Low molecular weight ε-caprolactone-p-coumaric acid copolymers as potential biomaterials for skin regeneration applications

PLoS One. 2019 Apr 8;14(4):e0214956. doi: 10.1371/journal.pone.0214956. eCollection 2019.

Abstract

ε-caprolactone-p-coumaric acid copolymers at different mole ratios (ε-caprolactone:p-coumaric acid 1:0, 10:1, 8:1, 6:1, 4:1, and 2:1) were synthesized by melt-polycondensation and using 4-dodecylbenzene sulfonic acid as catalyst. Chemical analysis by NMR and GPC showed that copolyesters were formed with decreasing molecular weight as p-coumaric acid content was increased. Physical characteristics, such as thermal and mechanical properties, as well as water uptake and water permeability, depended on the mole fraction of p-coumaric acid. The p-coumarate repetitive units increased the antioxidant capacity of the copolymers, showing antibacterial activity against the common pathogen Escherichia coli. In addition, all the synthesized copolyesters, except the one with the highest concentration of the phenolic acid, were cytocompatible and hemocompatible, thus becoming potentially useful for skin regeneration applications.

MeSH terms

  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Biocompatible Materials* / chemistry
  • Biocompatible Materials* / pharmacology
  • Caproates* / chemistry
  • Caproates* / pharmacology
  • Cell Line
  • Coumaric Acids
  • Escherichia coli / growth & development*
  • Humans
  • Lactones* / chemistry
  • Lactones* / pharmacology
  • Propionates* / chemistry
  • Propionates* / pharmacology
  • Skin* / injuries
  • Skin* / metabolism
  • Skin* / microbiology
  • Wound Healing / drug effects*

Substances

  • Anti-Bacterial Agents
  • Biocompatible Materials
  • Caproates
  • Coumaric Acids
  • Lactones
  • Propionates
  • caprolactone
  • p-coumaric acid

Grants and funding

The authors received no specific funding for this work.