Document Report Card

ID: ALA3286114

Journal: ACS Med Chem Lett

Title: Dual RXR Agonists and RAR Antagonists Based on the Stilbene Retinoid Scaffold.

Authors: Martínez C, Lieb M, Alvarez S, Rodríguez-Barrios F, Alvarez R, Khanwalkar H, Gronemeyer H, de Lera AR.

Abstract: Arotinoids containing a C5,C8-diphenylnaphthalene-2-yl ring linked to a (C3-halogenated) benzoic acid via an ethenyl connector (but not the corresponding naphthamides), which are prepared by Horner-Wadsworth-Emmons reaction of naphthaldehydes and benzylphosphonates, display the rather unusual property of being RXR agonists (15-fold induction of the RXR reporter cell line was achieved at 3- to 10-fold lower concentration than 9-cis-retinoic acid) and RAR antagonists as shown by transient transactivation studies. The binding of such bulky ligands suggests that the RXR ligand-binding domain is endowed with some degree of structural elasticity.

CiteXplore: 24900875

DOI: 10.1021/ml400521f