Synthesis and Characterization of Hybrid Glycolipids as Functional Organogelators and Hydrogelators
Synthesis and Characterization of Hybrid Glycolipids as Functional Organogelators and Hydrogelators
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DOI：
10.1021/acs.langmuir.9b02347
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发表时间：
2019-11-12
期刊：
影响因子：
3.9
通讯作者：
Wang, Guijun
中科院分区：
文献类型：
--
作者：
Morris, Joedian;Kozlowski, Paige;Wang, Guijun
碳水化合物基低分子质量凝胶剂是制备软材料的有用且用途广泛的化合物。以N-乙酰-D-氨基葡萄糖为原料，合成并表征了含有不同酯基的酰胺的15种糖脂。这些化合物包括具有不同链长的脂肪族衍生物和芳香族衍生物。大多数杂化酰胺-酯的相对分子质量小于500D，这些糖脂被发现是几种有机溶剂、水和水溶液的有效凝胶剂。在低浓度下也得到了两种高效的水凝胶剂。利用光学显微镜、原子力显微镜和流变学对几种具有代表性的凝胶进行了表征，以获得有关其形态和凝胶稳定性的信息。还用三种凝胶剂包埋了萘普生钠和甲苯胺蓝。用紫外-可见光谱监测药物从凝胶到水相的缓释过程。这些凝胶剂具有结构灵活性，可以对刺激做出反应。在碱性条件下，酯可以被水解，几种凝胶可以转化为溶液。这些设计合理的凝胶剂可用作具有控释性能的刺激响应型智能材料。
Carbohydrate-based low-molecular-weight gelators are useful and versatile compounds for the preparation of soft materials. Using N-acetyl-D-glucosamine as the starting material, we synthesized and characterized 15 glycolipids containing an amide with different ester functional groups. These include aliphatic derivatives with varying chain lengths and aromatic derivatives. Most of the hybrid amide-esters have molecular weights less than 500 D. These glycolipids were found to be effective gelators for several organic solvents, water, and aqueous solutions. Two efficient hydrogelators were also obtained at low concentrations. A few representative gels were characterized using optical microscopy, atomic force microscopy, and rheology to obtain information on their morphology and gel stability. Three gelators were also used to encapsulate naproxen sodium and toluidine blue. The sustained release of the drug from the gel to the aqueous phase was monitored by UV-vis spectroscopy. These gelators have structural flexibility that can be stimuli responsive. The esters can be hydrolyzed and several gels were converted to solutions under basic conditions. These rationally designed gelators could be utilized as stimuli-responsive smart materials with controlled release properties.