was achieved. The interaction between Cyt c and POA makes the formal potential shift negatively compared to that of Cyt c in solution. Spectrophotometric and electrochemical methods were used to investigate the interaction of Cyt c with POA. The immobilized Cyt c in the nano-networks POA film maintained its activity, showing a surface-controlled electrode process with the electron transfer rate constant (k(s)) of 21s(-1) and a of 0.53, and could be used for the electrocatalytic reduction of hydrogen peroxide. The quantitative determination of Cyt c by differential pulse voltammetry (DPV) using the fully sulfonated 3D POA nano-networks film coated platinum electrode was also studied.

Aniline Compounds↗

PubMed2004

Sulfatase-catalyzed assembly of regioselectively O-sulfonated p-nitrophenyl alpha-D-gluco- and alpha-D-mannopyranosides.

A chemoenzymic methodology is extended to the library synthesis of regioselectively O-sulfonated pNP D-gluco and D-mannopyranosides. The method involves the sequential reactions of chemical O-sulfonation and sulfatase-catalyzed O-desulfonation. pNP 2,6-di-O-sulfo-alpha-D-glucopyranoside and pNP 3,6-di-O-sulfo-alpha-D-mannopyranoside were obtained as sodium salts using chemical methods by way of dibutylstannylene acetals or tributylstannyl ethers. They were then applied to enzyme reactions using three molluscan enzymes (snail, limpet, and abalone). The sulfatase reactions cleaved a sulfate group at the secondary O-2 or O-3 position to yield the corresponding pNP 6-O-sulfo sugars. Neither pNP 6-O-sulfo-alpha-D-glucopyranoside nor 6-O-sulfo-alpha-D-mannopyranoside became the enzyme substrate. Evidently, the molluscan sulfatases have a tendency to cleave the secondary O-sulfo group with assistance from the 6-O-sulfo group.

Animals↗

PubMed2004

Molecularly imprinted solid-phase extraction of naphthalene sulfonates from water.

A new polymeric sorbent synthesised by exploiting molecular imprinting technology has been used to selectively extract naphthalene sulfonates (NSs) directly from aqueous samples. In the non-covalent molecular imprinting approach used to prepare this polymer, 1-naphthalene sulfonic acid (1-NS) and 4-vinylpyridine (4-VP) were used as a template molecule and functional monomer, respectively, and both dissolved in a mixture of methanol/water (4:1) as porogen together with the cross-linker ethylene glycol dimethacrylate. The new non-covalent molecularly imprinted polymer (MIP) prepared in aqueous environment was used as a sorbent in solid-phase extraction (SPE) to selectively extract a group of naphthalene mono- and disulfonates. When one litre of a standard aqueous solution, which contained a mixture of eight NSs, was percolated through the SPE cartridge, all the NSs were retained on the MIP because of the cross-reactivity of the polymer. Recoveries were higher than 80% for all the compounds even after a clean-up step with methanol (MeOH). The MIP was also used to analyse water from the Ebro river.

Naphthalenesulfonates↗

PubMed2005

Monitoring and toxicity of sulfonated derivatives of benzene and naphthalene in municipal sewage treatment plants.

Monitoring benzenesulfonates (BS) and naphthalenesulfonates (NS) took place in five municipal sewage treatment plants (STP). A previously optimized method based on solid phase extraction with polymeric cartridges followed by ion-pair liquid chromatography-electrospray-mass spectrometry (SPE-IPC-ESI-MS) was used. This work confirmed the little or no effect of primary settlement on total organic carbon (TOC) and monosulfonated compounds removal, whereas the main reduction is obtained at the biological stage. However, the most polar compounds, such as naphthalenedisulfonates (NDS), were not effectively removed using the biological treatment. An aromatic sulfonated compound is suggested to be used as a tracer of the origin of industrial pollutants discharged into STPs. A bioluminescence inhibition test, Microtox assay, allowed toxicity determination of the most relevant aromatic sulfonated compounds detected and toxicity comparison between primary and secondary effluents.

Benzenesulfonates↗

PubMed2006

Sorption of sodium dodecylbenzene sulfonate by montmorillonite.

Sorption of linear alkylbenzene sulfonates by soils and sediments is an important process that may affect their fate, transport, toxicity and their application in remediation of contaminated soil and groundwater. In this study, batch experiments were conducted to elucidate the sorption of a widely used anionic surfactant, sodium dodecylbenzene sulfonate (SDBS), by montmorillonite. It was observed that: (i) SDBS was sorbed significantly by montmorillonite saturated with Ca(2+), but little by Na-saturated montmorillonite; (ii) the amount of SDBS sorbed by Ca(2+)-montmorillonite was enhanced by NaCl; and (iii) no significant intercalation of SDBS into Ca(2+)-montmorillonite was observed by X-ray diffraction (XRD) analysis. These results indicate that the removal of SDBS by Ca(2+)-montmorillonite was primarily attributed to the precipitation between DBS(-) and Ca(2+) in solution which was released from montmorillonite via cation exchange. These results will help us to understand the sorption behavior and environmental effects of anionic surfactants.

