Benzimidazole-1,2,3-triazole hybrid molecules: synthesis and study of their interaction with G-quadruplex DNA
Literature Information
Publication Date
2021-02-22
DOI
10.1039/D0MD00414F
Impact Factor
0
Authors
Ushasri Chilakamarthi, Namita S. Mahadik, Bhamidipati Keerti, Santosh N. Mokale, Narayana Nagesh
View Original
Abstract
A series of new benzimidazole-1,2,3-triazole hybrid derivatives have been synthesized via ‘click’ reaction and evaluated for their in vitro cytotoxicity as well as DNA binding affinity. MTT assay showed that all the six compounds are cytotoxic to PC3 and B16-F10 cancer cell lines. Though all the compounds showed moderate interaction with G4, c-Myc promoter DNA and dsDNA, 4f exhibited selective interaction with G-quadruplex DNA over duplex DNA as demonstrated by spectroscopic experiments like UV-vis spectroscopy, fluorescence spectroscopy, CD spectroscopy, thermal melting and fluorescence lifetime experiments. They also confirm the G-quadruplex DNA stabilizing potential of 4f. Viscosity measurements also confirm that 4f exhibits high G-quadruplex DNA selectivity over duplex DNA. Docking studies supported the spectroscopic observations. Cell cycle analysis showed that 4f induces G2/M phase arrest and induces apoptosis. Hence, from these experimental results it is evident that compound 4f may be a G-quadruplex DNA groove binding molecule with anticancer activity.
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(3-{[4-(Aminomethyl)-6-(trifluoromethyl)-2-pyridinyl]oxy}phenyl)[(3R,4R)-3-fluoro-4-hydroxy-1-pyrrolidinyl]methanone
CAS Number:
2007885-39-2
Molecular Formula:
C18H17F4N3O3
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