Mechanism of action of the potent sodium-retaining steroid 11,19- oxidoprogesterone

Molecular Pharmacology

Volumn 58, Issue 1, 2000, Pages 58-70

  Galigniana, Mario D ^a,c   Vicent, Guillermo P ^a   Piwien Pilipuk, Graciela ^a   Burton, Gerardo ^b   Lantos, Carlos P ^a  

^a Depto de Farmacologia de las F   (Argentina)

^b UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^c UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOSTERONE; PROGESTERONE DERIVATIVE; TAUTOMYCIN;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG MECHANISM; DRUG POTENCY; DRUG RECEPTOR BINDING; HORMONE ACTION; INTRACELLULAR TRANSPORT; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN TRANSPORT; RAT; SODIUM RETENTION;

EID: 0033919249     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: 10.1124/mol.58.1.58     Document Type: Article

References (41)

1. Alnemri ES, Maksymowych AB, Robertson NM and Litwack G (1991) Overexpression and characterization of the human mineralocorticoid receptor. J Biol Chem 266:3925-3936.
2. Benhamou B, Garcia T, Lerouge T, Vergezac A, Gofflo D, Bigogne C, Chambon P and Gronemeyer H (1992) A single amino acid that determines the sensitivity of progesterone receptors. Science 255:206-209.
3. Binart N, Lombes M, Rafestin-Oblin ME and Baulieu EE (1991) Characterization of human mineralocorticoid receptor expressed in the baculovirus system. Proc Natl Acad Sci USA 88:10681-10685.
4. Brachet-Cota AL and Burton G (1990) An improved preparation of 11,19-oxidopregn-4-ene-3,20-dione and 6,19-oxidopregn-4-ene-3,11,20-trione. Z Naturforsch Teil [B] 45:711-715.
5. Burton G, Galigniana MD, de Lavallaz S, Brachet-Cota AL, Sproviero EM, Ghini AA, Lantos CP and Damasco MC (1995) Sodium-retaining activity of some natural and synthetic 21-deoxysteroids. Mol Pharmacol 47:535-543.
6. Colby H and Kitay J (1972) Sex and substrate effects on hepatic corticosteroid metabolism in rat. Endocrinology 90:473-478.
7. Czar MJ, Galigniana MD, Silverstein AM and Pratt WB (1997) Geldanamycin, a heat shock protein 90-binding benzoquinone ansamycin, inhibits steroid-dependent translocation of the glucocorticoid receptor from cytoplasm to the nucleus. Biochemistry 36:7776-7785.
8. Duax W, Cody V, Griffin J, Rohrer D and Weeks C (1978) Molecular conformation and protein binding affinity of progestins. J Toxicol Environ Health 4:205-227.
9. Funder JW, Pearce P, Smith R and Smith AI (1988) Mineralocorticoid action: Target tissue specificity is enzyme, not receptor, mediated. Science (Wash DC) 242:583-585.
10. Galigniana MD (1996) Stability study on renal type I mineralocorticoid receptor. Life Sci 59:511-521.
11. Galigniana MD (1998) Native rat kidney mineralocorticoid receptor is a phospho-protein whose transformation to a DNA-binding form is induced by phosphatases. Biochem J 333:555-563.
12. Galigniana MD, Housley PR, DeFranco DB and Pratt WB (1999) Inhibition of glucocorticoid receptor nucleocytoplasmic shuttling by okadaic acid requires intact cytoskeleton. J Biol Chem 274:16222-16227.
13. Galigniana MD and Piwien-Pilipuk G (1999) Comparative inhibition by hard and soft metal ions of steroid-binding capacity of renal mineralocorticoid receptor cross-linked to the 90-kDa heat-shock protein heterocomplex. Biochem J 341:585-592.
14. Galigniana MD, Vicent GP, Lantos CP and Burton G (1994) 11,19-Oxidoprogesterone: A potent sodium retaining steroid binding to an alternative site in kidney type I receptor. Eur J Endocrinol 130 (Suppl 2):260.
15. Galigniana MD, Vicent GP, Burton G and Lantos CP (1997) Features of the shuttle pair 11β-hydroxyprogesterone/11-ketoprogesterone. Steroids 62:358-364.
16. Galigniana MD, Scruggs JL, Herrington J, Welsh MJ, Carter-Su C, Housley PR and Pratt WB (1998) Heat shock protein 90-dependent (geldanamycin-inhibited) movement of the glucocorticoid receptor through the cytoplasm to the nucleus requires intact cytoskeleton. Mol Endocrinol 12:1903-1913.
17. Jones TR and Bell PA (1980) Glucocorticoid-receptor interactions: Studies of the negative cooperativity induced by steroid interactions with a secondary, hydrophobic, binding site. Biochem J 188:237-245.
18. Kato S, Endoh H, Masuhiro Y, Kitamoto T, Uchiyama S, Sasaki H, Masushige S, Gotoh Y, Nishida E, Kawashima H, Metzger D and Chambon P (1995) Activation of estrogen receptor through phosphorylation by mitogen-activated protein kinase. Science (Wash DC) 270:1491-1494.
