Lin Ching-Erh, Liao Wei-Ssu, Cheng Hsu-Tun, Kuo Chia-Ming, Liu Yu-Chih
Department of Chemistry, National Taiwan University, Taipei, Taiwan.
Electrophoresis. 2005 Oct;26(20):3869-77. doi: 10.1002/elps.200500087.
In this study, enantioseparations of five phenothiazines, including promethazine, ethopropazine, trimeprazine, methotrimeprazine, and thioridazine, in CD-modified CZE using dual CD systems consisting of randomly sulfate-substituted CD (MI-S-beta-CD) and a neutral CD as chiral selectors in a citrate buffer (100 mM) at pH 3.0 were investigated. The results indicate that MI-S-beta-CD is an excellent chiral selector for enantioseparation of ethopropazine. The enantiomers of promethazine can also be baseline-resolved with MI-S-beta-CD at concentrations in the range of 0.5-1.0% w/v. On the other hand, thioridazine and trimeprazine interact strongly with neutral CDs. As a result, the enantioselectivity of these two phenothiazines is remarkably and synergistically enhanced with increasing the concentration of neutral CDs in the presence of MI-S-beta-CD and simultaneous enantioseparations of these phenothiazines, except for methotrimeprazine, could favorably be achieved with the use of dual CD systems. Moreover, by varying the concentration of beta-CD or gamma-CD at a fixed concentration of MI-S-beta-CD (0.75% w/v) reversal of the enantiomer migration order of promethazine occurred. This may be attributable to the opposite effects of charged and neutral CDs on the mobility of the enantiomers of promethazine.
在本研究中，考察了在pH 3.0的100 mM柠檬酸盐缓冲液中，使用由随机硫酸根取代的环糊精（MI-S-β-CD）和中性环糊精组成的双环糊精体系，在CD修饰的毛细管区带电泳中对包括异丙嗪、乙丙嗪、异丁嗪、甲硫异丁嗪和硫利达嗪在内的五种吩噻嗪进行对映体分离。结果表明，MI-S-β-CD是乙丙嗪对映体分离的优良手性选择剂。异丙嗪对映体在0.5 - 1.0% w/v浓度范围内的MI-S-β-CD也能实现基线分离。另一方面，硫利达嗪和异丁嗪与中性环糊精强烈相互作用。因此，在MI-S-β-CD存在下，随着中性环糊精浓度的增加，这两种吩噻嗪的对映选择性显著协同增强，并且除甲硫异丁嗪外，使用双环糊精体系可以顺利实现这些吩噻嗪的同时对映体分离。此外，在固定MI-S-β-CD浓度（0.75% w/v）下改变β-CD或γ-CD的浓度，异丙嗪对映体迁移顺序发生了反转。这可能归因于带电和中性环糊精对异丙嗪对映体迁移率的相反影响。
