Navegar

Colección

Datos Estadísticas

Artículo

Brookes, J.C.; Galigniana, M.D.; Harker, A.H.; Stoneham, A.M.; Vinson, G.P. "System among the corticosteroids: Specificity and molecular dynamics" (2012) Journal of the Royal Society Interface. 9(66):43-53
Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Understanding how structural features determine specific biological activities has often proved elusive. With over 161 000 steroid structures described, an algorithm able to predict activity from structural attributes would provide manifest benefits. Molecular simulations of a range of 35 corticosteroids show striking correlations between conformational mobility and biological specificity. Thus steroid ring A is important for glucocorticoid action, and is rigid in the most specific (and potent) examples, such as dexamethasone. By contrast, ring C conformation is important for the mineralocorticoids, and is rigid in aldosterone. Other steroids that are less specific, or have mixed functions, or none at all, are more flexible. One unexpected example is 11-deoxycorticosterone, which the methods predict (and our activity studies confirm) is not only a specific mineralocorticoid, but also has significant glucocorticoid activity. These methods may guide the design of new corticosteroid agonists and antagonists. They will also have application in other examples of ligand-receptor interactions. This journal is © 2011 The Royal Society.

Registro:

Documento: Artículo
Título:System among the corticosteroids: Specificity and molecular dynamics
Autor:Brookes, J.C.; Galigniana, M.D.; Harker, A.H.; Stoneham, A.M.; Vinson, G.P.
Filiación:Department of Physics and Astronomy, University College London, Gower Street, London WC1E 6BT, United Kingdom
IBYME/CONICET Departamento de Química Biológica, Facultad de Ciencias Exactas Y Naturales, Buenos Aires C1428EGA, Argentina
London Centre for Nanotechnology, University College London, Gordon Street, London WC1E 6BT, United Kingdom
School of Biological and Chemical Sciences, Queen Mary University of London, London E1 4NS, United Kingdom
Palabras clave:Aldosterone; Conformational mobility; Cortisol; Deoxycorticosterone; Glucocorticoid; Mineralocorticoid; Molecular dynamics; Aldosterone; Conformational mobility; Cortisol; Deoxycorticosterone; Glucocorticoid; Mineralocorticoid; Drug products; aldosterone; betamethasone; corticosteroid; corticosteroid antagonist; corticosterone; deoxycorticosterone; dexamethasone; fludrocortisone; glucocorticoid; hydrocortisone; mineralocorticoid; prednisolone; prednisone; triamcinolone; article; drug activity; drug mechanism; molecular dynamics
Año:2012
Volumen:9
Número:66
Página de inicio:43
Página de fin:53
DOI: http://dx.doi.org/10.1098/rsif.2011.0183
Título revista:Journal of the Royal Society Interface
Título revista abreviado:J. R. Soc. Interface
ISSN:17425689
CAS:aldosterone, 52-39-1, 6251-69-0; betamethasone, 378-44-9; corticosterone, 50-22-6; deoxycorticosterone, 64-85-7; dexamethasone, 50-02-2; fludrocortisone, 127-31-1; hydrocortisone, 50-23-7; prednisolone, 50-24-8; prednisone, 53-03-2; triamcinolone, 124-94-7
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_17425689_v9_n66_p43_Brookes

Referencias:

