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Chemical Compound Review

Bibenzal     [(E)-2-phenylethenyl]benzene

Synonyms: STILBENE, Stilben, Toluylene, Bibenzylidene, Bibenzylidine, ...
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Disease relevance of stilbene


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


Biological context of stilbene


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


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].


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  2. Stilbene disulfonic acids. CD4 antagonists that block human immunodeficiency virus type-1 growth at multiple stages of the virus life cycle. Cardin, A.D., Smith, P.L., Hyde, L., Blankenship, D.T., Bowlin, T.L., Schroeder, K., Stauderman, K.A., Taylor, D.L., Tyms, A.S. J. Biol. Chem. (1991) [Pubmed]
  3. Diallyl sulfide inhibits the oxidation and reduction reactions of stilbene estrogens catalyzed by microsomes, mitochondria and nuclei isolated from breast tissue of female ACI rats. Thomas, R.D., Green, M.R., Wilson, C., Sadrud-Din, S. Carcinogenesis (2004) [Pubmed]
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  5. 11C-labeled stilbene derivatives as Abeta-aggregate-specific PET imaging agents for Alzheimer's disease. Ono, M., Wilson, A., Nobrega, J., Westaway, D., Verhoeff, P., Zhuang, Z.P., Kung, M.P., Kung, H.F. Nucl. Med. Biol. (2003) [Pubmed]
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  7. Blue-fluorescent antibodies. Simeonov, A., Matsushita, M., Juban, E.A., Thompson, E.H., Hoffman, T.Z., Beuscher, A.E., Taylor, M.J., Wirsching, P., Rettig, W., McCusker, J.K., Stevens, R.C., Millar, D.P., Schultz, P.G., Lerner, R.A., Janda, K.D. Science (2000) [Pubmed]
  8. Distance-dependent electron transfer in DNA hairpins. Lewis, F.D., Wu, T., Zhang, Y., Letsinger, R.L., Greenfield, S.R., Wasielewski, M.R. Science (1997) [Pubmed]
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  10. Evidence for carrier-mediated chloride/bicarbonate exchange in canalicular rat liver plasma membrane vesicles. Meier, P.J., Knickelbein, R., Moseley, R.H., Dobbins, J.W., Boyer, J.L. J. Clin. Invest. (1985) [Pubmed]
  11. Role of Na(+)HCO(3)(-) cotransporter NBC1, Na(+)/H(+) exchanger NHE1, and carbonic anhydrase in rabbit duodenal bicarbonate secretion. Jacob, P., Christiani, S., Rossmann, H., Lamprecht, G., Vieillard-Baron, D., Müller, R., Gregor, M., Seidler, U. Gastroenterology (2000) [Pubmed]
  12. Oestrogen inhibits resveratrol-induced post-translational modification of p53 and apoptosis in breast cancer cells. Zhang, S., Cao, H.J., Davis, F.B., Tang, H.Y., Davis, P.J., Lin, H.Y. Br. J. Cancer (2004) [Pubmed]
  13. Induction of epoxide hydrolase in cultured rat hepatocytes and hepatoma cell lines. Razzouk, C., McManus, M.E., Hayashi, S., Schwartz, D., Thorgeirsson, S.S. Biochem. Pharmacol. (1985) [Pubmed]
  14. Cross-reaction of chalcone synthase and stilbene synthase overexpressed in Escherichia coli. Yamaguchi, T., Kurosaki, F., Suh, D.Y., Sankawa, U., Nishioka, M., Akiyama, T., Shibuya, M., Ebizuka, Y. FEBS Lett. (1999) [Pubmed]
  15. Effects of 'DIDS', an anion transport blocker, on CSF [HCO3-] in respiratory acidosis. Javaheri, S., Weyne, J. Respiration physiology. (1984) [Pubmed]
  16. The gene stlA encodes a phenylalanine ammonia-lyase that is involved in the production of a stilbene antibiotic in Photorhabdus luminescens TT01. Williams, J.S., Thomas, M., Clarke, D.J. Microbiology (Reading, Engl.) (2005) [Pubmed]
  17. Directed tagging of the Arabidopsis FATTY ACID ELONGATION1 (FAE1) gene with the maize transposon activator. James, D.W., Lim, E., Keller, J., Plooy, I., Ralston, E., Dooner, H.K. Plant Cell (1995) [Pubmed]
  18. A stilbene synthase from Japanese red pine (Pinus densiflora): implications for phytoalexin accumulation and down-regulation of flavonoid biosynthesis. Kodan, A., Kuroda, H., Sakai, F. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  19. Human erythrocyte band 3 polymorphism (band 3 Memphis): characterization of the structural modification (Lys 56----Glu) by protein chemistry methods. Yannoukakos, D., Vasseur, C., Driancourt, C., Blouquit, Y., Delaunay, J., Wajcman, H., Bursaux, E. Blood (1991) [Pubmed]
