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

Research output: Contribution to journalResearch articleContributedpeer-review

Contributors

  • Ana Bratusa - , University of Maribor (Author)
  • Thomas Elschner - , Papiertechnische Stifung (PTS) (Author)
  • Thomas Heinze - , Friedrich Schiller University Jena (Author)
  • Eleonore Frohlich - , Medical University of Graz (Author)
  • Silvo Hribernik - , University of Maribor (Author)
  • Mojca Bozic - , University of Maribor (Author)
  • Ema Zagar - , National Institute of Chemistry Ljubljana (Author)
  • Karin Stana Kleinschek - , University of Maribor (Author)
  • Martin Thonhofer - , University of Maribor (Author)
  • Rupert Kargl - , Graz University of Technology (Author)

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 C-13 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, bioimaging or surface functionalization.

Details

Original languageEnglish
Pages (from-to)561-566
Number of pages6
JournalColloids and Surfaces B: Biointerfaces
Volume181
Publication statusPublished - 1 Sept 2019
Peer-reviewedYes
Externally publishedYes

External IDs

Scopus 85066940446

Keywords

Keywords

  • Dextran, Bio-Conjugation, Micro-/nano-particles, Emulsion precipitation, Cytotoxicity, Zeta-Potential, DRUG-DELIVERY, NANOPARTICLES, DERIVATIVES