Steroidal affinity labels of the estrogen receptor α. 4. Electrophilic 11β-aryl derivatives of estradiol

Journal of Medicinal Chemistry

Volumn 43, Issue 4, 2000, Pages 613-628

  Aliau, Sigrid ^a   Delettre, Georges ^b   Mattras, Hélène ^a   El Garrouj, Driss ^a,c   Nique, François ^b   Teutsch, Georges ^b   Borgna, Jean Louis ^a  

^a INSERM   (France)

^b SANOFI   (France)

^c SIDI MOHAMED BEN ABDELLAH UNIVERSITY   (Morocco)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMO N [2 [4 (3,17BETA DIHYDROXYESTRA 1,3,5(10) TRIEN 11BETA YL)PHENOXY]ETHYL] N METHYLACETAMIDE; 2 BROMO N [5 [4 (3,17BETA DIHYDROXYESTRA 1,3,5(10) TRIEN 11BETA YL)PHENOXY]PENTYL] N METHYLACETAMIDE; ACETAMIDE DERIVATIVE; CARBON; CHLOROACETAMIDE; CYSTEINE; ESTRADIOL DERIVATIVE; ESTROGEN RECEPTOR; IODIDE; PHENYL GROUP; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BINDING SITE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; FEMALE; LAMB; NONHUMAN;

AFFINITY LABELS; ANIMALS; CYTOSOL; ESTRADIOL; FEMALE; HUMANS; INDICATORS AND REAGENTS; METHYL METHANESULFONATE; RADIOLIGAND ASSAY; RECEPTORS, ESTROGEN; SHEEP; STRUCTURE-ACTIVITY RELATIONSHIP; UTERUS;

EID: 0034003129     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990179s     Document Type: Article

References (35)

