PH‐Universal Catechol‐Amine Chemistry for Versatile Hyaluronic Acid Bioadhesives. Issue 41 (21st August 2022)

• Record Type: Journal Article
• Authors: An, Soohwan; Jeon, Eun Je; Han, Seung Yeop; Jeon, Jihoon; Lee, Mi Jeong; Kim, Sooyeon; Shin, Mikyung; Cho, Seung‐Woo
• Is Part Of: Small. Volume 18:Issue 41(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-08-21
• Subjects: biomedical application -- catechol–amine chemistry -- hyaluronic acid hydrogels -- pH‐universal crosslinking; Nanotechnology -- Periodicals; Nanoparticles -- Periodicals; Microtechnology -- Periodicals; 620.5
• DOI: 10.1002/smll.202202729
• Languages: English
• ISSNs: 1613-6810

Abstract

Abstract: Catechol, a major mussel‐inspired underwater adhesive moiety, has been used to develop functional adhesive hydrogels for biomedical applications. However, oxidative catechol chemistry for interpolymer crosslinking and adhesion is exclusively effective under alkaline conditions, with limited applications in non‐alkaline conditions. To overcome this limitation, pH‐universal catechol–amine chemistry to recapitulate naturally occurring biochemical events induced by pH variation in the mussel foot is suggested. Aldehyde moieties are introduced to hyaluronic acid (HA) by partial oxidation, which enables dual‐mode catechol tethering to the HA via both stable amide and reactive secondary amine bonds. Because of the presence of additional reactive amine groups, the resultant aldehyde‐modified HA conjugated with catechol (AH‐CA) is effectively crosslinked in acidic and neutral pH conditions. The AH‐CA hydrogel exhibits not only fast gelation via active crosslinking regardless of pH conditions, but also strong adhesion and excellent biocompatibility. The hydrogel enables rapid and robust wound sealing and hemostasis in neutral and alkaline conditions. The hydrogel also mediates effective therapeutic stem cell and drug delivery even in dynamic and harsh environments, such as a motile heart and acidic stomach. Therefore, the AH‐CA hydrogel can serve as a versatile biomaterial in a wide range of pH conditions in vivo. Abstract : pH‐universal catechol–amine chemistry mimicking natural pH responses of mussel byssus is realized by hyaluronic acid (HA) ring opening and subsequent catechol conjugation to HA via amide and secondary amine linkages. This chemistry induced by both linkages enables oxidative crosslinking and adhesion of catechol‐functionalized HA hydrogel over a wide range of pH conditions with versatile biomedical applications.