1,2,3-Triazole naphthaldehyde compounds and their oxime derivatives: in vitro and in silico DNA binding properties.

Abstract

In this work, we report the synthesis and DNA binding properties of a series of 1,2,3-triazole naphthaldehyde compounds and their oxime derivatives. The 1,2,3-triazole naphthaldehyde compounds (1a-1f) were prepared by the Cu(I) catalysed click reactions. The 1,2,3-triazole naphthaldehyde compounds (1a-1f) were then reacted with hydroxyl amine to yield 1,2,3-triazole oxime compounds (2a-2f). The structures of all compounds were characterized by Fourier-transform ınfrared spectroscopy, Nuclear magnetic resonance and elemental analysis. Crystal structures of compounds 1a, 1c, 1f, 2c and 2d were investigated by single crystal X-ray crystallography. The compounds were evaluated for their DNA binding properties via in vitro spectrophotometric and in silico molecular docking studies. The compounds were found to interact with DNA via a groove binding mode with considerable the binding constants. The groove binding mode of interactions were also suggested by fluorescence ethidium bromide replacement experiments and viscosity studies. Binding interactions of the compounds with DNA have also been studied by molecular docking studies.