Artículo
Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18
Verlinden, Lieve; Verstuyf, Annemieke; Eelen, Guy; Bouillon, Roger; Ordóñez-Morán, Paloma; Larriba, María Jesús; Muñoz, Alberto; Rochel, Natacha; Sato, Yoshiteru; Moras, Dino; Maestro, Miguel; Seoane, Samuel; Dominguez, Fernando; Eduardo, Silvina Laura
; Nicoletti, Daniel; Moman, Edelmiro; Mouriño, Antonio
Fecha de publicación:
05/2011
Editorial:
Wiley VCH Verlag
Revista:
Chemmedchem
ISSN:
1860-7179
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
An improved synthetic route to 1α,25-dihydroxyvitamin D3 des-side chain analogues 2a and 2b with substituents at C18 is reported, along with their biological activity. These analogues display significant antiproliferative effects toward MCF-7 breast cancer cells and prodifferentiation activity toward SW480-ADH colon cancer cells; they are also characterized by a greatly decreased calcemic profile. The crystal structure of the human vitaminD receptor (hVDR) complexed to one of these analogues, 20(17→18)-abeo-1α,25-dihydroxy-22-homo-21-norvitamin D3 (2a) reveals that the side chain introduced at position C18 adopts the same orientation in the ligand binding pocket as the side chain of 1α,25-dihydroxyvitamin D3. Vitamin D3 supplements: The synthesis and biological activity of des-side chain analogues of 1α,25-dihydroxyvitamin D3 with substituents at C18 are described. Crystallographic analysis revealed that the new side chain introduced at C18 adopts the same orientation as the natural side chain at C17 in the parent molecule 1α,25-dihydroxyvitamin D3. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Palabras clave:
Biological Activity
,
Cancer
,
Steroids
,
Vitamind Analogues
,
Vitamins
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Articulos(UMYMFOR)
Articulos de UNID.MICROANAL.Y MET.FISICOS EN QUIM.ORG.(I)
Articulos de UNID.MICROANAL.Y MET.FISICOS EN QUIM.ORG.(I)
Citación
Verlinden, Lieve; Verstuyf, Annemieke; Eelen, Guy; Bouillon, Roger; Ordóñez-Morán, Paloma; et al.; Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18; Wiley VCH Verlag; Chemmedchem; 6; 5; 5-2011; 788-793
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