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Chiral nanocomposite of sulfobutyl ether-β-cyclodextrin embedded in carbon nanofibers for enantioselective electrochemical discrimination of amlodipine, metoprolol and clenbuterol enantiomers
Journal of Materiomics ( IF 9.4 ) Pub Date : 2020-09-24 , DOI: 10.1016/j.jmat.2020.09.004
Pramod K. Kalambate , Sharad S. Upadhyay , Yue Shen , Wanida Laiwattanapaisal , Yunhui Huang

A highly sensitive and selective electrochemical chiral sensor was developed based on the competitive supramolecular interaction of carbon nanofibers (CNFs) embedded sulfobutyl ether-β-cyclodextrin (SBE-β-CD) with optically active cationic drugs at glassy carbon electrode (GCE). The difference in intermolecular hydrogen bonding/stability constant/enantioselectivity coefficient and Gibbs free energy of anionic host SBE-β-CD with enantiomers of amlodipine (R-/S-AML), clenbuterol (R-/S-CBL) and metoprolol (R-/S-MET) as a guest paved the way for efficient discrimination. The proposed sensing platform (CNFs-SBE-β-CD/GCE) could recognize the aforementioned enantiomers based on the discernible difference of peak potential (S/R-AML (ΔEp = 135 mV), R/S-MET (ΔEp = 99 mV) and R/S-CBL (ΔEp = 111 mV). The binding mechanisms and thermodynamic study of the enantiospecific behavior have been investigated using the host-guest chemistry approach inside the nanocavity and results suggest that S-AML, R-MET, and R-CBL show stronger stability constants than their antipodes. Formation of the diastereomeric complex was taken as a measure of enantioselectivity and experimental results indicated that anionic SBE-β-CD is a better chiral ligand than neutral cyclodextrins. The fabricated sensor could be a useful low-cost electrochemical tool for molecular recognition of a variety of cationic species not only of drugs but also from other sources.



中文翻译:

嵌入碳纳米纤维中的磺基丁基醚-β-环糊精的手性纳米复合物,用于氨氯地平,美托洛尔和克仑特罗对映体的对映选择性电化学鉴别

基于碳纳米纤维(CNFs)嵌入的磺丁基醚-β-环糊精(SBE-β-CD)与光学活性阳离子药物在玻璃碳电极(GCE)上的竞争性超分子相互作用,开发了一种高灵敏度和选择性的电化学手性传感器。阴离子主体SBE-β-CD与氨氯地平(R- / S-AML),克仑特罗(R- / S-CBL)和美托洛尔(R)的分子间氢键键合/稳定性常数/对映选择性系数和吉布斯自由能的差异-/ S-MET)作为客人为有效的歧视铺平了道路。所提出的感测平台(的CNF-SBE-β-CD / GCE)可以基于峰值电势(S / R-AML(ΔE的可辨别的差异识别上述对映异构体p  = 135毫伏),R / S-MET(ΔE p  = 99 mV)和R / S-CBL(ΔEp  = 111 mV)。已使用纳米腔体内的客体-客体化学方法研究了对映体行为的结合机理和热力学研究,结果表明S-AML,R-MET和R-CBL的稳定常数比其对映体强。以非对映异构体的形成作为对映选择性的量度,实验结果表明,阴离子SBE-β-CD比中性环糊精更好。制成的传感器可能是一种有用的低成本电化学工具,不仅可以识别药物的各种阳离子种类,还可以用于其他来源的分子识别。

更新日期:2020-09-24
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