A new glucose-based bioadhesive, poly(glucosamine methacrylate-co-N-methacryloyl-3,4-dihydroxyl-l-phenylalanine-co-3-azidopropyl methacrylate) is synthesized by thermally initiated free radical polymerization. Adhesion strength of the synthesized terpolymer is finely controllable via crosslinking. The used crosslinking chemistry is strain-promoted azide-alkyne cycloaddition (SPAAC)) which has advantages of no releasing byproducts and no requiring chemical reagents and/or special stimulus. The SPAAC mediated crosslinking enhanced overall adhesion properties and the fine-tuning of adhesion enhancement was possible by employing various lengths of crosslinkers, concentrations of crosslinkers, and temperatures. The chemistry of covalent bond formation of SPAAC was clearly confirmed by 1H-NMR and FTIR. The glycopolymer segment in the new bioadhesive is highly hydrophilic polymer, which resembles chemical structure of natural saccharides. Due to high water solubility of the glycopolymer, the entire bioadhesive was able to be used as a form of water swollen bioadhesive presenting strong adhesion property on biological surfaces (porcine skins). The adhesion property of synthesized adhesive is examined by lap shear test on porcine skins after moistening the adhesive and crosslinker (PEG-Di BCN) with water. Poly(GM-co-MDOPA-co-AOM) adhesive has 25 times higher adhesion strength (120kPa) compared to rubber cement (4.5 kPa). Furthermore, addition of 20% mole of crosslinker in the poly(GM-co-MDOPA-co-AOM) increases the adhesion strength up to 1.5 times (180 kPa). Those revealed features, which include strong adhesion on biological surface, water compatibility, biocompatibility of each polymeric segment, non-toxic adhesion enhancement principle via SPAAC crosslinking, and potentials capability of glycopolymer segment in biological recognition, indicate that the new terpolymer bioadhesive can be successfully applied in biomedical fields.

Controllable glucose-based bioadhesive through strain-promoted azide-alkyne cycloaddition (SPAAC)

255th National Meeting (2018)

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