19. Krozowski ZS and Funder JW (1983) Renal mineralocorticoid receptors and hippocampal corticosterone binding species have identical intrinsic steroid specificity. Proc Natl Acad Sci USA 80:6056-6060.
20. Lantos CP, Burton G, Roldán A, Damasco MC and Aragonés A (1981) Structure-activity relationship in certain glucocorticoids and mineralocorticoids, in Physiopathology of Endocrine Diseases and Mechanisms of Hormone Action (Soto RJ, de Nicola A and Blaquier J, eds) pp 477-494, Alan R. Liss, New York.
21. Lilley KS and Engel PC (1992) The essential active-site lysines of clostridial glutamate dehydrogenase: A study with pyridoxal-5′-phosphate. Eur J Biochem 207: 533-540.
22. McDonnell D, Clemm D, Herman T, Goldman ME and Pike JW (1995) Analysis of estrogen receptor function in vitro reveals three distinct classes of antiestrogens. Mol Endocrinol 9:659-669.
23. Migliaccio A, Di Domenico M, Castoria G, de Falco A, Bontempo P, Nola E and Auricchio F (1996) Tyrosine kinase/p21ras/MAP-kinase pathway activation by estradiol-receptor complex in MCF-7 cells. EMBO J 15:1292-1300.
24. Morris D (1981) The metabolism and mechanism of action of aldosterone. Endocr Rev 2:234-247.
25. Morris DJ, Tsai R and De Conti G (1976) Regulation of plasma levels of aldosterone and its metabolites during the latent period of aldosterone. J Steroid Biochem 7:971-978.
26. Nemere I, Zhou L and Norman A (1993) Nontranscriptional effects of steroid hormones. Receptor 3:277-291.
27. Piwien-Pilipuk G and Galigniana MD (1998) Tautomycin inhibits phosphatase-dependent transformation of the rat kidney mineralocorticoid receptor. Mol Cell Endocrinol 144:119-130.
28. Piwien-Pilipuk G and Galigniana MD (2000) Oxidative stress induced by L-buthionine-(S,R)-sulfoximine, a selective inhibitor of the glutathione metabolism, inhibits the mouse kidney mineralocorticoid receptor function. Biochim Biophys Acta 1495:263-280.
29. Pratt WB and Toft DO (1997) Steroid receptor interactions with heat shock protein and immunophilin chaperones. Endocr Rev 18:306-360.
30. Renaud JP, Rochel N, Ruff M, Vivat V, Chambon P, Gronemeyer H and Moras D (1995) Crystal structure of the RAR-γ ligand-binding domain bound to all trans retinoic acid. Nature (Lond) 378:681-689.
31. Scherrer LC, Dalman FC, Massa E, Meshinchi S and Pratt WB (1990) Structural and functional reconstitution of the glucocorticoid receptor-hsp90 heterocomplex. J Biol Chem 267:21397-21400.
32. Souque A, Fagart J, Couette B and Rafestin-Oblin ME (1996) Sulfhydryl groups are involved in the binding of agonists and antagonists to the human mineralocorticoid receptor. J Steroid Biochem Mol Biol 67:315-321.
33. Svec F, Teubner V and Tate D (1989) Location of the second steroid-binding site on the glucocorticoid receptor. Endocrinology 125:3103-3108.
34. Teutsch G, Nique F, Lemoine G, Bouchoux F, Cérède, Gofflo D and Philibert D (1995) General structure-activity correlations of antihormones. Ann N Y Acad Sci 761: 5-28.
35. Vegeto E, Allan GF, Schrader WT, Tsai MJ, McDonnell D and O'Malley BW (1992) The mechanism of RU486 antagonism is dependent on the conformation of the carboxy-terminal tail of the human progesterone receptor. Cell 69:703-713.
36. Vicent GP, Burton G, Ghini A, Lantos CP and Galigniana MD (1998) Influence of calf serum on glucocorticoid-responses of certain progesterone derivatives. J Steroid Biochem Mol Biol 66:211-217.
37. Vicent GP, Monteserín MC, Veleiro AS, Burton G, Lantos CP and Galigniana MD (1997) 21-Hydroxy-6,19-oxidoprogesterone: A novel synthetic steroid with specific antiglucocorticoid properties in the rat. Mol Pharmacol 52:749-753.
38. Vicent GP, Pecci A, Ghini A, Piwien-Pilipuk G, Burton G, Lantos CP and Galigniana MD (1999) The glucocorticoid properties of the synthetic steroid pregna-1,4-diene-11β-ol-3,20-dione (ΔHOP) are not entirely correlated with the steroid binding to the glucocorticoid receptor. Mol Cell Endocrinol 149:207-219.
39. Waynforth HB (1980) Experimental and Surgical Technique in the Rat. Academic Press, London.
40. Williams SP and Sigler PB (1998) Atomic structure of progesterone complexed with its receptor. Nature (Lond) 393:392-396.
41. Yamakawa Y, Ezumi K, Shiro M, Nakai H, Kamata S, Matsui T and Haga N (1986) Relationships of the molecular structure of aldosterone derivatives with their binding affinity for mineralocorticoid receptor. Mol Pharmacol 30:585-589.