Preparation of a class of versatile, chemoselective, and amorphous polyketoesters.
A straightforward and versatile strategy for preparing a class of biodegradable and amorphous polyketoesters is reported. A series of ketone-containing diesters and diacids were combined with di(ethylene glycol) through condensation polymerization, achieving <Mn> values of up to 10.1 x 10(3) g/mol. Glass transition temperatures ranged from -41 to -6 degrees C, rendering all of the materials liquid at room temperature. By including ketone groups in the repeat unit, facile postpolymerization modifications were possible by reaction with oxyamine-tethered ligands through the formation of an oxime linkage. Upon reaction with molecules that contain oxyamines, under mild conditions, these polymers can easily have a diverse set of side chains appended without coreagents or catalysts. The chemoselective oxime-forming coupling strategy is compatible with physiological conditions and can be done in the presence of a wide range of functional groups and biomolecules, including proteins and nucleic acids. We demonstrate the utility of this strategy by immobilizing a cell adhesive peptide (H2NO-RGD) to polyketoester films, creating cell adhesive elastomers. This immobilization strategy is synthetically flexible for designing and tailoring polymers for targeted biological applications.
Barrett
Devin G
DG
Department of Chemistry, Carolina Center for Genome Science, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Yousaf
Muhammad N
MN
D016475:3T3 Cells; D000818:Animals; D001672:Biocompatible Materials / Q000138:chemical synthesis*; D001704:Biopolymers; D002448:Cell Adhesion / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D020724:Elastomers; D005347:Fibroblasts / Q000166:cytology / Q000187:drug effects*; D007659:Ketones; D051379:Mice; D009842:Oligopeptides; D010091:Oximes; D044367:Phase Transition; D011091:Polyesters / Q000138:chemical synthesis*
D001672:Biocompatible Materials; D001704:Biopolymers; D020724:Elastomers; D007659:Ketones; D009842:Oligopeptides; D010091:Oximes; D011091:Polyesters; C047981:arginyl-glycyl-aspartic acid