  • Lipkus, A.H., Yuan, Q., Lucas, K.A., Funk, S.A., Bartelt III, W.F., Schenck, R.J., Trippe, A.J., Structural diversity of organic chemistry. A scaffold analysis of the CAS Registry (2008) J. Org. Chem., 73, pp. 4443-4451. , doi:10.1021/jo8001276
  • Vinson, G.P., The adrenal cortex and life (2009) Mol. Cell. Endocrinol., 300, pp. 2-6. , doi:10.1016/j.mce.2008.09.008
  • Han, F., Ozawa, H., Matsuda, K., Nishi, M., Kawata, M., Colocalization of mineralocorticoid receptor and glucocorticoid receptor in the hippocampus and hypothalamus (2005) Neurosci. Res., 51, pp. 371-381. , doi:10.1016/j.neures.2004.12.013
  • Bureik, M., Bruck, N., Hubel, K., Bernhardt, R., The human mineralocorticoid receptor only partially differentiates between different ligands after expression in fission yeast (2005) FEMS Yeast Res., 5, pp. 627-633. , doi:10.1016/j.femsyr.2004.12.007
  • Fuller, P.J., Lim-Tio, S.S., Brennan, F.E., Specificity in mineralocorticoid versus glucocorticoid action (2000) Kidney Int., 57, pp. 1256-1264. , doi:10.1046/j.1523-1755.2000.00959.x
  • Nishi, M., Kawata, M., Dynamics of glucocorticoid receptor and mineralocorticoid receptor: Implications from live cell imaging studies (2007) Neuroendocrinology, 85, pp. 186-192. , doi:10.1159/000101917
  • Baxter, J.D., Funder, J.W., Apriletti, J.W., Webb, P., Towards selectively modulating mineralocorticoid receptor function: Lessons from other systems (2004) Mol. Cell. Endocrinol., 217, pp. 151-165. , doi:10.1016/j.mce.2003.10.044
  • Hellal-Levy, C., Couette, B., Fagart, J., Souque, A., Gomez-Sanchez, C., Rafestin-Oblin, M., Specific hydroxylations determine selective corticosteroid recognition by human glucocorticoid and mineralocorticoid receptors (1999) FEBS Lett., 464, pp. 9-13. , doi:10.1016/S0014-5793(99)01667-1
  • Krozowski, Z., The type I and type II 11 beta-hydroxysteroid dehydrogenase enzymes (1999) J. Steroid Biochem. Mol. Biol., 69, pp. 391-401. , doi:10.1016/S0960-0760(99)00074-6
  • Ferrari, P., Cortisol and the renal handling of electrolytes: Role in glucocorticoid-induced hypertension and bone disease (2003) Best Pract. Res. Clin. Endocrinol. Metab., 17, pp. 575-589. , doi:10.1016/S1521-690X(03)00053-8
  • Funder, J.W., Aldosterone action (1993) Annu. Rev. Physiol., 55, pp. 115-130. , doi:10.1146/annurev.ph.55.030193.000555
  • Funder, J.W., Mineralocorticoid receptors: Distribution and activation (2005) Heart Fail. Rev., 10, pp. 15-22. , doi:10.1007/s10741-005-2344-2
  • Roland, B.L., Krozowski, Z.S., Funder, J.W., Glucocorticoid receptor, mineralocorticoid receptors, 11 beta-hydroxysteroid dehydrogenase-1 and -2 expression in rat brain and kidney: In situ studies (1995) Mol. Cell. Endocrinol., 111, pp. R1-R7. , doi:10.1016/0303-7207(95)03559-P
  • Usa, K., Singh, R.J., Netzel, B.C., Liu, Y., Raff, H., Liang, M., Renal interstitial corticosterone and 11-dehydrocorticosterone in conscious rats (2007) Am. J. Physiol. Renal Physiol., 293, pp. F186-F192. , doi:10.1152/ajprenal.00484.2006
  • Galigniana, M.D., Piwien Pilipuk, G., Kanelakis, K.C., Burton, G., Lantos, C.P., Molecular mechanism of activation and nuclear translocation of the mineralocorticoid receptor upon binding of pregnanesteroids (2004) Mol. Cell. Endocrinol., 217, pp. 167-179. , doi:10.1016/j.mce.2003.10.041
  • Bledsoe, R.K., A ligand-mediated hydrogen bond network required for the activation of the mineralocorticoid receptor (2005) J. Biol. Chem., 280, pp. 31283-31293. , doi:10.1074/jbc.M504098200
  • Bledsoe, R.K., Crystal structure of the glucocorticoid receptor ligand binding domain reveals a novel mode of receptor dimerization and coactivator recognition (2002) Cell, 110, pp. 93-105. , doi:10.1016/S0092-8674(02)00817-6
  • Nabuurs, S.B., Wagener, M., De Vlieg, J., A flexible approach to induced fit docking (2007) J. Med. Chem., 50, pp. 6507-6518. , doi:10.1021/jm070593p
  • Duax, W.L., Weeks, C.M., Rohrer, D.C., Crystal structure of steroids: Molecular conformation and biological function (1976) Recent Progr. Hormone Res., 32, pp. 81-116
  • Brookes, J.C., Horsfield, A.P., Stoneham, A.M., Odour character differences for enantiomers correlate with molecular flexibility (2009) J. R. Soc. Interface, 6, pp. 75-86. , doi:10.1098/rsif.2008.0165
  • Ohloff, G., Maurer, B., Winter, B., Giersch, W., Structural and configurational dependence of the sensory process in steroids (1983) Helvetica Chimica Acta, 66 (1), pp. 192-217
