Issue 6, 2016

Multivalency in the recognition and antagonism of a HIV TAR RNA–TAT assembly using an aminoglycoside benzimidazole scaffold

Abstract

Recognition of RNA by high-affinity binding small molecules is crucial for expanding existing approaches in RNA recognition, and for the development of novel RNA binding drugs. A novel neomycin dimer benzimidazole conjugate 5 (DPA 83) was synthesized by conjugating a neomycin-dimer with a benzimidazole alkyne using click chemistry to target multiple binding sites on HIV TAR RNA. Ligand 5 significantly enhances the thermal stability of HIV TAR RNA and interacts stoichiometrically with HIV TAR RNA with a low nanomolar affinity. 5 displayed enhanced binding compared to its individual building blocks including the neomycin dimer azide and benzimidazole alkyne. In essence, a high affinity multivalent ligand was designed and synthesized to target HIV TAR RNA.

Graphical abstract: Multivalency in the recognition and antagonism of a HIV TAR RNA–TAT assembly using an aminoglycoside benzimidazole scaffold

Supplementary files

Article information

Article type
Paper
Submitted
28 Sep 2015
Accepted
18 Dec 2015
First published
14 Jan 2016

Org. Biomol. Chem., 2016,14, 2052-2056

Multivalency in the recognition and antagonism of a HIV TAR RNA–TAT assembly using an aminoglycoside benzimidazole scaffold

S. Kumar, N. Ranjan, P. Kellish, C. Gong, D. Watkins and D. P. Arya, Org. Biomol. Chem., 2016, 14, 2052 DOI: 10.1039/C5OB02016F

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