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Synthesis and ligand recognition of paracetamol selective polymers: semi-covalent versus non-covalent molecular imprinting.
University of Kalmar, School of Pure and Applied Natural Sciences.
University of Kalmar, School of Pure and Applied Natural Sciences. (BBCL)
Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences. (BBCL)ORCID iD: 0000-0003-1241-8888
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2009 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 7, p. 3148-3155Article in journal (Refereed) Published
Abstract [en]

Three molecular imprinting strategies, each based upon a series of ethylene glycol dimethacrylate (EGDMA) cross-linked co-polymers, have been used to produce materials selective for the commonly used analgesic and antipyretic agent paracetamol (p-acetaminophen or 4-acetamidophenol) (1). The polymers were synthesised using either a semi-covalent imprinting strategy based upon 4-acetamidophenyl-(4-vinylphenyl) carbonate (4) or a non-covalent strategy based on methacrylic acid (MAA) as the functional monomer, or by employing a combination of these strategies. Radioligand binding studies demonstrated low template affinity in polymers offering only a single electrostatic interaction point for recognition via the phenolic residue in the template, whereas binding was substantially increased upon the introduction of a second binding mode, namely interaction at the acetamide moiety. HPLC analyses revealed no imprinting effect in the purely semi-covalent system, and only a minor effect in the purely non-covalent systems. However, a pronounced imprinting effect was demonstrated for polymers prepared by a combination of semi-covalent and non-covalent imprinting. This study illustrates a limitation of both the non-covalent and the semi-covalent strategies when it comes to achieving imprinted selectivity for small and poorly functionalised templates such as paracetamol. Parallels with conclusions from studies with antibodies are discussed. 

Place, publisher, year, edition, pages
2009. Vol. 7, p. 3148-3155
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-7870DOI: 10.1039/b900014cOAI: oai:DiVA.org:lnu-7870DiVA, id: diva2:345900
Available from: 2010-08-27 Created: 2010-08-27 Last updated: 2017-12-12Bibliographically approved

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Rosengren-Holmberg, Jenny P.Karlsson, Jesper G.Andersson, Håkan S.Nicholls, Ian A.

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