Disease relevance of stilbene

• Estrogen 2- and 4-hydroxylase (ESH), a microsomal enzyme which mediates the formation of catechol estrogens, has been studied in the kidneys of castrated male Syrian hamsters, a species uniquely susceptible to induction of renal carcinomas by both steroidal and stilbene estrogens [1].
• The stilbene disulfonic acids are a novel class of site-specific CD4 antagonists that block multiple CD4-dependent events associated with acute and established HIV-1 infections [2].
• Stilbene disulfonic acids. CD4 antagonists that block human immunodeficiency virus type-1 growth at multiple stages of the virus life cycle [2].
• This inhibition may play a role in the chemoprevention of stilbene estrogen-induced breast cancer [3].
• The stilbene DIDS (4,4-diisothiocyanatostilbenedisulphonic acid, 200 microM) also partially inhibited pHi recovery following an induced intracellular acidosis [4].

Psychiatry related information on stilbene

• 11C-labeled stilbene derivatives as Abeta-aggregate-specific PET imaging agents for Alzheimer's disease [5].
• Inhibition studies with the specific anion transport blocker 4,4'-diisothiocyanto-2,2'-disulfonic acid stilbene (DIDS) demonstrated that the same degree of inhibition of chloride transport could be achieved at a much lower concentration of DIDS in Huntington's disease than in controls [6].

High impact information on stilbene

• The antibodies controlled the isomerization coordinate of trans-stilbene and dynamically coupled this manifold with an active-site residue [7].
• However, the introduction of a single deoxyguanosine-deoxycytidine base pair resulted in distance-dependent fluorescence quenching and the formation of the stilbene anion radical [8].
• Na+ uptake into hepatocytes was stimulated approximately 10-fold by 25 mM extracellular HCO3-.HCO3--stimulated Na+ uptake was saturable, abolished by 4-acetamido-4'-isothiocyano-2,2'-disulfonic acid stilbene (SITS), and unaffected by amiloride or Cl- removal [9].
• Initial rates of both pH and HCO3- gradient-stimulated Cl- uptake were completely inhibited by 4,4'-diisothiocyano-2,2'-disulfonic acid stilbene (DIDS) [10].
• METHODS & RESULTS: pH gradient-driven (22)Na(+) uptake into duodenal basolateral membrane vesicles was partly HCO(3)(-) dependent, stilbene sensitive, and therefore mediated by Na(+)HCO(3)(-) cotransport, and partly HCO(3)(-) independent, Hoechst 642 sensitive, and therefore mediated by the Na(+)/H(+) exchanger isoform NHE1 [11].

Chemical compound and disease context of stilbene

• Resveratrol, a naturally occurring stilbene, induced apoptosis in human breast cancer MCF-7 cells [12].
• Styrene 7,8-oxide hydrolase activity was increased in the McA-RH-7777 rat hepatoma cell line by phenobarbital, trans-stilbene oxide and 2-acetylaminofluorene treatment [13].
• Cross-reaction of chalcone synthase and stilbene synthase overexpressed in Escherichia coli [14].
• Since disulfonic stilbene derivatives combine selectively with the carrier involved in anion transport and inhibit inorganic anion exchange, the data in the present study suggest that in the central nervous system a DIDS-inhibitable carrier is involved in the rise of CSF [HCO3-] observed during acute respiratory acidosis [15].
• The gene stlA encodes a phenylalanine ammonia-lyase that is involved in the production of a stilbene antibiotic in Photorhabdus luminescens TT01 [16].

Biological context of stilbene

• The predicted amino acid sequence of the FAE1 protein shares homology with those of other condensing enzymes (chalcone synthase, stilbene synthases, and beta-ketoacyl-acyl carrier protein synthase III), supporting the notion that FAE1 is the structural gene for a synthase or condensing enzyme [17].
• A stilbene synthase from Japanese red pine (Pinus densiflora): implications for phytoalexin accumulation and down-regulation of flavonoid biosynthesis [18].
• Band 3 from a heterozygote subject for this polymorphism and that displays a normal reactivity towards stilbene disulfonates has been isolated and its primary structure determined by protein chemistry [19].
• Significant epoxide hydrolysis was observed in microsomal and cytosolic subcellular fractions assayed with cis- and trans-stilbene oxide, benzo(a)pyrene-4,5-oxide, and cholesterol epoxide [20].
• A trimodal distribution of trans-stilbene oxide-induced sister chromatid exchanges was observed in the population, including resistant, moderate, and highly sensitive groups [21].

