具有抗菌活性的新型两亲性葡聚糖酯。

Novel amphiphilic dextran esters with antimicrobial activity.

机构信息

"Petru Poni" Institute of Macromolecular Chemistry, Department of Natural Polymers, Bioactive and Biocompatible Materials, Gr. Ghica Voda Alley, no 41 A, 700457, Iasi, Romania.

"Al. I. Cuza" University of Iasi, Faculty of Chemistry, Department of Organic Chemistry, Bd. Carol I, no 11, 700506, Iasi, Romania.

出版信息

Int J Biol Macromol. 2020 May 1;150:746-755. doi: 10.1016/j.ijbiomac.2020.02.021. Epub 2020 Feb 6.

DOI:10.1016/j.ijbiomac.2020.02.021

PMID:32035962

Abstract

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 (H and C-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.

摘要

新型两亲性葡聚糖酯是通过多糖与不同取代的 1,2,3-三唑-4-羧酸在 N,N'-羰基二咪唑原位活化条件下反应得到的。含氮杂环衍生物是通过有机叠氮化物与丙炔酸乙酯的铜（I）催化环加成反应得到的。通过元素分析、傅里叶变换红外和核磁共振波谱（H 和 C-NMR）研究了化合物的结构特征。采用热重分析、差示扫描量热法和广角 X 射线衍射对酯进行了表征。通过动态光散射和透射电子显微镜研究了在水溶液中形成的聚合物自组装体的性质。通过荧光光谱法测定的葡聚糖酯的临界聚集浓度值在 4.1-9.5mg/dL 范围内。通过圆盘扩散法研究了一些聚合物的抗菌活性，表明多糖酯具有活性。