Recent advances in structure of progestins and their binding to progesterone receptors

References

• Graham JD, Clarke C. Progesterone receptors – animal models and cell signaling in breast cancer: expression and transcriptional activity of progesterone receptor A and progesterone receptor B in mammalian cells. Breast Cancer Res 2002;4:187–90
   PubMed Web of Science ®Google Scholar
• Wen DX, Xu YF, Mais DE, et al. The A and B isoforms of the human progesterone receptor operate through distinct signaling pathways within target cells. Mol Cell Biol 1994;14:8356–64
   PubMed Web of Science ®Google Scholar
• Sartorius CA, Melville MY, Hovland AR, et al. A third transactivation function (AF3) of human progesterone receptors located in the unique N-terminal segment of the B-isoform. Mol Endocrinol 1994;8:1347–60
   PubMed Web of Science ®Google Scholar
• Giangrande PH, Kimbrel EA, Edwards DP, McDonnell DP. The opposing transcriptional activities of the two isoforms of the human progesterone receptor are due to differential cofactor binding. Mol Cell Biol 2000;20:3102–15
   PubMed Web of Science ®Google Scholar
• Conneely OM. Perspective: female steroid hormone action. Endocrinology 2001;142:2194–9
   PubMed Web of Science ®Google Scholar
• Liu Z, Auboeuf D, Wong J, et al. Coactivator/corepressor ratios modulate PR-mediated transcription by the selective receptor modulator RU486. Proc Natl Acad Sci USA 2002;99:7940–4
   PubMed Web of Science ®Google Scholar
• Karteris E, Zervou S, Pang Y, et al. Progesterone signaling in human myometrium through two novel membrane G protein-coupled receptors: potential role in functional progesterone withdrawal at term. Mol Endocrinol 2006;20:1519–34
   PubMed Web of Science ®Google Scholar
• Hopp TA, Weiss HL, Hilsenbeck SG, et al. Breast cancer patients with progesterone receptor PR-A-rich tumors have poorer disease-free survival rates. Clin Cancer Res 2004;10:2751–60
   PubMed Web of Science ®Google Scholar
• Shyamala G, Yang X, Silberstein G, et al. Transgenic mice carrying an imbalance in the native ratio of A to B forms of progesterone receptor exhibit developmental abnormalities in mammary glands. Proc Natl Acad Sci USA 1998;95:696–701
   PubMed Web of Science ®Google Scholar
• Daniel AR, Knutson TP, Lange CA. Signaling inputs to progesterone receptor gene regulation and promoter selectivity. Mol Cell Endocrinol 2009;308:47–52
   PubMed Web of Science ®Google Scholar
• Hagan CR, Regan TM, Dressing GE, Lange CA. ck2-dependent phosphorylation of progesterone receptors (PR) on ser81 regulates PR-B isoform-specific target gene expression in breast cancer cells. Mol Cell Biol 2011;31:2439–52
   PubMed Web of Science ®Google Scholar
• Moore NL, Narayanan R, Weigel NL. Cyclin dependent kinase 2 and the regulation of human progesterone receptor activity. Steroids 2007;72:202–9
   PubMed Web of Science ®Google Scholar
• Obr AE, Grimm SL, Bishop KA, et al. Progesterone receptor and Stat5 signaling cross talk through RANKL in mammary epithelial cells. Mol Endocrinol 2013;27:1808–24
   PubMed Web of Science ®Google Scholar
• Zhu Y, Rice CD, Pang Y, et al. Cloning, expression, and characterization of a membrane progestin receptor and evidence it is an intermediary in meiotic maturation of fish oocytes. Proc Natl Acad Sci USA 2003;100:2231–6
   PubMed Web of Science ®Google Scholar
• Sleiter N, Pang Y, Park C, et al. Progesterone receptor A (PRA) and PRB-independent effects of progesterone on gonadotropin-releasing hormone release. Endocrinology 2009;150:3833–44
