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Molecular Imprinting Using a Functional Chain Transfer Agent.

Phonlakrit Muang-Non1,2, K Fremielle Lim1,3, Anthony Katselas1,4

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Summary
This summary is machine-generated.

This study shows molecular imprinting is feasible without functional monomers, using a functional chain transfer agent. Ethylene glycol dimethacrylate (EGDMA)-based polymers with thioglycolic acid (TGA) effectively imprinted R,S-(±)-propranolol (PNL).

Keywords:
MIPchain transfermolecular imprintingpropranololthioglycolic acid

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Analytical Chemistry

Background:

  • Molecular imprinting (MIP) typically requires functional monomers for template interaction.
  • Functional chain transfer agents (CTAs) offer an alternative approach for MIP synthesis.
  • Ethylene glycol dimethacrylate (EGDMA) is a common crosslinker in MIP synthesis.

Purpose of the Study:

  • To demonstrate the feasibility of molecular imprinting using a functional chain transfer agent (TGA) without a functional monomer.
  • To investigate the effect of TGA concentration on imprinting efficiency and polymer morphology.
  • To evaluate the binding affinity and selectivity of the synthesized MIPs for R,S-(±)-propranolol (PNL).

Main Methods:

  • Synthesis of EGDMA-based MIPs using thioglycolic acid (TGA) as a functional CTA.
  • Incorporation of TGA and template (PNL) assessed via quantitative 1H NMR.
  • Binding studies including imprinting factor (IF) determination, affinity measurements (Kd), and selectivity assays.
  • Morphological characterization of the synthesized polymers.

Main Results:

  • High incorporation of PNL and TGA confirmed efficient chain transfer and favorable PNL-TGA interaction.
  • The TGA-only MIPs exhibited an imprinting effect, with the lowest CTA concentration yielding the highest imprinting factor (IF = 2.1).
  • Addition of methacrylic acid (MAA) improved PNL binding capacity but slightly decreased IF (1.5) due to increased non-imprinted polymer binding.
  • TGA/MAA MIPs showed a two-fold lower dissociation constant (Kd = 10 ± 1 μM) for high-affinity sites compared to TGA-only MIPs, indicating enhanced affinity.
  • TGA-based MIPs demonstrated high selectivity for PNL against pindolol and moderate selectivity against atenolol.
  • Polymer morphology transitioned from aggregates to discrete macrospheres with increasing TGA concentration.

Conclusions:

  • Molecular imprinting is feasible using a functional CTA (TGA) without a functional monomer, enabling efficient imprinting of R,S-(±)-propranolol (PNL).
  • TGA concentration influences polymer morphology and imprinting efficiency, with optimal results observed at lower CTA levels.
  • Incorporating a functional monomer like MAA can enhance PNL binding affinity but requires careful optimization to balance specificity.
  • The synthesized TGA-based MIPs exhibit promising selectivity and affinity for PNL, suitable for potential separation applications.