Volume 18, Issue 41 2202729
Research Article

pH-Universal Catechol-Amine Chemistry for Versatile Hyaluronic Acid Bioadhesives

Soohwan An

Soohwan An

Department of Biotechnology, Yonsei University, Seoul, 03722 Republic of Korea

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Eun Je Jeon

Eun Je Jeon

Department of Biotechnology, Yonsei University, Seoul, 03722 Republic of Korea

CellArtgen Inc., Seoul, 03722 Republic of Korea

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Seung Yeop Han

Seung Yeop Han

Department of Biotechnology, Yonsei University, Seoul, 03722 Republic of Korea

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Jihoon Jeon

Jihoon Jeon

Department of Biotechnology, Yonsei University, Seoul, 03722 Republic of Korea

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Mi Jeong Lee

Mi Jeong Lee

Department of Biotechnology, Yonsei University, Seoul, 03722 Republic of Korea

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Sooyeon Kim

Sooyeon Kim

Department of Biotechnology, Yonsei University, Seoul, 03722 Republic of Korea

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Mikyung Shin

Mikyung Shin

Department of Biomedical Engineering, Sungkyunkwan University (SKKU), Suwon, 16419 Republic of Korea

Department of Intelligent Precision Healthcare Convergence, Sungkyunkwan University (SKKU), Suwon, 16419 Republic of Korea

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Seung-Woo Cho

Corresponding Author

Seung-Woo Cho

Department of Biotechnology, Yonsei University, Seoul, 03722 Republic of Korea

CellArtgen Inc., Seoul, 03722 Republic of Korea

Center for Nanomedicine, Institute for Basic Science (IBS), Seoul, 03722 Republic of Korea

Graduate Program of Nano Biomedical Engineering (NanoBME), Advanced Science Institute, Yonsei University, Seoul, 03722 Republic of Korea

E-mail: [email protected]

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First published: 21 August 2022
Citations: 16

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.

Conflict of Interest

S.-W.C. is a chief technology officer (CTO) of CellArtgen, Inc., Republic of Korea. S.A., E.J.J., and S.-W.C. are co-inventors on a Korean Patent Application (10-2022-0033370) related to the AH-CA hydrogel used in the manuscript.

Data Availability Statement

The data that support the findings of this study are available from the corresponding author upon reasonable request.

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