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

Agata Głuszyńska; Bernard Juskowiak

doi:10.3390/molecules24050965

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

Molecules. 2019 Mar 9;24(5):965. doi: 10.3390/molecules24050965.

Authors

Agata Głuszyńska¹, Bernard Juskowiak²

Affiliations

¹ Laboratory of Bioanalytical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Umultowska Street 89b, 61-614 Poznań, Poland. aglusz@amu.edu.pl.
² Laboratory of Bioanalytical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Umultowska Street 89b, 61-614 Poznań, Poland. juskowia@amu.edu.pl.

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.

Keywords: G-quadruplex ligands; carbazole derivatives; equilibrium dialysis method; microwave synthesis.

MeSH terms

Aldehydes / chemical synthesis*
Aldehydes / chemistry*
DNA / chemistry*
G-Quadruplexes
Microwaves*

Substances

Aldehydes
DNA

Grants and funding

(POMOST/2011-3/3)/Foundation for Polish Science