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PubMed2005

High potency of indolyl aryl sulfone nonnucleoside inhibitors towards drug-resistant human immunodeficiency virus type 1 reverse transcriptase mutants is due to selective targeting of different mechanistic forms of the enzyme.

Indolyl aryl sulfone (IAS) nonnucleoside inhibitors have been shown to potently inhibit the growth of wild-type and drug-resistant human immunodeficiency virus type 1 (HIV-1), but their exact mechanism of action has not been elucidated yet. Here, we describe the mechanism of inhibition of HIV-1 reverse transcriptase (RT) by selected IAS derivatives. Our results showed that, depending on the substitutions introduced in the IAS common pharmacophore, these compounds can be made selective for different enzyme-substrate complexes. Moreover, we showed that the molecular basis for this selectivity was a different association rate of the drug to a particular enzymatic form along the reaction pathway. By comparing the activities of the different compounds against wild-type RT and the nonnucleoside reverse transcriptase inhibitor-resistant mutant Lys103Asn, it was possible to hypothesize, on the basis of their mechanism of action, a rationale for the design of drugs which could overcome the steric barrier imposed by the Lys103Asn mutation.

Drug Resistance, Viral↗
PubMed1970

Growth responses of Escherichia coli to the surfactant dodecyl benzene sulfonate.

When strains of Escherichia coli are grown in broth cultures containing the anionic surfactant sodium dodecyl benzene sulfonate (NaDDBS), they exhibit unique growth responses. After 20 to 24 hr of incubation, they become slimy and viscous, and an addition of ethanol to the supernatant liquid yields a distinctive white, fibrous precipitate. The production of this material was shown to be dependent on the presence of NaDDBS in the medium. This precipitate from E. coli ATCC 11303 was found to contain 41 to 53% protein, 10 to 11% deoxyribonucleic acid, 6.8 to 7.4% ribonucleic acid, 15 to 25% carbohydrate, and 9% lipid. It is distinctive from naturally occurring E. coli slimes in several respects. Our data suggest that its formation is the primary result of the leakage of intracellular components into the medium. However, the rate of cell proliferation indicates a partial but not complete or lethal lysis. A limited utilization of NaDDBS as a carbon source was also shown.

Bacterial Proteins↗
PubMed1980

Protective effects of S-sulfonated human gamma globulin against experimental infections in mice.

S-sulfonated gamma globulin (GGS), newly developed as a safe drug for intravenous use, was studied for its protective effects against some experimental infections in mice. Gamma globulin showed a good protective activity against infections due to Streptococcus pneumoniae and Escherichia coli and was moderately active against infections due to Staphylococcus aureus and Pseudomonas aeruginosa. In most cases, the potency of GGS was almost the same as that of original native gamma globulin. The duration of GGS activity in vivo was found to be comparable to that of native gamma globulin and much higher than that of pepsin-digested gamma globulin. In the control of infection due to E. coli, specific antibody was found to play a central role in the antibacterial action of GGS. When GGS was administered in combination with the antibiotics gentamicin and cefazolin for the control of infections due to S. pneumoniae or E. coli, a clear synergistic effect was observed.

Animals↗
PubMed1969

Biochemical studies of bacterial sporulation and germination. XII. A sulfonic acid as a major sulfur compound of Bacillus subtilis spores.

A sulfonic acid found to be a major constituent of spores of Bacillus subtilis was provisionally identified as 3-l-sulfolactic acid. This compound was completely absent from vegetative cells during growth, but large amounts accumulated in sporulating cells just before the development of refractile spores. Essentially all of the accumulated sulfolactic acid was eventually incorporated into the nature spore, where it may represent more than 5% of the dry weight of the spore. Germination resulted in the rapid and complete release into the medium of unaltered sulfolactic acid. This compound was not found in spores of Bacillus megaterium, B. cereus, or B. thuringiensis.

Bacillus↗
PubMed1975

Inhibition by aurintricarboxylic acid and polyethylene sulfonate of RNA transcription of vesicular stomatitis virus.