  • Dewar, M.J., Zoebisch, E.G., Healy, E.F., Stewart, J.J., A new general quantum mechanical molecular model (1985) J. Am. Chem. Soc., 107, p. 3902
  • Becke, A.D., Density-functional thermochemistry. III. The role of exact exchange (1993) J. Chem. Phys., 98, pp. 5648-5652. , doi:10.1063/1.464913
  • Allen, M.P., Tildesley, D.J., (1989) Computer Simulation of Liquids, , Oxford, UK: Oxford Science Publications
  • Mayo, S.L., Olafson, B.D., Goddard III, W.A., DREIDING: A generic force field for molecular simulations (1990) J. Phys. Chem., 94, pp. 8897-8909. , doi:10.1021/j100389a010
  • Wang, J., Wolf, R.M., Caldwell, J.W., Kollman, P.A., Case, D.A., Development and testing of a general amber force field (2004) J. Comput. Chem., 25, pp. 1157-1174. , doi:10.1002/jcc.20035
  • Almenningen, A., Bastiansen, O., Skancke, P.N., Preliminary results of an electron diffraction reinvestigation of cyclobutane and cyclopentane (1961) Acta Chem. Scand., 15, p. 711
  • Eliel, E.L., Allinger, N.L., Angyal, S.J., Morrison, G.A., (1965) Conformational Analysis, , London, UK: John Wiley & Sons
  • Baxter, J.D., Rousseau, G.G., (1979) Glucocorticoid Hormone Action, , Berlin, Germany: Springer
  • Haynes, R.C., Murad, F., Adrenocorticotrophic hormone; adrenocortical steroids and their synthetic analogues; inhibitors of adrenocortical steroid biosynthesis (1985) The Pharmacological Basis of Therapeutics, , (eds A. G. Gilman, L. S. Goodman, T. W. Rall & F. Murad). New York, NY: Macmillan
  • Genest, J., The present status of aldosterone in clinical medicine (1955) Can. Med. Assoc. J., 73, pp. 876-883
  • Orth, D.N., Kovacs, W.J., The adrenal cortex (1998) Williams' Textbook of Endocrinology, pp. 517-664. , ed. J. D. Wilson, Philadelphia, PA: W.B. Saunders
  • Steele, R., Influence of corticosteroids on protein and carbohydrate metabolism (1975) Handbook of Physiology, pp. 135-167. , (eds H. Blaschko, A. D. Smith & G. Sayers), Washington, DC: American Physiological Society
  • Vicent, G.P., Pecci, A., Ghini, A.A., Piwien-Pilipuk, G., Veleiro, A.S., Burton, G., Lantos, C.P., Galigniana, M.D., The glucocorticoid properties of the synthetic steroid pregna-1,4-diene-11beta-ol-3,20-dione (deltaHOP) are not entirely correlated with the steroid binding to the glucocorticoid receptor (1999) Mol. Cell. Endocrinol., 149, pp. 207-219. , doi:10.1016/S0303-7207(98)00205-6
  • Krisman, C.R., A method for the colorimetric estimation of glycogen with iodine (1962) Anal. Biochem., 4, pp. 17-23
  • Galigniana, M.D., Vicent, G.P., Burton, G., Lantos, C.P., Features of the shuttle pair 11 beta-hydroxyprogesterone-11- ketoprogesterone (1997) Steroids, 62, pp. 358-364
  • Gallo, L.I., Ghini, A.A., Pilipuk, G.P., Galigniana, M.D., Differential recruitment of tetratricorpeptide repeat domain immunophilins to the mineralocorticoid receptor influences both heat-shock protein 90-dependent retrotransport and hormone-dependent transcriptional activity (2007) Biochemistry, 46, pp. 14044-14057. , doi:10.1021/bi701372c
  • Selye, H., Jensen, H., The chemistry of the hormones (1946) Ann. Rev. Biochem., 15, pp. 347-360
  • Purnell, J.Q., Kahn, S.E., Samuels, M.H., Brandon, D., Loriaux, D.L., Brunzell, J.D., Enhanced cortisol production rates, free cortisol, and 11beta-HSD-1 expression correlate with visceral fat and insulin resistance in men: Effect of weight loss (2009) Am J Physiol Endocrinol Metab, 296, pp. E351-E357. , doi:10.1152/ajpendo.90769.2008
  • Morris, D.J., Souness, G.W., Brem, A.S., Oblin, M.E., Interactions of mineralocorticoids and glucocorticoids in epithelial target tissues (2000) Kidney Int., 57, pp. 1370-1373. , doi:10.1046/j.1523-1755.2000.00977.x
  • Selye, H., The general adaptation syndrome and the diseases of adaptation (1946) J. Clin. Endocrinol. Metab., 6, pp. 117-230
  • Sigala, P.A., Kraut, D.A., Caaveiro, J.M., Pybus, B., Ruben, E.A., Ringe, D., Petsko, G.A., Herschlag, D., Testing geometrical discrimination within an enzyme active site: Constrained hydrogen bonding in the ketosteroid isomerase oxyanion hole (2008) J. Am. Chem. Soc., 130, pp. 13696-13708. , doi:10.1021/ja803928m
  • Barton, D.H., The principles of conformational analysis (1972) Nobel Lectures, 1963-1970, pp. 298-311. , Amsterdam, The Netherlands: Elsevier

