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Theoretical and experimental studies of an oseltamivir-triazole-based thermoresponsive organogel

机译：奥特拉米韦 - 三唑基热响应器有机凝胶的理论与实验研究

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摘要

Low-molecular weight organic gelators have been of significant interest in recent years because of their interesting properties and potential applications in sensing technology, biomedicine and drug delivery. Herein, the synthesis, characterization and gelation properties of new oseltamivir conjugates are reported. The oseltamivir-triazole conjugate 1 was synthesized via a click-reaction in a 75% yield. The key features of this conjugate include the presence of amide, flexible ester linkages and a triazole scaffold linking a hydrophobic alkyl chain. The conjugate 1, possessing a long alkyl chain, showed gelation properties in various apolar organic solvents. This gelation behavior was not observed in the case of the deesterified conjugate 2; this indicated the necessity of the alkyl chain for gelation. The gelator 1 showed thermoreversible gelation properties in a range of linear alkane solvents (from n-pentane to n-dodecane). A scanning electron microscopic study suggests that the gelator 1 exists as cross-linked structures, which are self-aggregated in the range of submicrometers, as supported by extensive H-1-NMR studies. The rheological parameters supported the occurrence of a soft gelation process, and the gel formed in n-decane was found to be stiffer than that formed in n-hexane. Computational studies suggested that the gelation behavior was indeed due to micelle formation and dependent on the lipophilicity of solvents.
机译：低分子量有机凝胶剂已经显著的兴趣，近年来由于其有趣的性质和传感技术，生物医学和药物传递的潜在应用。在这里，报道的新结合物奥司他韦的合成，表征和胶凝性质。奥司他韦三唑缀合物1经由产率为75％的点击反应合成。这种缀合物的主要功能包括酰胺的存在下，柔性酯键和三唑骨架连接的疏水烷基链。所述缀合物1，具有一个长烷基链，表现为凝胶化性能的各种非极性有机溶剂。在去酯化共轭2的情况下，没有观察到凝胶化此行为;这表明凝胶化烷基链的必要性。胶凝剂1的范围内的线性烷烃溶剂（从正戊烷到正十二烷）的显示热可逆胶凝性质。电镜观察的扫描表明，所述的胶凝剂1存在作为在亚微米的范围内交联结构，这是自聚集，通过广泛的H-1-NMR研究，作为支撑。流变参数支撑的软凝胶化过程的发生，以及形成于正癸烷的凝胶被发现是比形成于正己烷更硬。计算研究表明，凝胶化行为是确因胶束形成并依赖于溶剂的亲脂性。

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  • 来源
    《RSC Advances》 |2019年第36期|共11页
  • 作者

    Kumar Sumit; Wu Lidong; Sharma Neha; Ayushee; Kaushik Kumar; Grishina Maria; Chhikara Bhupendra S.; Poonam; Potemkin Vladimir; Rathi Brijesh;

  • 作者单位

    Univ Delhi Univ Enclave Hansraj Coll Lab Translat Chem &

    Drug DiscoveryDept Chem Delhi 110007 India;

    MIT Dept Chem Cambridge MA 02139 USA;

    Univ Delhi Univ Enclave Hansraj Coll Lab Translat Chem &

    Drug DiscoveryDept Chem Delhi 110007 India;

    Univ Delhi Univ Enclave Hansraj Coll Lab Translat Chem &

    Drug DiscoveryDept Chem Delhi 110007 India;

    Ctr Fire Explos &

    Environm Safety Fire Chem Grp Delhi 110054 India;

    South Ural State Univ Lab Computat Modeling Drugs Chelyabinsk 454080 Russia;

    Univ Delhi Aditi Mahavidyalaya Dept Chem Delhi 110039 India;

    Univ Delhi Dept Chem Miranda House Delhi 110007 India;

    South Ural State Univ Lab Computat Modeling Drugs Chelyabinsk 454080 Russia;

    Univ Delhi Univ Enclave Hansraj Coll Lab Translat Chem &

    Drug DiscoveryDept Chem Delhi 110007 India;

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