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首页> 外文学位 >Characterization of 3-Ester and 3-Carbamate Derivatives of N-acetyl-D-Glucosamine and Their Use in Controlled Drug Delivery
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Characterization of 3-Ester and 3-Carbamate Derivatives of N-acetyl-D-Glucosamine and Their Use in Controlled Drug Delivery

机译：N-乙酰基-D-氨基葡萄糖的3-酯和3-氨基甲酸酯衍生物的表征及其在药物控制中的应用

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摘要

Low molecular weight gelators (LMWGs) are a class of compounds which reversibly form a network that traps solvents to form gels. Gelation by LMWGs is driven solely by non-covalent interactions such as hydrogen bonding, pi-pi stacking, and hydrophobic interactions. LMWGs can be designed such that the gel-sol and sol-gel transitions happen as a response to a specific stimulus. These stimulus responsive gels or "smart" gels can be used in a wide variety of applications including tissue regeneration, biosensing, and controlled drug delivery.;Among the different types of compounds that are LMWGs, carbohydrate based systems are especially interesting. Carbohydrates are abundant, renewable, biocompatible, and have numerous hydroxyl groups which can be readily functionalized. Our group has previously found that organogelators and hydrogelators can be obtained from D-glucose and D-glucosamine by selectively functionalization of the hydroxyl groups. Various C-2 acyl derivatives including esters and carbamates are found to be effective LMWGs for both water and organic solvents. In this study, the functionalization at the C-3 position of glucosamine derivative was carried out. Two types of C-3 derivatives including esters and carbamates were synthesized and characterized by 1H and 13C NMR spectroscopy and LCMS. These compounds were then analyzed for gelation properties in a series of selected solvents. Several compounds were found to be effective organogelators, the resulting gels were characterized using IR, rheology, optical microscopy, etc. The use of these gelators for controlled drug delivery was tested and it was found that the gels loaded with naproxen sodium or chloramphenicol released the drug in an acidic environment.
机译：低分子量胶凝剂（LMWG）是一类可逆地形成网络的化合物，该网络会捕获溶剂以形成凝胶。 LMWG的胶凝作用仅由非共价相互作用（例如氢键，pi-pi堆积和疏水相互作用）驱动。可以设计LMWG，以使凝胶-溶胶和溶胶-凝胶转变作为对特定刺激的响应而发生。这些刺激响应性凝胶或“智能”凝胶可用于多种应用，包括组织再生，生物传感和受控的药物输送。在LMWGs化合物的不同类型中，基于碳水化合物的系统尤为有趣。碳水化合物丰富，可再生，具有生物相容性，并具有许多易于官能化的羟基。我们的小组先前发现，可以通过选择性地官能化羟基从D-葡萄糖和D-葡萄糖胺获得有机胶凝剂和水胶凝剂。发现各种C-2酰基衍生物（包括酯和氨基甲酸酯）对于水和有机溶剂都是有效的LMWG。在该研究中，进行了葡糖胺衍生物的C-3位的官能化。合成了两种类型的C-3衍生物，包括酯和氨基甲酸酯，并通过1H和13C NMR光谱以及LCMS对其进行了表征。然后在一系列选定的溶剂中分析这些化合物的胶凝特性。已发现几种化合物是有效的有机胶凝剂，使用红外光谱，流变学，光学显微镜等对所得的凝胶进行了表征。测试了这些胶凝剂在控制药物输送中的用途，发现载有萘普生钠或氯霉素的凝胶会释放出药物在酸性环境中。

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  • 作者

    Garcia, Consuelo.;

  • 作者单位

    Old Dominion University.;

  • 授予单位 Old Dominion University.;
  • 学科 Chemistry.;Organic chemistry.;Pharmaceutical sciences.
  • 学位 M.S.
  • 年度 2017
  • 页码 86 p.
  • 总页数 86
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 古生物学;
  • 关键词

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