The "Gatekeeper" Residue Influences the Mode of Binding of Acetyl Indoles to Bromodomains.

Basic Information

ID: ALA3808347

Journal: J Med Chem

Title: The "Gatekeeper" Residue Influences the Mode of Binding of Acetyl Indoles to Bromodomains.

Authors: Unzue A, Zhao H, Lolli G, Dong J, Zhu J, Zechner M, Dolbois A, Caflisch A, Nevado C.

Abstract: Small-molecule hits for the bromodomains of CREBBP and BAZ2B have been identified by scaffold hopping followed by docking of a set of ∼200 compounds containing the acetyl indole scaffold. Chemical synthesis of nearly 30 derivatives has resulted in ligands of representatives of three subfamilies of human bromodomains with favorable ligand efficiency. The X-ray crystal structures of three different bromodomains (CREBBP, BAZ2B, and BRPF1b) in complex with acetyl indole derivatives reveal the influence of the gatekeeper residue on the orientation of small-molecule ligands in the acetyl lysine binding site.

CiteXplore: 26982797

DOI: 10.1021/acs.jmedchem.5b01757

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