Synthesis and DNA Binding Properties of Terpyridine-naphthalimide Conjugates

doi:10.7517/j.issn.1674-0475.2017.04.018

Abstract

Abstract:

Two terpyridine-naphthalimide conjugates NPI1 and NPI2 are synthesized, and their interaction with duplexcalf thymus DNA (CT DNA) and Htelo G-quadruplex DNA are investigated by UV-Vis absorption spectroscopy, circular dichroism (CD) spectroscopy and fluorescence resonance energy transfer (FRET) assay. NPI1 and NPI2 possess high affinity to G-quadruplex and resonable selectivity over duplex. The association constant between NPI2 and G-quadruplex is 1.06×10⁸ L/mol in buffer solution containing K⁺, which is 268-fold as that between NPI2 and CT DNA. Circular dichroism results suggest that in the absence of K⁺, the Htelo DNA can form anti-parallel structure of G-quadruplex upon addition of NPI1 and NPI2. Molecular docking studies indicate that NPI1 and NPI2 interact with telomeric G-quadruplex through π-π stacking, electrostatic interaction and hydrogen bonding, resulting in the high affinity of these compounds to G-quadruplex (K_a>10⁷ L/mol).

Key words: naphthalimide, G-quadruplex DNA, terpyridine, molecular docking analysis

OU Zhize, LI Qingqing, YI Na, LI Zhiyuan, XU Moheng, CAI Wenjiao. Synthesis and DNA Binding Properties of Terpyridine-naphthalimide Conjugates[J]. Imaging Science and Photochemistry, 2017, 35(4): 563-573.

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