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Chiral separation of lobeline analogs using high performance capillary electrophoresis and derivatized cyclodextrins
C R McCurdy1, T G Venkateshwaran, J W Beach
1Department of Pharmaceutical and Biomedical Sciences, College of Pharmacy, University of Georgia, Athens 30602-2352, USA.
Abstract:
High performance capillary electrophoresis (HPCE) methods are described that will separate the enantiomers of various lobeline analogs synthesized in these laboratories. "Cyclodextrin array analysis" was used for preliminary screening and electrophoresis conditions were optimized for each investigated analog. The lobeline analogs under consideration were investigated as potential nicotinic agonists for the treatment of neurodegenerative disorders, such as Alzheimer's disease. Native alpha (alpha)-, beta (beta)-, and gamma (gamma)-cyclodextrins, methyl-beta-cyclodextrin (M-beta-CD), heptakis-(2,6-di-O-methyl)-beta-cyclodextrin (DM-beta-CD), and heptakis-(2,3,6-tri-O-methyl)-beta-cyclodextrin (TM-beta-CD), hydroxypropyl-alpha-cyclodextrin (HP-alpha-CD), hydroxypropyl-beta-cyclodextrin (HP-beta-CD) and hydroxypropl-gamma-cyclodextrin (HP-gamma-CD) were used as run buffer additives and their effect on the enantiomeric resolution of the lobeline analogs was investigated. The effect of pH, buffer concentration, voltage, temperature and organic modifier concentration on the enantiomeric resolution of the lobeline analogs was investigated. The most suitable conditions for each compound were chosen and, with detection at a wavelength of 200 nm, optimized.