Experimental and Computational Studies on Non-Covalent Imprinted Microspheres as Recognition System for Nicotinamide Molecules.docVIP

Molecules 2009, 14, 2632-2649; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Experimental and Computational Studies on Non-Covalent Imprinted Microspheres as Recognition System for Nicotinamide Molecules Roberta Del Sole 1,*, Maria Rosaria Lazzoi 1, Mario Arnone 1, Fabio Della Sala 2, Donato Cannoletta 1 and Giuseppe Vasapollo 1 1 Dipartimento di Ingegneria dell’Innovazione, Università del Salento, via per Monteroni, km 1, 73100, Lecce, Italy 2 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; E-mail: roberta.delsole@unile.it; Tel.: +39-832.297256; Fax: +39-832.325362 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