The in vitro activity of the ribonucleoprotein-dependent RNA transcriptase of vesicular stomatitis virions was found to be completely inhibited by low concentrations of aurintricarboxylic acid (ATA) and polyethylene sulfonic acid (PES) when these inhibitors were added before the start of the RNA polymerase reaction. However, if RNA synthesis was allowed to occur before ATA or PES was added, RNA synthesis continued for a short time (10 min or less) in the presence of either inhibitor at a concentration which completely inhibited uninitiated enzyme. The ability to continue to synthesize RNA in the presence of ATA or PES only developed if all four nucleoside triphosphates were present during the preincubation period prior to the addition of the inhibitors. The protection was apparently not due to the released products of RNA polymerization. The results are interpreted as indicating that ATA and PES probably inhibit some reaction other than elongation of RNA chains, and this reaction might be one involved at or near initiation sites.

Adenosine Triphosphate↗
PubMed1970

Genetic characteristics of conditional lethal mutants of vesicular stomatitis virus induced by 5-fluorouracil, 5-azacytidine, and ethyl methane sulfonate.

One hundred and seventy-five temperature-sensitive (ts) mutants of vesicular stomatitis virus (type Indiana-C) induced by 5-fluorouracil (FU), 5-azacytidine (ACR), and ethyl methane sulfonate (EMS) have been assigned to four complementation groups by a qualitative test. Group I contains 151 mutants; group II, 2 mutants; group III, 1 mutant; and group IV, 15 mutants; 6 are unclassified. FU was much more effective as a mutagen than either ACR or EMS. The proportion of the mutants belonging to groups I and IV, however, was similar in the case of all three mutagens. Fifteen mutants from groups I and IV have been used to obtain quantitative complementation data. Both groups appear to be homogeneous. Complementation yields increase with increasing multiplicity, but the number of particles per cell required to elicit maximal complementation is small. The pattern of genetic recombination parallels that of complementation. No recombination could be detected in crosses within group I (<0.001%) or group IV (<0.07%), whereas recombination (0.31 to 3.4%) was observed in crosses between groups I and IV. Recombination frequency did not increase with multiplicity above an input of 0.6 plaque-forming units per cell. Many group I mutants have very low reversion rates, and BHK 21 clone 13 cells infected with one of these mutants have been "cured" of infection by prolonged exposure at the restrictive temperature.

Animals↗
PubMed1998

New polyether sulfone dialyzers attenuate passage of cytokine-inducing substances from pseudomonas aeruginosa contaminated dialysate.

The use of bicarbonate dialysate and high-flux and reprocessed dialyzers has raised concerns about the reverse transfer of dialysate contaminants into the blood compartment. This in vitro study was performed to investigate the reverse transfer of soluble Pseudomonas aeruginosa bacterial products across a polyether sulfone (PES), a newly developed synthetic polymer dialyzer. In vitro dialysis was carried out at 37 degreesC in a closed countercurrent recirculating loop dialysis circuit with a new PES dialyzer. An equal mixture of heparinized whole blood (from healthy volunteers) with pyrogen-free tissue culture medium was circulated in the blood compartment, and bicarbonate dialysate was circulated in the dialysate compartment. After 15 min of dialysis, the dialysate was challenged sequentially with 10(-4), 10(-3), and 10(-2) dilutions of a P. aeruginosa culture supernatant. 1-ml samples were drawn from the blood compartment 5 and 15 min after each challenge and incubated upright at 37 degrees C. At the end of 24 h, Triton X-100 was added, in order to extract total interleukin (IL) 6 and IL-8 production by the whole-blood mixture. These cytokines were measured by electrochemiluminescence assays. At dilutions of 10(-4) and 10(-3), the reverse transfer of soluble bacterial products across the dialyzer was negligible. Five and 15 min after contaminating the dialysate with the highest concentration (10(-2) dilution), the increase in IL-6 production was 239 +/- 170% (p = 0.06) and 886 +/- 444% (p = 0.02), respectively. However, comparing the IL-6-inducing potency of the 10(-2) bacterial supernatant dilution to the spontaneous IL-6 production in the blood compartment during dialysis with the same dilution of dialysate contaminant, there was a dramatic reduction in IL-6 production by 94 and 89% at 5 and 15 min, respectively. Similarly, 5 and 15 min after contaminating the dialysate with the 10(-2) dilution, the increase in IL-8 production was 357 +/- 147% (p = 0.07) and 630 +/- 229% (p = 0.04), respectively. However, comparing the IL-8-inducing potency of the 10(-2) bacterial supernatant dilution to the spontaneous IL-8 production in the blood compartment during dialysis with the same dilution of dialysate contaminant, there was a dramatic reduction in IL-8 production by 93 and 92% at 5 and 15 min, respectively. These results demonstrate that PES dialyzers markedly attenuate passage of cytokine-inducing substances from contaminated dialysate, using a method that detects the entire cytokine synthetic output in the blood compartment.

