Cell surface glycans, glycoproteins or glycolipids, are commonly aberrant in diseases and can serve as biomarkers that facilitate diagnostics, selective cellular labeling and delivery. Boronic acids have been extensively utilized for the detection and separation for carbohydrates through reversible formation of boronate esters in the binding of diol moieties on glycans. However, the biological application of this sensing group is challenged by its relatively low binding affinity in aqueous media. Our lab designed and synthesized boronic acid materials that can enhance its avidity towards glycan through multivalent binding interaction.<br/>First, a boronic acid microplate assay for sensitive and high-throughput detection for cancerous glycoprotein MUC1 was developed. A multivalent surface for glycoprotein recruitment and detection was achieved by immobilization of biotinylated boronic acid onto streptavidin plates. In addition, novel boronic acid lipids were synthesized and incorporated into liposome as drug delivery platform. We validated boronic acid liposome efficacy by demonstrating dose-dependent release of encapsulated hydrophobic or hydrophilic fluorophores upon titration with the polysaccharide heparin. Finally, cellular delivery and labeling was visualized by confocal microscopy through a dramatic enhancement in fluorescence signal, showcasing the prospects of boronic acid lipids for drug delivery.

Boronic acid materials: Applications in glycoprotein recognition and enhanced cellular delivery

2019 Spring National Meeting

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