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At least 775 records · Page 43Linked to original sources
PubMed2000

SULT1A1 catalyzes 2-methoxyestradiol sulfonation in MCF-7 breast cancer cells.

In a previous study of nine human breast-derived cell lines, rates of metabolism of 17beta-estradiol (E(2)) were greatly enhanced when cultures were exposed to the aromatic hydrocarbon receptor agonist, 2,3,7,8-tetrachlorodibenzo-p-dioxin. Elevated rates of E(2) hydroxylation at the C-2, -4, -6alpha and -15alpha positions were observed concomitant with the induction of cytochromes P450 1A1 and 1B1. In each cell line, 2- and 4-hydroxyestradiol (2- and 4-OHE(2)) were converted to 2- and 4-methoxyestradiol (2- and 4-MeOE(2)) by the action of catechol O:-methyltransferase. In this study, conjugation of these estrogen metabolites was investigated. A comparison of the levels of metabolites determined with and without prior treatment of the media with a crude beta-glucuronidase/sulfatase preparation showed that most of the 2-MeOE(2) present was in conjugated form, whereas 4-MeOE(2), 6alpha-OHE(2) and 15alpha-OHE(2) were minimally conjugated. Inhibitor studies suggested that it was the sulfatase activity of the preparation that hydrolyzed the 2-MeOE(2) conjugates in MCF-7 cell media; the presence of 2-MeOE(2)-3-sulfate in MCF-7 culture media was confirmed by electrospray ion-trap mass spectrometry. To identify the enzyme catalyzing this conjugation, the expression of mRNAs encoding five sulfotransferases (SULT1A1, SULT1A2, SULT1A3, SULT1E1 and SULT2A1) was evaluated in the nine cell lines by use of the reverse transcription-polymerase chain reaction. Only expression of SULT1A1 mRNA correlated with the observed conjugation of nanomolar levels of 2-MeOE(2) in these cell lines. Cloning and sequencing of SULT1A1 cDNA from MCF-7 cells revealed that mRNAs encoding two previously identified allelic variants, SULT1A1*1 ((213)Arg) and SULT1A1*2 ((213)His), were expressed in these cells. Heterologous cDNA-directed expression of either variant in MDA-MB-231 cells, which do not normally express SULT1A1, conferred 2-MeOE(2) sulfonation activity. The SULT1A1 allelic variants were also expressed in SF:9 insect cells, from which post-microsomal supernatants were used to determine K:(m) values of 0.90 +/- 0.12 and 0.81 +/- 0.06 microM for SULT1A1*1 and SULT1A1*2, respectively, with 2-MeOE(2) as substrate. These results show that SULT1A1 is an efficient and selective catalyst of 2-MeOE(2) sulfonation and, as such, may be important in modulating the anticarcinogenic effects of 2-MeOE(2) that have been described recently.

2-Methoxyestradiol↗
PubMed1980

The case of sulfonation in the chemical synthesis of oligonucleotides.

The sulfonation of nucleosidic component, a side reaction during phosphotriester bond formation, as a function of the reactivity of the condensing agents and the kind of substituents in the starting phosphodiester is discussed. It was found that in the coupling reaction of nucleoside alkyl phosphodiesters, the degree of sulfonation of the nucleosidic component was very high; while under the same conditions when the aryl group was present in the corresponding phosphodiester, this side reaction practically did not occur.

Arylsulfonates↗
PubMed1980

Effect of lysolecithin on the binding of 1-anilino-8-naphthalene sulfonate to apoHDL, apoA-I or apoA-II from human serum high density lipoprotein.

The binding of 1-anilino-8-naphthalene sulfonate to human serum high density apolipoprotein and to apoA-I and apoA-II which are major protein components of high density apolipoprotein was measured by a fluorometric method. The maximum number of 1-anilino-8-naphthalene sulfonate bound to high density apolipoprotein was about 950 mumol per g of protein, and those to apoA-I and apoA-II were 27 and 13 mol per mol of protein (there values correspond to 964 for apoA-I and 765 for apoA-II in mumol per g of protein), respectively. After preincubation of apolipoprotein with lysolecithin (less than 10 microM), the binding affinities for the dye increased twice or more with all the proteins, but the maximum binding numbers changed little. With apoA-I, two mol of the dye were bound with high affinity and lysolecithin did not compete with the dye for the binding sites. The fluorescence intensity of tryptophanyl residues of apoA-I was changed by incubation with lysolecithin at concentrations lower than the critical micellar concentration. These results indicate that the binding of lysolecithin molecules to apoA-I or other proteins makes the protein conformation more suitable for the binding of hydrophobic ligands.

