Differential response of estrogen receptor subtypes to 1,3-diarylindene and 2,3-diarylindene ligands

Journal of Medicinal Chemistry

Volumn 48, Issue 19, 2005, Pages 5989-6003

  Clegg, Nicola J ^a   Paruthiyil, Sreenivasan ^a,b   Leitman, Dale C ^a,b   Scanlan, Thomas S ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 [6 HYDROXY 2 (4 HYDROXYPHENYL) 1H INDEN 3 YL]BENZAMIDE; 4 HYDROXYTAMOXIFEN; DIETHYLSTILBESTROL; ESTRADIOL; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; INDENE DERIVATIVE; INDENESTROL A; LIGAND; METHYL 4 [6 HYDROXY 2 (4 HYDROXYPHENYL) 1H INDEN 3 YL]BENZOATE; RALOXIFENE; RECEPTOR SUBTYPE; TAMOXIFEN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CELL PROLIFERATION; CONTROLLED STUDY; DEPROTECTION REACTION; DRUG ACTIVITY; ESTROGEN RESPONSIVE ELEMENT; HORMONE RECEPTOR INTERACTION; HUMAN; HUMAN CELL; HUMAN TISSUE; LIGAND BINDING; MOLECULAR MODEL; REPORTER GENE; REPRODUCTION; SIGNAL TRANSDUCTION; TRANSCRIPTION REGULATION;

ANTINEOPLASTIC AGENTS; BINDING, COMPETITIVE; CELL LINE, TUMOR; CELL PROLIFERATION; ESTRADIOL; ESTROGEN ANTAGONISTS; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; FLUORESCENCE POLARIZATION; FLUORESCENT DYES; GENES, REPORTER; HUMANS; INDENES; LIGANDS; RESPONSE ELEMENTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 24944569173     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050226i     Document Type: Article

References (65)

1. Weatherman, R. V.; Fletterick, R. J.; Scanlan, T. S. Nuclear-receptor ligands and ligand-binding domains. Annu. Rev. Biochem. 1999, 68, 559-581.
2. Jordan, V. C. Antiestrogens and selective estrogen receptor modulators as multifunctional medicines. 1. Receptor interactions. J. Med. Chem. 2003, 46, 883-908.
3. Smith, C. L.; O'Malley, B. W. Coregulator function: a key to understanding tissue specificity of selective receptor modulators. Endocr. Rev. 2004, 25, 45-71.
4. Paech, K.; Webb, P.; Kuiper, G. G.; Nilsson, S.; Gustafsson, J. et al. Differential ligand activation of estrogen receptors ERalpha and ERbeta at AP1 sites. Science 1997, 277, 1508-1510.
5. Weatherman, R. V.; Clegg, N. J.; Scanlan, T. S. Differential SERM activation of the estrogen receptors (ERalpha and ER-beta) at AP-1 sites. Chem. Biol. 2001, 8, 427-436.
6. Rosenfeld, M. G.; Glass, C. K. Coregulator codes of transcriptional regulation by nuclear receptors. J. Biol. Chem. 2001, 276, 36865-36868.
7. Glass, C. K.; Rosenfeld, M. G. The Coregulator exchange in transcriptional functions of nuclear receptors. Genes Dev. 2000, 14, 121-141.
8. Qiu, J.; Bosch, M. A.; Tobias, S. C.; Grandy, D. K.; Scanlan, T. S. et al. Rapid signaling of estrogen in hypothalamic neurons involves a novel G-protein-coupled estrogen receptor that activates protein kinase C. J. Neurosci. 2003, 23, 9529-9540.
9. Katzenellenbogen, J. A.; Carlson, K. E.; Katzenellenbogen, B. S. Facile geometric isomerization of phenolic nonsteroidal estrogens and antiestrogens: limitations to the interpretation of experiments characterizing the activity of individual isomers. J. Steroid Biochem. 1985, 22, 589-596.
10. Katzenellenbogen, B. S.; Norman, M. J.; Eckert, R. L.; Peltz, S. W.; Mangel, W. F. Bioactivities, estrogen receptor interactions, and plasminogen activator-inducing activities of tamoxifen and hydroxy-tamoxifen isomers in MCF-7 human breast cancer cells. Cancer Res. 1984, 44, 112-119.
11. Robertson, D. W.; Katzenellenbogen, J. A.; Long, D. J.; Rorke, E. A.; Katzenellenbogen, B. S. Tamoxifen antiestrogens. A comparison of the activity, pharmacokinetics, and metabolic activation of the cis and trans isomers of tamoxifen. J. Steroid Biochem. 1982, 16, 1-13.
