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Chemical Compound Review

Tamogel     4-[(Z)-1-[4-(2- dimethylaminoethoxy)phenyl]...

Synonyms: Afimoxifene, CHEMBL489, SureCN9189, Tamogel (TN), CCRIS 8580, ...
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Disease relevance of trans-Hydroxytamoxifen


High impact information on trans-Hydroxytamoxifen


Chemical compound and disease context of trans-Hydroxytamoxifen


Biological context of trans-Hydroxytamoxifen

  • The antiestrogens tamoxifen and hydroxytamoxifen inhibit cell proliferation below the control level only when cells are grown in the presence of phenol red; in the absence of phenol red, the antiestrogens do not suppress growth [15].
  • However, simultaneous treatment of cells expressing wild-type ER with trans-4-hydroxytamoxifen and dopamine resulted in transgene expression that was additive in nature compared to either compound alone; similar treatment of cells expressing [Val400]ER produced a synergistic increase [16].
  • We now show that in hydroxytamoxifen-treated cells, transduction of the cell cycle inhibitor p27(Kip1) induces quiescence and insensitivity to growth stimulation by insulin/insulin-like growth factor I and epidermal growth factor/transforming growth factor alpha [17].
  • Out of five estrogen conjugates, only 3-glucurono-estradiol partly suppressed the inhibition of hydroxytamoxifen; the conjugate also reduced the estrogen receptor content of the cells, probably by a down regulation process ("processing") [18].
  • Long-term hydroxytamoxifen treatment of an MCF-7-derived breast cancer cell line irreversibly inhibits the expression of estrogenic genes through chromatin remodeling [19].