Bacteriological Techniques↗
PubMed1983

Kinetic assay of aldehyde oxidase with 2,2'-azino-di-(3-ethylbenzthiazoline-6-sulfonate) as chromogen.

A new kinetic method for the assay of aldehyde oxidase (EC 1.2.3.1) is described. By the oxidation of pyridoxal as a substrate, pyridoxic acid and hydrogen peroxide are formed. Hydrogen peroxide is subsequently reduced to water by the action of peroxidase, while the chromogen 2,2'-azino-di-(3-ethylbenzthiazoline-6-sulfonate) (ABTS) is oxidized to a blue-greenish-dyed product. The absorbance increase of the oxidized form of ABTS, registered every minute at 410 nm, is proportional to aldehyde oxidase activity.

Aldehyde Oxidase↗
PubMed2001

Interaction of poly(2-acrylamido 2-methylpropane sulfonate)-grafted polystyrene beads with cationic complement proteins.

Influence of various biomaterials on the complement system in serum has been intensively studied by many research groups, since activation of the complement pathway in vivo has been known to give rise to some pathological conditions, such as inflammation and anaphylaxis. Much effort has been devoted to develop new materials that do not activate or deteriorate the complement system. The present work is aimed at revealing the mode of reactions of anionic poly(2-acrylamido 2-methylpropane sulfonate) grafted on polystyrene bead (PAMPS-g-bead) with serum complement. Complement activity assay, determination of complement proteins levels, and immunoblot analysis were carried out for sera pretreated with PAMPS-g-beads. The results clearly showed that, when PAMPS-g-beads were incubated with serum, those beads adsorbed several complement proteins, i.e. C1q, factor D, factor P, C6, and C8, but the generation of activation fragments of complement components was not observed. Especially, factor D was most effectively removed from serum, resulting in potential inhibition of the alternative pathway. A larger amount of PAMPS-g-beads was needed to decrease the serum CH50 level. That may be caused by removal of C6. Although some polyanions, such as dextran sulfate, were reported to activate the complement system, the obtained results indicate that the PAMPS-g-bead is not an activator of the complement pathway, but acts as an adsorbent of complement components. One possible clinical application of the PAMPS-g-beads is adsorption of serum factor D by extracorporeal treatment of patients with renal failure with a high level of factor D, because the increased quantity of factor D in serum may cause consistent activation of the alternative pathway.

Biocompatible Materials↗
PubMed2005

Interaction of poly(styrene sulfonic acid) with the alternative pathway of the serum complement system.

Bioartificial pancreas, in which the islets of Langerhans are enclosed in artificial membrane to be protected from the host immune system, is expected to be a promising medical device to treat patients who suffer from insulin-dependent diabetes. Our strategy for preparation of a bioartificial pancreas involves utilizing a membrane including polymeric materials that can inhibit the complement reaction. In this study, we examined the effects of poly(styrene sulfonic acid) (PSSa) on the alternative pathway of the serum complement system to identify the mechanism(s) involved. PSSa was dissolved in pooled normal human serum (NHS), and the mixtures were incubated at 37 degrees C for 30 min. Complement activities in sera were determined by hemolytic assays. Amounts of complement activation products released were determined by ELISA. Interactions of PSSa with complement components and fragments were examined with electrophoresis and immunoblotting. From these examinations, it appeared that the manner of PSSa effects on the alternative pathway (AP) highly depends on its concentration. PSSa seemingly acted as an activator when its concentration was 0.005 g/dl to 0.05 g/dl, while it acted as an inhibitor when its concentration was more than 0.1 g/dl. In terms of activation or inhibition of the AP, forming complex of PSSa with factor H induced activation, and that with factor D induced inhibition.

Biocompatible Materials↗
PubMed1995

Coadsorption of IgG and BSA onto sulfonated polystyrene latex: I. Sequential and competitive coadsorption isotherms.

