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PubMed1983

Kinetics and mechanism of erythrocyte anion exchange.

Steady state velocities for the rate of exchange of extracellular dithionite for intracellular sulfate through the red cell inorganic anion transport protein, known as band 3, were measured at increasing trans-sulfate concentrations at constant cis-sulfate concentration in order to directly discriminate between single and double displacement classes of mechanism. A 7-fold increase in trans-sulfate concentration resulted in intersecting Lineweaver-Burk plots under iso-osmotic conditions. This result argues against a double displacement or ping-pong mechanism. The specificity of the trans-anion effect for band 3 was illustrated by studying reversible 4-acetamido-4'-isothiocyano-2,2'-stilbene disulfonate inhibition of anion exchange. The increase in trans-sulfate increased 4-acetamido-4'-isothiocyano-2,2'-stilbene disulfonate affinity at the outer surface by about 4-fold under conditions where outside anion concentration was constant. A possible two-site ordered sequential mechanism for erythrocyte inorganic anion exchange is briefly discussed.

Anion Transport Proteins↗
PubMed1982

Comparative accumulation of uric acid and hypoxanthine by slices of avian renal cortex.

The purpose of the study was to compare the concentrative uptake processes of the 14C-labeled purines uric acid (UA) and hypoxanthine (HX) by slices of chicken renal cortex. It was found that both purines were accumulated by the slices and that, while UA was unaltered metabolically, HX was partially oxidized to UA during the incubation. Inhibition of the oxidation of HX to UA by use of the enzyme inhibitor allopurinol did not alter accumulation indicating that metabolism of HX did not drive accumulation. UA accumulation was eliminated by the presence of low concentrations of the organic anion transport inhibitors probenecid and 4-acetamido-4'-isothiocyano-stilbene-2,2'-disulfonic acid. However, HX accumulation was unaffected by probenecid and significantly decreased by 4-acetamido-4'-isothiocyano-stilbene-2,2'-disulfonic acid only at concentrations considerably in excess of those needed to eliminate UA accumulation. The lack of effect of probenecid is in contrast to its reported inhibitory action on HX excretion by the chicken in vivo, a difference which may reflect lack of luminal transport by in vitro slices. Neither was HX accumulation sensitive to the presence of high concentrations of the organic cations quinine and tetraethylammonium. Despite the insensitivity of the HX accumulation process to organic anions or cations, the process was blocked by cyanide and an N2 atmosphere indicating energy dependence. The results suggest that both UA and HX are accumulated by separable transport processes indicating that the renal tubules possess more than one system capable of contributing to purine excretion.

4-Acetamido-4'-isothiocyanatostilbene-2,2'-disulfo↗
PubMed1981

Neonatal estrogen treatment and epithelial abnormalities in the cervicovaginal epithelium of adult mice.

Female NMRI mice were given injections of different doses of 17 beta-estradiol, 17 alpha-estradiol, diethylstilbestrol (DES), dienestrol, trans-stilbene, progesterone, testosterone, 5 alpha-dihydrotestosterone, or olive oil for the first 5 days after birth. When the females were killed at 8 weeks after birth, all the estrogens, effective at different dose levels (10(-2) to 5 microgram/day), had resulted in the display by several of the cervicovaginal preparations studied of a heterotopic columnar epithelium (HCE) in regions where females given injections of olive oil, testosterone, 5 alpha-dihydrotestosterone, progesterone, or trans-stilbene had only the normal squamous epithelium. The further fate of the HCE was followed at two later age stages, 36 to 52 weeks and 14 to 17 months. The HCE developed into glandular-like structures penetrating into the stroma and justifying the designation of adenosis. DES resulted in a more pronounced adenosis than did 17 beta-estradiol; in both cases, metaplasia was a striking component of the adenosis regions. Development of adenosis from HCE was dependent upon presence of the ovaries. Some preparations from 44-week-old females given DES injections showed signs of a beginning malignant transformation in the adenosis regions, more evident in 17-month-old females. Among the 23 preparations in the latter group, 8 had changes morphologically indicating malignancy with examples of adenocarcinoma, mixed carcinoma, and squamous carcinoma. Because of the seemingly low aggressive nature of this malignancy, the term "pseudocarcinoma" is discussed. Ten- to 12-week-old BALB/c and C57BL/6 females given DES injections neonatally had HCE in the uterine cervix and vaginal fornices after neonatal DES injections. Differences in extension of HCE were observed after DES injections for three different 5-day periods in th neonatal and immature stages of NMRI females. An interaction between different DES-sensitive parameters to result in the pseudocarcinomas is discussed.

