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Issue 5, 2004
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The roles of template complexation and ligand binding conditions on recognition in bupivacaine molecularly imprinted polymers

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Abstract

A model for the molecular basis for ligand recognition in bupivacaine imprinted methacrylic acidethylene glycol dimethacrylate co-polymers has been developed based upon a series of 1H-NMR studies in conjunction with HPLC and radioligand binding analyses. 1H-NMR studies indicated that functional monomer-template complexes survive the polymerisation process, at least up until the stage of gelation. Polymers were synthesised and characterised by surface area analysis (BET), FT-IR and SEM. A combination of zonal and frontal chromatographic studies in aqueous and non-polar media indicate that selectivity arises from a combination of hydrophobic and electrostatic interactions. However, in the concentration regime employed for LC-based studies, ligand recognition in aqueous media was shown to be predominantly non-specific and hydrophobic in character. Radioligand binding studies, in lower ligand binding concentration regimes, permitted closer examination of the higher affinity binding sites. It was shown that the presence of a polar modifier in a non-polar solvent, or an organic modifier in water, produced enhanced selectivity. Variable temperature studies showed that the temperature of binding influences selectivity as well as the apparent number of sites available and that this effect is different in organic and aqueous environments. This indicates that the system studied is more complex in character than is generally appreciated. A comparison of the techniques employed here indicates that although chromatographic studies provide a valuable first-round screen for polymerligand selectivities, the level of detail obtainable using radioligand binding studies (lower concentrations and true equilibrium binding) makes them superior for detailed evaluations of molecularly imprinted polymers.

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Article information


Submitted
23 Dec 2004
Accepted
24 Mar 2004
First published
15 Apr 2004

Analyst, 2004,129, 456-462
Article type
Paper

The roles of template complexation and ligand binding conditions on recognition in bupivacaine molecularly imprinted polymers

J. G. Karlsson, B. Karlsson, L. I. Andersson and I. A. Nicholls, Analyst, 2004, 129, 456
DOI: 10.1039/B316716J

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