Inhibition of estrogen receptor α-mediated transcription by antiestrogenic 1,1-dichloro-2,2,3-triarylcyclopropanes

Molecular Pharmacology

Volumn 66, Issue 4, 2004, Pages 970-977

  Cheng, Peng ^b   Kanterewicz, Beatriz ^b   Hershberger, Pamela A ^b   McCarty Jr , Kenneth S ^b   Day, Billy W ^b   Nichols, Mark ^a  

^a UNIVERSITY OF PITTSBURGH CANCER INSTITUTE   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYTAMOXIFEN; ANTIESTROGEN; CYCLOPROPANE DERIVATIVE; ESTROGEN RECEPTOR ALPHA; FULVESTRANT; GLUTATHIONE TRANSFERASE; PHORBOL 13 ACETATE 12 MYRISTATE; PROTEIN P160; TRANSCRIPTION FACTOR AP 1;

ARTICLE; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG EFFECT; DRUG POTENTIATION; ENZYME ACTIVITY; ENZYME INHIBITION; ESTROGEN RESPONSIVE ELEMENT; HUMAN; HUMAN CELL; PRIORITY JOURNAL; PROTEIN BINDING; TRANSCRIPTION INITIATION;

ANIMALS; BENZENE DERIVATIVES; CYCLOPROPANES; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR MODULATORS; HUMANS; MICE; TRANSCRIPTION, GENETIC; TUMOR CELLS, CULTURED;

EID: 4944229974     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: 10.1124/mol.104.000752     Document Type: Article

References (42)