Absorption↗

PubMed2004

Distribution of metal-free sulfonated phthalocyanine in subcutaneously transplanted murine tumors.

Metal-free sulfonated phthalocyanine with the average number of sulfonate groups per molecule 2.4 (H(2)PcS(2.4)) was recently proved to be an efficient photosensitizer for the photodynamic therapy. Fluorescence spectral imaging microscopy was applied here to study localization and relative concentration of H(2)PcS(2.4) with micron-scale resolution in subcutaneously transplanted murine tumors: Ehrlich mammary gland carcinoma (EC), Lewis lung carcinoma (LLC), P388 lymphoid leukemia (P388) and B16 melanoma (B16). The study of cryogenic tissue sections prepared 24 h after H(2)PcS(2.4) intravenous injection revealed that H(2)PcS(2.4) was present in all tissue structures in the monomeric photoactive state. The preferential accumulation of H(2)PcS(2.4) was documented in tumor cells and adjacent non-tumor tissues (skin structures, fatty tissue, connective tissue enriched in fibrous component and infiltrated with fibroblasts and macrophages) for all the studied tumor models. P388 and B16 were stained with H(2)PcS(2.4) less than adjacent skin structures, whereas EC and LLC accumulated H(2)PcS(2.4) alike or higher than particular skin structures. Staining of EC and LLC was similar and ca. 1.4 and 2 times higher than that of B16 and P388, respectively, thus revealing the differences in ability of particular tumor strains to H(2)PcS(2.4) accumulation. The H(2)PcS(2.4) concentration in remote healthy tissues (skin, muscles and connective tissue) was 2-3 times lower as compared with the analogous tissue structures from the tumor area, whereas subcutaneous fatty tissue staining did not depend on the tissue-to-tumor distance. The tissue distribution of H(2)PcS(2.4) predefines the combined action of two photodynamic damage mechanisms: eradication of tumor due to the direct tumor cell destruction and suppression of tumor growth due to the injury of growth supporting system.

Animals↗

PubMed2006

Efficacy of topical pale sulfonated shale oil in the treatment of venous leg ulcers: a randomized, controlled, multicenter study.

BACKGROUND: Venous leg ulcers are a growing socioeconomic burden. Pale sulfonated shale oils (PSSO) are used for therapy of inflammatory skin diseases and have been shown to enhance wound healing in vitro and in vivo. The aim of this study was to investigate whether PSSO is capable of enhancing venous ulcer healing beyond compression therapy alone. METHODS: One hundred nineteen patients were enrolled in this randomized, multicenter, observer-blind study. In the treatment group, PSSO 10% was applied daily for 20 weeks, and the control group received the vehicle only. Wounds were covered by a nonadherent gauze dressing, and compression therapy with short-stretch elastic bandages was performed in an outpatient setting. The primary study end point was defined as cumulative reduction in wound area; the secondary study end point was treatment success as assessed by both physicians and patients. Additionally, adverse events, including changes with respect to physical examination and vital signs, were documented. RESULTS: At the end of the study period, ulcer size was significantly more reduced in the PSSO group compared with the vehicle group (15 +/- 15.9 to 6.2 +/- 12.9 cm(2) vs 11.4 +/- 14.5 to 10.8 +/- 15.7 cm(2); P = .0005). The cumulative relative reduction in ulcer area was significantly higher in the PSSO group (-4391 +/- 4748.7 vs -231.9 +/- 6283.6 % x days; P < .0001). Relative reduction in wound area was significantly greater in the PSSO group as early as 6 weeks after the beginning of treatment (-47.4 +/- 28.4 vs -23.8 +/- 42.2%; P < .001). PSSO was judged successful both by physicians and patients. There were no significant differences in adverse events (PSSO, 9 [12.2%]; vehicle, 7 [11.1%]. Similarly, tolerability of PSSO was equal to the tolerability of the vehicle. CONCLUSION: Pale sulfonated shale oils were capable of favoring venous ulcer healing in addition to compression therapy. PSSO should be considered for future wound care protocols for treatment of venous leg ulcers.

Administration, Topical↗

PubMed2006

Spectrophotometric determination of aminomethylbenzoic acid using sodium 1,2-naphthoquinone-4-sulfonate as the chemical derivative chromogenic reagent.

