Practical Microwave Synthesis of Carbazole Aldehydes for the Development of DNA-Binding Ligands

Abstract

Microwave formylation of carbazole derivatives was investigated and 3-monoaldehydes were obtained in high yield. A potential DNA-binding ligand, 3-[(3-ethyl)-2-vinylbenzothiazolium]-9-N-ethyl carbazole iodide, was synthesized and characterized including spectral properties (UV-Vis absorption and fluorescence spectra). The binding selectivity and affinity of three carbazole ligands for double-stranded and G-quadruplex DNA structures were studied using a competitive dialysis method in sodium- and potassium-containing buffer solutions.

Synthesis and evaluation of bis(imino)anthracene derivatives as G-quadruplex ligands

“…19 It was also shown that using piperidine as a N-propylamino attached to carbazoles gave the highest stabilizing ligands in a study. 20 Interestingly, however they did identify that there was an inverse correlation between G-tetrad stabilization and G4 DNA selectivity. 21 This is very interesting for our results, as it could begin to explain why we see that the relationship between the change in ppm does not correlate completely with IC 50 values, even showing an inverse relationship to what was expected from nemorubicin…”