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

Affiliation

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: [Email]

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,

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