title: Hydrophilization of poly(caprolactone) copolymers through introduction of oligo(ethylene glycol) moieties.
abstract: In this study, a new family of poly(ε-caprolactone) (PCL) copolymers that bear oligo(ethylene glycol) (OEG) moieties is described. The synthesis of three different oligo(ethylene glycol) functionalized epoxide monomers derived from 2-methyl-4-pentenoic acid, and their copolymerization with ε-caprolactone (CL) to poly(CL-co-OEG-MPO) copolymers is presented. The statistical copolymerization initiated with SnOct2/BnOH yielded the copolymers with varying OEG content and composition. The linear relationship between feed ratio and incorporation of the OEG co-monomer enables control over backbone functional group density. The introduction of OEG moieties influenced both the thermal and the hydrophilic characteristics of the copolymers. Both increasing OEG length and backbone content resulted in a decrease in static water contact angle. The introduction of OEG side chains in the PCL copolymers had no adverse influence on MC-3TE3-E1 cell interaction. However, changes to cell form factor (Φ) were observed. While unmodified PCL promoted elongated (anisotropic) morphologies (Φ = 0.094), PCL copolymer with tri-ethylene glycol side chains at or above seven percent backbone incorporation induced more isotropic cell morphologies (Φ = 0.184) similar to those observed on glass controls (Φ = 0.151).
authors.affiliation: Institute for Macromolecular Chemistry, University of Freiburg, Freiburg, Germany; BIOSS Centre for Biological Signaling Studies, University of Freiburg, Freiburg, Germany.
authors.forename: Jonathan J
authors.initials: JJ
authors.lastname: Wurth
authors.affiliation: Institute for Macromolecular Chemistry, University of Freiburg, Freiburg, Germany; BIOSS Centre for Biological Signaling Studies, University of Freiburg, Freiburg, Germany.
authors.forename: Nils R
authors.initials: NR
authors.lastname: Blumenthal
authors.affiliation: Institute for Macromolecular Chemistry, University of Freiburg, Freiburg, Germany; BIOSS Centre for Biological Signaling Studies, University of Freiburg, Freiburg, Germany.
authors.forename: V Prasad
authors.initials: VP
authors.lastname: Shastri
mesh_terms: D000818:Animals; D001672:Biocompatible Materials / Q000138:chemical synthesis*; D063566:Biodegradable Plastics / Q000138:chemical synthesis; D002152:Calorimetry, Differential Scanning; D002460:Cell Line; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D019855:Ethylene Glycol / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D008422:Materials Testing; D051379:Mice; D018625:Microscopy, Atomic Force; D019906:Nuclear Magnetic Resonance, Biomolecular; D010006:Osteoblasts / Q000187:drug effects; D011091:Polyesters / Q000737:chemistry*; D011108:Polymers / Q000138:chemical synthesis*
chemical_list: D001672:Biocompatible Materials; D063566:Biodegradable Plastics; D004852:Epoxy Compounds; D011091:Polyesters; D011108:Polymers; C016240:polycaprolactone; D019855:Ethylene Glycol