Hydrogels are used in many biomedical applications such as tissue engineering, drug delivery and wound healing. Controlling the mechanical and swelling properties of hydrogels is a critical component to determining appropriate applications for these materials. We hypothesized that introduction of methylene groups within a PEG crosslinker containing terminal NHS active esters will provide additional control of these properties when crosslinked with a multifunctional amine, such as a tri-lysine Dendron. The general synthetic route to the PEG crosslinkers is as follows: NHS-PEG-NHS is reacted with a thiol and base in dry methylene chloride to afford intermediate A. The crosslinker was obtained by reacting intermediate A with N,N’-dicyclohexylcarbodiimide and N-hydroxysuccinimide in dry methylene chloride. Three different PEG crosslinkers were synthesized and characterized by NMR, MALDI, TGA and DSC. The mechanical properties and swelling properties of the resulting hydrogels are dependent on added weight percent and on the number of methylenes present in the crosslinker. In addition, these hydrogels can be controllably dissolved on-demand via a thiol-thioester exchange reaction as an internal thioester is present within the PEG crosslinker. Finally, these hydrogels are non-toxic, biocompatible, and biodegradable.

Insertion of methylene groups into PEG crosslinkers allows for control of hydrogel swelling and mechanical properties

256th National Meeting (2018)

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