Abstract
This study demonstrates the feasibility of molecular imprinting using a functional chain transfer agent sans a functional monomer. Ethylene glycol dimethacrylate (EGDMA)-based MIPs were synthesised in the presence of thioglycolic acid (TGA) possessing a carboxylic acid group, capable of interacting with the chosen test template R,S-(±)-propranolol (PNL) and a labile S-H bond to facilitate an efficient chain transfer reaction. Quantitative 1H NMR measurements showed high PNL and TGA incorporation within the MIP, indicating an efficient chain transfer process and a favourable interaction between PNL and TGA. TGA-50, with the lowest amount of CTA, showed the largest imprinting effect and an imprinting factor (IF) of 2.1. The addition of MAA to the formulation improved the binding capacity of PNL to the MIP but also increased NIP binding, resulting in a slightly decreased IF of 1.5. The Kd for the high-affinity sites of the TGA/MAA MIP were found to be two times lower (10 ± 1 μM) than that for the high-affinity sites of the TGA-only MIPs, suggesting that the incorporation of the functional monomer MAA increases the affinity towards the PNL template. Selectivity studies, cross-reactivity as well as binary competitive and displacement assays showed the TGA-based MIPs to be highly selective towards PNL against pindolol and slightly competitive against atenolol. The morphologies of the polymers were shown to be affected by the concentration of the TGA, transforming into discrete macrospheres (from small aggregates) at a higher TGA concentration.
Highlights
The preparation of a molecularly imprinted polymer (MIP) by the self-assembly method is relatively simple, conventionally requiring four essential components: template, functional monomer(s), cross-linker, and porogenic solvent
R,S-(±)-PNL-imprinted thioglycolic acid (TGA)-MIPs and non-imprinted polymers (NIPs) were synthesised in the presence of various amounts of TGA: 50 (TGA-50), 100 (TGA-100), 200 (TGA-200), and 400 (TGA-400)
This study has demonstrated the feasibility of molecular imprinting using a functional thiol chain transfer agent, sans the conventional functional monomer, with Ethylene glycol dimethacrylate (EGDMA)
Summary
The preparation of a molecularly imprinted polymer (MIP) by the self-assembly method is relatively simple, conventionally requiring four essential components: template (i.e., usually the target molecule), functional monomer(s), cross-linker, and porogenic solvent. These formulations as well as their synthetic conditions have been widely studied, tailored, and optimised to enhance binding efficiencies. For the template to be incorporated into the polymer and form high-fidelity imprints, it must be able to strongly interact with the functional monomer prior to polymerisation in the presence of a high amount of crosslinkers. Bespoke stoichiometric functional monomers have been developed such as the 2,6-bis-(acrylamido)pyridine (BAAPy)-containing amide-based functional groups that allow a 1:1 interaction and an array of hydrogen bonding with an imide-based template such as fluorouracil and barbiturates [9,10,11,12]
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