Use of methylamino-beta-cyclodextrin in capillary electrophoresis. Resolution of acidic and basic enantiomers

Beta-cyclodextrin derivatives, namely 6(A) methylamino-beta-CD and hepta-methylamino-beta-CD have been used as chiral selectors for the enantiomeric separation of a number of acidic and basic compounds by capillary electrophoresis employing either coated or uncoated capillaries. The effects of the CD type and concentration and the pH of the background electrolyte on the mobility and chiral resolution of the analytes have been studied. The use of monomethylamino-beta-CD in a coated capillary allowed the enantiomeric resolution of phenyl lactic acid, warfarin and acenocoumarol but was not successful for tiaprofen and its 3-isomer. The heptamethylamino derivative, under the same experimental conditions, was a better chiral selector than the monosubstituted CD toward the arylpropionic acids and phenyl lactic acid while the anticoagulant drugs showed poor or no chiral resolution. Inversion of migration order was obtained for phenyl lactic acid, warfarin and acenocoumarol enantiomers. The enantiomers of basic compounds of pharmaceutical interest, namely propranolol, terbutaline, ketamine, chlorpheniramine and isoproterenol were only resolved using monomethylamino-beta-CD dissolved in a phosphate buffer containing tetramethylammonium ions.