Correlation between pregnanesteroid conformation, receptor affinity, and anti-natriuretic effect
The aim of this study was to correlate mineralocorticoid action and steroid structure. Inasmuch as Na+ retention follows a parabolic dose-response curve for most pregnanesteroids, the second-order coefficient of the function was used as a representative factor for this bipartite biological effect. T...
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2002
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| LEADER | 11528caa a22014537a 4500 | ||
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| 001 | PAPER-5167 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203447.0 | ||
| 008 | 190411s2002 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0037111505 | |
| 024 | 7 | |2 cas |a Pregnanes; Receptors, Mineralocorticoid | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a EJPHA | ||
| 100 | 1 | |a Piwien-Pilipuk, G. | |
| 245 | 1 | 0 | |a Correlation between pregnanesteroid conformation, receptor affinity, and anti-natriuretic effect |
| 260 | |c 2002 | ||
| 270 | 1 | 0 | |m Galigniana, M.D.; 1301 Med. Sci. Research Building III, Department of Pharmacology, Univ. of Michigan Medical School, Ann Arbor, MI 48109-0632, United States; email: mgali@umich.edu |
| 506 | |2 openaire |e Política editorial | ||
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| 504 | |a Burton, G., Galigniana, M.D., DeLavallaz, S., Brachet-Cota, A.L., Sproviero, E.M., Ghini, A.A., Lantos, C.P., Sodium-retaining activity of some natural and synthetic 21-deoxysteroids (1995) Mol. Pharmacol., 47, pp. 535-543 | ||
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| 504 | |a Dluhy, R.G., Glucocorticoid-remediable aldosteronism (2001) Endocrinologist, 11, pp. 263-268 | ||
| 504 | |a Fagart, J., Wurtz, J.M., Souque, A., Hellal-Levy, C., Moras, D., Rafestin-Oblin, M.E., Antagonism in the human mineralocorticoid receptor (1998) EMBO J., 17, pp. 3317-3325 | ||
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| 504 | |a Galigniana, M.D., Native rat kidney mineralocorticoid receptor is a phosphoprotein whose transformation to a DNA-binding form is induced by phosphatases (1998) Biochem. J., 333, pp. 555-563 | ||
| 504 | |a Galigniana, M.D., Functional regulation of corticosteroid receptors by phosphorylation and redox potential (2000) Curr. Top. Steroid Res., 3, pp. 1-22 | ||
| 504 | |a Galigniana, M.D., Piwien-Pilipuk, G., Comparative inhibition by hard and soft metal ions on steroid-binding capacity of renal mineralocorticoid receptor cross-linked to the 90-kDa heat-shock protein heterocomplex (1999) Biochem. J., 341, pp. 585-592 | ||
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| 504 | |a Galigniana, M.D., Vicent, G.P., Piwien-Pilipuk, G., Burton, G., Lantos, C.P., Mechanism of action of the potent sodium-retaining steroid 11,19-oxidoprogesterone (2000) Mol. Pharmacol., 58, pp. 58-70 | ||
| 504 | |a Grassy, G., Fagart, J., Calas, B., Adenot, M., Rafestin-Oblin, M.E., Auzou, G., Structure-activity relationships of steroids with mineralocorticoid activity (1997) Eur. J. Med. Chem., 32, pp. 869-879 | ||
