Comparative study of the complex forming ability and enantioselectivity of cyclodextrin polymers by CE and 1H NMR

The interactions between nine drugs (baclofen, bupivacaine, chlorpheniramine, ketoconazole, paliperidone, promethazine, propranolol, risperidone and verapamil) and six cyclodextrins (alpha-CD, beta-CD, gamma-CD, HP-beta-CD, HP-gamma-CD and Me-beta-CD) or six polymers of cyclodextrins (poly alpha-CD, poly beta-CD, poly gamma-CD, polyHP-beta-CD, polyHP-gamma-CD and polyMe-beta-CD) were studied by affinity capillary electrophoresis and/or H-1 NMR at pH 2.5. An exhaustive qualitative study was performed through the determination of the retardation factor. Then, four compounds and both beta-CD and poly beta-CD were selected for the quantitative study of the interactions at pH 2.5 and 7.0. By comparing the results obtained with the beta-CD and poly beta-CD, it appears that the apparent binding constants are up to five times higher with the polymer. The 2D-NMR results seem to indicate that the structure of the polymeric network favours the inclusion of the guest in the hydrophobic cavity of the CD units. Moreover, the poly-CDs have shown very high enantioselective abilities at both pH. (C) 2012 Elsevier Ltd. All rights reserved.