Due to their excellent biocompatibility, chemically cross-linked poly(ethylene glycol) based hydrogels are widely used for biomedical applications, especially as drug delivery systems or tissue engineering scaffolds. Despite their wide use, most cross-linking mechanisms are associated with significant disadvantages, such as the formation of potentially harmful radicals or unwanted side reactions with incorporated drug molecules. Here, we present an innovative method for the covalent cross-linking of hydrogels by exploiting the Diels-Alder click reaction. As a proof of concept, Diels-Alder hydrogels were loaded with different fluorescein isothiocyanate labeled macromolecules; the mobility of these substances was characterized by fluorescence recovery after photobleaching experiments. By fitting model equations to the experimental data, diffusion coefficients could be calculated for each probe molecule. With the help of these data and further mathematical models, release profiles were predicted. According to our calculations, a sustained release over several days can be expected.

Application of the Diels-Alder reaction as a new cross-linking mechanism for poly(ethylene glycol) based hydrogels

244th National Meeting (2012)

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