Functional dextran amino acid ester particles derived from N-protected S-trityl-L-cysteine

Ana Bratuša, Thomas Elschner, Thomas Heinze, Eleonore Fröhlich, Silvo Hribernik, Mojca Božič, Ema Žagar, Karin Stana Kleinschek, Martin Thonhofer, Rupert Kargl

Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

Abstract

This work describes the derivatization of dextran using N-(tert-butyloxycarbonyl)-S-(trityl)-L-cysteine in the presence of N,N′-carbonyldiimidazole (CDI) as a coupling agent. Homogeneous reactions in dimethyl sulfoxide allowed for an efficient coupling of the amino acid derivative to the polymer backbone. Derivatization was confirmed by infrared and 13C NMR spectroscopy, size exclusion chromatography and elemental analysis. The presence of hydrophobic protecting groups resulted in a product that can be shaped into water-insoluble particles stable in an aqueous environment and non-toxic for lung epithelial cells. It is suggested that materials composed of ester bonds between amino acids and polysaccharides are useful for targeted drug delivery, bio-imaging or surface functionalization.

Originalspracheenglisch
Seiten (von - bis)561-566
Seitenumfang6
FachzeitschriftColloids and Surfaces / B
Jahrgang181
DOIs
PublikationsstatusVeröffentlicht - 1 Sep 2019

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3-tritylthio-L-alanine
dextrans
Dextran
cysteine
Dextrans
amino acids
Amino acids
esters
Esters
Amino Acids
Dimethyl sulfoxide
Size exclusion chromatography
polysaccharides
Coupling agents
chromatography
Polysaccharides
Dimethyl Sulfoxide
exclusion
lungs
Nuclear magnetic resonance spectroscopy

Schlagwörter

    ASJC Scopus subject areas

    • Biotechnology
    • !!Surfaces and Interfaces
    • !!Physical and Theoretical Chemistry
    • !!Colloid and Surface Chemistry

    Fields of Expertise

    • Human- & Biotechnology

    Dies zitieren

    Functional dextran amino acid ester particles derived from N-protected S-trityl-L-cysteine. / Bratuša, Ana; Elschner, Thomas; Heinze, Thomas; Fröhlich, Eleonore; Hribernik, Silvo; Božič, Mojca; Žagar, Ema; Kleinschek, Karin Stana; Thonhofer, Martin; Kargl, Rupert.

    in: Colloids and Surfaces / B, Jahrgang 181, 01.09.2019, S. 561-566.

    Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

    Bratuša, Ana ; Elschner, Thomas ; Heinze, Thomas ; Fröhlich, Eleonore ; Hribernik, Silvo ; Božič, Mojca ; Žagar, Ema ; Kleinschek, Karin Stana ; Thonhofer, Martin ; Kargl, Rupert. / Functional dextran amino acid ester particles derived from N-protected S-trityl-L-cysteine. in: Colloids and Surfaces / B. 2019 ; Jahrgang 181. S. 561-566.
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    abstract = "This work describes the derivatization of dextran using N-(tert-butyloxycarbonyl)-S-(trityl)-L-cysteine in the presence of N,N′-carbonyldiimidazole (CDI) as a coupling agent. Homogeneous reactions in dimethyl sulfoxide allowed for an efficient coupling of the amino acid derivative to the polymer backbone. Derivatization was confirmed by infrared and 13C NMR spectroscopy, size exclusion chromatography and elemental analysis. The presence of hydrophobic protecting groups resulted in a product that can be shaped into water-insoluble particles stable in an aqueous environment and non-toxic for lung epithelial cells. It is suggested that materials composed of ester bonds between amino acids and polysaccharides are useful for targeted drug delivery, bio-imaging or surface functionalization.",
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    AU - Bratuša, Ana

    AU - Elschner, Thomas

    AU - Heinze, Thomas

    AU - Fröhlich, Eleonore

    AU - Hribernik, Silvo

    AU - Božič, Mojca

    AU - Žagar, Ema

    AU - Kleinschek, Karin Stana

    AU - Thonhofer, Martin

    AU - Kargl, Rupert

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    KW - Cytotoxicity

    KW - Dextran

    KW - Emulsion precipitation

    KW - Micro-/nano-particles

    KW - Zeta-Potential

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