The key to the antiestrogenic mechanism of raloxifene is amino acid 351 (Aspartate) in the estrogen receptor

Cancer Research

Volumn 58, Issue 9, 1998, Pages 1872-1875

  Levenson, Anait S ^a   Craig Jordan, V ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARTIC ACID; CANCER GROWTH FACTOR; ESTRADIOL; ESTROGEN RECEPTOR; FULVESTRANT; RALOXIFENE; TRANSFORMING GROWTH FACTOR ALPHA;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CANCER HORMONE THERAPY; DRUG MECHANISM; HUMAN; HUMAN CELL; LIGAND BINDING; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ASPARTIC ACID; BLOTTING, NORTHERN; BREAST NEOPLASMS; ESTRADIOL; ESTROGEN ANTAGONISTS; FEMALE; HUMANS; MUTAGENESIS, SITE-DIRECTED; PIPERIDINES; POINT MUTATION; RALOXIFENE; RECEPTORS, ESTROGEN; RNA, MESSENGER; TRANSFECTION; TRANSFORMING GROWTH FACTOR ALPHA; TUMOR CELLS, CULTURED;

EID: 2642593030     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. Jordan, V. C. Biochemical pharmacology of antiestrogen action. Pharmacol. Rev., 36: 245-276, 1984.
2. Lednicer, D., Lyster, S. C., Aspergren, B. D., and Duncan, G. W. Mammalian antifertility agents. III. 1-Anyl-2-phenyl-1,2,3,4-tetrahydro-1-naphthols, 1-anyl-2-phenyl-3,4-dihydronaphthalenes and their derivatives. J. Med. Chem., 9: 172-176, 1966.
3. Lednicer, D., Lyster, S. C., and Duncan, G. W. Mammalian antifertility agents. IV. Basic 3,4-dihydronaphthalenes and 1,2,3,4-tetrahydro-1-naphthols. J. Med. Chem., 10: 78-86, 1967.
4. Clark, E. R., and Jordan, V. C. Oestrogenic, antioestrogenic and antifertility properties of a series of compounds related to ethamoxytriphetol (MER-25). Br. J. Pharmacol., 57: 487-493, 1976.
5. Robertson, D. W., Katzenellenbogen, J. A., Hayes, J. R., and Katzehellenbogen, B. S. Antiestrogen basicity-activity relationships: a comparison of the estrogen receptor binding and antiuterotrophic potencies of several analogues of (Z)-1,2-diphenyl-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-butene (Tamoxifen, Nolvadex) having altered basicity. J. Med. Chem., 25: 167-171, 1982.
6. Jordan, V. C., and Gosden, B. Importance of the alkylaminoethoxy side chain for the estrogenic and antiestrogenic actions of tamoxifen and trioxifene in the immature rat uterus. Mol. Cell. Endocrinol., 27: 291-306, 1982.
7. Brzozowski, A. M., Pike, A. C. W., Dauter, Z., Hubbard, R. E., Bonn, T., Engstrom, O., Ohman, L., Greene, G. L., Gustafsson, J-A., and Carlquist, M. Molecular basis of agonism and antagonism in the oestrogen receptor. Nature (Lond.), 389: 753-758, 1997.
8. Lieberman, M. E., Gorski, J., and Jordan, V. C. An estrogen receptor model to describe the regulation of prolactin synthesis by antiestrogens in vitro. J. Biol. Chem., 258: 4741-4745, 1983.
9. Wolf, D. M., and Jordan, V. C. The estrogen receptor from a tamoxifen stimulated MCF-7 tumor variant contains a point mutation in the ligand binding domain. Breast Cancer Res. Treat., 31: 129-138, 1994.
10. Tora, L., Mullick, A., Metzger, D., Ponglikitmongkol, M., Park, I., and Chambon, P. The cloned human estrogen receptor contains a mutation which alters its hormone binding properties. EMBO J., 8: 1981-1986, 1989.
11. Jiang, S. Y., and Jordan, V. C. Growth regulation of estrogen receptor-negative breast cancer cells transfected with complementary DNAs for estrogen receptor. J. Natl. Cancer Inst., 84: 580-591, 1992.
12. Catherino, W. H., Wolf, D. M., and Jordan, V. C. A naturally occurring estrogen receptor mutation results in increased estrogenicity of a tamoxifen analogue. Mol. Endocrinol., 9: 1053-1063, 1995.
13. Levenson, A. S., Catherino, W. H., and Jordan, V. C. Estrogenic activity is increased for an antiestrogen by a natural mutation of the estrogen receptor. J. Steroid Biochem. Mol. Biol., 60: 261-268, 1997.
14. Jeng, M. H., Jiang, S. Y., and Jordan, V. C. Paradoxical regulation of estrogen-dependent growth factor gene expression in estrogen receptor (ER) negative human breast cancer cells stably expressing ER. Cancer Lett., 82: 123-128, 1994.
15. Pakdel, F., and Katzenellenbogen, B. S. Human estrogen receptor mutants with altered estrogen and antiestrogen ligand discrimination. J. Biol. Chem., 267: 3429-3437, 1992.