Age Factors↗
PubMed1994

Arachidonic acid blocks large-conductance chloride channels in L6 myoblasts.

Modulation of high-conductance chloride channels by eicosanoids, stilbene derivatives and Zn2+ ions was studied in cultured myoblasts (L6 rat muscle cell line) in excised and cell-attached membrane patches using a conventional patch clamp method. Arachidonic acid (AA) blocked the channel at concentrations 1-50 mumol/l from the internal side of the membrane in excised (inside out) patches with a time constant of about 20 s. The block was absent when arachidonic acid was applied to the bathing solution in cell attached patches, or to the pipette solution, respectively. Arachidonic acid changed the probability of the channel being in the open state (Popen) in dependence on the applied voltage (V). The asymmetric bell-shaped Popen - V relationship showed a steeper dependence on both the negative and positive voltage, respectively, in arachidonic acid solutions. The midpoint potentials (Vh) of the Popen - V relationship were shifted towards lower membrane potential displacements from the holding potential. The recovery from the block was very slow but was found to be enhanced by application of a symmetric voltage ramp pulse. The stilbene derivative (DIDS) blocked the channel at mu molar concentrations (10-100 mumol/l) applied from the internal side of the membrane. The onset and recovery of the DIDS block showed characteristics similar to the AA block. The channel was found to be blocked reversibly by short application of Zn+ ions (1-10 mmol/l) from the internal side of the membrane.

4,4'-Diisothiocyanostilbene-2,2'-Disulfonic Acid↗
PubMed1996

Activation of the Na(+)/H(+) antiporter, Na+/HCO3(-)/CO3(2-) cotransporter, or Cl(-)/HCO3(-) exchanger in spontaneous thymocyte apoptosis.

This study was undertaken to define the role of ion transporters on the apoptosis of thymocytes. Culture conditions, such as the ionic strength of NaCl, Ca2+, the buffer system (HCO3-/CO2), and the pH, could influence the spontaneous apoptosis of thymocytes. Depletion of NaCl in the culture medium either delayed or completely inhibited the apoptotic process of thymocytes, while its restoration led to a dose-dependent apoptosis. A high concentration (100 microM) of Ca2+ induced thymocyte apoptosis in the nominal absence of NaCl, whereas a low concentration (10 microM) enhanced apoptosis in the presence of 138 mM NaCl. Thymocytes had a higher spontaneous apoptotic rate in cultures without HCO3-/CO2 than in those with HCO3-/CO2. The thymocyte apoptosis completely ceased in medium at pH 6.0 and was considerably enhanced at pH 7.6. Intracellular pH, determined with the pH-sensitive bis-carboxyethyl carboxyfluorescein probe, was higher in apoptotic thymocytes than in nonapoptotic cells. Spontaneous apoptosis occurred in cells with alkaline intracellular condition, whereas it was considerably retarded in cells under acidified conditions. Amiloride analogue, including 5-(N,N-dimethyl)-amiloride (Na+/H+ antiporter), 4,4'-diisothiocyanato-stilbene-2,2'-disulfonic acid (Cl-/HCO3- exchanger), and 4-acetamido-4'-isothiocyanato-stilbene-2,2'-disulfonic acid (Na+/HCO3-/CO3(2-) cotransporter), inhibited the spontaneous thymocyte apoptosis. In contrast, neither cycloheximide nor actinomycin D had the same effect. In addition, thymocyte apoptosis was enhanced by PMA, but inhibited by forskolin. Taken together, thymocytes cultured in vitro underwent apoptosis with increased intracellular pH via activation of Na+/H+ antiporter, Na+/HCO3-/CO3(2-) cotransporter, or Cl-/HCO3- exchanger. This process does not require de novo protein synthesis.

