2,5-Diphenylfuran-based pure antiestrogens with selectivity for the estrogen receptor α

Journal of Steroid Biochemistry and Molecular Biology

Volumn 94, Issue 1-3 SPEC. ISS., 2005, Pages 57-66

  Zimmermann, Jochen ^a   Liebl, Renate ^a   Von Angerer, Erwin ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Antiestrogen; Diphenylfuran; Estrogen receptor ; Hormone dependent breast cancer; Structure activity relationship

Indexed keywords

2,5 BIS(4 HYDROXYPHENYL) 3 ETHYL 4 (6 PYRROLIDINOHEXYL)FURAN; 2,5 BIS(4 HYDROXYPHENYL) 3 ETHYL 4 [10 (PENTYLSULFONYL)DECYL]FURAN; 2,5 BIS(4 HYDROXYPHENYL) 3 ETHYL 4 [6 [N METHYL N (3 PENTYLSULFANYLPROPYL) AMINO]HEXYL]FURAN; 2,5 BIS(4 HYDROXYPHENYL) 3 METHYL 4 (6 PYRROLIDINOHEXYL)FURAN; 2,5 BIS(4 HYDROXYPHENYL) 3 [10 (PENTYLSULFONYL)DECYL] 4 PROPYLFURAN; 2,5 BIS(4 HYDROXYPHENYL) 3 [6 [N METHYL N (3 PENTYLSULFANYLPROPYL)AMINO] HEXYL] 4 PROPYLFURAN; 2,5 BIS(4 HYDROXYPHENYL) 4 METHYL 3 [10 (PENTYLSULFONYL)DECYL]FURAN; 2,5 BIS(4 HYDROXYPHENYL) 4 METHYL 3 [6 [N METHYL N (3 PENTYLSULFANYLPROPYL) AMINO]HEXYL]FURAN; ANTIESTROGEN; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; FURAN DERIVATIVE; LUCIFERASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BREAST CANCER; CANCER CELL; CANCER INHIBITION; CELL STIMULATION; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG TARGETING; ESTROGEN RESPONSIVE ELEMENT; FEMALE; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; IC 50; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; WILD TYPE;

MINK CELL FOCUS-FORMING VIRUS;

EID: 18144382577     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2004.12.018     Document Type: Article

References (24)

