Injectable Self-Healing Hydrogels Based on Boronate Ester Formation between Hyaluronic Acid Partners Modified with Benzoxaborin Derivatives and Saccharides

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Figueiredo, Tamiris | Jing, Jing | Jeacomine, Isabelle | Olsson, Johan | Gerfaud, Thibaud | Boiteau, Jean-Guy | Rome, Claire | Harris, Craig | Auzély-Velty, Rachel

Edité par CCSD ; American Chemical Society -

International audience. We demonstrate here, for the first time, formation of injectable dynamic covalent hydrogels at physiological pH using benzoxaborin-saccharide complexation as a reversible crosslinking method. The gels were prepared by simply mixing hyaluronic acid modified with an original boronic acid derivative, 3,4-dihydro-2H-benzo[e][1,2]oxaborinin-2-ol (1,2-ABORIN), and HA functionalized with 1-amino-1-deoxy-D-fructose. Dynamic rheological experiments confirmed the gel-like behavior (storage modulus (G’) > loss modulus (G’) in the frequency window explored) for the designed HA-1,2-ABORIN/HA-fructose network. Furthermore, this hydrogel exhibited excellent self-healing and injectability behaviors in aqueous conditions and was found to be responsive to pH. Additionally, fibroblast cells encapsulated in the HA network showed high viability (> 80 % after 7 days of cell culture), as monitored by Live/Dead staining. Taken together, this new class of boronate ester crosslinked hydrogel provides promising future for diverse biomedical applications.

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