Oral Selective Estrogen Receptor Downregulators (SERDs), a Breakthrough Endocrine Therapy for Breast Cancer

Journal of Medicinal Chemistry

Volumn 58, Issue 12, 2015, Pages 4883-4887

  McDonnell, Donald P ^a   Wardell, Suzanne E ^a   Norris, John D ^a  

^a DUKE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

11 [4 [[5 [(4,4,5,5,5 PENTAFLUOROPENTYL)SULFONYL]PENTYL]OXY]PHENYL]ESTRADIOL; 4 (1,2 DIPHENYL 1 BUTENYL)CINNAMIC ACID; ACOLBIFENE; ANTIESTROGEN; ANTINEOPLASTIC HORMONE AGONISTS AND ANTAGONISTS; ARZOXIFENE; AZD9496; BAZEDOXIFENE; ESTROGEN RECEPTOR ALPHA; FULVESTRANT; GDC 0810; GW7604; HORMONE RECEPTOR STIMULATING AGENT; PIPENDOXIFENE; SELECTIVE ESTROGEN RECEPTOR DOWNREGULATOR; STEROID HORMONE RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG; AROMATASE INHIBITOR; SELECTIVE ESTROGEN RECEPTOR MODULATOR; TAMOXIFEN;

ANTINEOPLASTIC ACTIVITY; BREAST CANCER; CANCER HORMONE THERAPY; CLINICAL TRIAL (TOPIC); CONFORMATIONAL TRANSITION; DRUG BIOAVAILABILITY; HUMAN; NONHUMAN; PHASE 1 CLINICAL TRIAL (TOPIC); PROTEIN CONFORMATION; PROTEIN EXPRESSION; PROTEIN PROTEIN INTERACTION; REVIEW; SIGNAL TRANSDUCTION; ANALOGS AND DERIVATIVES; ANIMAL; BREAST; BREAST NEOPLASMS; CHEMISTRY; DRUG DEVELOPMENT; DRUG EFFECTS; FEMALE; METABOLISM;

ANIMALS; ANTINEOPLASTIC AGENTS, HORMONAL; AROMATASE INHIBITORS; BREAST; BREAST NEOPLASMS; DRUG DISCOVERY; ESTROGEN RECEPTOR ALPHA; FEMALE; HUMANS; SELECTIVE ESTROGEN RECEPTOR MODULATORS; TAMOXIFEN;

EID: 84933073465     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b00760     Document Type: Review

References (27)