Animals↗
PubMed1996

Glutathione S-transferases in the Japanese quail: tissue distribution and purification of the liver isozymes.

Cytosolic glutathione S-transferase (GST) activities toward 1-chloro-2,4-dinitro-benzene (CDNB), 1,2-dichloro-4-nitrobenzene (DCNB), ethacrynic acid (EA), 1,2-epoxy-3-(p-nitrophenoxyl)propane (EPNP), trans-4-phenyl-3-buten-2-one(t-PBO), delta 5-androstene-3,17-dione (ASD) and trans-stilbene oxide (t-SO); cytosolic glutathione peroxidase activity toward cumene hydroperoxide (CuOOH); and microsomal GST activity toward CDNB were examined in liver, kidney, brain, and lung of adult male and female Japanese quail. In all cases, the renal specific activity per milligram protein was higher than the hepatic activity and was the highest among the four tissues examined. No consistent sex differences in GST activity were observed. The GSTs were purified from quail liver cytosol by S-hexylglutathione and glutathione affinity chromatography. Total GSTs eluted from the S-hexylglutathione affinity column were further separated by chromatofocusing, and the microheterogeneity of the GST isozymes was shown by high-resolution native isoelectrofocusing (IEF) in polyacrylamide slab gels and by SDS-PAGE. Five subunits were identified: QL1 (30.5 kDa), QL2 (27.2 kDa), QL3a (26.8 kDa), QL3b (26.5 kDa), and QL4 (25.5 kDa). Western blot analysis revealed that QL1 and QL2 reacted with antibodies raised against the rat Mu class GSTs (Yb1 and Yb2), and QL3a and QL3b reacted with those raised against the Alpha class (rat Ya and mouse a). Substrate specific activity of each isoform was determined with CDNB, DCNB, CuOOH, EA, t-PBO, ASD, and t-SO. QL3a and QL3b have high reactivity toward CuOOH, while QL1 and QL2 showed high activity toward t-SO. The N-terminal amino acid sequence of QL2 was identical to that of the chicken Mu class GST subunit CL2. However, no sequence was obtained with QL1 due to possible N-terminal blockage.

Amino Acid Sequence↗
PubMed1980

Anion channel blockade: effects upon erythrocyte membrane calcium response.

The influx of small amounts of calcium into normal human red cells adversely affects cellular metabolism, shape, ion and water content, and deformability. Because restriction of cation (potassium) efflux moderates these deleterious effects of Ca++ influx, we investigated the possibility that inhibition of anion permeability might be similarly beneficial. Human red cells were treated with 4,4'-diisothiocyano-2,2'-stilbene disulfonate (DIDS), which reacts preferentially with external sites on the transmembrane protein, band 3, and specifically inhibits inorganic anion transport. DIDS-treated and control cells were then exposed to the ionophore A23187 and Ca++. We find that DIDS treatment blocks Ca++-induced K+ and water loss and diminishes changes in osmotic fragility and cellular elasticity. Furthermore, DIDS reduces the "trapping" of hemoglobin by red cell membranes and increases the apparent affinity of the cell membrane for glyceraldehyde-3-phosphate dehydrogenase.

4,4'-Diisothiocyanostilbene-2,2'-Disulfonic Acid↗
PubMed2004

Styrylquinazolines: a new class of inhibitors on prostaglandin E2 production in lipopolysaccharide-activated macrophage cells.

A series of styrylquinazoline derivatives (2a-k) were prepared and evaluated for their inhibiton of prostaglandin E(2) (PGE(2)) production by cyclooxygenase-2 (COX-2). The latter was induced by lipopolysaccharide-stimulated macrophage cells RAW264.7. 3', 4'-Dihydroxylated styrylquinazolines (2a-c), 3'-hydroxylated styrylquinazolines (2h, 2i), and 3'-acetoxy-styrylquinazolines (2j, 2k) exhibited good inhibitory effects of PGE(2) production by COX-2 with a range of IC(50) values of 1.19 approximately 3.56 microM. The potencies were comparable or better than that of the representative stilbene resveratrol (IC(50) = 3.07 microM). These results indicate that styrylquinazolines can be considered as potential resveratrol analogues in the modulation of prostaglandin production by COX-2.

