Crosslinkable/functionalizable poly(2-oxazoline)­based micelles

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

Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

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.

Originalspracheenglisch
Aufsatznummer109305
Seitenumfang9
FachzeitschriftEuropean polymer journal
Jahrgang121
DOIs
PublikationsstatusVeröffentlicht - 1 Dez 2019

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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

Schlagwörter

    ASJC Scopus subject areas

    • !!Physics and Astronomy(all)
    • Organische Chemie
    • !!Polymers and Plastics
    • !!Materials Chemistry

    Fields of Expertise

    • Advanced Materials Science

    Kooperationen

    • NAWI Graz

    Dies zitieren

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

    in: European polymer journal, Jahrgang 121, 109305, 01.12.2019.

    Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

    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 ; Jahrgang 121.
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    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.",
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    T1 - Crosslinkable/functionalizable poly(2-oxazoline)­based micelles

    AU - Rossegger, Elisabeth

    AU - Pirolt, Franz

    AU - Hoeppener, Stephanie

    AU - Schubert, Ulrich S.

    AU - Glatter, Otto

    AU - Wiesbrock, Frank

    PY - 2019/12/1

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    N2 - 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.

    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.

    KW - Block copoly(2-oxazoline)s

    KW - Critical micellar concentration

    KW - Crosslinked micelles

    KW - Dynamic light scattering

    KW - Thiol-ene click reaction

    KW - Worm-shaped micelles

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    U2 - 10.1016/j.eurpolymj.2019.109305

    DO - 10.1016/j.eurpolymj.2019.109305

    M3 - Article

    VL - 121

    JO - European polymer journal

    JF - European polymer journal

    SN - 0014-3057

    M1 - 109305

    ER -