Novel amphiphilic dextran esters with antimicrobial activity.

New amphiphilic dextran esters were obtained by polysaccharide functionalization with different substituted 1,2,3-triazoles-4-carboxylic acid via in situ activation with N, N′-carbonyldiimidazole. Nitrogen-containing heterocyclic derivatives were achieved by copper(I)-catalyzed cycloaddition reaction between organic azides and ethyl propiolate. Structural characteristics of the compounds were studied by elemental analysis, Fourier transform infrared and nuclear magnetic resonance spectroscopy (1H and 13C‐NMR). Thermogravimetric analysis, differential scanning calorimetry and wide-angle X-ray diffraction were used for esters characterization. Properties of polymeric self-associates, formed in aqueous solution, were studied by dynamic light scattering and transmission electron microscopy. The critical aggregation concentration values for dextran esters, determined by fluorescence spectroscopy, were in the range of 4.1-9.5 mg/dL. Antimicrobial activity, investigated for some of the polymers by disc-diffusion method, pointed out that polysaccharide esters were active. • Dextrans with 1,4-disubstituted 1,2,3-triazoles as side-chains were obtained. • 13C-NMR, FTIR, thermal studies and WAXD were used for esters characterization. • Polymeric self-associates, formed in aqueous media, were studied by DLS and TEM. • CAC for the dextran esters demonstrated lower values (4.1–9.5 mg/dL) • Some of the polymers showed a moderate to good antimicrobial activity. [ABSTRACT FROM AUTHOR]