1. Mayer, E. L. Targeting breast cancer with CDK inhibitors Curr. Oncol. Rep. 2015, 17, 443
2. Baselga, J.; Campone, M.; Piccart, M.; Burris, H. A., 3rd; Rugo, H. S.; Sahmoud, T.; Noguchi, S.; Gnant, M.; Pritchard, K. I.; Lebrun, F.; Beck, J. T.; Ito, Y.; Yardley, D.; Deleu, I.; Perez, A.; Bachelot, T.; Vittori, L.; Xu, Z.; Mukhopadhyay, P.; Lebwohl, D.; Hortobagyi, G. N. Everolimus in postmenopausal hormone-receptor-positive advanced breast cancer N. Engl. J. Med. 2012, 366, 520-529
3. Johnston, S. R. Endocrine manipulation in advanced breast cancer: recent advances with SERM therapies Clin. Cancer Res. 2001, 7, 4376s-4387s (discussion 4411s-4412s)
4. Deshmane, V.; Krishnamurthy, S.; Melemed, A. S.; Peterson, P.; Buzdar, A. U. Phase III double-blind trial of arzoxifene compared with tamoxifen for locally advanced or metastatic breast cancer J. Clin. Oncol. 2007, 25, 4967-4973
5. DeFriend, D. J.; Howell, A.; Nicholson, R. I.; Anderson, E.; Dowsett, M.; Mansel, R. E.; Blamey, R. W.; Bundred, N. J.; Robertson, J. F.; Saunders, C.; Baum, M.; Walton, P.; Sutcliffe, F.; Wakeling, A. E. Investigation of a new pure antiestrogen (ICI 182780) in women with primary breast cancer Cancer Res. 1994, 54, 408-414
6. Robertson, J. F. R. Fulvestrant (Faslodex)-how to make a good drug better Oncologist 2007, 12, 774-784
7. Lai, A.; Kahraman, M.; Govek, S.; Nagasawa, J.; Bonnefous, C.; Julien, J.; Douglas, K.; Sensintaffar, J.; Lu, N.; Lee, K.-j.; Aparicio, A.; Kaufman, J.; Qian, J.; Shao, G.; Prudente, R.; Moon, M. J.; Joseph, J. D.; Darimont, B.; Brigham, D.; Grillot, K.; Heyman, R.; Rix, P. J.; Hager, J. H.; Smith, N. D. Identification of GDC-0810 (ARN-810), an orally bioavailable selective estrogen receptor degrader (SERD) that demonstrates robust activity in tamoxifen-resistant breast cancer xenografts J. Med. Chem. 2015, 10.1021/acs.jmedchem.5b00054
8. McDonnell, D. P.; Wardell, S. E. The molecular mechanisms underlying the pharmacological actions of ER modulators: implications for new drug discovery in breast cancer Curr. Opin. Pharmacol. 2010, 10, 620-628
9. Gottardis, M. M.; Robinson, S. P.; Satyaswaroop, P. G.; Jordan, V. C. Contrasting actions of tamoxifen on endometrial and breast tumor growth in the athymic mouse Cancer Res. 1988, 48, 812-815
10. Love, R. R.; Mazess, R. B.; Barden, H. S.; Epstein, S.; Newcomb, P. A.; Jordan, V. C.; Carbone, P. P.; DeMets, D. L. Effects of tamoxifen on bone mineral density in postmenopausal women with breast cancer N. Engl. J. Med. 1992, 326, 852-856
11. Musgrove, E. A.; Sutherland, R. L. Biological determinants of endocrine resistance in breast cancer Nat. Rev. Cancer 2009, 9, 631-643
12. Norris, J. D.; Paige, L. A.; Christensen, D. J.; Chang, C.-Y.; Huacani, M. R.; Fan, D.; Hamilton, P. T.; Fowlkes, D. M.; McDonnell, D. P. Peptide antagonists of the human estrogen receptor Science 1999, 285, 744-746
13. 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
14. Connor, C. E.; Norris, J. D.; Broadwater, G.; Willson, T. M.; Gottardis, M. M.; Dewhirst, M. W.; McDonnell, D. P. Circumventing tamoxifen resistance in breast cancers using antiestrogens that induce unique conformational changes in the estrogen receptor Cancer Res. 2001, 61, 2917-2922
15. Willson, T. M.; Henke, B. R.; Momtahen, T. M.; Charifson, P. S.; Batchelor, K. W.; Lubahn, D. B.; Moore, L. B.; Oliver, B. B.; Sauls, H. R.; Triantafillou, J. A.; Wolfe, S. G.; Baer, P. G. 3-[4-(1,2-Diphenylbut-1- enyl)phenyl]acrylic acid: A non-steroidal estrogen with functional selectivity for bone over uterus in rats J. Med. Chem. 1994, 37, 1550-1552
