Synthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen

Abstract

The development of sensors that recognize Lewis oligosaccharides can help the diagnosis and early detection of cancer. Herein, we reported the design and synthesis of a series of anthracene-based bisboronic acids (9a—9e) with different N-substituents near the boronic acid unit. Among them, compound 9a could recognize sialyl Lewis X(sLe^x) with selectivity over other Lewis sugars, and could significantly stain sLe^x-expressing HEPG2 cells with selectivity over the range of 0.1—10 μmol/L. Compound 9a possibly has two properly positioned boronic acids caused by the steric hindrance by the near N-benzyl substituent group, which empower its sLe^x selectivity and higher binding affinity.

Keywords

Lewis sugar / Bisboronic acid / Anthracene-based fluorescent probe / Biochemical recognition

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