   PubMed Web of Science ®Google Scholar
• Frye CA, Sumida K, Lydon JP, et al. Mid-aged and aged wild-type and progestin receptor knockout (PRKO) mice demonstrate rapid progesterone and 3α,5α-THP-facilitated lordosis. Psychopharmacology 2006;185:423–32
   PubMed Web of Science ®Google Scholar
• Pang Y, Dong J, Thomas P. Characterization, neurosteroid binding and brain distribution of human membrane progesterone receptors δ and ε (mPRδ and mPRε) and mPRδ involvement in neurosteroid inhibition of apoptosis. Endocrinology 2012;154:283–95
   PubMed Web of Science ®Google Scholar
• Peluso JJ, Romak J, Liu X. Progesterone receptor membrane component-1 (PGRMC1) is the mediator of progesterone’s antiapoptotic action in spontaneously immortalized granulosa cells as revealed by PGRMC1 small interfering ribonucleic acid treatment and functional analysis of PGRMC1 mutations. Endocrinology 2008;149:534–43
   PubMed Web of Science ®Google Scholar
• Dressing G, Alyea R, Pang Y, Thomas P. Membrane progesterone receptors (mPRs) mediate progestin induced antimorbidity in breast cancer cells and are expressed in human breast tumors. Horm Cancer 2012;3:101–12
   PubMed Web of Science ®Google Scholar
• Dressing GE, Pang Y, Dong J, Thomas P. Progestin signaling through mPRα in Atlantic Croaker Granulosa/Theca cell cocultures and its involvement in progestin inhibition of apoptosis. Endocrinology 2010;151:5916–26
   PubMed Web of Science ®Google Scholar
• Thomas P, Pang Y, Dong J. Enhancement of cell surface expression and receptor functions of membrane progestin receptor alpha (mPRα) by progesterone receptor membrane component 1 (PGRMC1): evidence for a role of PGRMC1 as an adaptor protein for steroid receptors. Endocrinology 2014:155:1107–19
   Google Scholar
• Stanczyk FZ. All progestins are not created equal. Steroids 2003;68:879–90
   PubMed Web of Science ®Google Scholar
• Gagne D, Pons M, Philibert D. RU 38486: a potent antiglucocorticoid in vitro and in vivo. J Steroid Biochem 1985;23:247–51
   PubMedGoogle Scholar
• Lebeau M-C, Baulieu EE. Steroid antagonists and receptor-associated proteins. Hum Reprod 1994;9:437–44
   PubMed Web of Science ®Google Scholar
• Cadepond PF, Ulmann MDPA, Baulieu MDPEE. RU486 (MIFEPRISTONE): mechanisms of action and clinical uses. Annu Rev Med 1997;48:129–56
   PubMed Web of Science ®Google Scholar
• Gravanis A, Schaison G, George M, et al. Endometrial and pituitary responses to the steroidal antiprogestin RU 486in postmenopausal women. J Clin Endocrinol Metab 1985;60:156–63
   PubMed Web of Science ®Google Scholar
• Attardi BJ, Burgenson J, Hild SA, Reel JR. In vitro antiprogestational/antiglucocorticoid activity and progestin and glucocorticoid receptor binding of the putative metabolites and synthetic derivatives of CDB-2914, CDB-4124, and mifepristone. J Steroid Biochem Mol Biol 2004;88:277–88
   PubMed Web of Science ®Google Scholar
• Attardi BJ, Burgenson J, Hild SA, et al. CDB-4124 and its putative monodemethylated metabolite, CDB-4453, are potent antiprogestins with reduced antiglucocorticoid activity: in vitro comparison to mifepristone and CDB-2914. Mol Cell Endocrinol 2002;188:111–23
   PubMed Web of Science ®Google Scholar
• Melis GB, Piras B, Marotto MF, et al. Pharmacokinetic evaluation of ulipristal acetate for uterine leiomyoma treatment. Expert Opin Drug Metab Toxicol 2012;8:901–8
   PubMed Web of Science ®Google Scholar