12. Lednicer, D.; Lyster, S. C.; Aspergren, B. D.; Duncan, G. W. Mammalian antifertility agents. 3. 1-Aryl-2-phenyl-1,2,3,4-tetrahydro-1-naphthols, 1-aryl-2-phenyl-3,4-dihydronaphthalenes, and their derivatives. J. Med. Chem. 1966, 9, 172-176.
13. Lednicer, D.; Lyster, S. C.; Duncan, G. W. Mammalian antifertility agents. IV. Basic 3,4-dihydronaphthalenes and 1,2,3,4-tetrahydro-1-naphthols. J. Med. Chem. 1967, 10, 78-84.
14. McCague, R.; Kuroda, R.; Leclercq, G.; Stoessel, S. Synthesis and estrogen receptor binding of 6,7-dihydro-8-phenyl-9-[4-[2-(dimethylamino)ethoxy] phenyl]-5H-benzocycloheptene, a nonisomerizable analogue of tamoxifen. X-ray crystallographic studies. J. Med. Chem. 1986, 29, 2053-2059.
15. Adler, E.; Hagglund, B. Ark Kemi Mineral Geol. 1945, 19A, 1.
16. Korach, K. S.; Metzler, M.; McLachlan, J. A. Estrogenic activity in vivo and in vitro of some diethylstilbestrol metabolites and analogs. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 468-471.
17. Korach, K. S.; Metzler, M.; McLachlan, J. A. Diethylstilbestrol metabolites and analogues. New probes for the study of hormone action. J. Biol. Chem. 1979, 254, 8963-8968.
18. Korach, K. S.; Fox-Davies, C.; Quarmby, V. E.; Swaisgood, M. H. Diethylstilbestrol metabolites and analogs. Biochemical probes for differential stimulation of uterine estrogen responses. J. Biol. Chem. 1985, 260, 15420-15426.
19. Korach, K. S.; Levy, L. A.; Sarver, P. J. Estrogen receptor stereochemistry, receptor binding and hormonal responses. J. Steroid Biochem. 1987, 27, 281-290.
20. Curtis, S. W.; Shi, H.; Teng, C.; Korach, K. S. Promoter and species specific differential estrogen-mediated gene transcription in the uterus and cultured cells using structurally altered agonists. J. Mol. Endocrinol. 1997, 18, 203-211.
21. Chae, K.; Gibson, M. K.; Korach, K. S. Estrogen Receptor Stereochemistry -Ligand Binding Orientation and Influence on Biological Activity. Mol. Pharmacol. 1991, 40, 806-811.
22. Kohno, H.; Bocchinfuso, W. P.; Gandini, O.; Curtis, S. W.; Korach, K. S. Mutational analysis of the estrogen receptor ligand-binding domain: influence of ligand structure and stereochemistry on transactivation. J. Mol. Endocrinol. 1996, 16, 277-285.
23. Mueller, S. O.; Hall, J. M.; Swope, D. L.; Pedersen, L. C.; Korach, K. S. Molecular determinants of the stereoselectivity of agonist activity of estrogen receptors (ER) alpha and beta. J. Biol. Chem. 2003, 278, 12255-12262.
24. Korach, K. S.; Chae, K.; Levy, L. A.; Duax, W. L.; Sarver, P. J. Diethylstilbestrol metabolites and analogs. Stereochemical probes for the estrogen receptor binding site. J. Biol. Chem. 1989, 264, 5642-5647.
25. Chae, K.; Johnston, S. H.; Korach, K. S. Multiple estrogen binding sites in the uterus: stereochemistry of receptor and nonreceptor binding of diethylstilbestrol and its metabolites. J. Steroid Biochem. Mol. Biol. 1991, 38, 35-42.
26. Sadler, B. R.; Cho, S. J.; Ishaq, K. S.; Chae, K.; Korach, K. S. Three-dimensional quantitative structure-activity relationship study of nonsteroidal estrogen receptor ligands using the comparative molecular field analysis/cross-validated r2-guided region selection approach. J. Med. Chem. 1998, 41, 2261-2267.
27. Lednicer, D.; Babcock, J. C.; Marlatt, P. E.; Lyster, S. C.; Duncan, G. W. Mammalian Antifertility Agents. I. Derivatives of 2,3-Diphenylindenes. J. Med. Chem. 1965, 39, 52-57.
