Enantioseparation of phenothiazines in CD-modified CZE using single isomer sulfated CD as a chiral selector.
Enantioseparations of five chiral phenothiazines in CD-modified CZE using the single isomer sulfate-substituted beta-CD (heptakis(2,3-dihydroxy-6-O-sulfo)-beta-CD, SI-S-beta-CD) and dual CD systems consisting of SI-S-beta-CD and a neutral CD as chiral selectors in a citrate buffer at pH 3.0 were investigated. The results indicate that SI-S-beta-CD is an excellent chiral selector for enantioseparation of promethazine. The enantiomers of trimeprazine were well separated, while those of ethopropazine could also be baseline-resolved with SI-S-beta-CD. With dual CD systems, especially with hydroxypropyl-beta-CD (HP-beta-CD) as neutral CD, the enantioselectivity of thioridazine and ethopropazine was considerably enhanced. Effective enantioseparation of phenothiazines, except for methotrimeprazine, could thus be favorably and simultaneously achieved. Moreover, reversal of the enantiomer migration order of ethopropazine and thioridazine occurred by varying the concentration of gamma-CD in the presence of SI-S-beta-CD. These phenomena may be attributable to the opposite effects of sulfated beta-CD and gamma-CD on the mobility of the enantiomers of ethopropazine and of thioridazine. Comparative studies on the enantioseparations of phenothiazines with single CD and dual CD systems containing SI-S-beta-CD and randomly sulfate-substituted beta-CD (MI-S-beta-CD) were made.
Liao
Wei-Ssu
WS
Department of Chemistry, National Taiwan University, Taipei, Taiwan.
Lin
Chen-Hsing
CH
Chen
Chih-Yu
CY
Kuo
Chia-Ming
CM
Liu
Yu-Chih
YC
Wu
Jong-Chang
JC
Lin
Ching-Erh
CE
D004573:Electrolytes; D019075:Electrophoresis, Capillary / Q000295:instrumentation* / Q000379:methods*; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D015394:Molecular Structure; D010640:Phenothiazines / Q000737:chemistry / Q000302:isolation & purification*; D011398:Promethazine / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D013431:Sulfates / Q000737:chemistry; D013881:Thioridazine / Q000737:chemistry / Q000302:isolation & purification; D014291:Trimeprazine / Q000737:chemistry / Q000302:isolation & purification; D047392:beta-Cyclodextrins / Q000737:chemistry*; D047408:gamma-Cyclodextrins / Q000737:chemistry*
D004573:Electrolytes; D007202:Indicators and Reagents; D010640:Phenothiazines; D013431:Sulfates; D047392:beta-Cyclodextrins; D047408:gamma-Cyclodextrins; D014291:Trimeprazine; C084820:profenamine; D011398:Promethazine; D013881:Thioridazine