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

文献类型： 外文期刊

作者： Kumar, Sumit 1 ; Wu, Lidong 3 ; Sharma, Neha 1 ; Ayushee 1 ; Kaushik, Kumar 5 ; Grishina, Maria 6 ; Chhikara, Bhupendr 1 ;

作者机构： 1.Univ Delhi, Univ Enclave, Hansraj Coll, Lab Translat Chem & Drug DiscoveryDept Chem, Delhi 110007, India

2.Univ Delhi, Dept Chem, Miranda House, Delhi 110007, India

3.MIT, Dept Chem, Cambridge, MA 02139 USA

4.Chinese Acad Fishery Sci, Minist Agr, Key Lab Control Qual & Safety Aquat Prod, Beijing 100141, Peoples R China

5.Ctr Fire Explos & Environm Safety, Fire Chem Grp, Delhi 110054, India

6.South Ural State Univ, Lab Computat Modeling Drugs, Chelyabinsk 454080, Russia

7.Univ Delhi, Aditi Mahavidyalaya, Dept Chem, Delhi 110039, India

期刊名称：RSC ADVANCES （ 影响因子：3.361； 五年影响因子：3.39 ）

ISSN： 2046-2069

年卷期： 2019 年 9 卷 36 期

页码：

收录情况： SCI

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.

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