PEG- and peptide-grafted aliphatic polyesters by click chemistry.
Novel aliphatic polyesters with pendent acetylene groups were prepared by controlled ring-opening polymerization and subsequently used for grafting poly(ethylene glycol) and oligopeptide moieties by the Cu(I)-catalyzed addition of azides and alkynes, a type of "click" chemistry. These aliphatic polyesters possess an acetylene graft density that can be tailored by ring-opening copolymerization of alpha-propargyl-delta-valerolactone (1) with epsilon-caprolactone. Since the mild conditions associated with the click reaction are shown to be compatible with the polyester backbone, this method is a generally useful means for grafting numerous types of functionality onto aliphatic polyesters. The amphiphilic graft polyesters prepared in this study are shown to be biocompatible by in vitro cytotoxicity evaluation, suggesting their suitability for a range of biomaterial applications.
Parrish
Bryan
B
Polymer Science & Engineering Department, University of Massachusetts, Conte Center for Polymer Research, Amherst, 01003, USA.
Breitenkamp
Rebecca B
RB
Emrick
Todd
T
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000818:Animals; D001672:Biocompatible Materials / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D002384:Catalysis; D002460:Cell Line; D003300:Copper / Q000737:chemistry; D005347:Fibroblasts / Q000187:drug effects; D051379:Mice; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000737:chemistry* / Q000633:toxicity; D011091:Polyesters / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D011092:Polyethylene Glycols / Q000737:chemistry* / Q000633:toxicity
D001672:Biocompatible Materials; D009842:Oligopeptides; D011091:Polyesters; D011092:Polyethylene Glycols; D003300:Copper; D000114:Acetylene