Polymersome‐forming amphiphilic glycosylated polymers: Synthesis and characterization. Issue 24 (16th October 2013)

• Record Type: Journal Article
• Authors: Eissa, Ahmed M.; Smith, Michael J.P.; Kubilis, Artur; Mosely, Jackie A.; Cameron, Neil R.
• Is Part Of: Journal of polymer science. Volume 51:Issue 24(2013:Dec.)
• Page Start: 5184
• Page End: 5193
• Publication Date: 2013-10-16
• Subjects: 547
• DOI: 10.1002/pola.26959
• Languages: English
• ISSNs: 0887-624X

Abstract

<abstract abstract-type="main"> <title>ABSTRACT</title> <p>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‐<italic>b</italic>‐PEG followed by CuAAC reaction with different azide functionalized sugars. The alkyne‐terminated PE‐<italic>b</italic>‐PEG was prepared by etherification reaction between hydroxyl‐terminated PE‐<italic>b</italic>‐PEG (<italic>M</italic><sub>n</sub> ∼ 875 g mol<sup>−1</sup>) 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‐<italic>b</italic>‐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. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. <bold>2013</bold>, <italic>51</italic>, 5184–5193</p> </abstract>