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 Simon Thonhofer, Rupert Kargl

Research output: Contribution to journalArticleResearchpeer-review

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.

Original languageEnglish
Pages (from-to)561-566
Number of pages6
JournalColloids and Surfaces / B
Volume181
DOIs
Publication statusPublished - 1 Sep 2019

    Fingerprint

Keywords

  • Bio-Conjugation
  • Cytotoxicity
  • Dextran
  • Emulsion precipitation
  • Micro-/nano-particles
  • Zeta-Potential

ASJC Scopus subject areas

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

Fields of Expertise

  • Human- & Biotechnology

Cite this