Synthesis of fluorescent bisboronic acid sensors and their recognition of mono-/oligo-saccharides

Sensors capable of recognizing cell surface carbohydrates, such as sialyl Lewis X (sLex), are invaluable research tools and for the diagnosis and early detection of many forms of cancer. In this paper, we report the design and synthesis of a series of bisboronic acids 6(a-f) as fluorescent sensors towards mono-/oligosaccharides. Among them, compounds 6d and 6e showed strong binding affinities with glucose and fructose, while compound 6c, in which two anthracene-based boronic acid units were linked by a hexamethylene spacer, was able to recognize sLex selectivity and stained HEPG2 cells at 1 mu mol/L. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.