The complexation system between levosulpiride (L-SUL) and different cyclodextrins (CDs) was investigated with the aim of evaluating the intermolecular interactions involved in enantioseparation by capillary electrophoresis (CE). A molecular modeling study made it possible to explain the different affinities of L-SUL for several cyclodextrins tested during CE method scouting. The calculated binding energies showed the most stable complexes, obtained with sulfated-β-CD and methyl-β-CD. A correlation between CE migration time and stability complex of analyte–CDs complexes was postulated. Furthermore, rotating-frame Overhauser effect spectroscopy NMR (ROESY) experiments were carried out to confirm the mechanism of separation, providing valuable and complementary information. 2-D NMR ROESY spectra clearly indicated the formation of complexes, highlighting the presence of the benzene sulfonamides moiety of L-SUL inside the hydrophobic cavity of the CDs.
Evaluation of the inclusion complex formation of levosulpiride and cyclodextrins by capillary electrophoresis, molecular modeling and NMR / Benedetta Pasquini; Fabrizio Melani; Serena Orlandini; Sergio Pinzauti; Sandra Furlanetto. - ELETTRONICO. - (2014), pp. 229-229. (Intervento presentato al convegno XXV Congresso Nazionale della Società Chimica Italiana tenutosi a Arcavacata di Rende (CS) nel 7-12 Settembre 2014).
Evaluation of the inclusion complex formation of levosulpiride and cyclodextrins by capillary electrophoresis, molecular modeling and NMR
PASQUINI, BENEDETTA;MELANI, FABRIZIO;ORLANDINI, SERENA;PINZAUTI, SERGIO;FURLANETTO, SANDRA
2014
Abstract
The complexation system between levosulpiride (L-SUL) and different cyclodextrins (CDs) was investigated with the aim of evaluating the intermolecular interactions involved in enantioseparation by capillary electrophoresis (CE). A molecular modeling study made it possible to explain the different affinities of L-SUL for several cyclodextrins tested during CE method scouting. The calculated binding energies showed the most stable complexes, obtained with sulfated-β-CD and methyl-β-CD. A correlation between CE migration time and stability complex of analyte–CDs complexes was postulated. Furthermore, rotating-frame Overhauser effect spectroscopy NMR (ROESY) experiments were carried out to confirm the mechanism of separation, providing valuable and complementary information. 2-D NMR ROESY spectra clearly indicated the formation of complexes, highlighting the presence of the benzene sulfonamides moiety of L-SUL inside the hydrophobic cavity of the CDs.
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