In this work the sequential and competitive coadsorption of IgG and BSA proteins on a sulfonate polystyrene latex with high surface charge density have been studied. For sequential coadsorption the IgG/a-CRP was first adsorbed and then the free surface of the particle was saturated by redispersion of the pellet in a solution with a high concentration of monomeric BSA (m-BSA). The competitive coadsorption experiments were carried out in two separate experiments by changing the initial concentration of one protein when the concentration of other protein was high and constant. During the incubation the pH was 5 or 6, and the ionic strength 2 mM, as in previous studies the adsorption of BSA was very low at neutral or basic pH regardless of the amount of adsorbed IgG. From these coadsorption experiments it was possible to obtain latex-protein complexes with a similar degree of coverage by each protein, high adsorption of IgG and different amounts of BSA, or high adsorption of BSA and a low, but significant, amount of IgG. The latex-protein complexes were electrokinetically characterized by measuring the electrophoretic mobility of each complex vs the pH of redispersion. In that way we can detect the i.e.p. of the complexes and the pH range in which the electrostatic repulsion can make them colloidally stable.

Adsorption↗
PubMed2000

Epoxide formation from diallyl sulfone is associated with CYP2E1 inactivation in murine and human lungs.

We tested the hypothesis that an epoxide formed from diallyl sulfone (DASO(2)) is responsible for inactivation of CYP2E1 in murine and human lungs. An epoxide (1,2-epoxypropyl-3,3'-sulfonyl-1'-propene [DASO(3)]) was synthesized from DASO(2) and conjugated with glutathione (GSH) to produce the conjugates S-(1R, S-[[1-hydroxymethyl-2,3' -sulfonyl]-1' -propenyl]ethyl)glutathione (diastereomers) and S-(1-[[2R,S-hydroxypropyl]-3, 3'-sulfonyl]-1'-propenyl)glutathione (diastereomers). Analysis of these conjugates by high performance liquid chromatography revealed a major peak eluting at 20.5 min. This peak was detected in incubations of murine and human lung microsomes containing DASO(2) and nicotinamide adenine dinucleotide phosphate (NADPH), and was not detected in incubations performed in the absence of DASO(2) or NADPH. The amounts of epoxide-derived GSH conjugates formed in the incubations were concentration-dependent and achieved saturation at 0.75 mM DASO(2). Formation of the conjugates was also time-dependent and peaked at 2.0 h after DASO(2). The peak containing the GSH conjugates was also detected in incubations of CYP2E1-expressed lymphoblastoid microsomes, NADPH, and DASO(2). Maximal amounts of DASO(3), as estimated by formation of a 4-(p-nitrobenzyl)pyridine derivatized product, were detected in murine lung microsomes incubated for 35 min with 1 mM DASO(2). The derivatized DASO(3) was not detectable in incubations of human lung microsomes. p-Nitrophenol hydroxylation, a catalytic activity associated with CYP2E1, was reduced in murine and human lung microsomes incubated with DASO(2), with decreases that were concentration-dependent. Dose-dependent decreases in hydroxylase activity were also found in microsomes from mice treated in vivo with DASO(2) (25 to 200 mg/kg). These results supported the premise that an epoxide formed from DASO(2) mediates inactivation of lung CYP2E1. Furthermore, the findings suggested that the mouse model is relevant for studies of DASO(2) in human lung.

Allyl Compounds↗
PubMed1984

The oxidative generation of sulfonic acid groups in neuromelanin and lipofuscin in the human brain.

Sulfonic acid groups were oxidatively generated in the soluble lipid-free lipofuscin component of neuromelanin of human substantia nigra and in lipofuscin of human inferior olive. Exposure of these oxidized, intraneuronal pigments to low pH Alcian blue or aldehyde fuchsin demonstrated an intensity of staining that related to the type of oxidant and the conditions of its use. Utilization of the following oxidants generated increasingly strong staining reactions as signified by the following sequence; periodic acid under mild conditions, bromine in carbon tetrachloride, hydrogen peroxide, periodic acid under drastic conditions, potassium permanganate followed by oxalic acid, hydrogen peroxide followed by bromine in carbon tetrachloride, potassium permanganate followed by metabisulfite or bisulfite, and performic acid. Neither Alcian blue nor aldehyde fuchsin revealed oxidatively generated aldehyde as judged by 1) their failure or near failure to stain inferior olive lipofuscin following mildly applied periodic acid, and 2) the increase in staining intensity, from moderate to strong, displayed by the soluble lipid-free lipofuscin component of neuromelanin and by inferior olive lipofuscin when potassium permanganate was followed by a rinse with metabisulfite or bisulfite in place of one with oxalic acid.

