Capillary electrophoretic enantioseparation of basic drugs using a new single-isomer cyclodextrin derivative and theoretical study of the chiral recognition mechanism.
Capillary electrophoretic enantioseparation of basic drugs using a new single-isomer cyclodextrin derivative and theoretical study of the chiral recognition mechanism.
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DOI：
10.1002/jssc.201501026
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发表时间：
2016-05
影响因子：
3.1
通讯作者：
Yongjing Liu;Miaoduo Deng;Jia Yu;Zhen Jiang;Xingjie Guo
中科院分区：
文献类型：
--
作者：
Yongjing Liu;Miaoduo Deng;Jia Yu;Zhen Jiang;Xingjie Guo
合成了一种新型单异构体环糊精衍生物heptakis{2,6-二o -[3-（1,3-二羧基丙基氨基）-2-羟丙基]}-β-环糊精（谷氨酸-β-环糊精），并将其作为手性选择剂用于毛细管电泳，用于特布他林、氯丙那林、妥洛布特罗、克仑特罗、普罗卡特罗、卡维地洛、康康唑、咪康唑、甲基溴homatropine、溴苯那敏、氯苯那敏和苯那敏等12种基本药物的对映分离。考察了背景电解液pH、谷氨酸-β-环糊精浓度和磷酸盐缓冲液浓度对分离效率的影响。采用50 cm（有效长度40 cm） × 50 μm的未涂覆熔融石英毛细管，以含0.5-4.5 mM谷氨酸-β-环糊精的120 mM磷酸盐缓冲液（pH 2.5-4.0）作为背景电解质，获得了满意的对映体分离。施加20 kV电压，毛细管温度保持在20℃。结果表明，谷氨酸-β-环糊精是12种基本药物的有效手性选择剂。此外，采用半经验参数法考察了溴苯那敏、氯苯那敏和苯那敏对谷氨酸-β-环糊精可能的手性识别机理。
A novel single-isomer cyclodextrin derivative, heptakis {2,6-di-O-[3-(1,3-dicarboxyl propylamino)-2-hydroxypropyl]}-β-cyclodextrin (glutamic acid-β-cyclodextrin) was synthesized and used as a chiral selector in capillary electrophoresis for the enantioseparation of 12 basic drugs, including terbutaline, clorprenaline, tulobuterol, clenbuterol, procaterol, carvedilol, econazole, miconazole, homatropine methyl bromide, brompheniramine, chlorpheniramine and pheniramine. The primary factors affecting separation efficiency, which include the background electrolyte pH, the concentration of glutamic acid-β-cyclodextrin and phosphate buffer concentration, were investigated. Satisfactory enantioseparations were obtained using an uncoated fused-silica capillary of 50 cm (effective length 40 cm) × 50 μm id with 120 mM phosphate buffer (pH 2.5-4.0) containing 0.5-4.5 mM glutamic acid-β-cyclodextrin as background electrolyte. A voltage of 20 kV was applied and the capillary temperature was kept at 20°C. The results proved that glutamic acid-β-cyclodextrin was an effective chiral selector for studied 12 basic drugs. Moreover, the possible chiral recognition mechanism of brompheniramine, chlorpheniramine and pheniramine on glutamic acid-β-cyclodextrin was investigated using the semi-empirical Parametric Method 3.