Carbohydrates play a crucial role in many biological processes, including cell-cell communication, cellular adhesion, cancer metastasis, inflammation and immunoregulation.  Consequently, one area glycoscience aims to study is the identification of functional glycans on the cell surface and their role in immunoregulation.  Lectins have been used in the past to study a wide range of biological processes and are known to bind to cell surface glycans and induce signal transduction.  However, the number of natural lectins is still limited compared with the diversity of native glycans giving rise to a demand for a more comprehensive and complete catalogue for detailed glycan analysis.  Boronic acid derivatives, often termed boronolectins, are regarded as synthetic lectin mimetics for their ability to form reversible complexes with saccharides. Specifically, boronic acid derivatives have shown to preferentially bind terminal sialic acid residues at physiologic pH.  Sialic acids are the most abundant terminal residue of glycans and could therefore be useful for diagnostic and therapeutic applications related to disease based on their large role in multiple pathological and physiological conditions.  This research proposes a focused synthetic approach to model boronic acid-containing proteins for carbohydrate-recognition and/or cellular activation application. Specifically, BSA-boronic acid conjugates were synthesized by modifying different amino acids to afford the lectin mimetics. The resultant BSA-boronic acid conjugates were characterized by sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE), matrix-assisted laser desorption/ionization - time of flight (MALDI-TOF) to determine success of the synthetic route and quantify BA density. MTT assay showed biocompatibility of the BSA-boronic acid conjugates as well. These novel lectin mimetics will inevitably find a role in theranostic applications given they do not suffer from the drawbacks of natural lectins and they can be wittingly modified altering binding specificity and capacity.

Synthesis of and evaluation of boronic acid derived lectin mimetics

253rd National Meeting (2017)

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