Synthesis and G-quadruplex binding study of a novel full visible absorbing perylene diimide dye

Abstract

A novel perylene diimide dye containing glucopyranosyl groups in 1- and 7-positions of the perylene ring has been synthesized and characterized to obtain highly efficient and stable photosensitized material in photodynamic therapy. Solvatochromic studies on this dye in solvents of different polarities have indicated that absorption bands of the dye cover the whole visible spectrum in more polar organic solvents. It shows absorption bands localized at 350-500 nm and 600-850 urn in benzonitrile giving a green color. Also, the dye has a wide absorption region which covers the wavelength between 400 and 800 nm in more polar solvents by changing the dye concentration in the solvents. Singlet oxygen generation efficiency and G-quadruplex binding affinity of the dye have been tested. Theoretical calculations through semi-empirical methods have been performed and a detailed spectroscopic assignment of the molecule has been also presented. (C) 2012 Elsevier B.V. All rights reserved.