Anatomical context of trans-Hydroxytamoxifen


Associations of trans-Hydroxytamoxifen with other chemical compounds


Gene context of trans-Hydroxytamoxifen


Analytical, diagnostic and therapeutic context of trans-Hydroxytamoxifen


  1. Antagonism by suramin of the growth-inhibitory effect of hydroxytamoxifen and doxorubicin in human MCF-7 breast cancer cells. Berthois, Y., Dong, X.F., Martin, P.M., Cvitkovic, E. J. Natl. Cancer Inst. (1992) [Pubmed]
  2. Stimulatory effects of 4-hydroxytamoxifen on proliferation of human endometrial adenocarcinoma cells (Ishikawa line). Anzai, Y., Holinka, C.F., Kuramoto, H., Gurpide, E. Cancer Res. (1989) [Pubmed]
  3. Tamoxifen might influence the affinity of LPL for heparin-sepharose. Kawano, M., Hozumi, Y., Itoh, K. Clin. Chim. Acta (2003) [Pubmed]
  4. Hydroxytamoxifen interaction with human erythrocyte membrane and induction of permeabilization and subsequent hemolysis. Cruz Silva, M.M., Madeira, V.M., Almeida, L.M., Custódio, J.B. Toxicology in vitro : an international journal published in association with BIBRA. (2001) [Pubmed]
  5. The estrogen receptor binds tightly to its responsive element as a ligand-induced homodimer. Kumar, V., Chambon, P. Cell (1988) [Pubmed]
  6. Ectopic expression of activated Stat6 induces the expression of Th2-specific cytokines and transcription factors in developing Th1 cells. Kurata, H., Lee, H.J., O'Garra, A., Arai, N. Immunity (1999) [Pubmed]
  7. Antiestrogenic action of 3-hydroxytamoxifen in the human breast cancer cell line MCF-7. Roos, W., Oeze, L., Löser, R., Eppenberger, U. J. Natl. Cancer Inst. (1983) [Pubmed]
  8. The N-terminal part of TIF1, a putative mediator of the ligand-dependent activation function (AF-2) of nuclear receptors, is fused to B-raf in the oncogenic protein T18. Le Douarin, B., Zechel, C., Garnier, J.M., Lutz, Y., Tora, L., Pierrat, P., Heery, D., Gronemeyer, H., Chambon, P., Losson, R. EMBO J. (1995) [Pubmed]
  9. A second binding site for hydroxytamoxifen within the coactivator-binding groove of estrogen receptor beta. Wang, Y., Chirgadze, N.Y., Briggs, S.L., Khan, S., Jensen, E.V., Burris, T.P. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  10. Binding of antiestrogens exposes an occult antigenic determinant in the human estrogen receptor. Martin, P.M., Berthois, Y., Jensen, E.V. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  11. Selective estrogen receptor modulators in the ruthenocene series. Synthesis and biological behavior. Pigeon, P., Top, S., Vessières, A., Huché, M., Hillard, E.A., Salomon, E., Jaouen, G. J. Med. Chem. (2005) [Pubmed]
  12. Inhibition of the estradiol-induced growth of cultured human breast cancer cells by the anti-estrogens tamoxifen, desmethyl-tamoxifen, 4-hydroxy-tamoxifen and enclomiphene. Marth, C., Daxenbichler, G., Buehring, G.C., Hofstädter, F., Dapunt, O. Biochem. Pharmacol. (1984) [Pubmed]
  13. EM-652 (SCH 57068), a third generation SERM acting as pure antiestrogen in the mammary gland and endometrium. Labrie, F., Labrie, C., Bélanger, A., Simard, J., Gauthier, S., Luu-The, V., Mérand, Y., Giguere, V., Candas, B., Luo, S., Martel, C., Singh, S.M., Fournier, M., Coquet, A., Richard, V., Charbonneau, R., Charpenet, G., Tremblay, A., Tremblay, G., Cusan, L., Veilleux, R. J. Steroid Biochem. Mol. Biol. (1999) [Pubmed]
  14. Antiestrogenic properties of keoxifene, trans-4-hydroxytamoxifen, and ICI 164384, a new steroidal antiestrogen, in ZR-75-1 human breast cancer cells. Poulin, R., Merand, Y., Poirier, D., Levesque, C., Dufour, J.M., Labrie, F. Breast Cancer Res. Treat. (1989) [Pubmed]
  15. Phenol red in tissue culture media is a weak estrogen: implications concerning the study of estrogen-responsive cells in culture. Berthois, Y., Katzenellenbogen, J.A., Katzenellenbogen, B.S. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  16. Modulation of the ligand-independent activation of the human estrogen receptor by hormone and antihormone. Smith, C.L., Conneely, O.M., O'Malley, B.W. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  17. p27(Kip1) induces quiescence and growth factor insensitivity in tamoxifen-treated breast cancer cells. Carroll, J.S., Lynch, D.K., Swarbrick, A., Renoir, J.M., Sarcevic, B., Daly, R.J., Musgrove, E.A., Sutherland, R.L. Cancer Res. (2003) [Pubmed]
  18. Estrogen conjugates and serum factors mediating the estrogenic trophic effect on MCF-7 cell growth. Devleeschouwer, N., Legros, N., Olea-Serrano, N., Paridaens, R., Leclercq, G. Cancer Res. (1987) [Pubmed]
