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2006:
Moss Jason A; Stokols Shula; Hixon Mark S; Ashley Fawn T; Chang Jason Y; Janda Kim D
Solid-phase synthesis and kinetic characterization of fluorogenic enzyme-degradable hydrogel cross-linkers.
Biomacromolecules 2006;
7(
4):.
Of critical importance in drug delivery and tissue engineering applications is the degradability of implanted polymeric materials. The use of peptide-derived cross-linkers in hydrogel design is a valuable approach by which polymeric carriers can be endowed with enzymatic degradability in a predictable, "programmable" fashion. The solid-phase synthesis strategy described herein allows for an expeditious, flexible synthesis of bis-acrylamide-derivatized peptides with complex modifications, as exemplified by the incorporation of fluorophore and quencher moieties into a matrix metalloprotease (MMP)-degradable cross-linker. The crude synthetic product was obtained in high yield and purity and purified by standard methods; it was then used directly for polymerization without the need for tedious and often nonchemoselective solution-phase modifications. Functional appendages incorporated for detection provided a direct, quantitative link between enzymatic activity and hydrogel degradation using routine methods for identification of optimal enzyme-specific degradability.
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