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


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.

SUBMITTER: Martinez C 

PROVIDER: S-EPMC4027779 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

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

Martínez Claudio C   Lieb Michele M   Alvarez Susana S   Rodríguez-Barrios Fátima F   Alvarez Rosana R   Khanwalkar Harshal H   Gronemeyer Hinrich H   de Lera Angel R AR  

ACS medicinal chemistry letters 20140319 5


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 transact  ...[more]

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