Brain↗
PubMed2003

Virus concentration using sulfonated magnetic beads to improve sensitivity in nucleic acid amplification tests.

To enhance the sensitivity of virus detection by polymerase chain reaction (PCR) and reverse-transcriptional (RT)-PCR, we developed a novel virus-concentration method using sulfonated (SO-) magnetic beads in the presence of divalent cations. In the presence of either Zn(2+) or Cu(2+) ions, we showed that SO-magnetic beads were able to concentrate non-enveloped model viruses, such as porcine parvovirus (PPV) and poliovirus, which were not concentrated by polyethyleneimine (PEI)-magnetic beads.(1)) Using the SO-magnetic beads, the sensitivity of virus genome detection by PCR or RT-PCR can be enhanced. Therefore, an efficient virus concentration method using either SO-magnetic beads or PEI-magnetic beads enhances the sensitivity of virus detection by PCR or RT-PCR.

Animals↗
PubMed2003

pH-dependent long-term radical scavenging activity of AA-2G and 6-Octa-AA-2G against 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation.

The 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS (radical +)) decolorization assay was applied to evaluate the stoichiometric radical scavenging activity of ascorbic acid (AA) and two AA derivatives, 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G) and 2-O-alpha-D-glucopyranosyl-6-O-octanoyl-L-ascorbic acid (6-Octa-AA-2G). AA rapidly reacted with ABTS (radical +), and the reaction was completed within 10 min. In contrast, AA-2G and 6-Octa-AA-2G continuously reacted with ABTS (radical +), and the reaction was not completed after 2 h. The radical scavenging activity of AA-2G and 6-Octa-AA-2G in aqueous solutions at pH 4.0 and above was higher than that at pH 3.0, whereas AA showed no difference in the pH range 3 to 6. The amounts of ABTS (radical +) scavenged by one molecule of AA, AA-2G and 6-Octa-AA-2G after 2 h of reaction at pH 6.0 were approximately 2.0, 3.4 or 3.9 molecules, respectively. This study demonstrates that the quantity of ABTS (radical +) quenched by AA-2G and 6-Octa-AA-2G is superior to that of AA in a long-term reaction.

Ascorbic Acid↗
PubMed2003

Reaction of magnesium alkylidene carbenoids with lithium alpha-sulfonyl carbanions: a novel synthesis of tri- and tetra-substituted allenes from 1-chlorovinyl p-tolyl sulfoxides and sulfones.

Treatment of 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from ketones and chloromethyl p-tolyl sulfoxide, with ethylmagnesium chloride or isopropylmagnesium chloride at below -78 degrees C gave magnesium alkylidene carbenoids in about 90% yields. The reaction of the generated carbenoids with lithium alpha-sulfonyl carbanions was found to afford tri- and tetra-substituted allenes. Both cyclic ketones and acyclic ketones were useful in this procedure. However, the 1-chlorovinyl p-tolyl sulfoxides derived from aldehydes gave only rearranged products, acetylenes, under the reaction conditions. The magnesium alkylidene carbenoid derived from an optically active 1-chlorovinyl p-tolyl sulfoxide was treated with lithium alpha-carbanion of 1-naphthyl phenyl sulfone; however, the obtained allene was found to be racemic. The mechanism of this reaction is also discussed.

Lithium↗
PubMed2003

A novel isoindoline, porritoxin sulfonic acid, from Alternaria porri and the structure-phytotoxicity correlation of its related compounds.

Novel zinniol-related compound 3, named porritoxin sulfonic acid, with an isoindoline skeleton was isolated from the culture liquid of Alternaria porri. The structure was determined to be 2-(2"-sulfoethyl)-4-methoxy-5-methyl-6-(3'-methyl-2'-butenyloxy)-2,3-dihydro-1H-isoindol-1-one. The phytotoxic activities of three isoindolines (1-3) were evaluated in a seedling-growth assay against stone leek and lettuce.

Alternaria↗