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Synthesis and self-assembly study of zwitterionic amphiphilic derivatives of chitosan

机译：壳聚糖两性离子两亲衍生物的合成与自组装研究

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New zwitterionic derivatives of chitosan (CH) were synthesized through the Michael addition reaction of 1-(3-sulfopropyl)2-vinylpyridine hydroxide (SPP) with primary amines of deacetylated CHs (with weight-average molecular weights of 46 and 216 kDa) to obtain SPP-substituted CHs. The hydrophilic derivatives were subsequently modified with 2.1, 4.6, and 9.7% of dodecyl groups [degree of substitution by dodecyl groups (DSDod)]. The SPP-substituted CH derivatives were characterized by H-1-NMR, Fourier transform infrared spectroscopy, and gel permeation chromatography. Aqueous solutions of SPP-substituted CH samples remained clear, independently of the pH (3.0< pH< 12.0). The self-association study of the amphiphilic derivatives was performed in aqueous buffered solution at pH 5.0 and 7.4, and the critical aggregation concentration values varied from 5.6 x 10(-3) to 0.02 g/L. The measurements of dynamic light scattering and zeta potentials showed that the self-assembly behavior was dependent on the pH and DSDod. At pH 7.4, the measured zeta potentials were near zero, and colloidal stability was provided by the hydrated zwitterionic shell of the aggregates. Transmission electron microscopy revealed spherelike microsized particles of broad distribution. The amphiphilic SPP-substituted CH samples were shown to be nontoxic with a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay performed with HeLa cells. The remarkable water solubility and nontoxicity displayed by the new SPP-substituted CH derivatives showed promising properties for the design of CH-based biomaterials and nanoparticles. (C) 2016 Wiley Periodicals, Inc.
机译：通过1-（3-磺丙基）2-乙烯基吡啶氢氧化物（SPP）与脱乙酰基CHs的伯胺（重均分子量分别为46和216 kDa）的迈克尔加成反应合成了壳聚糖（CH）的新两性离子衍生物获得SPP取代的CH。随后用2.1、4.6和9.7％的十二烷基[十二烷基取代度（DSDod）]修饰亲水性衍生物。通过H-1-NMR，傅立叶变换红外光谱和凝胶渗透色谱法对SPP取代的CH衍生物进行了表征。 SPP取代的CH样品的水溶液保持澄清，与pH无关（3.0 H <12.0）。两性衍生物的自缔合研究是在pH 5.0和7.4的缓冲水溶液中进行的，关键的聚集浓度值从5.6 x 10（-3）到0.02 g / L不等。动态光散射和ζ电势的测量表明，自组装行为取决于pH和DSSd。在pH 7.4时，测得的ζ电位接近于零，胶体稳定性由聚集体的水合两性离子壳提供。透射电子显微镜显示分布广泛的球形微粒。用HeLa细胞进行的3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物测定显示，两亲SPP取代的CH样品无毒。新的SPP取代的CH衍生物显示出显着的水溶性和无毒性，这些特性为基于CH的生物材料和纳米颗粒的设计展示了令人鼓舞的特性。 （C）2016威利期刊公司

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