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

13 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

Cite this

Eissa, Ahmed M. ; Smith, Michael J. P. ; Kubilis, Artur ; Mosely, Jackie A. ; Cameron, Neil R. / Polymersome-forming amphiphilic glycosylated polymers : Synthesis and characterization. In: Journal of Polymer Science, Part A: Polymer Chemistry. 2013 ; Vol. 51, No. 24. pp. 5184-5193.
@article{660a0e5705f34382ba734cf076deca42,
title = "Polymersome-forming amphiphilic glycosylated polymers: Synthesis and characterization",
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. ",
keywords = "Amphiphiles, Amphiphilic copolymers, ASAP mass spectrometry, Block copolymers, Click glycosylation reaction, Electro-formation, Functionalization of polymers, Giant vesicles, Polymersomes, Self-assembly, Vesicles",
author = "Eissa, {Ahmed M.} and Smith, {Michael J. P.} and Artur Kubilis and Mosely, {Jackie A.} and Cameron, {Neil R.}",
year = "2013",
month = "12",
day = "15",
doi = "10.1002/pola.26959",
language = "English",
volume = "51",
pages = "5184--5193",
journal = "Journal of Polymer Science, Part A: Polymer Chemistry",
issn = "0887-624X",
publisher = "Wiley-Blackwell",
number = "24",

}

Polymersome-forming amphiphilic glycosylated polymers : Synthesis and characterization. / Eissa, Ahmed M.; Smith, Michael J. P.; Kubilis, Artur; Mosely, Jackie A.; Cameron, Neil R.

In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 51, No. 24, 15.12.2013, p. 5184-5193.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Polymersome-forming amphiphilic glycosylated polymers

T2 - Synthesis and characterization

AU - Eissa, Ahmed M.

AU - Smith, Michael J. P.

AU - Kubilis, Artur

AU - Mosely, Jackie A.

AU - Cameron, Neil R.

PY - 2013/12/15

Y1 - 2013/12/15

N2 - 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. 

AB - 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. 

KW - Amphiphiles

KW - Amphiphilic copolymers

KW - ASAP mass spectrometry

KW - Block copolymers

KW - Click glycosylation reaction

KW - Electro-formation

KW - Functionalization of polymers

KW - Giant vesicles

KW - Polymersomes

KW - Self-assembly

KW - Vesicles

UR - http://www.scopus.com/inward/record.url?scp=84887461206&partnerID=8YFLogxK

U2 - 10.1002/pola.26959

DO - 10.1002/pola.26959

M3 - Article

VL - 51

SP - 5184

EP - 5193

JO - Journal of Polymer Science, Part A: Polymer Chemistry

JF - Journal of Polymer Science, Part A: Polymer Chemistry

SN - 0887-624X

IS - 24

ER -