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Chemical Compound Review

ACMC-1AOGF     1,2-diphenylethenylbenzene

Synonyms: T82805_ALDRICH, AG-K-08869, ANW-33024, NSC-17535, KST-1B6131, ...
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Disease relevance of Triphenylethene


High impact information on Triphenylethene

  • The triphenylethylene antiestrogen tamoxifen and its major metabolite N-desmethyltamoxifen at concentrations of 4-6 microM enhance the intracellular concentration of natural-product antineoplastics and augment the cytotoxicity of such drugs three-fold to 10-fold in a variety of human and murine cell lines [5].
  • Other study results indicate that both progestins and triphenylethylene antiestrogens may be substrates for P-glycoprotein, the product of the MDR1 gene [6].
  • Although the mechanism of inhibition of PKC by triphenylethylenes clearly involves nonspecific interactions between the antiestrogens and the lipid cofactor of PKC, we recently demonstrated that PKC itself has specific triphenylethylene-binding sites, suggesting that the inhibitory mechanism also involves specific drug-protein interactions [7].
  • It is proposed that the double binding of Tam and OH-Tam to ER and ABS in estrogen target cells may be related to the complex double series of estrogenic and "antiestrogenic" activities displayed by nonsteroidal triphenylethylene derivatives [8].
  • Induction of virus could be inhibited by the triphenylethylene anti-estrogen tamoxifen at concentrations that had minimal effects on cellular DNA synthetic responses and cell cycle kinetics [9].

