Polymersome-forming amphiphilic glycosylated polymers: Synthesis and characterization

Ahmed M. Eissa, Michael J. P. Smith, Artur Kubilis, Jackie A. Mosely, Neil R. Cameron

Research output: Contribution to journalArticleResearchpeer-review

16 Citations (Scopus)

Abstract

Copper-catalyzed azide-alkyne cycloaddition (CuAAC) was used to prepare glycosylated polyethylene (PE)-poly(ethylene glycol) (PEG) amphiphilic block copolymers. The synthetic approach involves preparation of alkyne-terminated PE-b-PEG followed by CuAAC reaction with different azide functionalized sugars. The alkyne-terminated PE-b-PEG was prepared by etherification reaction between hydroxyl-terminated PE-b-PEG (Mn ∼ 875 g mol-1) and propargyl bromide and azidoethyl glycosides were prepared by glycosylation of 2-azidoethanol. Atmospheric pressure solids analysis probe-mass spectrometry was used as a novel solid state characterization tool to determine the outcome of the CuAAC click reaction and end-capping of PE-b-PEG by the azidoethyl glycoside group. The aqueous solution self-assembly behavior of these amphiphilic glycosylated polymers was explored by TEM and dye solubilization studies. Carbohydrate-bearing spherical aggregates with the ability to solubilize a hydrophobic dye were observed. The potential of these amphiphilic glycosylated polymers to self-assemble via electro-formation into giant carbohydrate-bearing polymersomes was also investigated using confocal fluorescence microscopy. An initial bioactivity study of the carbohydrate-bearing aggregates is furthermore presented. 

Original languageEnglish
Pages (from-to)5184-5193
Number of pages10
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume51
Issue number24
DOIs
Publication statusPublished - 15 Dec 2013
Externally publishedYes

Keywords

  • Amphiphiles
  • Amphiphilic copolymers
  • ASAP mass spectrometry
  • Block copolymers
  • Click glycosylation reaction
  • Electro-formation
  • Functionalization of polymers
  • Giant vesicles
  • Polymersomes
  • Self-assembly
  • Vesicles

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