| 504 | |a Koshida, H., Miyamori, I., Soma, R., Matsubara, T., Ikeda, M., Takeda, R., Nakamura, S., Tsuda, Y., Mineralocorticoid and renal receptor binding activity of 21-deoxyaldosterone (1990) Endocrinology, 126, pp. 1410-1415 | ||
| 504 | |a Lantos, C.P., Burton, G., Roldán, A., Damasco, M.C., Aragonés, A., Structure-activity relationship in certain glucocorticoids and mineralocorticoids (1981) Physiopathology of Endocrine Diseases and Mechanisms of Hormone Action, pp. 477-494. , R.J. Soto, A. de Nicola, & J. Blaquier. New York: Alan R. Liss | ||
| 504 | |a Lombès, M., Kenouch, S., Souque, A., Farman, N., Rafestin-Oblin, M.E., The mineralocorticoid receptor discriminates aldosterone from glucocorticoids independently of the 11β-hydroxysteroid dehydrogenase (1994) Endocrinology, 135, pp. 834-840 | ||
| 504 | |a Piwien-Pilipuk, G., Galigniana, M.D., Tautomycin inhibits phosphatase-dependent transformation of the rat kidney mineralocorticoid receptor (1998) Mol. Cell. Endocrinol., 144, pp. 119-130 | ||
| 504 | |a Piwien-Pilipuk, G., Kanelakis, K.C., Ghini, A.A., Lantos, C.P., Litwack, G., Burton, G., Galigniana, M.D., Modification of an essential amino group in the mineralocorticoid receptor evidences a differential conformational change of the receptor protein upon binding of antagonists, natural agonists and the synthetic agonist 11,19-oxidoprogesterone (2001) Biochim. Biophys. Acta, 1589, pp. 31-48 | ||
| 504 | |a Robertson, N.M., Schulman, G., Karnik, S., Alnemri, E., Litwack, G., Demonstration of nuclear translocation of the mineralocorticoid receptor (MR) using anti-MR antibody and confocal scanning microscopy (1993) Mol. Endocrinol., 7, pp. 1226-1239 | ||
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| 504 | |a Souque, A., Fagart, J., Coutte, B., Davioud, E., Marquet, A., Rafestin-Oblin, M.E., The mineralocorticoid activity of progesterone derivatives depends on the nature of the C18 substituent (1995) Endocrinology, 136, pp. 5651-5658 | ||
| 504 | |a Struhl, K., Histone acetylation and transcriptional regulatory mechanisms (1998) Genes Dev., 12, pp. 599-606 | ||
| 504 | |a Teutsch, G., Nique, F., Lemoine, G., Bouchoux, F., Cérède, E., Gofflo, D., Philibert, D., General structure-activity correlations of antihormones (1995) Ann. N.Y. Acad. Sci., 761, pp. 5-28 | ||
| 504 | |a Veleiro, A.S., Nevado, M.V., Monteserín, M.C., Burton, G., Syntheses of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione (1995) Steroids, 60, pp. 358-364 | ||
| 504 | |a Young, D.B., Quantitative analysis of aldosterone's role in potassium regulation (1988) Am. J. Physiol., 255, pp. F811-F822 | ||
| 520 | 3 | |a The aim of this study was to correlate mineralocorticoid action and steroid structure. Inasmuch as Na+ retention follows a parabolic dose-response curve for most pregnanesteroids, the second-order coefficient of the function was used as a representative factor for this bipartite biological effect. The C3=O/D angle of the ligands was correlated with both Na+-retaining activity and binding affinity for the mineralocorticoid receptor. Because some steroids exhibit identical functional groups and different conformational structure, we also postulate that the flat conformation of a pregnanesteroid determines its Na+-retaining capacity in vivo. No correlations were found in vitro, which demonstrates the multifactorial nature of the second-order coefficient determined in vivo under more complex and interactive conditions that include various pre-receptor variables. These findings may allow the estimation of the putative biological activity of a given steroid simply by knowing its conformational structure, which may be important for designing compounds in a pharmaceutical setting. © 2002 Elsevier Science B.V. All rights reserved. |l eng | |