16. Wrenn, C. K., and Katzenellenbogen, B. S. Structure-function analysis of the hormone binding domain of the estrogen receptor by region-specific mutagenesis and phenotypic screening in yeast. J. Biol. Chem., 268: 24089-24098, 1993.
17. Zhuang, Y., Katzenellenbogen, B. S., and Shapiro, D. Estrogen receptor mutants which do not bind 17β-estradiol dimerize and bind to the estrogen response element in vivo. Mol. Endocrinol., 9: 457-566, 1995.
18. Danielian, P. S., White, R., Lees, J. A., and Parker, M. G. Identification of a conserved region required for hormone dependent transcriptional activation by steroid hormone receptors. EMBO J., 11: 1025-1033, 1992.
19. Tzukerman, M. T., Esty, A., Santiso-Mere, D., Danielian, P., Parker, M. G., Stein, R. B., Pike, J. W., and McDonnell, D. P. Human estrogen receptor transactivational capacity is determined by both cellular and promoter context and mediated by two functionally distinct intramolecular regions. Mol. Endocrinol., 8: 21-30, 1994.
20. Mahfoudi, A., Roulet, E., Dauvois, S., Parker, M. G., and Wahli, W. Specific mutations in the estrogen receptor change the properties of antiestrogens to full agonists. Proc. Natl. Acad. Sci. USA, 92: 4206-4210, 1995.
21. Montano, M. M., Ekena, K., Krueger, K. D., Keller, A. L., and Katzenellenbogen, B. S. Human estrogen receptor ligand activity inversion mutants: receptors that interpret antiestrogens as estrogens and estrogens as antiestrogens and discriminate among different antiestrogens. Mol. Endocrinol., 10: 230-242, 1996.
22. Early Breast Cancer Trials Collaborative Group. Systemic therapy of early breast cancer by hormonal, cytotoxic and immune therapy: 133 randomized trials involving 331,000 recurrences and 24,000 deaths among 75,000 women. Lancet, 339: 1-15, 1992.
23. Canney, P. A., Griffiths, T., Latief, T. N., and Priestman, T. J. Clinical significance of tamoxifen withdrawal response. Lancet, i: 36, 1987.
24. Howell, A., Dodwell, D. J., Anderson, H., and Redford, J. Response after withdrawal of tamoxifen and progestogens in advanced breast cancer. Ann. Oncol., 3: 611-617, 1992.
25. Osborne, C. K., Coronado, E. B., and Robinson, J. P. Human breast cancer in the athymic nude mouse: cytostatic effects of long-term antiestrogen therapy. Eur. J. Cancer Clin. Oncol., 23: 1189-1196, 1987.
26. Gottardis, M. M., and Jordan, V. C. Development of tamoxifen-stimulated growth of MCF-7 tumors in athymic mice after long-term antiestrogen administration. Cancer Res., 48: 5183-5187, 1988.
27. Gottardis, M. M., Jiang, S. Y., Jeng, M. H., and Jordan, V. C. Inhibition of tamoxifen-stimulated growth of an MCF-7 tumor variant in athymic mice by novel steroidal antiestrogens. Cancer Res., 49: 4090-4093, 1989.
28. Howell, A., DeFriend, D., Robertson, J., Blarney, R., and Walton, P. Response to a specific antioestrogen (ICI 182,780) in tamoxifen-resistant breast tumor. Lancet, 345: 29-30, 1995.
29. Howell, A., DeFriend, D. J., Robertson, J. F. R., Blamey, R. W., Anderson, L., Anderson, E., Sutcliffe, F. A., and Walton, P. Pharmacokinetics, pharmacological and anti-tumour effects of the specific anti-oestrogen ICI 182,780 in women with breast cancer. Br. J. Cancer, 74: 300-308, 1996.
30. Tonetti, D. A., and Jordan, V. C. Possible mechanisms in the emergence of tamoxifen-resistant breast cancer. Anticancer Drugs, 6: 498-507, 1995.
31. Catherine, W. H., and Jordan, V. C. Increasing the number of tandem estrogen response elements increases the estrogenic aclivity of a tamoxifen analogue. Cancer Lett., 92: 39-47, 1995.
32. Levenson, A. S., Tonetti, D. A., and Jordan, V. C. The estrogen-like effect of 4-hydroxylamoxifen on induction of transforming growth factor α mRNA in MDA-MB-231 breast cancer cells stably expressing the oestrogen receptor. Br. J. Cancer, in press.
33. Jordan, V. C., and Gosden, B. Differential antiestrogen actions in the immature rat uterus: a comparision of hydroxylated antiestrogens with high affinity for the estrogen receptor. J. Steroid Biochem., 19: 1249-1258, 1983.
34. Jordan, V. C., and Gosden, B. Inhibition of the uterotrophic activity of estrogens and antiestrogens by the short acting antiestrogen LY 117018. Endocrinology, 113: 463-468, 1983.