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First aldol cross-linked hyaluronic acid hydrogel: Fast and hydrolytically stable hydrogel with tissue adhesive properties

Bermejo-Velasco, Daniel, Kadekar, Sandeep, da Costa, Marcus Vinicius Tavares, Oommen, Oommen P. ORCID: https://orcid.org/0000-0003-2768-0133, Gamstedt, Kristofer, Hilborn, Jöns and Varghese, Oommen P. 2019. First aldol cross-linked hyaluronic acid hydrogel: Fast and hydrolytically stable hydrogel with tissue adhesive properties. ACS Applied Materials & Interfaces 11 (41) , pp. 38232-38239. 10.1021/acsami.9b10239

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Abstract

Currently, there are limited approaches to tailor 3D scaffolds cross-linked with a stable covalent C–C bond that does not require any catalysts or initiators. We present here the first hydrogels employing aldol condensation chemistry that exhibit exceptional physicochemical properties. We investigated the aldol-cross-linking chemistry using two types of aldehyde-modified hyaluronic acid (HA) derivatives, namely, an enolizable HA-aldehyde (HA-Eal) and a non-enolizable HA-aldehyde (HA-Nal). Hydrogels formed using HA-Eal demonstrate inferior cross-linking efficiency (due to intramolecular loop formation), when compared with hydrogels formed by mixing HA-Eal and HA-NaI leading to a cross-aldol product. The change in mechanical properties as a result of cross-linking at different pH values is determined using rheological measurements and is interpreted in terms of molecular weight between cross-links (Mc). The novel HA cross-aldol hydrogel demonstrate excellent hydrolytic stability and favorable mechanical properties but allow hyaluronidase-mediated enzymatic degradation. Interestingly, residual aldehyde functionality within the aldol product rendered the tissue-adhesive properties by bonding two bone tissues. The aldehyde functionality also facilitated facile post-synthetic modifications with nucleophilic reagents. Finally, we demonstrate that the novel hydrogel is biocompatible with encapsulated stem cells that show a linear rate of expansion in our 3–6 days of study.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Pharmacy
Publisher: American Chemical Society
ISSN: 1944-8252
Last Modified: 25 Oct 2024 10:00
URI: https://orca.cardiff.ac.uk/id/eprint/172999

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