Synthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen
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.
KeywordsLewis sugar Bisboronic acid Anthracene-based fluorescent probe Biochemical recognition
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We also thanks Professor WANG Binghe(Georgia State University, USA) for his help in revising the manuscript.
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