Simultaneous Enantiospecific Recognition of Several β-Blocker Enantiomers Using Molecularly Imprinted Polymer-Based Electrochemical Sensor

Abstract

The development of a chiral electrochemical sensor using an electrogenerated molecularly imprinted polymer (MIP)-based ultrathin film using R(+)-atenolol (ATNL) as a template was reported. The proposed sensor exhibited distinctive enantiospecific oxidation peaks toward the R-antipodes of four β-blocker representatives and additional oxidation peaks common to both enantiomers of each studied β-blocker, allowing thus the simultaneous analysis of all of their enantiomers in a single analysis. The specific preconditioning of the polymer by alternative exposure to aqueous and nonaqueous medium was proven to be essential for the chiral recognition ability of the obtained sensor. The rebinding property of the MIP film was studied by using a well-known redox probe, a change in the morphology and diffusive permeability of the thin polymeric layer in the presence of its template being observed. The applicability of the optimized analytical procedure was demonstrated by the analysis of ATNL's enantiomers in the range of 1.88 × 10(-7)-1.88 × 10(-5) mol/L. The developed polymeric interface is the first reported transductor of a chiral electrochemical sensor able to exhibit simultaneous enantiospecificity toward several β-blocker representatives extensively used in the pharmaceutical and biomedical fields, offering good prospects in the simple, cost-effective, and fast assessment of their enantiomeric ratio and total concentration.

Betamethasone‐based chiral electrochemical sensor coupled to chemometric methods for determination of mandelic acid enantiomers

“…The results confirm the efficient performance of OPPy‐BMZ/GR as chiral sensing platform for MA detection and further prove the enantioselectivity character of BMZ. Previous mechanisms describing three‐point interaction for chiral discrimination on the basis of the Dagliesh model, include occurrence of 3 interactions which at least one of them is stereoselective . It is presumed that the diastereomeric complexes with MA enantiomers can be formed via multiple hydrogen bonding interactions between hydroxyl, fluorine, and carboxylic acid units of BMZ and the carboxyl and hydroxyl moiety of MA enantiomers.…”

A Voltammetric Sensory System for Recognition of Propranolol Enantiomers Based on Glassy Carbon Electrodes Modified by Polyarylenephthalide Composites of Melamine and Cyanuric Acid

“…Propranolol (1‐isopropylamino‐3‐(1‐naphthoxy)‐2‐propanol) is known to be irreversibly oxidised on the modified GCE in a potential range from 1–2 V, with the transfer of two electrons . The majority of the publications attribute the oxidation peak to the hydroxyl group directly bonded to the chiral center , whereas a few papers assign it to the secondary amine . For some electrodes, the voltammograms of the propranolol enantiomers differ among themselves .…”

New Materials for the Construction of Electrochemical Biosensors

“…Due to their low conductivity, sensors based on such MIPs usually use optical, piezoelectric or impedimetric signal transduction. However, as long as they are electrodeposited in a thickness that does not insulate the underlying conductive electrode surface (<10 nm) [162], a successful voltamperometric signal transduction may also be performed [163].…”

“…Nevertheless, very recently an MIP-based electrochemical sensor has been reported for the simultaneous enantiospecific recognition of several β-blocker enantiomers [163].…”