Anilino Naphthalenesulfonates↗
PubMed1989

Positive inotropic and hemodynamic properties of flosequinan, a new vasodilator, and a sulfone metabolite.

Flosequinan, a new orally active vasodilator, and its sulfone metabolite were evaluated for inotropic activity in isolated ferret papillary muscles and pentobarbital anesthetized open-chest dogs. In vitro, flosequinan and its sulfone derivative increased tension development in a concentration-dependent manner (1-50 microM) in electrically stimulated papillary muscles pretreated with the beta-adrenergic blocking agent atenolol (2 microM). Peak increases in tension of 75 +/- 17%, and 111 +/- 46% with potencies (EC50) of 15 and 10 microM were observed for flosequinan and its metabolite, respectively. In vivo, flosequinan increased left ventricular dP/dtmax (74 +/- 12%) and right ventricular contractile force (CF) (104 +/- 10%) after administration of 1.875 mg/kg, i.v. Inotropic activity was dose-dependent and remained elevated for at least 60 min postinfusion. Flosequinan also increased heart rate (HR) (14 +/- 2%) and reduced mean arterial pressure (-9 +/- 3%). The i.v. potency of flosequinan (ED50 = 0.45 mg/kg) and its metabolite (ED50 = 0.38 mg/kg) were similar to that of the inotropic vasodilator amrinone (ED50 = 0.38 mg/kg). Inotropic activity was not significantly altered by pretreatment with propranolol (0.5 mg/kg) and atropine (1.0 mg/kg), further supporting the in vitro data indicating that flosequinan can directly stimulate myocardial contractility independent of beta-adrenergic receptor activation. Additional hemodynamic studies were conducted in an acute heart failure model produced by an overdose of propranolol. Flosequinan (2 mg/kg, i.v.) increased cardiac output (CO) (50 +/- 9%) and stroke volume (SV) (29 +/- 8%) while reducing total peripheral vascular resistance (TPR) (-36 +/- 4%), right atrial pressure (-62 +/- 5%), and left ventricular end-diastolic pressure (LVEDP) (-41 +/- 2%).(ABSTRACT TRUNCATED AT 250 WORDS)

Amrinone↗
PubMed2001

Oxonium 5-aminouracil-6-sulfonate hydrate.

In the title compound, oxonium 5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-sulfonate hydrate, H3O(+)-C4H4N3O5S(-)-H2O, the sulfonate group is in the anionic form and charge balance is provided by an oxonium cation, H3O(+). Screw-related molecules overlap significantly and are hydrogen bonded to form a zigzag chain of the uracil skeleton along the direction of the c screw axis. The partially stacked bases and their glide-related equivalents run parallel to the a axis to form hydrophobic zones separated by hydrophilic zones built up by a network of hydrogen bonds.

Crystallography, X-Ray↗
PubMed2004

Hydrogen-bonded supramolecular motifs in 4,4'-bipyridinium 8-hydroxy-7-iodoquinoline-5-sulfonate dihydrate.

In the title compound, C(10)H(9)N(2)(+).C(9)H(5)INO(4)S(-).2H(2)O, the 4,4'-bipyridine molecule is protonated at one of the pyridine N atoms. These moieties self-assemble into a supramolecular chain along the a axis through N-H.N hydrogen bonds. The quinolinol OH group acts as a donor with respect to a sulfonate O atom [O-H.O(sulfonate)] and acts as an acceptor with respect to a C-H group of ferron [C-H.O(hydroxy)], forming a supramolecular chain along the b axis. These two types of supramolecular chains (one type made up of bipyridine motifs and the other made up of sulfoxine motifs) interact via pi-pi stacking, generating a three-dimensional framework. These chains are further crosslinked by C-H.O hydrogen bonds and O-H.O hydrogen bonds involving water molecules.

Journal Article↗
PubMed2006

Diaquabis(ethylenediamine)cadmium(II) bis(4-aminonaphthalene-1-sulfonate) dihydrate.

In the title compound, [Cd(C2H8N2)2(H2O)2](C10H8NO3S)2.2H2O, the CdII atom, located on an inversion centre, has a distorted octahedral coordination geometry formed by two ethylenediamine and two water molecules. 4-aminonaphthalene-1-sulfonate acts as a counter-ion to balance the charge, and two antiparallel anions showing strong pi-pi stacking interactions are linked by paired N-H...O(sulfonate) hydrogen bonds into an isolated R2(2)(16) dimer. The crystal structure is stabilized by the pi-pi stacking interactions and hydrogen bonds.