  19. Long-term hydroxytamoxifen treatment of an MCF-7-derived breast cancer cell line irreversibly inhibits the expression of estrogenic genes through chromatin remodeling. Badia, E., Duchesne, M.J., Semlali, A., Fuentes, M., Giamarchi, C., Richard-Foy, H., Nicolas, J.C., Pons, M. Cancer Res. (2000) [Pubmed]
  20. Hydroxytamoxifen induces a rapid and irreversible inactivation of an estrogenic response in an MCF-7-derived cell line. Badia, E., Duchesne, M.J., Fournier-Bidoz, S., Simar-Blanchet, A.E., Terouanne, B., Nicolas, J.C., Pons, M. Cancer Res. (1994) [Pubmed]
  21. Differential recruitment of coregulator proteins steroid receptor coactivator-1 and silencing mediator for retinoid and thyroid receptors to the estrogen receptor-estrogen response element by beta-estradiol and 4-hydroxytamoxifen in human breast cancer. Fleming, F.J., Hill, A.D., McDermott, E.W., O'Higgins, N.J., Young, L.S. J. Clin. Endocrinol. Metab. (2004) [Pubmed]
  22. 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]
  23. Interindividual variation in the isomerization of 4-hydroxytamoxifen by human liver microsomes: involvement of cytochromes P450. Williams, M.L., Lennard, M.S., Martin, I.J., Tucker, G.T. Carcinogenesis (1994) [Pubmed]
  24. Hydroxytamoxifen protects against oxidative stress in brain mitochondria. Moreira, P.I., Custódio, J.B., Oliveira, C.R., Santos, M.S. Biochem. Pharmacol. (2004) [Pubmed]
  25. Estrogen receptor alpha and beta heterodimers exert unique effects on estrogen- and tamoxifen-dependent gene expression in human U2OS osteosarcoma cells. Monroe, D.G., Secreto, F.J., Subramaniam, M., Getz, B.J., Khosla, S., Spelsberg, T.C. Mol. Endocrinol. (2005) [Pubmed]
  26. Microsomal and peroxidase activation of 4-hydroxy-tamoxifen to form DNA adducts: comparison with DNA adducts formed in Sprague-Dawley rats treated with tamoxifen. Pathak, D.N., Pongracz, K., Bodell, W.J. Carcinogenesis (1995) [Pubmed]
  27. Nonsteroidal antiestrogen inhibition of protein kinase C in human corpus luteum and placenta. Eyster, K.M., Clark, M.R. Biochem. Pharmacol. (1989) [Pubmed]
  28. Hoxa9 and Meis1 are key targets for MLL-ENL-mediated cellular immortalization. Zeisig, B.B., Milne, T., García-Cuéllar, M.P., Schreiner, S., Martin, M.E., Fuchs, U., Borkhardt, A., Chanda, S.K., Walker, J., Soden, R., Hess, J.L., Slany, R.K. Mol. Cell. Biol. (2004) [Pubmed]
  29. Constitutive overexpression of cyclin D1 does not prevent inhibition of hormone-responsive human breast cancer cell growth by antiestrogens. Pacilio, C., Germano, D., Addeo, R., Altucci, L., Petrizzi, V.B., Cancemi, M., Cicatiello, L., Salzano, S., Lallemand, F., Michalides, R.J., Bresciani, F., Weisz, A. Cancer Res. (1998) [Pubmed]
  30. An estrogen-responsive element-targeted histone deacetylase enzyme has an antiestrogen activity that differs from that of hydroxytamoxifen. Demirpence, E., Semlali, A., Oliva, J., Balaguer, P., Badia, E., Duchesne, M.J., Nicolas, J.C., Pons, M. Cancer Res. (2002) [Pubmed]
  31. Identification and characterization of a novel factor that regulates quinone reductase gene transcriptional activity. Montano, M.M., Wittmann, B.M., Bianco, N.R. J. Biol. Chem. (2000) [Pubmed]
  32. Expression of insulin-like growth factors and their binding proteins in the estrogen responsive Ishikawa human endometrial cancer cell line. Hana, V., Murphy, L.J. Endocrinology (1994) [Pubmed]
  33. trans-4-Hydroxytamoxifen concentration and metabolism after local percutaneous administration to human breast. Mauvais-Javis, P., Baudot, N., Castaigne, D., Banzet, P., Kuttenn, F. Cancer Res. (1986) [Pubmed]
  34. Bioactivities, estrogen receptor interactions, and plasminogen activator-inducing activities of tamoxifen and hydroxy-tamoxifen isomers in MCF-7 human breast cancer cells. Katzenellenbogen, B.S., Norman, M.J., Eckert, R.L., Peltz, S.W., Mangel, W.F. Cancer Res. (1984) [Pubmed]
  35. Early alterations at the plasma membrane of breast cancer cell lines in response to estradiol and hydroxytamoxifen. Pourreau-Schneider, N., Berthois, Y., Gandilhon, P., Cau, P., Martin, P.M. Mol. Cell. Endocrinol. (1986) [Pubmed]
  36. Mechanisms governing the accumulation of estrogen receptor alpha in MCF-7 breast cancer cells treated with hydroxytamoxifen and related antiestrogens. Laïos, I., Journe, F., Laurent, G., Nonclercq, D., Toillon, R.A., Seo, H.S., Leclercq, G. J. Steroid Biochem. Mol. Biol. (2003) [Pubmed]
  37. Flow cytometry analysis of the growth inhibitory effect of 4-hydroxy-tamoxifen on a human breast carcinoma cell line. Vicard, E., Hijazi, A., Muchada, E., Chouvet, C., Devonec, M., Saez, S. Anticancer Res. (1988) [Pubmed]
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