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ACS Med Chem Lett. 2014 Mar 19;5(5):533-7. doi: 10.1021/ml400521f. eCollection 2014.

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

Author information

1
Departamento de Química Orgánica, Facultade de Química, CINBIO, Universidade de Vigo, and Instituto de Investigación Biomédica de Vigo (IBIV) , 36310 Vigo, Spain.
2
Equipe Labellisée Ligue Contre le Cancer, Department of Functional Genomics and Cancer, Institut de Génétique et de Biologie Moléculaire et Cellulaire (IGBMC)/CNRS/INSERM/UdS , BP 10142, 67404 Illkirch, Cedex, C. U. de Strasbourg, France.

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.

KEYWORDS:

Retinoid receptor subtypes; agonists; antagonists; arotinoids; molecular modeling; transactivation

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