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

doi:10.1016/j.colsurfb.2019.06.005

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

Colloids Surf B Biointerfaces. 2019 Sep 1:181:561-566. doi: 10.1016/j.colsurfb.2019.06.005. Epub 2019 Jun 4.

Authors

Affiliations

¹ Laboratory for Characterization and Processing of Polymers (LCPP), Faculty of Mechanical Engineering, University of Maribor, Smetanova ulica 17, SI-2000, Maribor, Slovenia.
² Papiertechnische Stiftung Pirnaer Straße 37, D-01809, Heidenau, Germany.
³ Center of Excellence for Polysaccharide Research, Institute for Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University of Jena, Humboldtstraße 10, D-07743, Jena, Germany.
⁴ ZMF - Center for Medical Research, Stiftingtalstraße 24, A-8010, Graz, Austria.
⁵ National Institute of Chemistry, Department of Polymer Chemistry and Technology, Hajdrihova 19, SI-1000, Ljubljana, Slovenia.
⁶ Laboratory for Characterization and Processing of Polymers (LCPP), Faculty of Mechanical Engineering, University of Maribor, Smetanova ulica 17, SI-2000, Maribor, Slovenia; Institute of Paper, Pulp and Fibre Technology (IPZ), Graz University of Technology, Inffeldgasse 23, A - 8010, Graz, Austria. Electronic address: rupert.kargl@um.si.

PMID: 31185448
DOI: 10.1016/j.colsurfb.2019.06.005

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.

Keywords: Bio-Conjugation; Cytotoxicity; Dextran; Emulsion precipitation; Micro-/nano-particles; Zeta-Potential.

MeSH terms

Amino Acids / chemistry*
Cysteine / analogs & derivatives*
Cysteine / chemistry
Dextrans / chemistry
Esters / chemistry*
Particle Size
Surface Properties

Substances

Amino Acids
Dextrans
Esters
3-tritylthio-L-alanine
Cysteine