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. 2019 Jan 12;19(2):283.
doi: 10.3390/s19020283.

Dopamine/2-Phenylethylamine Sensitivity of Ion-Selective Electrodes Based on Bifunctional-Symmetrical Boron Receptors

Martyna Durka  1 , Krzysztof Durka  2 , Agnieszka Adamczyk-Woźniak  3 , Wojciech Wróblewski  4
Affiliations

Dopamine/2-Phenylethylamine Sensitivity of Ion-Selective Electrodes Based on Bifunctional-Symmetrical Boron Receptors

Martyna Durka et al. Sensors (Basel). .

Abstract

Piperazine-based compounds bearing two phenylboronic acid or two benzoxaborole groups (PBPA and PBBB) were applied as dopamine receptors in polymeric membranes (PVC/DOS) of ion-selective electrodes. The potentiometric sensitivity and selectivity of the sensors towards dopamine were evaluated and compared with the results obtained for 2-phenylethylamine. Since the developed electrodes displayed strong interference from 2-phenylethylamine, single-molecule geometry optimizations were performed using the density functional theory (DFT) method in order to investigate the origin of dopamine/2-phenylethylamine selectivity. The results indicated that phenylboronic acid and benzoxaborole receptors bind dopamine mainly through the dative B⁻N bond (like 2-phenylethylamine) and the potentiometric selectivity is mainly governed by the higher lipophilicity of 2-phenylethylamine.

Keywords: dopamine; ion-selective electrodes; organoboron receptors.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of the studied organoboron receptors.
Figure 2
Figure 2
Potentiometric responses of ion-selective electrodes formulated with organoboron receptors (PVC/DOS, 10 mol% KTFPB) towards dopamine.
Figure 3
Figure 3
Potentiometric responses of ion-selective electrodes formulated with PBPA receptor (PVC/DOS, with and without KTFPB) towards dopamine and 2-phenylethylamine.
Figure 4
Figure 4
Semi-transparent representation of electrostatic potential (eÅ−1) mapped onto the electron density surface (ρ = 0.003 eÅ−3) generated for: (a) dopamine, (b) phenylethylamine and their corresponding cationic forms (c,d).
See this image and copyright information in PMC

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