Anatomical context of stilbene

• We reconstituted erythrocyte band 3 into liposomes using apical and basolateral types of lipids and examined the inhibitory potency of 4, 4'-dinitorsostilbene-2,2'-disulfonic acid (DNDS; a reversible stilbene) on 35SO4/SO4 exchange [22].
• Transient expression of AE2 in a eukaryotic cell line leads to an increase in stilbene inhibitable whole cell 35SO4(2-)-efflux consistent with its function as a plasma membrane anion exchanger [23].
• Anion transport in oocytes of Xenopus laevis induced by expression of mouse erythroid band 3 protein--encoding cRNA and of a cRNA derivative obtained by site-directed mutagenesis at the stilbene disulfonate binding site [24].
• Mitochondria can import artificial precursor proteins containing a branched polypeptide chain or a carboxy-terminal stilbene disulfonate [25].
• Although all the RNA samples examined contained class-alpha GT mRNA, class-mu GT mRNA was found only in individuals whose peripheral leukocytes expressed GT activity on the substrate trans-stilbene oxide [26].

Associations of stilbene with other chemical compounds

• We report that functional studies in Xenopus oocytes show INDY is a metabolite transporter that mediates the high-affinity, disulfonic stilbene-sensitive flux of dicarboxylates and citrate across the plasma membrane by a mechanism that is not coupled to Na(+), K(+), or Cl(-) [27].
• Resveratrol, an edible polyphenolic stilbene, has been reported to possess substantial antileukemic activities in different leukemia cell lines [28].
• Treatment of animals with trans-stilbene oxide or phenobarbital (a) increased the total amount of metabolites per protein mass and time, (b) changed the pattern of metabolites, but (c) induced a pattern of metabolites which was again very similar in rough and smooth endoplasmic reticulum [29].
• Lymphocytes account for most of the epoxide hydrolase activity towards cis-stilbene oxide, and all of the activity towards trans-stilbene oxide is in the human mononuclear cell fractions [30].
• Human erythrocyte epoxide hydrolase did not hydrate either styrene oxide or trans-stilbene oxide [31].

Gene context of stilbene

• Expression of mNBC3 cRNA in Xenopus laevis oocytes demonstrated that the protein encodes a novel stilbene-insensitive 5-(N-ethyl-N-isopropyl)-amiloride-inhibitable sodium bicarbonate cotransporter [32].
• Compounds 3e and 4e are fluorinated stilbene derivatives displaying high binding affinities for Abeta plaques in AD brain homogenates (Ki = 15 +/- 6 and 5.0 +/- 1.2 nM, respectively) [33].
• The GSTM1 activity toward the substrate trans-stilbene oxide was 5- to 7-fold lower than in the parental cells [34].
• The stilbene activated MAPK and caused increased abundance of p53 and serine-15 phosphorylated p53 [35].
• Sex and species differences in hepatic epoxide hydrolase activities towards cis- and trans-stilbene oxide were examined in common laboratory animals, as well as in monkey and man [36].

Analytical, diagnostic and therapeutic context of stilbene

• Site-directed mutagenesis studies indicate the involvement of specific amino acid residues in the proposed transmembrane segment 6 for disulfonic stilbene blockade and segments 6 and 12 for arylaminobenzoate blockade [37].
• About 10% of the protein is present at the plasma membrane as determined by immunoprecipitation of covalently bound 4,4'-diisothiocyano-2,2'-disulfonic acid stilbene (DIDS) with anti-DIDS antibody [38].
• As an independent measure of inhibitor binding, we titrated the red shift in the optical spectrum of ferrocytochrome b with methoxyacrylate stilbene and thus confirmed the results of the inhibition of activity titrations [39].
• Characterization of semiquinone free radicals formed from stilbene catechol estrogens. An ESR spin stabilization and spin trapping study [40].
• Modulation of the covalent binding of aryl hydrocarbon metabolites to DNA in vitro after treatment of rats and mice with trans-stilbene oxide [41].

References