Introduction

For the last two decades, the concept of designing synthetic molecular recognition materials that can mimic biological functions has generated substantial interest (1-7) and stimulated research on structurally organized materials. Particularly at a nanoscale level, the technique of molecular imprinting—cre-ating synthetic recognition sites within macromolecular matrices by template inclusion during polymerization—has demonstrated potential for a variety of

From: Methods in Molecular Biology, vol. 300: Protein Nanotechnology, Protocols, instrumentation, and Applications Edited by: T. Vo-Dinh © Humana Press Inc., Totowa, NJ

Fig. 1. Schematic concept of molecular imprinting.

applications (8,9). Generally, this methodology is based on utilizing the functionalities of a target molecule (template) to assemble its own recognition cavity by forming interactions with "complementary" functional groups of appropriate functional monomers. These interactions are provided by either cleavable covalent bonds or noncovalent interactions, which are then "frozen" in position by polymerization carried out in the presence of a high concentration of crosslinker (10-13). Subsequent removal of the template creates binding pockets within the polymer matrix that memorize the spatial arrangement of functional groups and the size and shape of the target molecule. Ideally, highly selective recognition of the imprinted analyte is thereby ensured, which favors a reversible rebinding process and selective retention of the templated analyte within the biomimetic recognition matrix (see Fig. 1).

So far, molecular imprinting has mainly been demonstrated for templates with a relatively low molecular weight (14-16). In the past few years, successful preparation of molecularly imprinted polymers (MlPs) specifically targeting practically relevant biomolecules such as flavonoids (17,18), mycotoxins (19), proteins, or carbohydrates (20-26) has been discussed in the literature. Nevertheless, the formation of synthetic receptors for macromolecules remains a challenging task, and appropriate procedures for the preparation of MlPs selective for specific biomolecules are of substantial biological and biomedical interest.

In the present study, imprinted polymers against the flavonol quercetin were successfully synthesized and characterized via high-performance liquid chromatography (HPLC) experiments. Because quercetin represents a biomolecule with several functionalities enabling noncovalent interactions with functional monomers, this approach is a suitable example for the formation of synthetic recognition matrices selective for biomolecules.

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