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Molecules 2018, 23(8), 1875; https://doi.org/10.3390/molecules23081875

Improved Enantioselectivity for Atenolol Employing Pivot Based Molecular Imprinting

1
Department of Inorganic Chemistry, Faculty of Pharmacy, “Iuliu Haţieganu” University of Medicine and Pharmacy, 12 Ion Creangă St., Cluj-Napoca 400010, Romania
2
Department of Analytical Chemistry, Faculty of Pharmacy, “Iuliu Haţieganu” University of Medicine and Pharmacy, 4 Pasteur St., Cluj-Napoca 400349, Romania
3
Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editors: Maria Elizabeth Tiritan, Madalena Pinto and Carla Sofia Garcia Fernandes
Received: 3 June 2018 / Revised: 20 July 2018 / Accepted: 26 July 2018 / Published: 27 July 2018
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Abstract

In the last few decades, molecular imprinting technology went through a spectacular evolution becoming a well-established tool for the synthesis of highly selective biomimetic molecular recognition platforms. Nevertheless, there is still room for advancement in the molecular imprinting of highly polar chiral compounds. The aim of the present work was to investigate the favorable kosmotropic effect of a ternary complex involving a polar chiral template (eutomer of atenolol) and a functional monomer, bridged by a central metal ion through well-defined, spatially directional coordinate bonds. The efficiency of the chiral molecular recognition was systematically assessed on polymers obtained both by non-covalent and metal-mediated molecular imprinting. The influence on the chromatographic retention and enantioselectivity of different experimental variables (functional monomers, cross-linkers, chaotropic agents, metal ions, porogenic systems, etc.) were studied on both slurry packed and monolithic HPLC columns. Deliberate changes in the imprinting and rebinding (chromatographic) processes, along with additional thermodynamic studies shed light on the particularities of the molecular recognition mechanism. The best performing polymer in terms of enantioselectivity (α = 1.60) was achieved using 4-vinyl pyridine as functional monomer and secondary ligand for the Co(II)-mediated imprinting of S-atenolol in the presence of EDMA as cross-linker in a porogenic mixture of [BMIM][BF4]:DMF:DMSO = 10:1:5, v/v/v. View Full-Text
Keywords: metal-mediated molecular imprinting; hydrophilic template; atenolol; chiral separation; β-blockers; molecularly imprinted polymers; molecular recognition metal-mediated molecular imprinting; hydrophilic template; atenolol; chiral separation; β-blockers; molecularly imprinted polymers; molecular recognition
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
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Bodoki, A.E.; Iacob, B.-C.; Gliga, L.E.; Oprean, S.L.; Spivak, D.A.; Gariano, N.A.; Bodoki, E. Improved Enantioselectivity for Atenolol Employing Pivot Based Molecular Imprinting. Molecules 2018, 23, 1875.

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