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四甲基铵羧甲基-β-环糊精的合成及应用:毛细管电泳手性拆分中的一种新型离子液体。

Synthesis and application of tetramethylammonium-carboxymethylated-β-cyclodextrin: A novel ionic liquid in capillary electrophoresis enantioseparation.

机构信息

Key Laboratory of Drug Quality Control and Pharmacovigilance (Ministry of Education), China Pharmaceutical University, Nanjing, 210009, PR China; State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 210009, PR China.

Key Laboratory of Drug Quality Control and Pharmacovigilance (Ministry of Education), China Pharmaceutical University, Nanjing, 210009, PR China; State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 210009, PR China.

出版信息

J Pharm Biomed Anal. 2020 Feb 20;180:113030. doi: 10.1016/j.jpba.2019.113030. Epub 2019 Dec 5.

DOI:10.1016/j.jpba.2019.113030
PMID:31851909
Abstract

In this study, a carboxymethylated-β-cyclodextrin-based chiral ionic liquid (CIL), tetramethylammonium-carboxymethylated-β-cyclodextrin (TMA-CM-β-CD) was successfully designed and synthesized. This cyclodextrin-based ionic liquids (ILs) was used as the sole chiral selector in capillary electrophoresis, and it is very interesting to find that the chiral separation capability can be remarkably improved when a conventional cyclodextrin chiral selector evolved into an IL chiral selector. The ionic liquid showed satisfactory separation performance towards twelve tested drugs. A series of parameters affecting the enantioseparation, such as the type and proportion of organic modifier, buffer pH, chiral selector concentration, as well as applied voltage were systematically investigated. Additionally, the molecular docking program Autodock was applied to further demonstrate the mechanism of chiral recognition and the enhanced enantioselectivity of TMA-CM-β-CD, which kept in agreement with our experimental results.

摘要

在这项研究中,成功设计并合成了基于羧甲基-β-环糊精的手性离子液体(CIL),即四甲基铵羧甲基-β-环糊精(TMA-CM-β-CD)。这种基于环糊精的离子液体(ILs)被用作毛细管电泳中的唯一手性选择剂,非常有趣的是,当传统的环糊精手性选择剂演变成 IL 手性选择剂时,手性分离能力可以显著提高。该离子液体对 12 种测试药物表现出良好的分离性能。系统研究了一系列影响对映体分离的参数,例如有机改性剂的类型和比例、缓冲液 pH 值、手性选择剂浓度以及施加电压。此外,应用分子对接程序 Autodock 进一步证明了 TMA-CM-β-CD 的手性识别机制和增强的对映选择性,这与我们的实验结果一致。

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