Cell Line↗
PubMed2006

Resveratrol is efficiently glucuronidated by UDP-glucuronosyltransferases in the human gastrointestinal tract and in Caco-2 cells.

Resveratrol (3, 5, 4'-trihydroxy-trans-stilbene), a natural polyphenol present in grapes and peanuts, has been reported to exert a variety of potentially therapeutic effects. The aim of this study was to determine the contribution of the gastrointestinal (GI) tract to the glucuronidation of this compound and its cis-isomer, which also occurs naturally. For this purpose, glucuronidation of the two resveratrol isomers was investigated in human microsomes prepared from: stomach, duodenum, four segments of the remaining small intestine (S-1 to S-4) and colon, and from the human intestinal cell lines Caco-2 and PD-7. cis- and trans-Resveratrol were efficiently glucuronidated in the GI tract with the formation of both 3-O- and 4'-O-glucuronides, however, the two stereoisomers were glucuronidated at different rates depending on the donor and the segment considered. Microsomes prepared from Caco-2 and PD-7 cells also efficiently glucuronidated cis-resveratrol and, to a lesser extent, the trans-isomer, however, only the 3-O-glucuronide was formed. Among the UDP-glucuronosyltransferases (UGT) that are known to be expressed in the GI tract, the isoforms UGT1A1, 1A6, 1A8, 1A9 and 1A10 were active in glucuronidating trans- and/or cis-resveratrol. The results demonstrate that the GI tract may contribute significantly to the first pass metabolism of these naturally occurring polyphenols.

Caco-2 Cells↗
PubMed2004

Enhancement of tyrosinase inhibition of the extract of Veratrum patulum using cellulase.

Inhibitors of melanin biosynthesis were screened by using three different methods. The extract of Veratrum patulum contains hydroxystilbene compounds that are potent tyrosinase inhibitors. We evaluated the enzyme inhibitory property on the mushroom tyrosinase of hydroxystilbene compounds including resveratrol, oxyresveratrol, and their analogs. Biotransformation using cellulase of the whole extract brought about an increase in the inhibitory activity of the products on mushroom tyrosinase. The enhancement of tyrosinase inhibition is supposed to increase the concentration of aglycon, which has superior inhibitory activity to its glycoside. Eventually, melanin biosynthesis was inhibited by the enhanced tyrosinase inhibitory activity of the extract. This result indicated that deglycosylation of stilbene compounds has exerted more effective inhibition on the enzyme than that of the unprocessed plant extract.

Agaricales↗
PubMed2006

Tuning the reaction site for enzyme-free primer-extension reactions through small molecule substituents.

The replication of genetic information relies on the template-directed extension of DNA primers catalyzed by polymerases. The active sites of polymerases accept four different substrates and ensure fidelity and processivity for each of them. Because of the pivotal role of catalyzed primer extension for life, it is important to better understand this reaction on a molecular level. Here we present results from primer-extension reactions performed with chemical systems that show high reactivity in the absence of polymerases. Small molecular caps linked to the 5'-terminus of templates are shown to enhance the rate and selectivity of primer extension driven by 2-methylimidazolides as activated monomers for any of the four different templating bases (A, C, G, and T). The most consistent effect is provided by a stilbene carboxamide residue, rather than larger aromatic or aliphatic substituents. Up to 20-fold rate enhancements were achieved for the reactions at the terminus of the template. The preference for a medium size cap can be explained by competing interactions with both the oligonucleotides and the incoming deoxynucleotide. The data also show that there is no particularly intractable problem in combining promiscuity with fidelity. Exploratory experiments involving a longer template and a downstream-binding strand with a 5'-cap show up to 38-fold rate acceleration over the same reaction templated by a single overhanging nucleotide.

5' Flanking Region↗
PubMed1998

Fluorescence imaging of light absorption for axial-beam geometry in capillary electrophoresis.

