Polymer Science

Degradable Glycopolyester-Like Nanoparticles by Radical Ring-Opening Polymerization

Authors

  • Théo Pesenti University of Paris-Saclay & CNRS & Institut Galien Paris-Saclay ,
  • Daniel Domingo-Lopez University of Paris-Saclay & CNRS & Institut Galien Paris-Saclay ,
  • Emilie Gillon Grenoble Alpes University & CNRS & CERMAV ,
  • Nada Ibrahim University of Paris-Saclay & CNRS & Institut Galien Paris-Saclay ,
  • Samir Messaoudi University of Paris-Saclay & CNRS & BioCIS ,
  • Anne Imberty Grenoble Alpes University & CNRS & CERMAV ,
  • Julien Nicolas CNRS & University of Paris-Saclay & Institut Galien Paris-Saclay

Abstract

A small library of degradable polyester-like glycopolymers was successfully prepared by the combination of radical ring-opening copolymerization (rROP) of 2-methylene-1,3-dioxepane (MDO) with vinyl ether (VE) derivatives, and a Pd-catalyzed thioglycoconjugation. The resulting thioglycopolymers were formulated into self-stabilized thioglyconanoparticles which were stable up to 4 months and were enzymatically degraded. Nanoparticles and their degradation products exhibited a good cytocompatibility on two healthy cell lines. Interactions between thioglyconanoparticles and lectins were investigated and highlighted the presence of both specific carbohydrate/lectin interactions and non-specific hydrophobic interactions. Fluorescent thioglyconanoparticles were also prepared either by encapsulation of Nile Red, or by the functionalization of the polymer backbone with Rhodamine B. Such nanoparticles were used to prove the cell internalization of the thioglyconanoparticles by lung adenocarcinoma (A549) cells which underlined the great potential of P(CKA-co-VE) copolymers for biomedical applications

Content

Thumbnail image of GlycoNPs_rROP_F.pdf

Supplementary material

Thumbnail image of GlycoNPs_rROP_ESI_F.pdf
Supporting Information
1H NMR spectra, SEC chromatograms, estimation of the fraction of glycoside residues on the surface of nanoparticles, ITC thermograms.