• Donnez J, Tatarchuk TF, Bouchard P, et al. Ulipristal acetate versus placebo for fibroid treatment before surgery. N Engl J Med 2012;366:409–20
   PubMed Web of Science ®Google Scholar
• Lusher SJ, Raaijmakers HCA, Vu-Pham D, et al. X-ray structures of progesterone receptor ligand binding domain in its agonist state reveal differing mechanisms for mixed profiles of 11β-substituted steroids. J Biol Chem 2012;287:20333–43
   PubMed Web of Science ®Google Scholar
• Han SJ, Tsai SY, Tsai M-J, O’Malley BW. Distinct temporal and spatial activities of RU486 on progesterone receptor function in reproductive organs of ovariectomized mice. Endocrinology 2007;148:2471–86
   PubMed Web of Science ®Google Scholar
• Meyer ME, Pornon A, Ji J, et al. Agonistic and antagonistic activities of RU486 on the functions of the human progesterone receptor. EMBO J 1990;9:3923–32
   PubMed Web of Science ®Google Scholar
• Robertson JFR, Willsher PC, Winterbottom L, et al. Onapristone, a progesterone receptor antagonist, as first-line therapy in primary breast cancer. Eur J Cancer 1999;35:214–18
   PubMed Web of Science ®Google Scholar
• Chen W, Ohara N, Wang J, et al. A novel selective progesterone receptor modulator asoprisnil (J867) inhibits proliferation and induces apoptosis in cultured human uterine leiomyoma cells in the absence of comparable effects on myometrial cells. J Clin Endocrinol Metab 2006;91:1296–304
   PubMed Web of Science ®Google Scholar
• Afhüppe W, Beekman JM, Otto C, et al. In vitro characterization of ZK 230211 – A type III progesterone receptor antagonist with enhanced antiproliferative properties. J Steroid Biochem Mol Biol 2010;119:45–55
   PubMed Web of Science ®Google Scholar
• Jonat W, Bachelot T, Ruhstaller T, et al. Randomized phase II study of lonaprisan as second-line therapy for progesterone receptor-positive breast cancer. Ann Oncol 2013;24:2543–8
   PubMed Web of Science ®Google Scholar
• Klijn JGM, Setyono-Han B, Foekens JA. Progesterone antagonists and progesterone receptor modulators in the treatment of breast cancer. Steroids 2000;65:825–30
   PubMed Web of Science ®Google Scholar
• Yuan H, Upadhyay G, Lu J, et al. The chemopreventive effect of mifepristone on mammary tumorigenesis is associated with an anti-invasive and anti-inflammatory gene signature. Cancer Prev Res 2012;5:754–64
   PubMed Web of Science ®Google Scholar
• Chwalisz K, Perez MC, DeManno D, et al. Selective progesterone receptor modulator development and use in the treatment of leiomyomata and endometriosis. Endocr Rev 2005;26:423–38
   PubMed Web of Science ®Google Scholar
• Williams ARW, Critchley HOD, Osei J, et al. The effects of the selective progesterone receptor modulator asoprisnil on the morphology of uterine tissues after 3 months treatment in patients with symptomatic uterine leiomyomata. Hum Reprod 2007;22:1696–704
   PubMed Web of Science ®Google Scholar
• Pasqualini JR. Progestins in the menopause in healthy women and breast cancer patients. Special issue: progestogens and the climacteric female. Maturitas 2009;62:343–8
   PubMed Web of Science ®Google Scholar
• Klein-Hitpass L, Cato ACB, Henderson D, Ryffel GU. Two types of antiprogestins identified by their differential action in transcriptionally active extracts from T47D cells. Nucleic Acids Res 1991;19:1227–34
   PubMed Web of Science ®Google Scholar
• Trussell J. Update on and correction to the cost effectiveness of contraceptives in the United States. Contraception 2012;85:218
