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

The Diels-Alder (DA) reaction was investigated as a cross-linking mechanism for poly(ethylene glycol) (PEG) based hydrogels. Two complementary macromonomers were synthesized by functionalizing star-shaped PEG with furyl and maleimide groups. Gel formation occurred in water at 37 degrees C; the gelation time ranged between 171 +/- 25 min and 14 +/- 1 min depending on the used hydrogel formulation. The complex shear modulus was dependent on the concentration, branching factor and molecular weight of the macromonomers; values between 2821 +/- 1479 Pa and 37097 +/- 6698 Pa were observed. Hydrogel swelling and degradation were influenced by the same parameters; the degradation time varied between a few days and several weeks. Gel dissolution was found to occur by retro-DA reaction and subsequent hydrolysis of maleimide groups. Calculations of the network mesh size revealed that the prepared hydrogels would be suitable for the controlled release of therapeutic proteins.