Azlactone-functionalized polymers, like poly(2-vinyl-4,4-dimethylazlactone) (PVDMA), undergo rapid ring opening reactions in the presence of nucleophiles, such as primary amines, alcohols, and thiols. The reactivity of these materials make them useful for the fabrication of scaffolds functionalized with a broad range of chemical and biological moieties. We recently demonstrated the assembly, topographical patterning, and chemical functionalization of soft hydrogel scaffolds using PVDMA and a diamine of interest in the context of advanced cell culture platforms. The work described here builds on these previous studies to develop a photocontrolled approach for both the assembly and post-fabrication modification of azlactone-functionalized gel materials. This approach involves the use of photocaged amines for the fabrication and functionalization of PVDMA-based gel materials. Preliminary experiments using hexamethylenediamine protected with the photolabile group, 2-(2-nitrophenyl)propyloxycarbonyl, mixed with PVDMA in DMF demonstrated gelation upon irradiation with UV light at 365 nm. This presentation will describe the synthesis of a series of photocaged mono- and diamines and the feasibility of using these reactions to fabricate gel scaffolds patterned with a range of chemical and biological functionality, in addition to the resulting differences in gelation kinetics and gel moduli.

Photocontrolled ring-opening reactions of poly(2-alkenyl azlactone)s with photocaged amines for hydrogel formation and modification

256th National Meeting (2018)

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