Abstract
Molecular imprinting is one of the most efficient methods for preparing synthetic receptors that possess user defined recognition properties. Despite general success of non-covalent imprinting for a large variety of templates, some groups of compounds remain difficult to tackle due to their structural complexity. In this study we investigate preparation of molecularly imprinted polymers that can bind sulfonamide compounds, which represent important drug candidates. Compared to the biological system that utilizes metal coordinated interaction, the imprinted polymer provided pronounced selectivity when hydrogen bond interaction was employed in an organic solvent. Computer simulation of the interaction between the sulfonamide template and functional monomers pointed out that although methacrylic acid had strong interaction energy with the template, it also possessed high non-specific interaction with the solvent molecules of tetrahydrofuran as well as being prone to self-complexation. On the other hand, 1-vinyl-imidazole was suitable for imprinting sulfonamides as it did not cross-react with the solvent molecules or engage in self-complexation structures.
Highlights
Molecular imprinting is one of the most efficient methods for preparing synthetic receptors that possess user-defined recognition properties [1,2,3]
When sulfonamide 1 was used as template, it could be dissolved in THF at a relatively low concentration in the presence of
The total binding in THF was quite limited due to the rather weak interactions. This result is in line with a study carried out by Dirion et al [33], where the weakly acidic estradiol template generated low imprinting effect when Methacrylic acid (MAA) was used as the functional monomer in THF
Summary
Molecular imprinting is one of the most efficient methods for preparing synthetic receptors that possess user-defined recognition properties [1,2,3]. In this study we intended to prepare molecularly imprinted polymers using a “rational design” approach, where we utilize the hydrogen bond interactions between template and functional monomers. Methacrylic acid (MAA) has been used as a universal functional monomer to prepare imprinted polymers against both weakly acidic [31] and basic molecules [32] employing hydrogen bond interactions, because it can act as both a hydrogen bond donor and acceptor.
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