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

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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… Click to show full 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(sLex) with selectivity over other Lewis sugars, and could significantly stain sLex-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 sLex selectivity and higher binding affinity.

Keywords: acids selective; synthesis bisboronic; sialyl lewis; selective recognition; recognition sialyl; bisboronic acids

Journal Title: Chemical Research in Chinese Universities
Year Published: 2018

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