Citas:

---------- APA ----------
Brookes, J.C., Galigniana, M.D., Harker, A.H., Stoneham, A.M. & Vinson, G.P. (2012) . System among the corticosteroids: Specificity and molecular dynamics. Journal of the Royal Society Interface, 9(66), 43-53.
http://dx.doi.org/10.1098/rsif.2011.0183
---------- CHICAGO ----------
Brookes, J.C., Galigniana, M.D., Harker, A.H., Stoneham, A.M., Vinson, G.P. "System among the corticosteroids: Specificity and molecular dynamics" . Journal of the Royal Society Interface 9, no. 66 (2012) : 43-53.
http://dx.doi.org/10.1098/rsif.2011.0183
---------- MLA ----------
Brookes, J.C., Galigniana, M.D., Harker, A.H., Stoneham, A.M., Vinson, G.P. "System among the corticosteroids: Specificity and molecular dynamics" . Journal of the Royal Society Interface, vol. 9, no. 66, 2012, pp. 43-53.
http://dx.doi.org/10.1098/rsif.2011.0183
---------- VANCOUVER ----------
Brookes, J.C., Galigniana, M.D., Harker, A.H., Stoneham, A.M., Vinson, G.P. System among the corticosteroids: Specificity and molecular dynamics. J. R. Soc. Interface. 2012;9(66):43-53.
http://dx.doi.org/10.1098/rsif.2011.0183