A new method has been established for the determination of aminomethylbenzoic acid using sodium 1,2-naphthoquinone-4-sulfonate as the chemical derivative chromogenic reagent. This method is based on the formation of a pink compound from the reaction of aminomethylbenzoic acid and sodium 1,2-naphthoquinone-4-sulfonate. The nucleophilic substitution reaction proceeds quantitatively in pH 12.0 buffer solution. The stoichiometric ratio of the reaction, maximum absorption wavelength and the value of epsilon(430) were 1:1, 430 nm, and 2.87 x 10(3)L mol(-1)cm(-1), respectively. Beer's law was obeyed in the range of 0.80-80 mg/L of aminomethylbenzoic acid. The data have been filled to a linear regression equation A=0.03183+0.01658C (mg/L), with a correlation coefficient of 0.9996. The detection limit is 0.11 mg/L, R.S.D. is 0.54%, and average recovery is over 99.6%. This paper further improves the determination of aminomethylbenzoic acid compared to the previous methods. The kinetic property and reaction mechanism have also been discussed. This proposed method has been successfully applied to the determination of aminomethylbenzoic acid in injection of aminomethylbenzoic acid with satisfactory results.

4-Aminobenzoic Acid↗

PubMed2003

Sulfonation of polyvinylidene difluoride resin and its application in extraction of restriction enzymes from DNA digestion solutions.

Sulfonation of polyvinylidene difluoride (PVDF) resin was achieved by incubation of the resin with sulfuric acid at a moderately high temperature. The sulfonated PVDF (SPVDF) resin was studied for its ability to extract restriction enzymes from DNA digestion solutions. The SPVDF resin was effective in adsorbing restriction enzymes such as EcoRI and BamHI and the extraction procedure was easy and simple to perform. The adsorption depended upon the amount of the resin added. We found that 1 mg of the SPVDF resin could completely remove all restriction enzyme activity routinely used in DNA digestion within 2 min after its addition. Treatment of a digestion solution with the SPVDF resin did not change the reaction solution and the same digestion buffer could be used for another digestion of the same DNA with other enzymes. We also found that, in comparison with normal PVDF, the SPVDF resin adsorbed less DNA, resulting in less loss of DNA in the extraction step. The potential application of the SPVDF resin in other procedures of molecular cloning and enzyme purification is discussed.

Absorption↗

PubMed1999

Kinetic and equilibrium studies of incorporation of di-sulfonated aluminum phthalocyanine into unilamellar vesicles.

The interactions of cis-di-sulfonated aluminum phthalocyanine (PcS(2)Al) with dimyristoylphosphatidylcholine (DMPC) unilamellar vesicles have been investigated by fluorescence spectroscopy. At pH 7.0, PcS(2)Al incorporates into the vesicles with a high affinity constant (2.7x10(6) M(-1), in terms of phospholipid concentration). The fluorescence changes following rapid mixing of PcS(2)Al with vesicles are biphasic. The first phase is attributed to the entry of PcS(2)Al into the vesicles, as deduced from the linear dependence of the rate upon lipid concentration. More surprisingly, this rate is strongly pH dependent with a marked maximum around pH 7.3, a result interpreted in terms of the coordination state of the aluminum ion in aqueous solutions. At this pH, a hydroxide ion neutralizes the residual positive charge of the metal ion that remains unbalanced after coordination by the phthalocyanine cycle. A water molecule is likely to complete the metal coordination sphere. Only this form, PcAl(+)(OH(-))(OH(2)), with an uncharged core is quickly incorporated into the vesicles. The protonation of OH(-) or the deprotonation of the coordinated H(2)O leading to a positively or negatively charged core, respectively, account for the observed pH effect. Studies on the effect of cholesterol addition and exchange of PcS(2)Al between vesicles and albumin all indicate the absence of transfer of the phthalocyanine between the vesicle hemileaflets, a result expected from the presence of the two negatively charged sulfonated groups at the ring periphery. Instead, the slower kinetic phase is likely due to the movement of the phthalocyanine becoming more buried within the outer leaflet upon the loss of the water molecule coordinated to the aluminum ion.

Biological Transport, Active↗

PubMed2003

Solution structure and biological activity of recombinant salmon calcitonin S-sulfonated analog.

Salmon calcitonin S-sulfonated analog (abbreviated as [S-SO(3)(-)]rsCT) was prepared by introducing two sulfonic groups into the side chains of Cys1 and Cys7 of recombinant salmon calcitonin. The hypocalcemic potency of this open-chain analog is 5500IU/mg, which is about 30% higher than that (4500IU/mg) of the wild type. The solution conformation of [S-SO(3)(-)]rsCT was studied in aqueous trifluoroethanol solution by CD, 2D-NMR spectroscopy, and distance geometry calculations. In the mixture of 60% TFE and 40% water, the peptide assumes an amphipathic alpha-helix in the region of residues 4-22, which is one turn longer than that of the native sCT. The structural feature analysis of the peptide revealed the presence of hydrophobic surface composed of five hydrophobic side chains of residues Leu4, Leu9, Leu12, Leu16, and Leu19, and a network of salt-bridges that consisted of a tetrad of oppositely charged side chains (Cys7-SO(3)(-)-Lys11(+)-Glu15(-)-Lys18(+)). The multiple salt bridges resulted in the stabilization of the longer amphipathic alpha-helix. Meanwhile, the higher hypocalcemic potency of the peptide could be attributed to the array of hydrophobic side chains of five leucine residues of the amphipathic alpha-helix.

Amino Acid Sequence↗