Osteoarthritis (OA) is one of the ten most disabling diseases in developed countries, which mainly affects the articular cartilage (AC) of joints continually stressed over time. It contributes to functional impairment and loss of independence in the middle-aged and the elderly and represents an immense burden to patients, thus having a major impact on society. In this regard, porous 3D hydrogels that display high water content, injectability, load-bearing properties and encourage tissue repair are promising biomaterials for cartilage regeneration. Within this context, click hydrogels, which form rapidly under physiological conditions by covalently bonding non-toxic polymeric chains through easily accessible functional groups, are envisaged as promising load-bearing soft tissue scaffolds. However, their poor mechanical properties and their ability to swell when immersed in aqueous environments still limit their bioapplication. To overcome these drawbacks, the nucleophilic thiol-yne reaction, which is highly suitable for hydrogel synthesis because of its efficiency and rapid nature, have been investigated. By using this approach, a range of robust poly(ethylene glycol) (PEG) hydrogels with tunable properties were easily prepared while retaining high water content (ca. 90%). Remarkably, the optimization of the molecular weight, architecture, and composition of the PEG precursors resulted in strong hydrogels (i.e. compressive strengths in the range of MPa) with different storage moduli and tailored stiffness. Moreover, through the judicious choice of the PEG precursor, our robust thiol-yne hydrogels showed non-swellable properties. Not only did they retain their excellent compressive strength in the swollen state, but also displayed enhanced mechanical performance over time. Overall, the versatile and robust nature of the PEG hydrogels designed through efficient thiol-yne chemistry highlights their potential application to resolve the major concerns of hydrogels as biomaterials.

Efficient in situ nucleophilic thiol-yne click chemistry for the synthesis of strong hydrogel materials with tunable properties

254th National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.