Chemical compound and disease context of Triphenylethene


Biological context of Triphenylethene


Anatomical context of Triphenylethene


Associations of Triphenylethene with other chemical compounds


Gene context of Triphenylethene


Analytical, diagnostic and therapeutic context of Triphenylethene


  1. MCF7/LCC9: an antiestrogen-resistant MCF-7 variant in which acquired resistance to the steroidal antiestrogen ICI 182,780 confers an early cross-resistance to the nonsteroidal antiestrogen tamoxifen. Brünner, N., Boysen, B., Jirus, S., Skaar, T.C., Holst-Hansen, C., Lippman, J., Frandsen, T., Spang-Thomsen, M., Fuqua, S.A., Clarke, R. Cancer Res. (1997) [Pubmed]
  2. Okadaic acid-sensitive activation of Maxi Cl(-) channels by triphenylethylene antioestrogens in C1300 mouse neuroblastoma cells. Diaz, M., Bahamonde, M.I., Lock, H., Muñoz, F.J., Hardy, S.P., Posas, F., Valverde, M.A. J. Physiol. (Lond.) (2001) [Pubmed]
  3. Desmoid tumours treated with triphenylethylenes. Brooks, M.D., Ebbs, S.R., Colletta, A.A., Baum, M. Eur. J. Cancer (1992) [Pubmed]
  4. Effects of tamoxifen on steroid hormone receptors and hormone concentration and the results of DNA analysis by flow cytometry in endometrial carcinoma. Nola, M., Jukić, S., Ilić-Forko, J., Babić, D., Uzarević, B., Petrovecki, M., Suchanek, E., Skrablin, S., Dotlić, S., Marusić, M. Gynecol. Oncol. (1999) [Pubmed]
  5. High-dose oral tamoxifen, a potential multidrug-resistance-reversal agent: phase I trial in combination with vinblastine. Trump, D.L., Smith, D.C., Ellis, P.G., Rogers, M.P., Schold, S.C., Winer, E.P., Panella, T.J., Jordan, V.C., Fine, R.L. J. Natl. Cancer Inst. (1992) [Pubmed]
  6. Effect of P-glycoprotein expression on sensitivity to hormones in MCF-7 human breast cancer cells. Clarke, R., Currier, S., Kaplan, O., Lovelace, E., Boulay, V., Gottesman, M.M., Dickson, R.B. J. Natl. Cancer Inst. (1992) [Pubmed]
  7. Role of specific interactions between protein kinase C and triphenylethylenes in inhibition of the enzyme. O'Brian, C.A., Ward, N.E., Anderson, B.W. J. Natl. Cancer Inst. (1988) [Pubmed]
  8. Physicochemical and genetic evidence for specific antiestrogen binding sites. Faye, J.C., Jozan, S., Redeuilh, G., Baulieu, E.E., Bayard, F. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  9. Effect of tamoxifen on regulation of viral replication and human immunodeficiency virus (HIV) long terminal repeat-directed transcription in cells chronically infected with HIV-1. Laurence, J., Cooke, H., Sikder, S.K. Blood (1990) [Pubmed]
  10. Cytochrome P-450-mediated activation and irreversible binding of the antiestrogen tamoxifen to proteins in rat and human liver: possible involvement of flavin-containing monooxygenases in tamoxifen activation. Mani, C., Kupfer, D. Cancer Res. (1991) [Pubmed]
  11. Tamoxifen and hydroxytamoxifen isomers versus estradiol effects on normal human breast cells in culture. Malet, C., Gompel, A., Spritzer, P., Bricout, N., Yaneva, H., Mowszowicz, I., Kuttenn, F., Mauvais-Jarvis, P. Cancer Res. (1988) [Pubmed]
  12. Cross-resistance of triphenylethylene-type antiestrogens but not ICI 182,780 in tamoxifen-stimulated breast tumors grown in athymic mice. Lee, E.S., Schafer, J.M., Yao, K., England, G., O'Regan, R.M., De Los Reyes, A., Jordan, V.C. Clin. Cancer Res. (2000) [Pubmed]
  13. Inhibition of protein kinase C and calmodulin by the geometric isomers cis- and trans-tamoxifen. O'Brian, C.A., Ioannides, C.G., Ward, N.E., Liskamp, R.M. Biopolymers (1990) [Pubmed]
  14. Correlation of the antiproliferative action of diphenylmethane-derivative antiestrogen binding site ligands with antagonism of histamine binding but not of protein kinase C-mediated phosphorylation. Brandes, L.J., Gerrard, J.M., Bogdanovic, R.P., Lint, D.W., Reid, R.E., LaBella, F.S. Cancer Res. (1988) [Pubmed]
  15. Calmodulin antagonism and growth-inhibiting activity of triphenylethylene antiestrogens in MCF-7 human breast cancer cells. Gulino, A., Barrera, G., Vacca, A., Farina, A., Ferretti, C., Screpanti, I., Dianzani, M.U., Frati, L. Cancer Res. (1986) [Pubmed]
