College of Pharmacy, Shenyang Pharmaceutical University, Shenyang, China.
Chirality. 2021 May;33(5):188-195. doi: 10.1002/chir.23300. Epub 2021 Feb 18.
In this study, a novel hydroxypropyl-γ-cyclodextrin (HP-γ-CD) functionalized monolithic capillary column was prepared by one-pot sequential strategy and used for chiral separation in capillary electrochromatography for the first time. In one pot, GMA-HP-γ-CD as functional monomer was allowed to be formed via the ring opening reaction between HP-γ-CD and glycidyl methacrylate (GMA) catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and then copolymerized directly with ethylene dimethacrylate (EDMA) and 2-acrylamido-2-methyl propane sulfonic acid (AMPS) in the presence of porogenic solvents via thermally initiated free radical polymerization. The preparation conditions of monoliths were optimized. Enantiomer separations of six chiral drugs including pindolol, clorprenaline, tulobuterol, clenbuterol, propranolol, and tropicamide were achieved on the monolith. Among them, pindolol, clorprenaline, and tropicamide were baseline separated with resolution values of 1.62, 1.73, and 1.55, respectively. The mechanism of enantiomer separation was discussed by comparison of the HP-γ-CD and HP-β-CD functionalized monoliths.
在这项研究中,通过一锅顺序策略制备了一种新型的羟丙基-γ-环糊精(HP-γ-CD)功能化整体毛细管柱,并首次将其用于毛细管电色谱中的手性分离。在一锅反应中,HP-γ-CD 与甲基丙烯酸缩水甘油酯(GMA)在 1,8-二氮杂双环[5.4.0]十一-7-烯(DBU)的催化作用下通过开环反应形成 GMA-HP-γ-CD 作为功能单体,然后在致孔剂溶剂的存在下直接与乙二醇二甲基丙烯酸酯(EDMA)和 2-丙烯酰胺基-2-甲基丙磺酸(AMPS)共聚通过热引发自由基聚合。优化了整体柱的制备条件。在手性药物分离方面,在该整体柱上实现了六种手性药物包括匹哚洛尔、氯普洛尔、妥布特罗、克仑特罗、普萘洛尔和托吡卡胺的对映体分离。其中,匹哚洛尔、氯普洛尔和托吡卡胺的分离度分别为 1.62、1.73 和 1.55。通过比较 HP-γ-CD 和 HP-β-CD 功能化整体柱,讨论了手性分离的机制。