| 593 | |a Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428, Buenos Aires, Argentina | ||
| 593 | |a Department of Pharmacology, University of Michigan Medical School, Ann Arbor, MI 48109, United States | ||
| 593 | |a 1301 Medical Science Research Building III, Department of Pharmacology, University of Michigan Medical School, Ann Arbor, MI 48109-0632, United States | ||
| 690 | 1 | 0 | |a ALDOSTERONE |
| 690 | 1 | 0 | |a MINERALOCORTICOID RECEPTOR |
| 690 | 1 | 0 | |a NATRIURESIS |
| 690 | 1 | 0 | |a STEROID CONFORMATION |
| 690 | 1 | 0 | |a 11BETA,17BETA DIHYDROXY 6 METHYL 17ALPHA (1 PROPYNYL)ANDROSTA 1,4,6 TRIEN 3 ONE |
| 690 | 1 | 0 | |a FUNCTIONAL GROUP |
| 690 | 1 | 0 | |a LIGAND |
| 690 | 1 | 0 | |a MINERALOCORTICOID RECEPTOR |
| 690 | 1 | 0 | |a PREGNANE DERIVATIVE |
| 690 | 1 | 0 | |a PREGNANESTEROID |
| 690 | 1 | 0 | |a SODIUM ION |
| 690 | 1 | 0 | |a STEROID |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a MINERALOCORTICOID RECEPTOR |
| 690 | 1 | 0 | |a PREGNANE DERIVATIVE |
| 690 | 1 | 0 | |a ANIMAL CELL |
| 690 | 1 | 0 | |a ANIMAL EXPERIMENT |
| 690 | 1 | 0 | |a ANTIDIURESIS |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a BINDING AFFINITY |
| 690 | 1 | 0 | |a CONCENTRATION RESPONSE |
| 690 | 1 | 0 | |a CONTROLLED STUDY |
| 690 | 1 | 0 | |a CORRELATION ANALYSIS |
| 690 | 1 | 0 | |a DRUG CONFORMATION |
| 690 | 1 | 0 | |a DRUG MECHANISM |
| 690 | 1 | 0 | |a DRUG RECEPTOR BINDING |
| 690 | 1 | 0 | |a DRUG STRUCTURE |
| 690 | 1 | 0 | |a IN VITRO STUDY |
| 690 | 1 | 0 | |a IN VIVO STUDY |
| 690 | 1 | 0 | |a MALE |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a SODIUM RETENTION |
| 690 | 1 | 0 | |a ANIMAL |
| 690 | 1 | 0 | |a CELL STRAIN COS1 |
| 690 | 1 | 0 | |a CERCOPITHECUS |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a DOSE RESPONSE |
| 690 | 1 | 0 | |a DRUG EFFECT |
| 690 | 1 | 0 | |a HUMAN |
| 690 | 1 | 0 | |a METABOLISM |
| 690 | 1 | 0 | |a NATRIURESIS |
| 690 | 1 | 0 | |a PHYSIOLOGY |
| 690 | 1 | 0 | |a PROTEIN BINDING |
| 690 | 1 | 0 | |a RAT |
| 690 | 1 | 0 | |a SPRAGUE DAWLEY RAT |
| 690 | 1 | 0 | |a STRUCTURE ACTIVITY RELATION |
| 690 | 1 | 0 | |a ANIMALS |
| 690 | 1 | 0 | |a CERCOPITHECUS AETHIOPS |
| 690 | 1 | 0 | |a COS CELLS |
| 690 | 1 | 0 | |a DOSE-RESPONSE RELATIONSHIP, DRUG |
| 690 | 1 | 0 | |a HUMANS |
| 690 | 1 | 0 | |a MALE |
| 690 | 1 | 0 | |a NATRIURESIS |
| 690 | 1 | 0 | |a PREGNANES |
| 690 | 1 | 0 | |a PROTEIN BINDING |
| 690 | 1 | 0 | |a RATS |
| 690 | 1 | 0 | |a RATS, SPRAGUE-DAWLEY |
| 690 | 1 | 0 | |a RECEPTORS, MINERALOCORTICOID |
| 690 | 1 | 0 | |a STRUCTURE-ACTIVITY RELATIONSHIP |
| 653 | 0 | 0 | |a ru 28362, Roussel Uclaf, France |
| 700 | 1 | |a Kanelakis, K.C. | |
| 700 | 1 | |a Galigniana, M.D. | |
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