NMR studies of chiral recognition mechanisms: interaction of enantiomers of N-imidazole derivatives with cyclodextrin hosts. Correlation with the CD-EKC studies |
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| Affiliation: | 1. Laboratoire de Chimie Analytique, EA 4034, Faculté des Sciences Pharmaceutiques et Biologiques, Université de Lille 2, 3 rue du Pr. Laguesse, BP 83, 59006 Lille Cédex, France;2. Laboratoire de Physique, UMR CNRS 8009, Faculté des Sciences Pharmaceutiques et Biologiques, Université de Lille 2, BP 83, 59006 Lille Cédex, France;1. Laboratory for the Analysis of Medicines, Department of Pharmacy, Faculty of Medicine, CIRM, University of Liège, Avenue Hippocrate 15, B36-+3-T4, 4000 Liège, Belgium;2. Department of Analytical Chemistry and Instrumental Analysis, Faculty of Pharmacy, “Iuliu Hațieganu” University of Medicine and Pharmacy Cluj-Napoca, 4 Louis Pasteur Street, 400349 Cluj-Napoca, Romania;1. Department of Chemistry, Virginia Tech, Blacksburg, VA 24061, USA;2. Department of Sustainable Biomaterials, Virginia Tech, Blacksburg, VA 24061, USA;3. Department of Industrial and Physical Pharmacy, College of Pharmacy, Purdue University, West Lafayette, IN 47907, USA;4. Macromolecules Innovation Institute, Virginia Tech, Blacksburg, VA 24061, USA;1. Department of Chemistry, St. Joseph University, Nagaland, 797 115, India;2. Department of Chemistry, Annamalai University, Annamalainagar, 608 002, India;3. PG & Research Department of Physics, Government Arts College, Melur, 625 106, India;4. Laboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad, 500 067, India;1. Laboratoire de Physicochimie des Polymères et des Interfaces (LPPI, I-MAT), University of Cergy-Pontoise, 95000 Cergy-Pontoise, France;2. Physics and Astronomy, University of British Columbia, Vancouver, BC V6T 1Z1, Canada |
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| Abstract: | The inclusion complexes formed between two chiral N-imidazole derivatives and four cyclodextrins (α-, β-, γ-, and highly sulfated-β-CDs) were investigated by one- and two-dimensional 1H NMR. With the additional results of an ESI-MS study, a 1:1 stoichiometry was proven for all the complexes studied. The complexes were also characterized in terms of binding constants and the results were compared to those obtained by CD-EKC. An identical affinity order for the various CDs was obtained with both techniques. Furthermore, the affinity order for both enantiomers determined by their binding constants values is confirmed by the enantiomer migration orders previously determined by CD-EKC. The structural data obtained by the 2D-ROESY experiments allowed us to understand the interaction mechanisms and to propose, for different analyte structures, theoretical models of inclusion orientation in the CD cavity. These models are in accordance with our previous hypothesis based on the analyte structure–enantioseparation relationships and the thermodynamic parameters determined by CD-EKC. |
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