Crosslinkable/functionalizable poly(2-oxazoline)­based micelles

Elisabeth Rossegger, Franz Pirolt, Stephanie Hoeppener, Ulrich S. Schubert, Otto Glatter, Frank Wiesbrock

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Considering the pseudo-livingness of the cationic ring-opening polymerization of various 2-oxazoline monomers, micelles formed by amphiphilic diblock copoly(2-oxazoline)s are potential candidates for drug delivery. Copoly(2-oxazoline)s of the composition poly(2-ethyl-2-oxazoline)100-n-block-poly(2-dec-9′-enyl-2-oxazoline)n (n = 5, 10, 15) were found to form micelles in aqueous solution. The hydrophobic cores of these non-spherical micelles could be crosslinked by the thiol-ene reaction with glycol dimercapto acetate, the ester bonds of which can be cleaved by esterases. While the hydrodynamic radii of the non-crosslinked micelles increased if the hydrophobic block of poly(2-dec-9′-enyl-2-oxazoline) grew larger, the opposite trend could be observed for the crosslinked micelles. In the course of an oil uptake study, the hydrodynamic radii of the crosslinked as well as non-crosslinked micelles increased. In oil-filled micelles of poly(2-ethyl-2-oxazoline)100-n-block-poly(2-dec-9′-enyl-2-oxazoline)n (n = 5, 10, 15), the hydrodynamic radii of the non-crosslinked micelles were significantly larger in comparison with the crosslinked ones in case of n = 5 and 10, while the hydrodynamic radii of non-crosslinked and crosslinked micelles were of the same range in case of n = 15. The changes of diameter in micelles with polar molecules such as Zidovudine covalently attached to the hydrophobic core support the proposed antagonism of the inclusion of non-polar/polar molecules into the micelles’ cores and the degree of crosslinking.

Original languageEnglish
Article number109305
Number of pages9
JournalEuropean polymer journal
Volume121
DOIs
Publication statusPublished - 1 Dec 2019

Fingerprint

Micelles
micelles
Hydrodynamics
hydrodynamics
radii
Oils
poly(2-oxazoline)
oils
Cationic polymerization
Molecules
Glycols
Zidovudine
Ring opening polymerization
Esterases
crosslinking
Drug delivery
Sulfhydryl Compounds
thiols
Crosslinking
glycols

Keywords

  • Block copoly(2-oxazoline)s
  • Critical micellar concentration
  • Crosslinked micelles
  • Dynamic light scattering
  • Thiol-ene click reaction
  • Worm-shaped micelles

ASJC Scopus subject areas

  • Physics and Astronomy(all)
  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

Fields of Expertise

  • Advanced Materials Science

Cooperations

  • NAWI Graz

Cite this

Crosslinkable/functionalizable poly(2-oxazoline)­based micelles. / Rossegger, Elisabeth; Pirolt, Franz; Hoeppener, Stephanie; Schubert, Ulrich S.; Glatter, Otto; Wiesbrock, Frank.

In: European polymer journal, Vol. 121, 109305, 01.12.2019.

Research output: Contribution to journalArticleResearchpeer-review

Rossegger, Elisabeth ; Pirolt, Franz ; Hoeppener, Stephanie ; Schubert, Ulrich S. ; Glatter, Otto ; Wiesbrock, Frank. / Crosslinkable/functionalizable poly(2-oxazoline)­based micelles. In: European polymer journal. 2019 ; Vol. 121.
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AB - Considering the pseudo-livingness of the cationic ring-opening polymerization of various 2-oxazoline monomers, micelles formed by amphiphilic diblock copoly(2-oxazoline)s are potential candidates for drug delivery. Copoly(2-oxazoline)s of the composition poly(2-ethyl-2-oxazoline)100-n-block-poly(2-dec-9′-enyl-2-oxazoline)n (n = 5, 10, 15) were found to form micelles in aqueous solution. The hydrophobic cores of these non-spherical micelles could be crosslinked by the thiol-ene reaction with glycol dimercapto acetate, the ester bonds of which can be cleaved by esterases. While the hydrodynamic radii of the non-crosslinked micelles increased if the hydrophobic block of poly(2-dec-9′-enyl-2-oxazoline) grew larger, the opposite trend could be observed for the crosslinked micelles. In the course of an oil uptake study, the hydrodynamic radii of the crosslinked as well as non-crosslinked micelles increased. In oil-filled micelles of poly(2-ethyl-2-oxazoline)100-n-block-poly(2-dec-9′-enyl-2-oxazoline)n (n = 5, 10, 15), the hydrodynamic radii of the non-crosslinked micelles were significantly larger in comparison with the crosslinked ones in case of n = 5 and 10, while the hydrodynamic radii of non-crosslinked and crosslinked micelles were of the same range in case of n = 15. The changes of diameter in micelles with polar molecules such as Zidovudine covalently attached to the hydrophobic core support the proposed antagonism of the inclusion of non-polar/polar molecules into the micelles’ cores and the degree of crosslinking.

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