1. Anzick SL, Kononen J, Walker RL, Azorsa DO, Tanner MM, Guan XY, Sauter G, Kallioniemi OP, Trent JM, and Meltzer PS (1997) AIB-1, a steroid receptor coactivator amplified in breast and ovarian cancer. Science (Wash DC) 277:965-968.
2. Berry M, Metzger D, and Chambon P (1990) Role of the two activating domains of the oestrogen receptor in the cell-type and promoter-context dependent agonistic activity of the anti-oestrogen 4-hydroxytamoxifen. EMBO (Eur Mol Biol Organ) J 9:2811-2818.
3. Brzozowski AM, Pike ACW, Dauter Z, Hubbard RE, Bonn T, Engstrom O, Ohman L, Greene GL, Gustafsson JA, and Carlquist M (1997) Molecular basis of agonism and antagonism in the oestrogen receptor. Nature (Lond) 389:753-758.
4. Darimont BD, Wagner RL, Apriletti JW, Stallcup MR, Kushner PJ, Baxter JD, Fletterick RJ, and Yamamoto KR (1998) Structure and specificity of nuclear receptor-coactivator interactions. Genes Dev 12:3343-3356.
5. Dauvois S, Danielian PS, White R, and Parker MG (1992) Antiestrogen ICI 164,384 reduces cellular estrogen receptor content by increasing its turnover. Proc Natl Acad Sci USA 89:4037-4041.
6. Dauvois S, White R, and Parker MG (1993) The antiestrogen ICI 182780 disrupts estrogen receptor nucleocytoplasmic shuttling. J Cell Sci 106:1377-1388.
7. Day BW, Magadan RA, Pento JT, Jain PT, Mousissian GK, and Meyer KL (1991) Synthesis and biological evaluation of 1,1-dichloro-2,2,3-triarylcycloprpanes as pure antiestrogens. J Med Chem 34:842-851.
8. Dubik D and Shiu RP (1988) Transcriptional regulation of c-myc oncogene expression by estrogen in hormone-responsive human breast cancer cells. J Biol Chem 263:12705-12708.
9. Eng FCS, Barsalou A, Akutsu N, Mercier I, Zechel C, Mader S, and White JH (1998) Different classes of coactivators recognize distinct overlapping binding sites on the estrogen receptor ligand binding domain. J Biol Chem 273:28371-28377.
10. Feng W, Ribeiro RCJ, Wagner RL, Nguyen H, Apriletti JW, Fletterick RJ, Baxter JD, Kushner PJ, and West BL (1998) Hormone-dependent coactivator binding to a hydrophobic cleft on nuclear receptors. Science (Wash DC) 280:1747-1749.
11. Fisch TM, Prywes R, and Roeder RG (1989) An AP1-binding site in the c-fos gene can mediate induction by epidermal growth factor and 12-O-tetradecanoyl phorbol-13-acetate. Mol Cell Biol 9:1327-1331.
12. Fisher B, Costantino JP, Wickerham DL, Redmond CK, Kavanah M, Cronin WM, Vogel V, Robidoux A, Dimitrov N, Atkins J, et al. (1999) Tamoxifen for prevention of breast cancer: report of the national surgical adjuvant breast and bowel project P-1 study. J Natl Cancer Inst 90:1371-1388.
13. Frasor J, Danes JM, Komm B, Chang KCN, Lyttle CR, and Katzenellenbogen BS (2003) Profiling of estrogen-up- and down-regulated gene expression in human breast cancer cells: insights into gene networks and pathways underlying estrogenic control of proliferation and cell phenotype. Endocrinology 144:4562-4574.
14. Gottardis MM, Robinson SP, Satyaswaroop PG, and Jordan VC (1988) Contrasting actions of tamoxifen on endometrial and breast tumor growth in the athymic mouse. Cancer Res 48:812-815.
15. Gronemeyer H and Laudet V (1995) Transcription factors 3: nuclear receptors. Protein Profile 2:1173-1308.
16. Hong H, Darimont BD, Ma H, Yang L, Yamamoto KR, and Stallcup MR (1999) An additional region of coactivator GRIP1 required for interaction with the hormone-binding domains of a subset of nuclear receptors. J Biol Chem 274:3496-3502.
17. Hong H, Kohli K, Trivedi A, Johnson DL, and Stallcup MR (1996) GRIP1, a novel mouse protein that serves as a transcriptional coactivator in yeast for the hormone binding domains of steroid receptors. Proc Natl Acad Sci USA 93:4948-4952.
18. Katzenellenbogen JA, O'Malley BW, and Katzenellenbogen BS (1996) Tripartite steroid hormone receptor pharmacology: interaction with multiple effector sites as a basis for the cell- and promoter-specific action of these hormones. Mol Endocrinol 10:119-131.
19. Kushner PJ, Agard DA, Greene GL, Scanlan TS, Shiau AK, Uht RM, and Webb P (2000) Estrogen receptor pathways to AP-1. J Steroid Biochem Mol Biol 74:311-317.
20. Magarian RA and Benjamin EJ (1975) Syntheses of cyclopropyl analogs of stilbene and stilbenediol as possible antiestrogens. J Pharm Sci 64:1626-1632.
21. McDonnell DP (1999) The molecular pharmacology of SERMs. Trends Endocrinol Metab 10:301-311.
22. McInerney EM, Rose DW, Flynn SE, Westin S, Mullen TM, Krones A, Inostroza J, Torchia J, Nolte RT, Assa-Munt N, et al. (1998) Determinants of coactivator LXXLL motif specificity in nuclear receptor transcriptional activation. Genes Dev 12:3357-3368.
23. Morris JD, Fan D, Stallcup MR, and McDonnell DP (1998) Enhancement of estrogen receptor transcriptional activity by the coactivator GRIP-1 highlights the role of activation function 2 in determining estrogen receptor pharmacology. J Biol Chem 273:6679-6688.
24. Onate SA, Tsai SY, Tsai MJ, and O'Malley BW (1995) Sequence and characterization of a coactivator for the steroid hormone receptor superfamily. Science (Wash DC) 270:1354-1357.
25. Overacre LB and Magarian RA (1998) Synthesis and biological evaluation of cyclopropyl analogs of the antiestrogen MER 25. Bioorg Chem 26:15-31.
26. Paech K, Webb P, Kuiper GGJM, Nilsson S, Gustafsson J-Å, Kushner PJ, and Scanlan TS (1997) Differential ligand activation of estrogen receptors ERα and ERβ at AP1 sites. Science (Wash DC) 277:1508-1510.
27. Saville B, Wormke M, Wang F, Nguyen T, Enmark E, Kuiper G, Gustafsson JA, and Safe S (2000) Ligand-, cell- and estrogen receptor subtype (α/β)-dependent activation at GC-rich (Sp1) promoter elements. J Biol Chem 275:5379-5387.
28. Shang Y, Hu X, DiRenzo J, Lazar MA, and Brown M (2000) Cofactor dynamics and sufficiency in estrogen receptor-regulated transcription. Cell 103:843-852.
29. Shang Y and Brown M (2002) Molecular determinants for the tissue specificity of SERMs. Science (Wash DC) 295:2465-2468.
30. Shiau AK, Barstad D, Loria PM, Cheng L, Kushner PJ, Agard DA, and Greene GL (1998) The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell 95:927-937.
31. Singh S, Meyer KL, and Magarian RA (1996) Synthesis and chiral separation of some antitumor agents. Bioorg Chem 24:81-94.
32. Smith CL and O'Malley BW (2004) Coregulator function: a key to understanding tissue specificity of selective receptor modulators. Endocrine Rev 25:45-71.
33. Smith CL, Oñate SA, Tsai MJ, and O'Malley BW (1998) CREB binding protein acts synergistically with steroid coactivator-1 to enhance steroid receptor dependent transcription. Proc Natl Acad Sci USA 93:8884-8888.
34. Suen C-S, Berrodin TJ, Mastroeni R, Cheskis BJ, Lyttle CR, and Frail DE (1998) A transcriptional coactivator, steroid receptor coactivator-3, selectively augments steroid receptor transcriptional activity. J Biol Chem 273:27645-27653.
35. Ter Haar E, Hamel E, Balachandran R, and Day BW (1997) Cellular targets of the anti-breast cancer agent Z-1,1-dichloro-2,3-diphenylcyclopropane: type II estrogen binding sites and tubulin. Anticancer Res 17:1861-1870.
36. Tonetti DA and Jordan VC (1996) Targeted anti-estrogens to treat and prevent diseases in women. Mol Med Today 2:218-223.
37. Tsai M-J and O'Malley BW (1994) Molecular mechanisms of action of steroid/thyroid receptor superfamily members. Annu Rev Biochem 63:451-486.
38. Tzukerman MT, Esty A, Santiso-Mere D, Danielian P, Parker MG, Stein RB, Pike JW, and McDonnell DP (1994) 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.
39. Voegel JJ, Heine MJS, Zechel C, Chambon P, and Gronemeyer H (1996) TIF2, a 160 kDa transcriptional mediator for the ligand-dependent activation function AF-2 of nuclear receptors. EMBO (Eur Mol Biol Organ) J 15:3667-3675.
40. Wärnmark A, Almlöf T, Leers J, Gustafsson JÅ and Treuter E (2001) Differential recruitment of the mammalian mediator subunit TRAP220 by estrogen receptors ERα and ERβ. J Biol Chem 276:23397-23404.
41. Wong C-W, Komm B, and Cheskis BJ (2001) Structure-function evaluation of ERα and ERβ interplay with SRC family coactivators: ER selective ligands. Biochemistry 40:6756-6765.
42. Yao TP, Ku G, Zhou ND, Scully R, and Livingston DM (1996) The nuclear hormone receptor coactivator SRC-1 is a specific target of p300. Proc Natl Acad Sci USA 93:10626-10631.