Biostability enhancement of oil core - polysaccharide multilayer shell via photoinitiator free thiol-ene 'click' reaction

Colloids Surf B Biointerfaces. 2016 Jun 1:142:281-289. doi: 10.1016/j.colsurfb.2016.02.063. Epub 2016 Mar 2.

Abstract

Layer-by-layer of polyelectrolytes has emerged as one of the easiest and most controlled techniques to deposit ultrathin polymer layers mainly driven by electrostatic interactions. However, this kind of interaction results to be weak and easily breakable in physiological environment. Here we report on the preparation of nanocapsules completely made of natural biomaterials: a lipophilic core (soybean oil and egg lecithin as surfactant) as nanometric template and a polysaccharide-based multilayer shell (glycol chitosan and heparin) covalently cross-linked. We first modified glycol chitosan with a thiol moiety and heparin with an alkene moiety, respectively, and then we built a polymer multilayer film with a covalent cross-linkage among layers, exploiting the light initiated thiol-ene reaction, known as click chemistry. We showed the possibility to perform the covalent cross-linkage without any photoinitiator or metal catalyst, thus avoiding cytotoxic effects and further purification steps. The so realized nanocapsules resulted to be stable and completely biocompatible and, therefore, of interest for the biotechnology fields, mainly for drug delivery.

Keywords: Biocompatible polymers; Glycol chitosan; Layer by layer; Oil-in-water nanoemulsion; Thiol-ene click chemistry; Thiolated chitosan.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Animals
  • Biocompatible Materials / chemical synthesis*
  • Biocompatible Materials / pharmacology
  • Brain / cytology
  • Cell Line
  • Cell Survival / drug effects
  • Chitosan / chemistry*
  • Click Chemistry
  • Emulsions
  • Endothelial Cells / drug effects
  • Heparin / chemistry*
  • Lecithins / chemistry*
  • Mice
  • Nanocapsules / chemistry*
  • Soybean Oil / chemistry*
  • Sulfhydryl Compounds / chemistry
  • Surface-Active Agents / chemistry
  • Ultraviolet Rays

Substances

  • Alkenes
  • Biocompatible Materials
  • Emulsions
  • Lecithins
  • Nanocapsules
  • Sulfhydryl Compounds
  • Surface-Active Agents
  • Soybean Oil
  • Heparin
  • Chitosan