Okafor Ifeanyi S, Wang Guijun
Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, VA 23529, USA.
Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, VA 23529, USA.
Carbohydr Res. 2017 Nov 8;451:81-94. doi: 10.1016/j.carres.2017.09.008. Epub 2017 Sep 15.
Low molecular weight gelators are important for the study of supramolecular chemistry and have useful applications for biomaterials. Glycomimetics that are easily accessible and have useful gelation properties are especially interesting molecules. In this research, nine per-O-acetyl lactosyl- and thirteen per-O-acetyl maltosyl triazole derivatives were synthesized and analyzed. Most of the maltosyl triazoles and one of the lactosyl derivatives were found to be effective molecular gelators. The supramolecular gels were characterized using rheology and optical microscopy and they exhibited morphologies ranging from fibers to planar sheets. The self-assembling properties of selected lactosyl and maltosyl triazole derivatives were studied using H NMR spectroscopy at different temperatures. The NMR studies revealed that the triazole moiety in these compounds played an important role in the formation of the supramolecular assembly, but the sugar moiety configurations are more influential towards gelation. Naproxen and chloramphenicol were used as the model drugs to assess the potential of these compounds in drug delivery applications. A pH responsive gelator showed faster delivery of chloramphenicol at mild basic conditions than neutral conditions. The effective disaccharide triazole-based molecular gelators are useful for the preparation of advanced soft materials that have potential applications as matrix for immobilization of drugs or biomolecules.
低分子量凝胶剂对于超分子化学的研究很重要，并且在生物材料方面有实用的应用。易于获取且具有有用凝胶化性质的糖模拟物是特别有趣的分子。在本研究中，合成并分析了九种全 -O - 乙酰乳糖基和十三种全 -O - 乙酰麦芽糖基三唑衍生物。发现大多数麦芽糖基三唑和一种乳糖基衍生物是有效的分子凝胶剂。使用流变学和光学显微镜对超分子凝胶进行了表征，它们呈现出从纤维到平面片的形态。在不同温度下使用核磁共振氢谱（¹H NMR）研究了选定的乳糖基和麦芽糖基三唑衍生物的自组装性质。核磁共振研究表明，这些化合物中的三唑部分在超分子组装的形成中起重要作用，但糖部分的构型对凝胶化更具影响力。使用萘普生和氯霉素作为模型药物来评估这些化合物在药物递送应用中的潜力。一种pH响应型凝胶剂在温和碱性条件下比中性条件下能更快地递送氯霉素。有效的基于二糖三唑的分子凝胶剂可用于制备具有作为固定药物或生物分子基质潜在应用的先进软材料。
