Artículo

Dansey, M.V.; del Fueyo, M.C.; Veleiro, A.S.; Di Chenna, P.H."Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR" (2017) Steroids. 121:40-46
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Abstract:

A new methodology to obtain C-25 and C-26 steroidal acids starting from pregnenolone is described. Construction of the side chain was achieved by applying the Mukaiyama aldol reaction with a non-hydrolytic work-up to isolate the trapped silyl enol ether with higher yields. Using this methodology we synthesized three new steroidal acids as potential ligands of DAF-12, Liver X and Glucocorticoid nuclear receptors and studied their activity in reporter gene assays. Our results show that replacement of the 21-CH3 by a 20-keto group in the side chains of the cholestane scaffold of DAF-12 or Liver X receptors ligands causes the loss of the activity. © 2017 Elsevier Inc.

Registro:

Documento: Artículo
Título:Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR
Autor:Dansey, M.V.; del Fueyo, M.C.; Veleiro, A.S.; Di Chenna, P.H.
Filiación:Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Biológica, Buenos Aires, Argentina
Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Pabellón 2, Ciudad Universitaria, Buenos Aires, C1428EG, Argentina
CONICET – Universidad de Buenos Aires, Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (UMYMFOR), Buenos Aires, Argentina
Palabras clave:Dafachronic acids; Glucocorticoids; Mukaiyama reaction; Oxysterols; Steroidal acids; cell nucleus receptor; cholestane derivative; ether derivative; glucocorticoid receptor; ligand; liver X receptor; nuclear receptor DAF 12; pregnenolone; silane derivative; steroid; unclassified drug; cell receptor; dafachronic acid; glucocorticoid receptor; liver X receptor; steroid; Article; biological activity; chemical modification; drug receptor binding; drug synthesis; Mukaiyama reaction; quantum yield; reporter gene; chemical structure; chemistry; hydrolysis; metabolism; nuclear magnetic resonance spectroscopy; synthesis; Cholestenes; Hydrolysis; Liver X Receptors; Magnetic Resonance Spectroscopy; Molecular Structure; Receptors, Cytoplasmic and Nuclear; Receptors, Glucocorticoid; Steroids
Año:2017
Volumen:121
Página de inicio:40
Página de fin:46
DOI: http://dx.doi.org/10.1016/j.steroids.2017.03.003
Handle:http://hdl.handle.net/20.500.12110/paper_0039128X_v121_n_p40_Dansey
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS:pregnenolone, 145-13-1; Cholestenes; dafachronic acid; Liver X Receptors; Receptors, Cytoplasmic and Nuclear; Receptors, Glucocorticoid; Steroids
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v121_n_p40_Dansey

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Citas:

---------- APA ----------
Dansey, M.V., del Fueyo, M.C., Veleiro, A.S. & Di Chenna, P.H. (2017) . Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR. Steroids, 121, 40-46.
http://dx.doi.org/10.1016/j.steroids.2017.03.003
---------- CHICAGO ----------
Dansey, M.V., del Fueyo, M.C., Veleiro, A.S., Di Chenna, P.H. "Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR" . Steroids 121 (2017) : 40-46.
http://dx.doi.org/10.1016/j.steroids.2017.03.003
---------- MLA ----------
Dansey, M.V., del Fueyo, M.C., Veleiro, A.S., Di Chenna, P.H. "Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR" . Steroids, vol. 121, 2017, pp. 40-46.
http://dx.doi.org/10.1016/j.steroids.2017.03.003
---------- VANCOUVER ----------
Dansey, M.V., del Fueyo, M.C., Veleiro, A.S., Di Chenna, P.H. Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR. Steroids. 2017;121:40-46.
http://dx.doi.org/10.1016/j.steroids.2017.03.003