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Bioorg Med Chem ; 24(4): 768-78, 2016 Feb 15.
Artículo en Inglés | MEDLINE | ID: mdl-26810832

RESUMEN

The epidermal growth factor receptor (EGFR) is part of an extended family of proteins that together control aspects of cell growth and development, and thus a validated target for drug discovery. We explore in this work the suitability of a molecular dynamics-based end-point binding free energy protocol to estimate the relative affinities of a virtual combinatorial library designed around the EGFR model inhibitor 6{1} as a tool to guide chemical synthesis toward the most promising compounds. To investigate the validity of this approach, selected analogs including some with better and worse predicted affinities relative to 6{1} were synthesized, and their biological activity determined. To understand the binding determinants of the different analogs, hydrogen bonding and van der Waals contributions, and water molecule bridging in the EGFR-analog complexes were analyzed. The experimental validation was in good qualitative agreement with our theoretical calculations, while also a 6-dibromophenyl-substituted compound with enhanced inhibitory effect on EGFR compared to the reference ligand was obtained.


Asunto(s)
Antineoplásicos/síntesis química , Diseño de Fármacos , Receptores ErbB/antagonistas & inhibidores , Simulación de Dinámica Molecular , Inhibidores de Proteínas Quinasas/síntesis química , Pirimidinas/síntesis química , Antineoplásicos/farmacología , Sitios de Unión , Pruebas de Enzimas , Receptores ErbB/química , Humanos , Ligandos , Simulación del Acoplamiento Molecular , Unión Proteica , Inhibidores de Proteínas Quinasas/farmacología , Estructura Secundaria de Proteína , Estructura Terciaria de Proteína , Pirimidinas/farmacología , Proteínas Recombinantes/química , Relación Estructura-Actividad , Termodinámica
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