Synthesis and modification of functional poly(lactide) copolymers: toward biofunctional materials.
A polylactide copolymer with pendant benzyloxy groups has been synthesized by the copolymerization of a benzyl-ether substituted monomer with lactide. Debenzylation of the polymer to provide pendant hydroxyl groups followed by modification with succinic anhydride affords the corresponding carboxylic acid functionalized copolymer that is amenable to standard carbodiimide coupling conditions to attach amine-containing biological molecules. An amino-substituted biotin derivative was coupled to the carboxyl functional groups of copolymer films as proof-of-concept. In a demonstration of the function of these new materials, an RGD-containing peptide sequence was tethered to copolymer films at various densities and was shown to enhance the adhesion of epithelial cells. This strategy provides the opportunity for the attachment of a variety of ligands, allowing for the fabrication of a versatile class of biodegradable, biocompatible materials.
Noga
David E
DE
School of Chemistry and Biochemistry, George W Woodruff School of Mechanical Engineering, Petit Institute for Bioengineering and Bioscience, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, USA.
Petrie
Timothy A
TA
Kumar
Anjli
A
Weck
Marcus
M
García
Andrés J
AJ
Collard
David M
DM
D000818:Animals; D001672:Biocompatible Materials / Q000138:chemical synthesis*; D019921:Biotinylation; D002448:Cell Adhesion; D004285:Dogs; D004847:Epithelial Cells / Q000166:cytology; D009842:Oligopeptides / Q000737:chemistry; D011091:Polyesters / Q000138:chemical synthesis* / Q000737:chemistry
D001672:Biocompatible Materials; D009842:Oligopeptides; D011091:Polyesters; C033616:poly(lactide); C047981:arginyl-glycyl-aspartic acid