28. Duncan, G. W.; Lednicer, D. Method for Controlling Birds and Rodents; US Patent Office, 1967; p 46.
29. Anstead, G. M.; Altenbach, R. J.; Wilson, S. R.; Katzenellenbogen, J. A. 2,3-Diarylindenes and 2,3-diarylindenones: synthesis, molecular structure, photochemistry, estrogen receptor binding affinity, and comparisons with related triarylethylenes. J. Med. Chem. 1988, 31, 1316-1326.
30. Anstead, G. M.; Katzenellenbogen, J. A. Fluorescence Properties of 2,3-Diarylindenes. J. Phys. Chem. 1988, 92, 6249-6258.
31. Anstead, G. M.; Peterson, C. S.; Pinney, K. G.; Wilson, S. R.; Katzenellenbogen, J. A. Torsionally and hydrophobically modified 2,3-diarylindenes as estrogen receptor ligands. J. Med. Chem. 1990, 33, 2726-2734.
32. Anstead, G. M.; Wilson, S. R.; Katzenellenbogen, J. A. 2-Arylindenes and 2-arylindenones: molecular structures and considerations in the binding orientation of unsymmetrical non-steroidal ligands to the estrogen receptor. J. Med. Chem. 1989, 32, 2163-2171.
33. Anstead, G. M.; Peterson, C. S.; Katzenellenbogen, J. A. Hydroxylated 2,3-diarylindenes: synthesis, estrogen receptor binding affinity, and binding orientation considerations. J. Steroid Biochem. 1989, 33, 877-887.
34. Kirkiacharian, S.; Koutsourakis, P. G.; Philibert, D.; Bouchoux, F.; Van de Velde, P. Synthesis and relative binding affinity to steroid receptors and antiproliferative activity on MCF-7 cells of 2,3-disubstituted indenes. Farmaco 1999, 54, 678-683.
35. Bryant, H. U.; Jones, C. D.; Pennington, P. A. Indene compounds having activity as SERMs; European Patent Office: London, Great Britain, 1998; p 33.
36. Shiau, A. K.; Barstad, D.; Loria, P. M.; Cheng, L.; Kushner, P. J. et al. The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell 1998, 95, 927-937.
37. Pike, A. C.; Brzozowski, A. M.; Hubbard, R. E.; Bonn, T.; Thorsell, A. G. et al. Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist. EMBO J. 1999, 18, 4608-4618.
38. Brzozowski, A. M.; Pike, A. C.; Dauter, Z.; Hubbard, R. E.; Bonn, T. et al. Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 1997, 389, 753-758.
39. Korach, K. S.; Chae, K.; Gibson, M.; Curtis, S. Estrogen Receptor Stereochemistry - Ligand Binding and Hormonal Responsiveness. Steroids 1991, 56, 263-270.
40. Chae, K.; Levy, L. A.; Korach, K. S. Chromatographic separation and isolation of the enantiomers of diethylstilbestrol metabolites. J. Chromatogr. 1988, 439, 484-487.
41. Parker, C. E.; Levy, L. A.; Smith, R. W.; Yamaguchi, K.; Gaskell, S. J. et al. Separation and detection of enantiomers of stilbestrol analogues by combined high-performance liquid chromatography-thermospray mass spectrometry. J. Chromatogr. 1985, 344, 378-384.
42. Sadler, B. R.; Chae, K.; Ishaq, K. S.; Korach, K. S. Separation of indenestrol A and B isomers and enantiomers by high-performance liquid chromatography. J. Chromatogr. A 1998, 799, 117-124.
43. Anstead, G. M.; Ensign, J. L.; Peterson, C. S.; Katzenellenbogen, J. A. 2-Arylindenes and 2-arylindenones: synthesis of probes to study the binding orientation of unsymmetrical nonsteroidal ligands to the estrogen receptor. J. Org. Chem. 1989, 54, 1495-1491.
44. Plentl, A. A.; Bogert, M. T. The Synthesis of Tricyclic Hydrocarbons Related to Stilbestrol. J. Am. Chem. Soc. 1941, 63, 989-995.
45. Meurling, L. Alkylation of Indenyllithium and Alkylindenyllithium Compounds. Acta Chem. Scand., Ser. B, Org. Chem. Biochem. 1974, B28, 295-300.
46. Cedheim, L.; Eberson, L. Simple Procedure for Preparation of 1-Alkylindenes. Synthesis (Stuttgart) 1973, 159-159.
47. Silverman, T.; Bogert, M. T. The Synthesis of Some Indene and Dihydronaphthalene Derivatives Related to Stilbestrol. J. Org. Chem. 1948, 11, 34-49.
48. Brown, D. W.; Denman, C.; O'Donnell, H. The Chemistry of Indanones. Part 1. The Ring Closure of 2-(4-Methoxyphenyl)-3-(3-Methoxyphenyl)propionic Acid. J. Chem. Soc. C 1971, 19, 3195-3198.
