Pyridyl-indolizine derivatives as DNA binders and pH-sensitive fluorescent dyes

• DOI: 10.1016/j.tet.2016.10.052
• Publication Date: 2016-11-04T01:46:12Z
• Authors: Narcisa-Laura Mar...; Lacramioara Popovici; Elena-Laura Ursu; Ramona Danac; Lilia Clima; Corneliu Cojocaru; Adina Coroaba; Andrei Neamtu; Ionel Mangalagiu; Mariana Pinteala; Alexandru Rotaru
• Keywords: Indolizine; Moiety; Dissociation constant; Agarose gel electrophoresis

New fluorescent anthracene-based indolizine derivative has been synthesized by appendix of the anthracene moiety via “click” chemistry at the first position of indolizinic core. The new product has been carefully characterized and its absorption-emission properties studied in aqueous buffer solutions at different pH values and also compared to its precursor containing only pyridyl-indolizinic core. The anthracenemodified indolizine and its precursor were tested for DNA binding using agarose gel electrophoresis, UV–vis and fluorescence experiments. The comparative experimental data were in accordance to the molecular docking simulation of the corresponding systems using the Yassara computer program. Both experimental and simulation results suggest that the anthracene-modified indolizine has a superior affinity for the DNA than its precursor due to much lower values of binding energy and dissociation constant of the corresponding complex.