Journal Article↗
PubMed1996

8-Hydroxy-7-nitroquinoline-5-sulfonic acid monohydrate.

The title compound, C9H6N2O6S.H2O, is zwitterionic (i.e. 8-hydroxy-7-nitroquinolinium-5-sulfonate monohydrate) with a deprotonated sulfonic group and a protonated quinoline N atom which interacts with the hydroxy O atom. The H atom of the hydroxy group is distal to the N atom and is involved in an interaction with an O atom of the nitro group, which is oriented at 32.2(1) degrees with respect to the quinoline ring system.

Anti-Infective Agents↗
PubMed1977

Development of an intravenous gamma-globulin with Fc activities. II. Reconversion of S-sulfonated human gamma-globulin into the original gamma-globulin.

The reconversion of S-sulfonated antitetanus gamma-globulin (S-GG) into the original gamma-globulin was studied. S-sulfonate groups in S-GG could be converted into disulfide bonds in vitro. The conversion restored the greater part of both complement-fixing and skin-sensitizing activities. S-GG administered intravenously formed interchain disulfide bonds again in vivo, which was accompanied by restoration of the C-dependent passive hemolytic activity. Intravenous injection of S-GG did not cause a significant decrease in serum complement level.

Biotransformation↗
PubMed1981

Induction of polymerization of purified tubulin by sulfonate buffers. Marked differences between 4-morpholineethanesulfonate (Mes) and 1,4-piperazineethanesulfonate (Pipes).

Interactions of both purified tubulin and microtubule protein (tubulin plus associated proteins) with two commonly used sulfonate buffers were examined. 1,4-Piperazineethanesulfonate (Pipes) and 4-morpholineethanesulfonate (Mes) at high concentrations induce the polymerization of purified tubulin in reactions requiring only buffer, tubulin and GTP. While both reactions were temperature-dependent, cold-reversible and inhibited by GDP, colchicine or Ca2+, there were significant differences between them. Substantially lower tubulin and buffer concentrations were required for Pipes-induced polymerization; and turbidity was much more intense in the Pipes-induced than in the Mes-induced reaction at the same protein concentration. Electron microscopy demonstrated that for the most part typical smooth-walled microtubules were formed in Mes, while aberrant forms were the predominant structures formed in Pipes. When the polymerization of microtubule protein was examined as a function of buffer concentration, biphasic patterns were observed with both Pipes and Mes: polymerization occurred at both low and high, but not intermediate, buffer concentrations. The turbidity observed at high concentrations of Pipes greatly exceeded that at low concentrations. With Mes, equivalent turbidity developed at both high and low buffer concentrations. Although associated proteins copolymerized with tubulin at low buffer concentrations, they were excluded from the polymerized material at high buffer concentrations. Pipes and Mes were compared to sodium phosphate, Tris/HCl and imidazole/HCl buffers at 0.1 M in several polymerization systems using both purified tubulin and microtubule protein. The sulfonate buffers were invariably associated with more vigorous reactions than the other buffers.

Alkanesulfonates↗
PubMed1982

Fluorescence of intramolecular and intermolecular interactions of aminonaphthyl-sulfonate with nucleotides.

Fluorescence studies of the intramolecular and intermolecular interactions between aminonaphthylsulfonate and nucleotides of uracil or adenine are described. The fluorescence originates solely from the naphthyl moiety and is intramolecularly quenched by the base, uracil being more effective than adenine. The enzymatic splitting of the molecule into a nucleoside monophosphate and the pyrophosphate product of the aminonaphthylsulfonate removes the intramolecular quenching and, especially in the case of uracil, a drastic increase of the fluorescence intensity results. The intact molecule exists predominantly in the folded form except in cases where electrostatic repulsion exceeds the stacking attraction. This is borne out by the pH dependence and the existence of a pronounced solvent-isotope effect of the fluorescence quantum yield for the uracil derivative at basic pH. At pH values above the pK of the enol proton of the uracil base the fluorescent properties of the intact and phosphodiesterase-digested molecules are very similar. The intermolecular interactions between 1-aminonaphthalene-5-sulfonate with AMP and UMP can be explained on the basis of dynamic quenching (collisional quenching) without any significant participation of ground-state complexes (static quenching). The interaction of the pyrophosphate adduct of 1-aminonaphthalene-5-sulfonate with UMP can best be explained by invoking two interacting nucleotide species: the free nucleotide and a sodium-nucleotide complex.

