In vitro and in vivo characterization of novel nonsteroidal progesterone receptor antagonists derived from the fungal metabolite PF1092C

Journal of Steroid Biochemistry and Molecular Biology

Volumn 82, Issue 2-3, 2002, Pages 217-223

  Tabata, Yuji ^a   Iizuka, Yumiko ^a   Masuda, Naomi Takei ^a   Shinei, Rie ^a   Kurihara, Ken Ichi ^a   Okonogi, Tsuneo ^a   Hoshiko, Shigeru ^a   Kurata, Yasushi ^a  

^a MEIJI SEIKA KAISHA LTD   (Japan)

Author keywords

McPhail test; Nonsteroidal progesterone receptor antagonist; PF1092; T47D; Tetrahydrobenzindolone; Tetrahydronaphthofuranone

Indexed keywords

ANDROGEN RECEPTOR; ANTIGESTAGEN; CP 8661; CP 8754; ESTROGEN RECEPTOR; FUNCTIONAL GROUP; GLUCOCORTICOID RECEPTOR; MIFEPRISTONE; PROGESTERONE; PROGESTERONE RECEPTOR; TRITIUM; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING ASSAY; BREAST CARCINOMA; CONTROLLED STUDY; DOSE RESPONSE; DRUG ACTIVITY; DRUG EFFECT; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENDOMETRIUM; FEMALE; HUMAN; HUMAN CELL; NONHUMAN; PROTEIN EXPRESSION; RABBIT; RECEPTOR AFFINITY; STRUCTURE ANALYSIS;

ANIMALS; BIOLOGICAL ASSAY; DOSE-RESPONSE RELATIONSHIP, DRUG; ENDOMETRIUM; ESTROGENS; FEMALE; GENE EXPRESSION REGULATION; GENES, REPORTER; HORMONE ANTAGONISTS; HUMANS; MOLECULAR STRUCTURE; NAPHTHOLS; PROGESTERONE; RABBITS; RECEPTORS, ANDROGEN; RECEPTORS, ESTROGEN; RECEPTORS, PROGESTERONE; SESQUITERPENES; TUMOR CELLS, CULTURED;

ORYCTOLAGUS CUNICULUS;

EID: 0036816016     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-0760(02)00157-7     Document Type: Article

References (26)

