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Characterization of 3-Ester and 3-Carbamate Derivatives of N-acetyl-D-Glucosamine and Their Use in Controlled Drug Delivery

機譯：N-乙?；?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藥物控制中的應用

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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.
機譯：低分子量膠凝劑（LMWG）是一類可逆地形成網(wǎng)絡的化合物，該網(wǎng)絡會捕獲溶劑以形成凝膠。 LMWG的膠凝作用僅由非共價相互作用（例如氫鍵，pi-pi堆積和疏水相互作用）驅動?？梢栽O計LMWG，以使凝膠-溶膠和溶膠-凝膠轉變作為對特定刺激的響應而發(fā)生。這些刺激響應性凝膠或“智能”凝膠可用于多種應用，包括組織再生，生物傳感和受控的藥物輸送。在LMWGs化合物的不同類型中，基于碳水化合物的系統(tǒng)尤為有趣。碳水化合物豐富，可再生，具有生物相容性，并具有許多易于官能化的羥基。我們的小組先前發(fā)現(xiàn)，可以通過選擇性地官能化羥基從D-葡萄糖和D-葡萄糖胺獲得有機膠凝劑和水膠凝劑。發(fā)現(xiàn)各種C-2酰基衍生物（包括酯和氨基甲酸酯）對于水和有機溶劑都是有效的LMWG。在該研究中，進行了葡糖胺衍生物的C-3位的官能化。合成了兩種類型的C-3衍生物，包括酯和氨基甲酸酯，并通過1H和13C NMR光譜以及LCMS對其進行了表征。然后在一系列選定的溶劑中分析這些化合物的膠凝特性。已發(fā)現(xiàn)幾種化合物是有效的有機膠凝劑，使用紅外光譜，流變學，光學顯微鏡等對所得的凝膠進行了表征。測試了這些膠凝劑在控制藥物輸送中的用途，發(fā)現(xiàn)載有萘普生鈉或氯霉素的凝膠會釋放出藥物在酸性環(huán)境中。

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  • 作者

    Garcia, Consuelo.;

  • 作者單位

    Old Dominion University.;

  • 授予單位 Old Dominion University.;
  • 學科 Chemistry.;Organic chemistry.;Pharmaceutical sciences.
  • 學位 M.S.
  • 年度 2017
  • 頁碼 86 p.
  • 總頁數(shù) 86
  • 原文格式 PDF
  • 正文語種 eng
  • 中圖分類 古生物學;
  • 關鍵詞

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