title: Capillary electrophoretic enantioseparation of basic drugs using a new single-isomer cyclodextrin derivative and theoretical study of the chiral recognition mechanism.
abstract: 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.
authors.affiliation: Department of Pharmaceutical Analysis, School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, Liaoning Province, P. R. China.|Fujian University of Traditional Chinese Medicine, Fuzhou, Fujian Province, P. R. China.
authors.forename: Yongjing
authors.initials: Y
authors.lastname: Liu
authors.affiliation: Department of Pharmaceutical Analysis, School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, Liaoning Province, P. R. China.
authors.forename: Miaoduo
authors.initials: M
authors.lastname: Deng
authors.affiliation: Department of Pharmaceutical Analysis, School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, Liaoning Province, P. R. China.
authors.forename: Jia
authors.initials: J
authors.lastname: Yu
authors.affiliation: Department of Pharmaceutical Analysis, School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, Liaoning Province, P. R. China.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Jiang
authors.affiliation: Department of Pharmaceutical Analysis, School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, Liaoning Province, P. R. China.
authors.forename: Xingjie
authors.initials: X
authors.lastname: Guo
mesh_terms: D001977:Brompheniramine / Q000737:chemistry / Q000302:isolation & purification; D002227:Carbazoles / Q000737:chemistry / Q000302:isolation & purification; D000077261:Carvedilol; D002744:Chlorpheniramine / Q000737:chemistry / Q000302:isolation & purification; D002976:Clenbuterol / Q000737:chemistry / Q000302:isolation & purification; D003505:Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry*; D004464:Econazole / Q000737:chemistry / Q000302:isolation & purification; D019075:Electrophoresis, Capillary; D007545:Isoproterenol / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D008825:Miconazole / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D010632:Pheniramine / Q000737:chemistry / Q000302:isolation & purification; D017265:Procaterol / Q000737:chemistry / Q000302:isolation & purification; D011412:Propanolamines / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D013726:Terbutaline / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D014326:Tropanes / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D002227:Carbazoles; D003505:Cyclodextrins; D011412:Propanolamines; D014326:Tropanes; D000077261:Carvedilol; D010632:Pheniramine; D002744:Chlorpheniramine; C004350:clorprenaline; C010809:tulobuterol; C056244:homatropine methylbromide; D004464:Econazole; D008825:Miconazole; D001977:Brompheniramine; D007545:Isoproterenol; D013726:Terbutaline; D017265:Procaterol; D002976:Clenbuterol
keywords: Capillary electrophoresis; Enantioseparation; Glutamic acid-cyclodextrin; Semi-empirical Parametric Method 3