  16. Autocrine regulation of cell proliferation by estradiol and hydroxytamoxifen of transformed mouse Leydig cells in serum-free culture. Nishizawa, Y., Sato, B., Miyashita, Y., Tsukada, S., Hirose, T., Kishimoto, S., Matsumoto, K. Endocrinology (1988) [Pubmed]
  17. Characterization of a triphenylethylene-antiestrogen-binding site on rat serum low density lipoprotein. Winneker, R.C., Guthrie, S.C., Clark, J.H. Endocrinology (1983) [Pubmed]
  18. Inhibition of prolactin-induced mammary cancer in C3Hf (XVII) mice with the trans isomer of bromotriphenylethylene. Drosdowsky, M., Edery, M., Guggiari, M., Montes-Rendon, A., Rudali, G., Vives, C. Cancer Res. (1980) [Pubmed]
  19. Inhibition of rat uterine gland genesis by tamoxifen. Branham, W.S., Sheehan, D.M., Zehr, D.R., Medlock, K.L., Nelson, C.J., Ridlon, E. Endocrinology (1985) [Pubmed]
  20. Disparate effects of triphenylethylene antiestrogens on estrogen and progestin biosyntheses by cultured rat granulosa cells. Welsh, T.H., Jia, X.C., Jones, P.B., Zhuang, L.Z., Hsueh, A.J. Endocrinology (1984) [Pubmed]
  21. Inhibition of prostaglandin synthetase by di- and triphenylethylene derivatives: a structure-activity study. Gilbert, J., Miquel, J.F., Précigoux, G., Hospital, M., Raynaud, J.P., Michel, F., Crastes de Paulet, A. J. Med. Chem. (1983) [Pubmed]
  22. Alterations of drug metabolizing and antioxidant enzyme activities during tamoxifen-induced hepatocarcinogenesis in the rat. Ahotupa, M., Hirsimäki, P., Pärssinen, R., Mäntylä, E. Carcinogenesis (1994) [Pubmed]
  23. Toremifene: pharmacologic and pharmacokinetic basis of reversing multidrug resistance. DeGregorio, M.W., Ford, J.M., Benz, C.C., Wiebe, V.J. J. Clin. Oncol. (1989) [Pubmed]
  24. Selective estrogenic effects of a novel triphenylethylene compound, FC1271a, on bone, cholesterol level, and reproductive tissues in intact and ovariectomized rats. Qu, Q., Zheng, H., Dahllund, J., Laine, A., Cockcroft, N., Peng, Z., Koskinen, M., Hemminki, K., Kangas, L., Väänänen, K., Härkönen, P. Endocrinology (2000) [Pubmed]
  25. Different interaction of estradiol and antiestrogens with the estrogen receptor of rat uterus. Faye, J.C., Fargin, A., Bayard, F. Mol. Cell. Endocrinol. (1986) [Pubmed]
  26. Differential effects of ovarian steroids and triphenylethylene compounds on macromolecular uptake and thymidine incorporation in the mouse uterus. Huet-Hudson, Y.M., Dey, S.K. J. Steroid Biochem. (1990) [Pubmed]
  27. Molecular classification of estrogens. Jordan, V.C., Schafer, J.M., Levenson, A.S., Liu, H., Pease, K.M., Simons, L.A., Zapf, J.W. Cancer Res. (2001) [Pubmed]
  28. Modulation of estrogen receptor transactivation and estrogen-induced gene expression by ormeloxifene-A triphenylethylene derivative. Blesson, C.S., Awasthi, S., Kharkwal, G., Daverey, A., Dwivedi, A. Steroids (2006) [Pubmed]
  29. Structure-activity relationships for triphenylethylene antiestrogens on hepatic phase-I and phase-II enzyme expression. Nuwaysir, E.F., Dragan, Y.P., McCague, R., Martin, P., Mann, J., Jordan, V.C., Pitot, H.C. Biochem. Pharmacol. (1998) [Pubmed]
  30. The dissociation rate of estrogen receptor-ligand complexes is increased by high concentrations of steroids and antiestrogens. Borgna, J.L., Ladrech, S. Mol. Cell. Endocrinol. (1982) [Pubmed]
  31. Frequent and specific mutations of the rat p53 gene in hepatocarcinomas induced by tamoxifen. Vancutsem, P.M., Lazarus, P., Williams, G.M. Cancer Res. (1994) [Pubmed]
  32. Gap junction modulation in rat uterus. II. Effects of antiestrogens on myometrial and serosal cells. Burghardt, R.C., Mitchell, P.A., Kurten, R. Biol. Reprod. (1984) [Pubmed]
  33. Subcellular and extracellular localization of specific binding sites for triphenylethylene antiestrogens in human breast cancer. Gulino, A., Vacca, A., Modesti, A., Screpanti, I., Farina, A., Frati, L. Biochem. Pharmacol. (1986) [Pubmed]
  34. Protein kinase C subspecies in estrogen receptor-positive and -negative human breast cancer cell lines. Bignon, E., Ogita, K., Kishimoto, A., Nishizuka, Y. Biochem. Biophys. Res. Commun. (1990) [Pubmed]
  35. GLC assay for fenclorac. Visalli, A.J., Patel, D.M., Reavey-Cantwell, N.H. Journal of pharmaceutical sciences. (1976) [Pubmed]
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