Adenine Nucleotides↗
PubMed1996

Desulfonation of aliphatic sulfonates by Pseudomonas aeruginosa PAO.

Pseudomonas aeruginosa PAO1 used a broad range of alkanesulfonic acids as sole sulfur source for growth, with molar growth yields of 2.2 to 2.9 kg protein per mol sulfur. 4-Phenylbutane-1-sulfonate was desulfonated in vivo to yield 4-phenyl-1-butyric acid quantitatively as the sole product, suggesting that the desulfonation mechanism is the same as when alkanesulfonates serve as a carbon source for growth. This contrasts with aromatic sulfonate utilization in other organisms, where different desulfonation reactions are used to provide carbon and sulfur. Desulfonation of alkanesulfonates to provide sulfur was repressed by sulfate or thiocyanate, and derepressed in their absence. The alkanesulfonatase system is hence controlled as part of the sulfate starvation-induced stimulon.

Alkanesulfonates↗
PubMed2007

Protective effects of vitamin E on ethane dimethane sulfonate-induced testicular toxicity in rats.

AIM: To evaluate the protective/ameliorative effects of vitamin E (vit E) on ethane dimethane sulfonate (EDS)-induced testicular toxicity in rats. METHODS: The rats were assigned to eight groups, seven rats in each, and were injected intraperitoneally with vehicle, a single dose of ethane dimethane sulfonate (EDS) (75 mg/kg bodyweight), vit E (100 mg/kg bodyweight) or EDS + vit E for 3? days. Thereafter, the rats were weighed, anaesthetized with ether and killed by cervical dislocation. The left testis weights were recorded and the relative testis weights were calculated. The left testes were processed for routine paraffin embedding. Three right testes from each group were taken randomly and then processed for routine electron microscopy. Tissue sections were examined using light and electron microscopy, and were scored for histopathological changes. RESULTS: Vit E coadministration did not prevent the bodyweight loss on days 3 and 7. However, vit E administration prevented the EDS-induced testicular-weight loss in rats that received vit E for 3 days but not 7 days. The relative testis weight was higher on day 3 (instead of on day 7) than other groups. Nevertheless, the testis histology was not markedly protected by vit E in the EDS-treated rats. Detailed microscopic assessment showed few Leydig cells and abundant fibroblast-like cells indicating only some protection. CONCLUSION: Vit E cotreatment showed partial protective effects on the testicular weight and testicular histology in rats that received EDS.

Animals↗
PubMed1990

Biological activities of phthalocyanines--XI. Phototoxicity of sulfonated aluminum naphthalocyanines towards V-79 Chinese hamster cells.

The phototoxicity of sulfonated aluminum naphthalocyanines towards V-79 Chinese hamster cells is investigated. The disulfonated naphthalocyanine exhibits similar photostability, but better cell penetrating properties than the tetrasulfonated dyes. The capacity of the naphthalocyanines to generate singlet oxygen is comparable to that of the corresponding phthalocyanines. However, in contrast to the phthalocyanine dyes, the sulfonated aluminum naphthalocyanines show very little phototoxicity towards the V-79 cells, suggesting close association with non-vital cell constituents or extensive formation of photoinactive adducts and aggregates.

Aluminum↗
PubMed1990

Cellular uptake and relative efficiency in cell inactivation by photoactivated sulfonated meso-tetraphenylporphines.

The cellular uptake, relative fluorescence quantum yields and photosensitizing efficiencies of meso-tetraphenylporphines sulfonated to different degrees (TPPSn) have been investigated using the human carcinoma cell line NHIK 3025. The efficiencies of these dyes in photoinactivation of cells were highly dependent on the number of sulfonate groups on the derivatives. These differences in phototoxicity were primarily due to different abilities to be taken up by cells, but were also dependent upon the cellular localization of the dyes. TPPS1 and TPPS2a were more efficiently taken up by the cells than TPPS2o and TPPS4. Plasma membrane associated TPPS4 was less efficient in cell inactivation per quantum of fluorescence emitted than intracellularly located dye. This was also to some extent the case for TPPS1 but not for TPPS2a and TPPS2o. The results presented here indicate that TPPS2a and TPPS1 are the most promising of the TPPSns for possible future use in photodynamic therapy.