  20. Epoxide-metabolizing enzymes in mammary gland and liver from BALB/c mice and effects of inducers on enzyme activity. Silva, M.H., Wixtrom, R.N., Hammock, B.D. Cancer Res. (1988) [Pubmed]
  21. Human glutathione S-transferase deficiency as a marker of susceptibility to epoxide-induced cytogenetic damage. Wiencke, J.K., Kelsey, K.T., Lamela, R.A., Toscano, W.A. Cancer Res. (1990) [Pubmed]
  22. The effect of apical and basolateral lipids on the function of the band 3 anion exchange protein. van't Hof, W., Malik, A., Vijayakumar, S., Qiao, J., van Adelsberg, J., Al-Awqati, Q. J. Cell Biol. (1997) [Pubmed]
  23. Functional activation of plasma membrane anion exchangers occurs in a pre-Golgi compartment. Ruetz, S., Lindsey, A.E., Ward, C.L., Kopito, R.R. J. Cell Biol. (1993) [Pubmed]
  24. 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. Bartel, D., Lepke, S., Layh-Schmitt, G., Legrum, B., Passow, H. EMBO J. (1989) [Pubmed]
  25. Mitochondria can import artificial precursor proteins containing a branched polypeptide chain or a carboxy-terminal stilbene disulfonate. Vestweber, D., Schatz, G. J. Cell Biol. (1988) [Pubmed]
  26. Hereditary differences in the expression of the human glutathione transferase active on trans-stilbene oxide are due to a gene deletion. Seidegård, J., Vorachek, W.R., Pero, R.W., Pearson, W.R. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  27. Functional characterization and immunolocalization of the transporter encoded by the life-extending gene Indy. Knauf, F., Rogina, B., Jiang, Z., Aronson, P.S., Helfand, S.L. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  28. Resveratrol blocks interleukin-1beta-induced activation of the nuclear transcription factor NF-kappaB, inhibits proliferation, causes S-phase arrest, and induces apoptosis of acute myeloid leukemia cells. Estrov, Z., Shishodia, S., Faderl, S., Harris, D., Van, Q., Kantarjian, H.M., Talpaz, M., Aggarwal, B.B. Blood (2003) [Pubmed]
  29. Metabolism of benzo(a)pyrene by subcellular fractions of rat liver: evidence for similar patterns of cytochrome P-450 in rough and smooth endoplasmic reticulum but not in nuclei and plasma membrane. Oesch, F., Bentley, P., Golan, M., Stasiecki, P. Cancer Res. (1985) [Pubmed]
  30. Measurement and characterization of membrane-bound and soluble epoxide hydrolase activities in resting mononuclear leukocytes from human blood. Seidegård, J., DePierre, J.W., Pero, R.W. Cancer Res. (1984) [Pubmed]
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  33. F-18 stilbenes as PET imaging agents for detecting beta-amyloid plaques in the brain. Zhang, W., Oya, S., Kung, M.P., Hou, C., Maier, D.L., Kung, H.F. J. Med. Chem. (2005) [Pubmed]
  34. Decreased expression of glutathione S-transferase M1 in HPV16-transfected human cervical keratinocytes in culture. Chen, C., Nirunsuksiri, W. Carcinogenesis (1999) [Pubmed]
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  38. Lysine 539 of human band 3 is not essential for ion transport or inhibition by stilbene disulfonates. Garcia, A.M., Lodish, H.F. J. Biol. Chem. (1989) [Pubmed]
  39. Inhibitory analogs of ubiquinol act anti-cooperatively on the Yeast cytochrome bc1 complex. Evidence for an alternating, half-of-the-sites mechanism of ubiquinol oxidation. Gutierrez-Cirlos, E.B., Trumpower, B.L. J. Biol. Chem. (2002) [Pubmed]
  40. Characterization of semiquinone free radicals formed from stilbene catechol estrogens. An ESR spin stabilization and spin trapping study. Kalyanaraman, B., Sealy, R.C., Liehr, J.G. J. Biol. Chem. (1989) [Pubmed]
  41. Modulation of the covalent binding of aryl hydrocarbon metabolites to DNA in vitro after treatment of rats and mice with trans-stilbene oxide. Lesca, P., Guenthner, T.M., Oesch, F. Carcinogenesis (1981) [Pubmed]
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