1. Christin-Maitre S., Bouchard P., Spitz I.M. Medical termination of pregnancy. N. Engl. J. Med. 342:2000;946-956.
2. Klijn J.G.M., Setyono-Han B., Sander H.J., Lamberts S.W.J., de Jong F.H., Deckers G.H., Foekens J.A. Pre-clinical and clinical treatment of breast cancer with antiprogestins. Hum. Reprod. 9(Suppl. 1):1994;181-189.
3. Kettel L.M., Murphy A.A., Morales A.J., Ulmann A., Baulieu E.E., Yen S.S.C. Treatment of endometriosis with the antiprogesterone mifepristone (RU486). Fertil. Steril. 65(Suppl. 1):1996;23-28.
4. Murphy A.A., Morales A.J., Kettel L.M., Yen S.S.C. Regression of uterine leiomyomata to the antiprogesterone RU486: dose-response effect. Fertil. Steril. 64:1995;187-190.
5. Grunberg S.M., Weiss M.H., Spitz I.M., Ahmadi J., Sadun A., Russell C.A., Lucci L., Stevenson L.L. Treatment of unresectable meningiomas with the antiprogesterone agent mifepristone. J. Neurosurg. 74:1991;861-866.
6. Wiechert R., Neef G. Synthesis of antiprogestational steroids. J. Steroid Biochem. 27:1987;851-858.
7. Teutsch G., Philibert D. History and perspectives of antiprogestins from the chemist's point of view. Hum. Reprod. 9:1994;12-31.
8. Hackenberg R., Hannig K., Beck S., Schmidt-Rhode P., Scholz A., Schulz K.-D. Androgen-like and anti-androgen-like effects of antiprogestins in human mammary cancer cells. Eur. J. Cancer. 32A:1996;696-701.
9. Spitz I.M., Bardin C.W. Clinical pharmacology of RU486: an antiprogestin and antiglucocorticoid. Contraception. 48:1993;403-444.
10. Pathirana C., Stein R.B., Berger T.S., Fenical W., Ianiro T., Mais D.E., Torres A., Goldman M.E. Nonsteroidal human progesterone receptor modulators from the marine alga Cymopolia barbata. Mol. Pharmacol. 47:1995;630-635.
11. Combs D.W., Reese K., Phillips A. Nonsteroidal progesterone receptor ligands. 1. 3-Aryl-1-benzoyl-1,4,5,6-tetrahydropyridazines. J. Med. Chem. 38:1995;4878-4879.
12. Hamann L.G., Farmer L.J., Johnson M.G., Bender S.L., Mais D.E., Wang M.W., Crombie D., Goldman M.E., Jones T.K. Synthesis and biological activity of novel nonsteroidal progesterone receptor antagonists based on cyclocymopol monomethyl ether. J. Med. Chem. 39:1996;1778-1789.
13. Pooley C.L.F., Edwards J.P., Goldman M.E., Wang M.W., Marschke K.B., Crombie D.L., Jones T.K. Discovery and preliminary SAR studies of a novel, nonsteroidal progesterone receptor antagonist pharmacophore. J. Med. Chem. 41:1998;3461-3466.
14. Zhi L., Tegley C.M., Marschke K.B., Mais D.E., Jones T.K. 5-Aryl-1,2,3,4-tetrahydrochromeno[3,4-f]quinolin-3-ones as a novel class of nonsteroidal progesterone receptor agonists: effect of A-ring modification. J. Med. Chem. 42:1999;1466-1472.
15. Palmer S., Campen C.A., Allan G.F., Rybczynski P., Haynes-Johnson D., Hutchins A., Kraft P., Kiddoe M., Lai M., Lombardi E., Pedersen P., Hodgen G., Combs D.W. Nonsteroidal progesterone receptor ligands with unprecedented receptor selectivity. J. Steroid Biochem. Mol. Biol. 75:2000;33-42.
16. Tabata Y., Miike N., Hatsu M., Kurata Y., Yaguchi T., Someya A., Miyadoh S., Hoshiko S., Tsuruoka T., Omoto S. PF1092A, B and C, new nonsteroidal progesterone receptor ligands produced by Penicillium oblatum. I. Taxonomy of producing strain, fermentation, isolation and biological activities. J. Antibiot. 50:1997;304-308.
17. Tabata Y., Hatsu M., Kurata Y., Miyajima K., Tani M., Sasaki T., Kodama Y., Tsuruoka T., Omoto S. PF1092A, B and C, new nonsteroidal progesterone receptor ligands produced by Penicillium oblatum. II. Physico-chemical properties and structure elucidation. J. Antibiot. 50:1997;309-313.
18. Kurihara K., Tanabe K., Shinei R., Okonogi T., Ohtsuka Y., Omoto S., Yasuda S., Tatsuta K. Synthesis of (±)-PF1092A, B, and C; new nonsteroidal progesterone receptor ligands. J. Antibiot. 50:1997;360-362.
19. Harimaya K., Magome E., Tabata Y., Sasaki T., Tsuruoka T. Chemical conversion of PR toxin into new eremophilanolides as progesterone receptor ligands. Sci. Rep. Meiji Seika Kaisha. 36:1997;19-27.
20. Tatsuta K., Yasuda S., Kurihara K., Tanabe K., Shinei R., Okonogi T. Total synthesis of progesterone receptor ligands, (-)-PF1092A, B, and C. Tetrahedron Lett. 38:1997;1439-1442.
21. Kurihara K., Tanabe K., Yamamoto Y., Shinei R., Ajito K., Okonogi T. Synthesis and structure-activity relationships of new nonsteroidal progesterone receptor ligands. Bioorg. Med. Chem. Lett. 9:1999;1837-1842.
22. Tabata Y., Iizuka Y., Kashiwa J., Takei Masuda N., Shinei R., Kurihara K., Okonogi T., Hoshiko S., Kurata Y. Fungal metabolite, PF1092 compounds and their derivatives, are nonsteroidal and selective progesterone receptor modulators. Eur. J. Pharmacol. 430:2001;159-165.
23. Markiewicz L., Gurpide E. Estrogenic and progestagenic activities coexisting in steroidal drugs: quantitative evaluation by in vitro bioassays with human cells. J. Steroid Biochem. Mol. Biol. 48:1994;89-94.
24. McPhail M.K. The assay of progestin. J. Physiol. 83:1934;145-156.
25. Michna H., Nishino Y., Neef G., McGuire W.L., Schneider M.R. Progesterone antagonist: tumor-inhibiting potential and mechanism of action. J. Steroid Biochem. Mol. Biol. 41:1992;339-348.
26. McDonnel D.P., Goldman M.E. RU486 exerts antiestrogenic activities through a novel progesterone receptor A form-mediated mechanism. J. Biol. Chem. 269:1994;11945-11949.