49. Hwang, K. J.; Oneil, J. P.; Katzenellenbogen, J. A. 5, 6, 11, 12-Tetrahydrochrysenes - Synthesis of Rigid Stilbene Systems Designed to Be Fluorescent Ligands for the Estrogen-Receptor. J. Org. Chem. 1992, 57, 1262-1271.
50. Blizzard, T. A.; Mosley, R. T.; Birzin, E. T.; Chan, W.; Hammond, M. L. Comparison of 2-phenylspiroindenes and 2-phenylspiroindenediones as estrogen receptor ligands-modeling and binding data don't agree! Bioorg. Med. Chem. Lett. 2004, 14, 1317-1321.
51. Muthyala, R. S.; Sheng, S.; Carlson, K. E.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Bridged bicyclic cores containing a 1,1-diarylethylene motif are high-affinity subtype-selective ligands for the estrogen receptor. J. Med. Chem. 2003, 46, 1589-1602.
52. Mortensen, D. S.; Rodriguez, A. L.; Carlson, K. E.; Sun, J.; Katzenellenbogen, B. S. et al. Synthesis and biological evaluation of a novel series of furans: ligands selective for estrogen receptor alpha. J. Med. Chem. 2001, 44, 3838-3848.
53. Sun, J.; Meyers, M. J.; Fink, B. E.; Rajendran, R.; Katzenellenbogen, J. A. et al. Novel ligands that function as selective estrogens or antiestrogens for estrogen receptor-alpha or estrogen receptor-beta. Endocrinology 1999, 140, 800-804.
54. Shiau, A. K.; Barstad, D.; Radek, J. T.; Meyers, M. J.; Nettles, K. W. et al. Structural characterization of a subtype-selective ligand reveals a novel mode of estrogen receptor antagonism. Nat. Struct. Biol. 2002, 9, 359-364.
55. Nettles, K. W.; Sun, J.; Radek, J. T.; Sheng, S.; Rodriguez, A. L. et al. Allosteric control of ligand selectivity between estrogen receptors alpha and beta: implications for other nuclear receptors. Mol. Cell 2004, 13, 317-327.
56. Webb, P.; Lopez, G. N.; Uht, R. M.; Kushner, P. J. Tamoxifen Activation of the Estrogen Receptor/AP-1 Pathway - Potential Origin For the Cell-Specific Estrogen-Like Effects of Antiestrogens. Mol. Endocrinol. 1995, 9, 443-456.
57. Paruthiyil, S.; Parmar, H.; Kerekatte, V.; Cunha, G. R.; Firestone, G. L. et al. Estrogen receptor beta inhibits human breast cancer cell proliferation and tumor formation by causing a G2 cell cycle arrest. Cancer Res. 2004, 64, 423-428.
58. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Safe and convenient procedure for solvent purification. Organometallics 1996, 15, 1518-1520.
59. Hone, N. D.; Baxter, A. D. Organosilicon Compounds and Their Use in Combinatorial Chemistry; European Patent Office: London, Great Britain, 1998.
60. Myers, T. C.; Pratt, R. J.; Morgan, R. L.; O'Donnell, J.; Jensen, E. V. Hormone Analogues. I. Preparation of Intermediate Ketones for the Synthesis of Stilbestrol Analogues. J. Am. Chem. Soc. 1955, 77, 5655-5657.
61. Skaddan, M. B.; Katzenellenbogen, J. A. Integrated "3+1" oxorhenium(V) complexes as estrogen mimics. Bioconjugate Chem. 1999, 10, 119-129.
62. Matsuo, J.; Koga, K. Enantioselective alpha-alkylation of phenylacetic acid using a chiral bidentate lithium amide as a chiral auxiliary. Chem. Pharm. Bull. 1997, 45, 2122-2124.
63. Hauser, C. R.; Chambers, W. J. Alkylations of the α-Carbon of Phenylacetic and Diphenylacetic Acids with Benzyl Chloride and Related Halides by Alkali Amides. J. Am. Chem. Soc. 1956, 78, 4942-4944.
64. Carpino, L. A.; Lin, Y. Z. Benz[/]Indene. J. Org. Chem. 1990, 55, 247-250.
65. Garro-Helion, F.; Merzouk, A.; Guibe, F. Mild and selective palladium(0)-catalyzed deallylation of allylic amines. Allylamine and diallylamine as very convenient ammonia equivalents for the synthesis of primary amines. J. Org. Chem. 1993, 58, 6109-6113.