Abstract
Fmoc-3-nitrotyrosine (Fmoc-3-NT) molecularly imprinted polymers (MIPs) were synthesized to understand the influence of several functional monomers on the efficiency of the molecular imprinting process. Acidic, neutral and basic functional monomers, such as acrylic acid (AA), methacrylic acid (MAA), methacrylamide (MAM), 2-vinylpyridine (2-VP), 4-vinylpyridine (4-VP), have been used to synthesize five different polymers. In this study, the MIPs were tested in batch experiments by UV-visible spectroscopy in order to evaluate their binding properties. The MIP prepared with 2-VP exhibited the highest binding affinity for Fmoc-3NT, for which Scatchard analysis the highest association constant (2.49 × 104 M−1) was obtained. Furthermore, titration experiments of Fmoc-3NT into acetonitrile solutions of 2-VP revealed a stronger bond to the template, such that a total interaction is observed. Non-imprinted polymers as control were prepared and showed no binding affinities for Fmoc-3NT. The results are indicative of the importance of ionic bonds formed between the –OH residues of the template molecule and the pyridinyl groups of the polymer matrix. In conclusion, 2-VP assists to create a cavity which allows better access to the analytes.
Highlights
Imprinted polymers (MIPs) are a promising alternative to provide tailor-made receptor binding sites via the rearrangement of the template and functional monomer [1,2,3,4]
Imprinted technique is based on a process where functional monomer and cross-linker are copolymerized in the presence of the template molecules, involving the formation of cavities in which the template is arranged
It was seen that the polymer’s affinity is directly related to the strength of the complex formed between template and monomer, so the choice of functional monomer is very important for the molecular recognition of Molecularly imprinted polymers (MIPs)
Summary
Imprinted polymers (MIPs) are a promising alternative to provide tailor-made receptor binding sites via the rearrangement of the template and functional monomer [1,2,3,4]. Because the influence of functional monomers in the formation of the monomer-template complexes is an important key in the creation of binding sites, in the present work, acidic, neutral and basic functional monomers, such as acrylic acid (AA), methacrylic acid (MAA), methacrylamide (MAM), 2-vinylpyridine (2-VP) and 4-vinylpyridine (4-VP) (Figure 1) have been chosen to test and define the most successful functional monomer. In this way it was possible to investigate which functional monomer establishes most interactions with the template and to develop the best procedure of synthesis. The MIPs prepared were tested in batch experiments by UV-vis spectroscopy and the binding characteristics of the MIPs were examined by Scatchard analysis
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