16. Wu, Y. V. L.; Yang, X.; Ren, Z.; McDonnell, D. P.; Norris, J. D.; Willson, T. M.; Greene, G. L. Structural basis for an unexpected mode of SERM-mediated ER antagonism Mol. Cell 2005, 18, 413-424
17. Schafer, J. M.; Lee, E. S.; Dardes, R. C.; Bentrem, D.; ORegan, R. M.; De Los Reyes, A.; Jordan, V. C. Analysis of cross-resistance of the selective estrogen receptor modulators arzoxifene (LY353381) and LY117018 in tamoxifen-stimulated breast cancer xenografts Clin. Cancer Res. 2001, 7, 2505-2512
18. Masamura, S.; Santner, S. J.; Heitjan, D. F.; Santen, R. J. Estrogen deprivation causes estradiol hypersensitivity in human breast cancer cells J. Clin. Endocrinol. Metab. 1995, 80, 2918-2925
19. Jeselsohn, R.; Yelensky, R.; Buchwalter, G.; Frampton, G.; Meric-Bernstam, F.; Gonzalez-Angulo, A. M.; Ferrer-Lozano, J.; Perez-Fidalgo, J. A.; Cristofanilli, M.; Gomez, H.; Arteaga, C. L.; Giltnane, J.; Balko, J. M.; Cronin, M. T.; Jarosz, M.; Sun, J.; Hawryluk, M.; Lipson, D.; Otto, G.; Ross, J. S.; Dvir, A.; Soussan-Gutman, L.; Wolf, I.; Rubinek, T.; Gilmore, L.; Schnitt, S.; Come, S. E.; Pusztai, L.; Stephens, P.; Brown, M.; Miller, V. A. Emergence of constitutively active estrogen receptor-alpha mutations in pretreated advanced estrogen receptor-positive breast cancer Clin. Cancer Res. 2014, 20, 1757-1767
20. Freedman, R. A.; Anders, C. K. Treatment of breast cancer brain metastases Curr. Breast Cancer Rep. 2012, 4, 1-9
21. Duchnowska, R.; Dziadziuszko, R.; Trojanowski, T.; Mandat, T.; Och, W.; Czartoryska-Arlukowicz, B.; Radecka, B.; Olszewski, W.; Szubstarski, F.; Kozlowski, W.; Jarosz, B.; Rogowski, W.; Kowalczyk, A.; Limon, J.; Biernat, W.; Jassem, J.; Polish Brain Metastasis Consortium. Conversion of epidermal growth factor receptor 2 and hormone receptor expression in breast cancer metastases to the brain Breast Cancer Res. 2012, 14, R119
22. Simpson, E. R. Sources of estrogen and their importance J. Steroid Biochem. Mol. Biol. 2003, 86, 225-230
23. Creighton, C. J.; Hilger, A. M.; Murthy, S.; Rae, J. M.; Chinnaiyan, A. M.; El-Ashry, D. Activation of mitogen-activated protein kinase in estrogen receptor alpha-positive breast cancer cells in vitro induces an in vivo molecular phenotype of estrogen receptor alpha-negative human breast tumors Cancer Res. 2006, 66, 3903-3911
24. Xia, W.; Bacus, S.; Hegde, P.; Husain, I.; Strum, J.; Liu, L.; Paulazzo, G.; Lyass, L.; Trusk, P.; Hill, J.; Harris, J.; Spector, N. L. A model of acquired autoresistance to a potent ErbB2 tyrosine kinase inhibitor and a therapeutic strategy to prevent its onset in breast cancer Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 7795-7800
25. Bosch, A.; Li, Z.; Bergamaschi, A.; Ellis, H.; Toska, E.; Prat, A.; Tao, J. J.; Spratt, D. E.; Viola-Villegas, N. T.; Castel, P.; Minuesa, G.; Morse, N.; Rodon, J.; Ibrahim, Y.; Cortes, J.; Perez-Garcia, J.; Galvan, P.; Grueso, J.; Guzman, M.; Katzenellenbogen, J. A.; Kharas, M.; Lewis, J. S.; Dickler, M.; Serra, V.; Rosen, N.; Chandarlapaty, S.; Scaltriti, M.; Baselga, J. PI3K inhibition results in enhanced estrogen receptor function and dependence in hormone receptor-positive breast cancer Sci. Transl. Med. 2015, 7, 283ra51
26. Wijayaratne, A. L.; Nagel, S. C.; Paige, L. A.; Christensen, D. J.; Norris, J. D.; Fowlkes, D. M.; McDonnell, D. P. Comparative analyses of the mechanistic differences among antiestrogens Endocrinology 1999, 140, 5828-5840
27. Wittmann, B. M.; Sherk, A.; McDonnell, D. P. Definition of functionally important mechanistic differences among selective estrogen receptor down-regulators Cancer Res. 2007, 67, 9549-9560