Synthesis and characterization of divinyl-fumarate poly-ε-caprolactone for scaffolds with controlled architectures

J Tissue Eng Regen Med. 2018 Jan;12(1):e523-e531. doi: 10.1002/term.2322. Epub 2017 Apr 3.

Abstract

A vinyl-terminated polycaprolactone has been developed for tissue engineering applications using a one-step synthesis and functionalization method based on ring opening polymerization (ROP) of ε-Caprolactone, with hydroxyl ethyl vinyl ether (HEVE) acting both as the initiator of ROP and as photo-curable functional group. The proposed method employs a catalyst based on aluminium, instead of the most popular Tin(II) 2-ethylhexanoate, to reduce the cytotoxicity. Following the synthesis of the vinyl-terminated polycaprolactone, its reaction with fumaryl chloride (FuCl) results in a divinyl-fumarate polycaprolactone (VPCLF). The polymers obtained were thoroughly characterized using Fourier transform infrared spectroscopy (FTIR) and gel permeation chromatography (GPC) techniques. The polymer has been successfully employed, in combination with N-vinyl pyrrolidone (NVP), to fabricate films and computer-designed porous scaffolds by micro-stereolithography (μ-SL) with gyroid and diamond architectures. Characterization of the networks indicated the influence of NVP content on the network properties. Human mesenchymal stem cells adhered and spread onto VPCLF/NVP networks showing good biological properties and no cytotoxic effect. Copyright © 2016 John Wiley & Sons, Ltd.

Keywords: biocompatibility; cell-material interactions; mathematically defined scaffold; photocrosslinkable polymer; polycaprolactone fumarate; stereolithography.

MeSH terms

  • Butadienes / chemical synthesis*
  • Butadienes / chemistry
  • Cell Adhesion
  • Cell Survival
  • Cross-Linking Reagents / chemistry
  • Humans
  • Mesenchymal Stem Cells / cytology
  • Mesenchymal Stem Cells / metabolism
  • Polyesters / chemical synthesis*
  • Polyesters / chemistry
  • Pyrrolidinones / chemistry
  • Spectroscopy, Fourier Transform Infrared
  • Tissue Scaffolds / chemistry*
  • Transition Temperature

Substances

  • Butadienes
  • Cross-Linking Reagents
  • Polyesters
  • Pyrrolidinones
  • poly(caprolactone fumarate)
  • N-vinyl-2-pyrrolidinone
  • 1,3-butadiene