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Dimeric 1,3-phenylene-bis(piperazinyl benzimidazole)s: synthesis and structure-activity investigations on their binding with human telomeric G-quadruplex DNA and telomerase inhibition properties.

Abstract：

:Ligand-induced stabilization of G-quadruplex structures formed by the human telomeric DNA is an active area of research. The compounds which stabilize the G-quadruplexes often lead to telomerase inhibition. Herein we present the results of interaction of new monomeric and dimeric ligands having 1,3-phenylene-bis(piperazinyl benzimidazole) unit with G-quadruplex DNA (G4DNA) formed by human telomeric repeat d[(G(3)T(2)A)(3)G(3)]. These ligands efficiently stabilize the preformed G4DNA in the presence of 100 mM monovalent alkali metal ions. Also, the G4DNA formed in the presence of low concentrations of ligands in 100 mM K(+) adopts a highly stable parallel-stranded conformation. The G-quadruplexes formed in the presence of the dimeric compound are more stable than that induced by the corresponding monomeric counterpart. The dimeric ligands having oligo-oxyethylene spacers provide much higher stability to the preformed G4DNA and also exert significantly higher telomerase inhibition activity. Computational aspects have also been discussed.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Jain AK,Paul A,Maji B,Muniyappa K,Bhattacharya S

doi

10.1021/jm200860b

subject

Has Abstract

pub_date

2012-04-12 00:00:00

pages

2981-93

issue

7

eissn

0022-2623

issn

1520-4804

journal_volume

55

pub_type

杂志文章

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