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Experimental and Computational Studies on Non-Covalent Imprinted Microspheres as Recognition System for Nicotinamide Molecules
Dipartimento di Ingegneria dell’Innovazione, Università del Salento, via per Monteroni, km1, 73100, Lecce, Italy
National Nanotechnology Laboratory of CNR-INFM, Distretto Tecnologico ISUFI, Università del Salento, Via per Arnesano, km 1, 73100 Lecce, Italy
* Author to whom correspondence should be addressed.
Received: 4 June 2009; in revised form: 29 June 2009 / Accepted: 3 July 2009 / Published: 17 July 2009
Abstract: Molecularly imprinted microspheres obtained by precipitation polymerization using nicotinamide (nia) as template have been prepared and characterised by SEM. How various experimental parameters can affect microsphere morphology, reaction yield and re-binding capacity have been evaluated. Pre-polymerization interactions between template and functional monomer in chloroform and MeCN have been studied by 1H-NMR. The results suggest that the interaction between nia and methacrylic acid (MAA) is mainly based on hydrogen-bonding between amide protons and MAA. Computational density functional theory (DFT) studies on MAA-nia complexes have been also performed to better understand hydrogen-bonding interactions. The imprinted activity of the microspheres, synthesized in chloroform or acetonitrile (MeCN), has been evaluated by spectrophotometric analysis of nia solutions when chloroform or MeCN are used as incubation solvents. The results suggest that MeCN interferes with hydrogen bonding between template and MAA during either the polymerization step or re-binding process as also observed from theoretical results. Finally, the selectivity towards selected nia analogues has been also confirmed.
Keywords: molecular imprinting; UV-vis spectroscopy; NMR; nicotinamide (nia); theoretical DFT studies
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Del Sole, R.; Lazzoi, M.R.; Arnone, M.; Sala, F.D.; Cannoletta, D.; Vasapollo, G. Experimental and Computational Studies on Non-Covalent Imprinted Microspheres as Recognition System for Nicotinamide Molecules. Molecules 2009, 14, 2632-2649.
Del Sole R, Lazzoi MR, Arnone M, Sala FD, Cannoletta D, Vasapollo G. Experimental and Computational Studies on Non-Covalent Imprinted Microspheres as Recognition System for Nicotinamide Molecules. Molecules. 2009; 14(7):2632-2649.
Del Sole, Roberta; Lazzoi, Maria Rosaria; Arnone, Mario; Sala, Fabio Della; Cannoletta, Donato; Vasapollo, Giuseppe. 2009. "Experimental and Computational Studies on Non-Covalent Imprinted Microspheres as Recognition System for Nicotinamide Molecules." Molecules 14, no. 7: 2632-2649.