Dual-Oriented Solid-Phase Molecular Imprinting: Toward Selective Artificial Receptors for Recognition of Nucleotides in Water

Abstract

We describe the synthesis of water-soluble molecularly imprinted polymer nanoparticles (MIP-NPs) as a new artificial host receptor for the recognition of adenosine monophosphate (AMP), used herein, as a model nucleotide. MIP-NPs were prepared by solid-phase synthesis on glass beads (GB) using, for the first time, immobilized Fe(III)-chelate as an affinity ligand to orientate the AMP via its phosphate group. A polymerizable thymine monomer which can induce complementary base-pairing with the adenine moiety of the nucleotide was synthesized and incorporated in the polymerization mixture to constrain the AMP in a dual-orientated configuration. The MIP-NPs were remarkably selective toward AMP as they did not bind other nucleotides, GMP, UMP, and CMP. This strategy of using the phosphate group of AMP as a hinge enables unhindered pairing of the nucleobase with its corresponding complementary base monomer and can be extended to the preparation of specific MIP receptors for other key nucleotides in aqueous condi...