Department of Chemistry, Aligarh Muslim University, Aligarh 202002, India.
Department of Chemistry, Aligarh Muslim University, Aligarh 202002, India.
Chem Phys Lipids. 2022 Mar;243:105176. doi: 10.1016/j.chemphyslip.2022.105176. Epub 2022 Jan 31.
The renewable fatty acid-based surface-active ionic liquids (SAILs) containing ethyl-substituted imidazolium head groups were prepared and structurally analyzed by Fourier transform infrared spectroscopy (FTIR), HNMR and CNMR spectroscopy. The products were named as; 3-ethyl-1-(2-dodecanoyl oxy) ethylimidazolium bromide [CEeim]Br, 3-ethyl-1-(2-tetradecanoyl oxy) ethylimidazolium bromide [CEeim]Br and 3-ethyl-1-(2-hexadecanoyl oxy) ethylimidazolium bromide [CEeim]Br. The critical micelle concentration (cmc) values of the three SAILs have been evaluated using conductivity measurements, probe-less UV-visible spectroscopy and fluorescence spectroscopy. The obtained cmc values were compared with the earlier reported non-functionalized SAILs such as [Cmim]Br and [Ceim]Br where n = 12, 14, 16. The values were found to be 3-9 times lower mainly due to the presence of ester chain and also ethyl substituted imidazole ring. Thermodynamic parameters were evaluated by conductivity data at three different temperatures. Further, the aggregation behavior of SAILs with anesthetic drug, lidocaine hydrochloride (LC) has been studied using fluorescence. The fluorescence and UV-visible studies showed strong synergistic interactions operating between SAILs and drug molecules involving H bonding and cation-π interactions. The interactions grew stronger with the elongation of SAIL-chain length (12-16C). Dynamic light scattering (DLS) and transmission electron microscopy (TEM) measurements suggested the formation of vesicles in SAIL-LC mixtures. These studies may thus offer an effective candidate which would serve as vectors for drug molecules in terms of their enhanced solubilization, permeability and target-specific delivery.
含有乙基取代咪唑鎓头基的可再生脂肪酸基表面活性离子液体 (SAIL) 通过傅里叶变换红外光谱 (FTIR)、HNMR 和 CNMR 光谱进行了制备和结构分析。这些产物分别命名为：3-乙基-1-(2-十二烷氧基)乙基咪唑溴盐 [CEeim]Br、3-乙基-1-(2-十四烷氧基)乙基咪唑溴盐 [CEeim]Br 和 3-乙基-1-(2-十六烷氧基)乙基咪唑溴盐 [CEeim]Br。通过电导率测量、无探针紫外可见光谱和荧光光谱评估了三种 SAIL 的临界胶束浓度 (cmc) 值。所得 cmc 值与先前报道的非功能化 SAIL 如 [Cmim]Br 和 [Ceim]Br 进行了比较，其中 n=12、14、16。由于酯链和乙基取代的咪唑环的存在，这些值低了 3-9 倍。通过在三个不同温度下的电导率数据评估了热力学参数。此外，还通过荧光研究了 SAIL 与麻醉药物盐酸利多卡因 (LC) 的聚集行为。荧光和紫外可见研究表明，SAIL 和药物分子之间存在强烈的协同相互作用，涉及氢键和阳离子-π 相互作用。随着 SAIL 链长（12-16C）的延长，相互作用变得更强。动态光散射 (DLS) 和透射电子显微镜 (TEM) 测量表明，在 SAIL-LC 混合物中形成了囊泡。这些研究因此提供了一种有效的候选物，它将作为药物分子的载体，在增强其增溶、渗透和靶向递送上发挥作用。