A new method for investigation of axial-beam absorption detection for improved detection limits in microcolumn separations is reported. The method is based on fluorescence imaging of light absorption along a separation capillary. The probing UV light is introduced at one end of the capillary and shows an exponential fall-off along the capillary. As the UV light propagates through the sample peaks, an additional loss in intensity will be observed. In order to view the absorption profile along the capillary, a background fluorophore is added to the buffer. A charge-coupled device (CCD) detector and imaging optics are placed beside the capillary to view the capillary in a direction perpendicular to the capillary. Signal integration is employed for consecutive exposures as well as for neighboring detector pixels in order to increase the signal-to-noise ratio. Measurements for stilbene 3 with sulforhodamine B as a background fluorophore are presented. The characteristics of the detection method and potential improvements are discussed.

Electrophoresis, Capillary↗
PubMed1975

Chemical modification of membrane proteins in relation to inhibition of anion exchange in human red blood cells.

Mono-, di-, and trisulfonic acids, including 4,4'-diacetamido stilbene-2,2'-disulfonic acid (DAS) and 2-(4'-amino phenyl)-6-methylbenzene thiazol-3',7-disulfonic acid (APMB) produce a reversible inhibition of sulfate equilibrium exchange in human red cells. A study of the sidedness of the action of a number of these sulfonic acids in red cell ghosts revealed that some, like DAS, inhibit only at the outer membrane surface while others, like APMB, inhibit at either surface. This finding suggests that at least two different types of membrane sites are involved in the control of anion permeability. The nature of the anion permeability controlling sites in the outer cell surface was investigated by studying the effects of DAS on the inhibition by dinitrofluorobenzene (DNFB) of anion equilibrium exchange and on the binding of DNFB to the proteins of the red blood cell membrane. After exposure to DNFB in the presence of DAS for a certain period of time, there was a reduction of both the inhibitory effect of DNFB on sulfate exchange and the binding of DNFB to the protein in band 3 of SDS polyacrylamide gel electropherograms (nomenclature of Steck, J. Cell. Biol., 62: 1, '74). Since binding to other membrane proteins was not affected, this observation supports the assumption that the protein in band 3 plays some role in anion transport. In accordance with the absence of an inhibitory effect at the inner membrane surface, internal DAS does not affect DNFB binding to the protein in band 3. DAS protected the anion exchange system not only against inhibition by DNFB but also by m-isothiocyanato benzene sulfonic acid. In contrast to DAS, the equally inhibitory phlorizin does not reduce the rate of dinitrophenylation of the protein in band 3. This suggests that either not all inhibitors of anion exchange exert their action by a combination with sites on the protein in band 3 or that in spite of the described evidence this protein is not involved in the control of anion movements.

Anthraquinones↗
PubMed1977

Chloride-stimulated sulfate efflux in Ehrlich ascites tumor cells: evidence for 1:1 coupling.

The kinetics of Cl-SO4-(2) exchange in Ehrlich ascites tumor cells was investigated in an attempt to determine the stoichiometry of this process. When tumor cells, equilibrated in Cl--free, 25 mM SO4-(2) medium are placed in SO4-(2)-free, 25 mm Cl-medium, both the net amount and rate of Cl-uptake far exceeds SO4-(2) loss.. Addition of the anion transport inhibitor SITS (4-acetamido-4,-isothiocyano-stilbene-2,2'-disulfonic acid) greatly reduces sulfate efflux (97%), but has no measurable effect on chloride uptake. Addition of furosemide, a Cl-transport inhibitor, reduces chloride uptake 94% but is without effect on sulfate efflux. These findings suggest that a chloride permeability pathway exists distinct from that utilized by SO4-(2). SITS, when added to furosemide treated cells, further reduces chloride uptake as well as inhibiting sulfate efflux, and under these experimental conditions, a linear relationship exists between SITS-sensitive, net chloride uptake and sulfate loss. The slope of this line is 1.05 (correlation coefficient = 0.996) which suggests the stoichiometry of Cl-SO4-(2) exchange is 1:1. Assuming a 1:1 stoichiometry, measurement of the initial chloride influx and initial sulfate efflux indicate that 92% of net chloride uptake is independent of sulfate efflux. Taken altogether, these results support the contention that the tumor cell possesses a permeability pathway which facilitates the exchange of one sulfate for one chloride. Under conditions where anion transport is not inhibited, this coupling is obscured by a second and quantitatively more important pathway for chloride uptake. This pathway is SITS-insensitive, although partially inhibited by furosemide.

