Fluorescent conjugates of D-glucosamine with 3-thiazolylcoumarins: Synthesis, characterization and potential use as cell imaging agents

Abstract

Aim. Synthesis and study of glucosamine-coumarin conjugates as possible reagents for the fluorescent cell imaging. Methods. Organic synthesis, NMR, optical spectroscopy, confocal microscopy. Results. D-glucosamine conjugates with 7-substituted 3-thiazolylcoumarins were obtained in 55-82 % yield by the reaction of NHS active esters of carboxy-modified dyes with sugar amino group. The anomeric configuration of the products was elucidated by NMR. Their spectral properties were studied in methanol and phosphate buffer. Preliminary evaluation of possible use of the conjugates for cell staining was performed. Conclusion. Thiazolylcoumarin-labeled glucosamines with bright blue emission are promising reagents for cell imaging.