1. G. Cheng, Z. Weihua, M. Warner, and J.A. Gustafsson Estrogen receptors ERα and ERβ in proliferation in the rodent mammary gland Proc. Natl. Acad. Sci. U.S.A. 2004
2. A.M. Fowler, N. Solodin, M.T. Preisler-Mashek, P. Zhang, A.V. Lee, and E.T. Alarid Increases in estrogen receptor-alpha concentration in breast cancer cells promote serine 118/104/106-independent AF-1 transactivation and growth in the absence of estrogen FASEB J. 18 2004 81 93
3. S. Ali, and R.C. Coombes Estrogen receptor alpha in human breast cancer: occurrence and significance J. Mammary. Gland. Biol. Neoplasia 5 2000 271 281
4. S. Oesterreich, P. Zhang, R.L. Guler, X. Sun, E.M. Curran, W.V. Welshons, C.K. Osborne, and A.V. Lee Re-expression of estrogen receptor alpha in estrogen receptor alpha-negative MCF-7 cells restores both estrogen and insulin-like growth factor-mediated signaling and growth Cancer Res. 61 2001 5771 5777
5. C. Palmieri, G.J. Cheng, S. Saji, M. Zelada-Hedman, A. Warri, Z. Weihua, S. Van Noorden, T. Wahlstrom, R.C. Coombes, M. Warner, and J.A. Gustafsson Estrogen receptor beta in breast cancer Endocr. Relat. Cancer 9 2002 1 13
6. A.M. Shaaban, P.A. O'Neill, M.P. Davies, R. Sibson, C.R. West, P.H. Smith, and C.S. Foster Declining estrogen receptor-beta expression defines malignant progression of human breast neoplasia Am. J. Surg. Pathol. 27 2003 1502 1512
7. S. Paruthiyil, H. Parmar, V. Kerekatte, G.R. Cunha, G.L. Firestone, and D.C. Leitman Estrogen receptor beta inhibits human breast cancer cell proliferation and tumor formation by causing a G2 cell cycle arrest Cancer Res. 64 2004 423 428
8. J. Matthews, and J.A. Gustafsson Estrogen signaling: a subtle balance between ERα and ERβ Mol. Intervent. 3 2003 281 292
9. A. Strom, J. Hartman, J.S. Foster, S. Kietz, J. Wimalasena, and J.A. Gustafsson Estrogen receptor beta inhibits 17beta-estradiol-stimulated proliferation of the breast cancer cell line T47D Proc. Natl. Acad. Sci. U.S.A. 101 2004 1566 1571
10. I. Laios, F. Journe, G. Laurent, D. Nonclercq, R.A. Toillon, H.S. Seo, and G. Leclercq Mechanisms governing the accumulation of estrogen receptor alpha in MCF-7 breast cancer cells treated with hydroxytamoxifen and related antiestrogens J. Steroid Biochem. Mol. Biol. 87 2003 207 221
11. S.E. Jones Fulvestrant: an estrogen receptor antagonist that downregulates the estrogen receptor Semin. Oncol. 30 2003 14 20
12. J. Hoffmann, R. Bohlmann, N. Heinrich, H. Hofmeister, J. Kroll, H. Kunzer, R.B. Lichtner, Y. Nishino, K. Parczyk, G. Sauer, H. Gieschen, H.F. Ulbrich, and M.R. Schneider Characterization of new estrogen receptor destabilizing compounds: effects on estrogen-sensitive and tamoxifen-resistant breast cancer J. Natl. Cancer Inst. 96 2004 210 218
13. G.A. Nishiguchi, A.L. Rodriguez, and J.A. Katzenellenbogen Diaryl-dialkyl-substituted pyrazoles: regioselective synthesis and binding affinity for the estrogen receptor Bioorg. Med. Chem. Lett. 12 2002 947 950
14. J. Sun, Y.R. Huang, W.R. Harrington, S. Sheng, J.A. Katzenellenbogen, and B.S. Katzenellenbogen Antagonists selective for estrogen receptor alpha Endocrinology 143 2002 941 947
15. D.S. Mortensen, A.L. Rodriguez, K.E. Carlson, J. Sun, B.S. Katzenellenbogen, and J.A. Katzenellenbogen Synthesis and biological evaluation of a novel series of furans: ligands selective for estrogen receptor α J. Med. Chem. 44 2001 3838 3848
16. J. Renaud, S.F. Bischoff, T. Buhl, P. Floersheim, B. Fournier, C. Halleux, J. Kallen, H. Keller, J.M. Schlaeppi, and W. Stark Estrogen receptor modulators: identification and structure-activity relationships of potent ERα-selective tetrahydroisoquinoline ligands J. Med. Chem. 46 2003 2945 2957
17. C. Biberger, and E. von Angerer 2-Phenylindoles with sulfur containing side chains. Estrogen receptor affinity, antiestrogenic potency, and antitumor activity J. Steroid Biochem. Mol. Biol. 58 1996 31 43
18. F. Hafner, E. Holler, and E. von Angerer Effect of growth factors on estrogen receptor mediated gene expression J. Steroid Biochem. Mol. Biol. 58 1996 385 393
19. M.M. Bradford A rapid and sensitive method for quantification of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 72 1976 248
20. S. Leichtl, and E. von Angerer 2-Phenylbenzo[b]thiophene-based antiestrogens with mammary tumor inhibiting activity Arch. Pharm. Pharm. Med. Chem. 331 1998 283 289
21. T. Golob, C. Biberger, G. Walter, and E. von Angerer Antiestrogenic activities of 3,8-dihydroxy-6,11-dihydrobenzo[a]carbazoles with sulfur-containing side chains Arch. Pharm. Pharm. Med. Chem. 333 2000 305 311
22. Y. Nishino, M.R. Schneider, H. Michna, and E. von Angerer Pharmacological characterisation of a novel oestrogen antagonist, ZK 119010, in rats and mice J. Endocrinol. 130 1991 409 414
23. S.R. Stauffer, Y.R. Huang, Z.D. Aron, C.J. Coletta, J. Sun, B.S. Katzenellenbogen, and J.A. Katzenellenbogen Triarylpyrazoles with basic side chains: development of pyrazole-based estrogen receptor antagonists Bioorg. Med. Chem. 9 2001 151 161
24. D.S. Mortensen, A.L. Rodriguez, J. Sun, B.S. Katzenellenbogen, and J.A. Katzenellenbogen Furans with basic side chains: synthesis and biological evaluation of a novel series of antagonists with selectivity for the estrogen receptor α Bioorg. Med. Chem. Lett. 11 2001 2521 2524