1. Green, S.; Walter, P.; Kumar, V.; Krust, A.; Bornet, J.-M.; Argos, P.; Chambon, P. Human oestrogen receptor cDNA: sequence, expression and homology to v-erb-A. Nature 1986, 320, 134-139.
2. Greene, G. L.; Gilna, P.; Waterfield, M.; Baker, A.; Hort, Y.; Shine, J. Sequence and expression of human estrogen receptor complementary DNA. Science 1986, 231, 1150-1154.
3. Kuiper, G. G. J. M.; Enmark, E.; Pelto-Huikko, M.; Nilsson, S.; Gustafsson, J.-A. Cloning of a novel estrogen receptor expressed in rat prostate and ovary. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 5925-5930.
4. Tremblay, G. B.; Tremblay, A.; Copeland, N. G.; Gilbert, D. J.; Jenkins, N. A,; Labrie, F.; Giguère, V. Cloning, chromosomal localization and functional analysis of the murine estrogen receptor β. Mol. Endocrinol 1998, 11, 353-365.
5. Mosselman, S.; Polman, J.; Dijkema, R. ERβ: identification and characterization of a novel human estrogen receptor. FEBS Lett. 1996, 392, 49-53.
6. Kuiper, G. G. J. M.; Carlson, B.; Grandien, K.; Enmark, E.; Häggblad, J.; Nilsson, S.; Gustafsson, J.-A. Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors α and β. Endocrinology 1997, 138, 863-870.
7. Enmark, E.; Pelto-Huikko, M.; Grandien, K.; Lagercrantz, S.; Lagercrantz, J.; Fried, G.; Nordenskjöld, M.; Gustafsson, J.-A. Human estrogen receptor β gene structure, chromosomal localization and expression pattern. J. Clin. Endocrinol. Metab. 1997, 82, 4258-4265.
8. Tanenbaum, D. M.; Wang, Y.; Williams, S. P.; Sigler, P. Crystallographic comparison of the estrogen and progesterone receptor's ligand binding domains. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 5998-6003.
9. Brzozowski, A. M.; Pike, A. C. W.; Dauter, Z.; Hubbard, R. E.; Bonn, T.; Engström, O.; Öhman, L.; Greene, G. L.; Gustafsson, J.-A.; Carlquist, M. Molecular basis of agonism and antagonism in the estrogen receptor. Nature 1997, 389, 753-758.
10. Shiau, A. K.; Barstad, D.; Loria, P. M.; Cheng, L.; Kushner, P. J.; Agard, D. A.; Greene, G. L. The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell 1998, 95, 927-937.
11. Bourguet, W.; Ruff, M.; Chambon, P.; Gronemeyer, H.; Moras, D. Crystal structure of the ligand-binding domain of the human nuclear receptor RXRa, Nature 1995, 375, 377-382.
12. Renaud, J.-P.; Rochel, N.; Ruff, M.; Vivat, V.; Chambon, P.; Gronemeyer, H.; Moras, D. Crystal structure of the RAR-γ ligand binding domain bound to all-trans retinoic acid. Nature 1995, 378, 681-689.
13. Wagner, R. L.; Apriletti, J. W.; McGrath, M. E.; West, B. L.; Baxter, J. D.; Fletterick, R. J. A structural role for hormone in the thyroid hormone receptor. Nature 1995, 378, 690-697.
14. Uppenberg, J.; Svensson, C.; Jaki, M.; Bertilsson, G.; Jenderberg, L.; Berkenstam, A. Crystal structure of the ligand binding domain of the human nuclear receptor PPARγ. J. Biol. Chem. 1998, 273, 31108-31112.
15. Williams, S. P.; Sigler, P. B. Atomic structure of the progesterone complexed with its receptor. Nature 1998, 393, 392-396.
16. Nolte, R. T.; Wisely, G. B.; Westin, S.; Cobb, J. E.; Lambert, M. H.; Kurokawa, R.; Rosenfeld, M. G.; Willson, T. M.; Glass, C. K.; Milburn, M. V. Ligand binding and co-activator assembly of the peroxisome proliferator-activated receptor-γ. Nature 1998, 395, 137-143.
17. Harlow, K. W.; Smith, D. N.; Katzenellenbogen, J. A.; Greene, G. L.; Katzenellenbogen, B. S. Identification of cysteine 530 as the covalent attachment site of an affinity-labeling estrogen (ketononestrol aziridine) and antiestrogen (tamoxifen aziridine) in the human estrogen receptor. J. Biol. Chem. 1989, 264, 17476-17485.
18. Reese, J. C.; Wooge, C. H.; Katzenellenbogen, B. S. Identification of two cysteines closely positioned in the ligand binding pocket of the human estrogen receptor: roles in ligand binding and transcriptional activation. Mol. Endocrinol. 1992, 6, 2160-2166.
19. El Garrouj, D.; Aumelas, A.; Borgna, J.-L. Steroidal affinity labels of the estrogen receptor. 1. 17α-(bromoacetoxy)alkyl/ alkynylestradiols. J. Med. Chem. 1993, 36, 2973-2983.
20. El Garrouj, D.; Aliau, S.; Aumelas, A.; Borgna, J.-L. Steroidal affinity labels of the estrogen receptor. 2. 17α-[(haloacetamido)-alkyl]estradiols. J. Med. Chem. 1995, 38, 2339-2348.
21. Aliau, S.; El Garrouj, D.; Yasri, A.; Katzenellenbogen, B. S.; Borgna, J.-L. 17α-[(Haloacetamido)alkyl]estradiols alkylate the human estrogen receptor at cysteine residues 417 and 530. Biochemistry 1997, 36, 5861-5867.
22. Lobaccaro, C.; Pons, J.-F.; Duchesne, M.-J.; Auzou, G.; Pons, M.; Nique, F.; Teutsch, G.; Borgna, J.-L. Steroidal affinity labels of the estrogen receptor. 3. Estradiol 11β-n-alkyl derivatives bearing a terminal electrophilic group: antiestrogenic and cytotoxic properties. J. Med. Chem. 1997, 40, 2217-2227.
23. Nique, F.; Van de Velde, P.; Brémaud, J.; Hardy, M.; Philibert, D.; Teutsch, G. 11β-Amidoalkoxyphenyl estradiols, a new series of pure antiestrogens. J. Steroid Biochem. Mol. Biol. 1994, 50, 21-29.
24. Van de Velde, P.; Nique, F.; Bouchoux, F.; Brémaud, J.; Hameau, M.-C.; Lucas D.; Moratille C.; Viet, S.; Philibert, D.; Teutsch, G. RU 58668, a new pure antiestrogen inducing a regression of human mammary carcinoma implanted in nude mice. J. Steroid Biochem. Mol. Biol 1994, 48, 187-196.
25. Bélanger, A.; Philibert, D.; Teutsch, G. Regio and stereospecific synthesis of 11β-substituted 19-nor-steroids. Steroids 1981, 37, 361-382.
26. Claussner, A.; Nedelec, L.; Philibert, D.: Van de Velde, P. New 19-norsteroids. European Patent EP 0 384 842 (Priority 24/02/ 89, FR 8 902 384); Chem. Abstr. 1990, 115, 256464.
27. Korenman, S. G. Relation between estrogen receptor inhibitory activity and binding to cytosol of rabbit and human uterus. Endocrinology 1970, 87, 1119-1123.
28. Claussner, A.; Nedelec, L.; Nique, F.; Philibert, D.; Teutsch, G.; Van de Velde, P. 11β-Amidoalkyl estradiols, a new series of pure antiestrogens. J. Steroid Biochem. Mol. Biol. 1992, 41, 609-614.
29. Anstead, G. M.; Carlson, K. E.; Katzenellenbogen, J. A. The estradiol pharmacophore: ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site. Steroids 1997, 62, 268-303.
30. Reese, J. C.; Katzenellenbogen, B. S. Mutagenesis of cysteines in the hormone binding domain of the human estrogen receptor. J. Biol. Chem. 1991, 266, 10880-10887.
31. Zablocki, J. A.; Katzenellenbogen, J. A.; Carbon, K. E.; Norman, M. J.; Katzenellenbogen, B. S. Estrogenic affinity labels: synthesis, irreversible receptor binding, and bioactivity of aziridine substituted hexestrols derivatives. J. Med. Chem. 1987, 30, 829-838.
32. Madigou, T.; Tiffoche, C.; Lazennec, G.; Pelletier, J.; Thieulant, M.-L. The sheep estrogen receptor: cloning and regulation of expression in the hypothalamo-pituitary axis. Mol. Cell. Endocrinol. 1996, 121, 153-163.
33. Hegy, G.; Shackleton, C.; Carlquist, M.; Bonn, T.; Engstrom, O.; Sjoholm, P.; Witkowska, H. Carboxymethylation of the human estrogen receptor ligand-binding domain-estradiol complex: HPLC/ESMS peptide mapping shows that cysteine 447 does not react with iodoacetic acid. Steroids 1996, 61, 367-373.
34. Aliau, S.; Mattras, H.; Richard, E.; Borgna, J.-L. Cysteine 530 of the human estrogen receptor a is the main covalent attachment site of 11β-(aziridinylakoxyphenyl)estradiols. Biochemistry 1999, 38, 14752-14762.
35. Layne, E. Spectrophotometric and turbidimetric methods for measuring proteins. Methods Enzymol. 1957, 3, 444-454.