A fluorescent bisboronic acid compound that selectively labels cells expressing oligosaccharide Lewis X.

Two fluorescent diboronic acid compounds (6a and 6b) with a dipeptide linker were synthesized as potential sensors for cell surface saccharide Lewis X (Le(X)). Compound 6a with a dipeptide (H-Asp-Ala-) as the linker was found to selectively label CHOFUT4 cells, which express Le(x), at micromolar concentrations, while non-Le(x)-expressing control cells were not labeled.

The first fluorescent diboronic acid sensor specific for hepatocellular carcinoma cells expressing sialyl Lewis X.

Carbohydrate antigens with subterminal fucosylation have been implicated in the development and progression of several cancers, including hepatocellular carcinoma (HCC). Fluorescent sensors targeting fucosylated carbohydrate antigens could potentially be used for diagnostic and other applications. We have designed and synthesized a series of 26 diboronic acid compounds as potential fluorescent sensors for such carbohydrates.

A glucose-selective fluorescence sensor based on boronic acid-diol recognition.

A glucose selective diphenylboronic acid fluorescent sensor (10a) with a K(a) of 1472M(-1) has been synthesized and evaluated. This sensor shows a 43- and 49-fold selectivity for glucose over fructose and galactose, respectively. The binding affinity improvement is about 300-fold and the selectivity improvement for glucose over fructose is about 1400-fold compared with the monoboronic acid compound, phenylboronic acid.

Diboronic acids as fluorescent probes for cells expressing sialyl Lewis X.

A series of fluorescent diboronic acids was synthesized in nine steps as potential sensors for sialyl Lewis X (sLex). The fluorescent binding studies of these sensors with sLex were carried out in a mixed aqueous solution. Compound 7e was found to show the strongest fluorescence enhancement upon binding with sLex.