Cell Survival↗
PubMed1993

In vivo fluorescence kinetics of phthalocyanines in a skin-fold observation chamber model: role of central metal ion and degree of sulfonation.

The fluorescence pharmacokinetics of a series of metallosulfophthalocyanines, chelated with either aluminum or zinc and sulfonated to different degrees, was studied by fluorescence measurements in vivo. Dyes were administered systemically to female WAG/RIJ rats with an isogeneic mammary carcinoma transplanted into the subcutis in a transparent observation chamber located on their backs. Following an intravenous injection of 2.5 mumol/kg of the dye, fluorescence dynamics was observed up to 7 h postinjection. The phthalocyanines were excited at 610 nm with a power density of 0.1 mW/cm2 without causing photodynamic damage to the vasculature. Fluorescence was detected above 665 nm using a fluorescence imaging system based on an image intensifier. Dye retention in the blood vessels and tumor tissue was expressed as ratios relative to the fluorescence signal of the surrounding subcutaneous tissue. Phthalocyanines chelated with aluminum gave the highest fluorescence signal with tumor-over-subcutis ratios of up to a value of 4. The zinc complexes exhibited the highest vascular-over-subcutis ratios with maximum values exceeding a value of 6. They also displayed the longest retention times in the vascular system of well over 7 h. Overall, decreasing the degree of sulfonation of the metallophthalocyanines results in lower tumor-over-normal tissue fluorescence ratios, and furthermore aluminum-based dyes seem superior tumor localizers over zinc-based dyes. The advantages of phthalocyanines over porphyrins with respect to tumor localization and photodynamic therapy are discussed.

Animals↗
PubMed1997

[Anti-bacterial activities of a sulfonated human immunoglobulin preparation against penicillin resistant Streptococcus pneumoniae and Pseudomonas aeruginosa].

Anti-bacterial activities of a sulfonated human immunoglobulin preparation against penicillin resistant Streptococcus pneumoniae and Pseudomonas aeruginosa were examined. Five week old CBA/J mice were challenged by 10 times of 50% lethal doses of penicillin sensitive (SP1) and resistant (SP2) strains of Streptococcus pneumniae serotype 19, and were treated with a sulfonated human immunoglobulin preparation (hIg). Fifty % protective dose (ED50) were 2-4 mg hIg/ mouse. These doses were parallel with the challenged doses despite of the challenged bacteria, and it was calculated that 6 x 10(6) bacteria were killed by one mg of hIg in both bacteria. Minimal inhibitory concentrations (MIC) of piperacillin, flomoxef, imipenem, amikacin and ofloxacin against SP1 and SP2 were estimated under the presence of various concentrations of hIg. It was found that under the presence of over 10-20 mg/ml of hIg, SP1 and SP2 were not grown even without any antibiotic. That is, MIC of hIg itself against penicillin sensitive and resistant Streptococcus pneumoniae serotype 19 were 10-20 mg/ml. Since about 10(6) bacteria/ml were used for this test, it was calculated that 5-10 x 10(4) bacteria were killed by one mg of hIg in vitro. This result suggested that in vivo anti-bacterial activities of hIg could be 100 times higher than that in vitro. Synergistic or at least additive effects between hIg and all antibiotics tested were seen by the MIC. If hIg was 100 times effective in in vivo, these results suggested that hIg could improve the effect of chemotherapy in clinical cases. Similar in vitro test were carried out for Pseudomonas aeruginosa, and synergistic or at least additive effects between hIg and all antibiotics tested were also confirmed in Pseudomonas aeruginosa. This result suggested that hIg could be effective for clinical pseudomonas infection.

Animals↗
PubMed1997

Sulfur and hydrogen isotope anomalies in meteorite sulfonic acids.

Intramolecular carbon, hydrogen, and sulfur isotope ratios were measured on a homologous series of organic sulfonic acids discovered in the Murchison meteorite. Mass-independent sulfur isotope fractionations were observed along with high deuterium/hydrogen ratios. The deuterium enrichments indicate formation of the hydrocarbon portion of these compounds in a low-temperature environment that is consistent with that of interstellar clouds. Sulfur-33 enrichments observed in methanesulfonic acid could have resulted from gas-phase ultraviolet irradiation of a precursor, carbon disulfide. The source of the sulfonic acid precursors may have been the reactive interstellar molecule carbon monosulfide.

Alkanesulfonic Acids↗