   PubMed Web of Science ®Google Scholar
• Dahmoun M, Boman K, Cajander S, Bäckström T. Intratumoral effects of medroxy-progesterone on proliferation, apoptosis, and sex steroid receptors in endometrioid endometrial adenocarcinoma. Gynecol Oncol 2004;92:116–26
   PubMed Web of Science ®Google Scholar
• Katsuki Y, Shibutani Y, Aoki D, Nozawa S. Dienogest, a novel synthetic steroid, overcomes hormone-dependent cancer in a different manner than progestins. Cancer 1997;79:169–76
   PubMed Web of Science ®Google Scholar
• Nakamura M, Katsuki Y, Shibutani Y, Oikawa T. Dienogest, a synthetic steroid, suppresses both embryonic and tumor-cell-induced angiogenesis. Eur J Pharmacol 1999;386:33–40
   PubMed Web of Science ®Google Scholar
• Oettel M, Carol W, Elger W, et al. A 19-norprogestin without 17α-ethinyl group II: dienogest from a pharmacodynamic point of view. Drugs Today 1995;31:517–36
   Google Scholar
• Hapgood JP, Africander D, Louw R, et al. Potency of progestogens used in hormonal therapy: toward understanding differential actions. J Steroid Biochem Mol Biol. [Epub ahead of print]. doi: 10.1016/j.jsbmb.2013.08.001
   Google Scholar
• Escande A, Servant N, Rabenoelina F, et al. Regulation of activities of steroid hormone receptors by tibolone and its primary metabolites. J Steroid Biochem Mol Biol 2009;116:8–14
   PubMed Web of Science ®Google Scholar
• Rižner TL, Brožič P, Doucette C, et al. Selectivity and potency of the retroprogesterone dydrogesterone in vitro. Steroids 2011;76:607–15
   PubMed Web of Science ®Google Scholar
• Loose DS, Stancel GM. Estrogens and progestins. In: Brunton LL, Lazo JS, Parker KL, eds. Goodman & Gilman's the pharmacological basis of therapeutics. 11th ed. New York: McGraw-Hill; 2006:1541–71
   Google Scholar
• Wiebe J, Zhang G, Welch I, Cadieux-Pitre H-A. Progesterone metabolites regulate induction, growth, and suppression of estrogen- and progesterone receptor-negative human breast cell tumors. Breast Cancer Res 2013;15:R38
   PubMed Web of Science ®Google Scholar
• Cabeza M, García-Lorenzana M, García M, et al. New-D-homoandrost-4,6-diene derivatives as potent progesterone receptor antagonist. Steroids 2010;75:101–8
   PubMed Web of Science ®Google Scholar
• Garrido M, Cabeza M, Cortés F, et al. Cytotoxic effect of novel dehydroepiandrosterone derivatives on different cancer cell lines. Eur J Med Chem 2013;68:301–11
   PubMed Web of Science ®Google Scholar
• Chabbert-Buffet N, Meduri G, Bouchard P, Spitz IM. Selective progesterone receptor modulators and progesterone antagonists: mechanisms of action and clinical applications. Hum Reprod Update 2005;11:293–307
   PubMed Web of Science ®Google Scholar
• DeManno D, Elger W, Garg R, et al. Asoprisnil (J867): a selective progesterone receptor modulator for gynecological therapy. Steroids 2003;68:1019–32
   PubMed Web of Science ®Google Scholar
• Madauss KP, Grygielko ET, Deng S-J, et al. A structural and in vitro characterization of asoprisnil: a selective progesterone receptor modulator. Mol Endocrinol 2007;21:1066–81
   PubMed Web of Science ®Google Scholar
• Busia L, Faus H, Hoffmann J, Haendler B. The antiprogestin Lonaprisan inhibits breast cancer cell proliferation by inducing p21 expression. Mol Cell Endocrinol 2011;333:37–46
   PubMed Web of Science ®Google Scholar
• Van Look PFA, von Hertzen H. Clinical uses of antiprogestogens. Hum Reprod Update 1995;1:19–34
   PubMed Web of Science ®Google Scholar