Animals↗
PubMed2005

Effect of piceatannol in human monocyte-derived dendritic cells in vitro.

Piceatannol is an anti-inflammatory, immunomodulatory, and antiproliferative stilbene that has been shown to interfere with the cytokine signaling pathway. Dendritic cells (DCs) play a pivotal in the initiation of T-cell-mediated immune responses, making them an attractive cellular adjuvant for use in cancer vaccines. This study investigated the effect of piceatannol on the phenotypic and functional maturation of human monocyte-derived DCs in vitro. Human monocytes were cultured with GM-CSF and IL-4 for 6 days, followed by another 2 days in the presence of piceatannol or LPS. DCs harvested on day 8 were examined using functional assays. The expression levels of CD1a, CD80, CD83, and CD86 as expressed by mean fluorescence intensity (MFI) on DCs differentiated from immature DCs after culture with 1 muM of piceatannol for 2 days were enhanced and decreased endocytic activity. Piceatannol-treated DCs also displayed enhanced T-cell stimulatory capacity in a MLR, as measured by T-cell proliferation. Similar results were obtained with DCs differentiated with LPS from immature DCs. However, piceatannol did not inhibit phenotypic and functional maturation induced by LPS from immature DCs. Piceatannol-treated DCs induced the differentiation of naive T cells towards a helper T-cell type 1 (Th1) response at DCs/T (1:5) cells ratio depending on IL-12 secretion. These results demonstrate that piceatannol may be used on DC-based vaccine for cancer immunotherapy.

Antibodies, Monoclonal↗
PubMed2005

Molecular mechanisms of the chemopreventive effects of resveratrol and its analogs in carcinogenesis.

Resveratrol (3,4',5-trihydroxy-trans-stilbene), a phytoalexin found in grape skins, peanuts, and red wine, has been reported to exhibit a wide range of biological and pharmacological properties. It has been speculated that dietary resveratrol could be an explanation for the so-called 'French paradox' as it may act as an antioxidant, promote nitric oxide production, inhibit platelet aggregation, and increase high-density lipoprotein cholesterol, and thereby serve as a cardioprotective agent. Recently, it has been demonstrated that resveratrol can function as a cancer chemopreventive agent, and there has been a great deal of experimental effort directed toward defining this effect. It has been shown that resveratrol and some of its analogs interfere with signal transduction pathways, modulate cell cycle-regulating proteins, and is a potent inducer of apoptosis in multiple carcinoma cell lines. This review summarizes the recent advances that have provided new insights into the molecular mechanisms underlying the promising properties of resveratrol.

Animals↗
PubMed2005

Resveratrol as an anti-inflammatory and anti-aging agent: mechanisms and clinical implications.

Resveratrol is a phytoalexin polyphenolic compound found in various plants, including grapes, berries, and peanuts. Multiple lines of compelling evidence indicate its beneficial effects on neurological, hepatic, and cardiovascular systems. Also one of the most striking biological activities of resveratrol soundly investigated during the late years has been its cancer-chemopreventive potential. In fact, recently it has been demonstrated that this stilbene blocks the multistep process of carcinogenesis at various stages: tumor initiation, promotion, and progression. One of the possible mechanisms for its biological activities involves downregulation of the inflammatory response through inhibition of synthesis and release of pro-inflammatory mediators, modification of eicosanoid synthesis, inhibition of activated immune cells, or inhibiting such as inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) via its inhibitory effects on nuclear factor (kappa)B (NF-(kappa)B) or the activator protein-1 (AP-1). More recent data provide interesting insights into the effect of this compound on the lifespan of yeast and flies, implicating the potential of resveratrol as an anti-aging agent in treating age-related human diseases. It is worthy to note that the phenolic compound possesses a low bioavailability and rapid clearance from the plasma. As the positive effects of resveratrol on inflammatory response regulation may comprise relevant clinical implications, the purpose of this article is to review its strong anti-inflammatory activity and the plausible mechanisms of these effects. Also, this review is intended to provide the reader an up-date of the bioavailability and pharmacokinetics of resveratrol and its impact on lifespan.

Aging↗