Chymotrypsin responsive hydrogel: application of a disulfide exchange protocol for the preparation of methacrylamide containing peptides.
Methacrylamide groups were selectively coupled to cysteine residues in the presence of amines and alcohols by utilizing a disulfide exchange reaction in aqueous, acidic buffer. The tetrapeptide sequence, CYKC, was used as a cross-linker to create poly(acrylamide) hydrogels that dissolved when subjected to either a flowing or stationary solution of alpha-chymotrypsin. Control hydrogels that were cross-linked with the tetrapeptide, CSKC, were not affected by the same protease solution. In contrast, dissolution of both the CYKC and CSKC cross-linked hydrogel structures was accomplished by using the disulfide reducing agent tris(2-carboxyethyl) phosphine (TCEP). The chemoselective conjugation technique described could have utility for more advanced protease-responsive hydrogels as well as other hybrid materials composed of synthetic and biomacromolecules.
Plunkett
Kyle N
KN
The Department of Chemistry & The Beckman Institute for Advanced Science and Technology, The University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
Berkowski
Kimberly L
KL
Moore
Jeffrey S
JS
D000178:Acrylamides; D000595:Amino Acid Sequence; D002918:Chymotrypsin / Q000378:metabolism*; D003432:Cross-Linking Reagents / Q000737:chemistry; D004220:Disulfides; D020136:Hydrogel, Polyethylene Glycol Dimethacrylate / Q000138:chemical synthesis* / Q000378:metabolism*; D009842:Oligopeptides / Q000737:chemistry*
D000178:Acrylamides; D003432:Cross-Linking Reagents; D004220:Disulfides; D009842:Oligopeptides; D020136:Hydrogel, Polyethylene Glycol Dimethacrylate; D002918:Chymotrypsin; C045985:methacrylamide