Synthesis of bisquinoline–pyrrole oligoamide as G-quadruplex binding ligand

Ong, Chi Wi, Liu, Meng-Chi, Lee, Kun-Da, Chang, Keng Wei, Yang, Ya-Ting, Tung, Hung-Wei and Fox, Keith R. (2012) Synthesis of bisquinoline–pyrrole oligoamide as G-quadruplex binding ligand. Tetrahedron, 68 (27-28), 5453-5457. (doi:10.1016/j.tet.2012.05.001).

Abstract

A one-pot procedure using ammonium formate under palladium catalysis for the reductive dechlorination and reduction of nitro group of 4-chloro-8-nitro–quinoline derivatives has be successfully carried out. This has lead to the synthesis of bisquinoline–pyrrole oligoamide 1, which show significant G-quadruplex selectivity in preference to duplex DNA. The cooperativity between the bisquinoline and pyrrole oligoamide moieties for good binding affinity to G-quadruplex was proven by synthesizing 2 and 3 lacking a quinoline ring and pyrrole amide, respectively, and both show much reduce affinity to G-quadruplex. Altogether, the results demostrate that the appropriate combination of two chromophores to form the hybride can attenuate binding affinity and selectivity towards G-quadruplex, an important criteria for the rational drug design

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Contributors

Author: Keith R. Fox

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