Triggered Copolypeptide Hydrogel Degradation Using Photolabile Lysine Protecting Groups.
Published Web Locationhttps://doi.org/10.1021/acsmacrolett.6b00715
We have prepared a new l-lysine-based N-carboxyanhydride monomer containing a photolabile o-nitrobenzyloxycarbonyl protecting group. This monomer was used to prepare poly(l-lysine)-block-poly(oNB-l-lysine) block copolypeptides that formed hydrogels with tunable physical properties and the capability to be degraded by UV irradiation. In these materials, the oNB-lysine residues were found to be excellent surrogates for the hydrophobic residues typically used to form block copolypeptide hydrogels, thus adding functionality without adversely altering self-assembly characteristics. Upon irradiation, full cleavage of the o-nitrobenzyloxycarbonyl groups was observed, resulting in dissolution of the product, poly(l-lysine), and complete hydrogel disruption. When dye molecules were entrapped in the hydrogels, photolysis resulted in release and mixing of these molecules with the surrounding media.