Romanian Society of Pharmaceutical Sciences
 

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AMINO ACIDS BASED CHIRAL IONIC LIQUIDS FOR ENANTIOMER SEPARATION BY CAPILLARY ELECTROPHORESIS

MIHAI STĂNESCU1*, CRINA MARIA MONCIU1, MIHAI NIȚULESCU2, CONSTANTIN DRĂGHICI3, IRINA DOICIN4, GINA LUPAȘCU1, ALEXANDRA LUPU1, CORINA CRISTINA ARAMĂ1

1.Analytical Chemistry Department, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Bucharest, Romania
2.Pharmaceutical Chemistry Department, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Bucharest, Romania
3.”C. D. Nenițescu” Institute of Organic Chemistry of Romanian Academy, Bucharest, Romania
4.Zentiva Group - a Sanofi company, Bucharest, Romania

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Room temperature chiral ionic liquids (CILs) are a relatively new class of ionic compounds; they act as efficient chiral selectors and modifiers of the capacity of enantiodiscrimination in electrophoretic or chromatographic separations. The aim of this study was to synthesize and characterize according to literature new ionic liquids, tetrabutylammonium and tetramethylammonium amino acid salts (chiral anions: l-leucine, l-proline, l-histidine) and to investigate their effect on chiral separations of some pharmaceutical active ingredients racemates (ondansetron, mianserin, ofloxacin) using capillary electrophoresis. CILs alone were not able to discriminate the isomers of ondansetron, ofloxacin and mianserin, but the results proved that the enantioselectivity of hydroxypropyl-β-cyclodextrin (HPβCD) increased when CILs were added in the background electrolyte (BGE) containing cyclodextrin. Several parameters (pH, CIL and cyclodextrin concentration, applied voltage and temperature) were studied and their effect on enantioselectivity was highlighted. The obtained results proved the synergistic action of CIL and cyclodextrins in the chiral recognition and enantioseparation process.