“Inherently chiral” thiophene-based electrodes at work: a screening of enantioselection ability toward a series of pharmaceutically relevant phenolic or catecholic amino acids, amino esters, and amine

“Inherently chiral” thiophene-based electroactive oligomer films have recently been shown to exhibit outstanding chirality manifestations. One of the most exciting among them is an unprecedented enantioselection ability as electrode surfaces. In fact, in preliminary chiral voltammetry experiments, t...

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Bibliographic Details
Published in:Analytical and bioanalytical chemistry 2016-10, Vol.408 (26), p.7243-7254
Main Authors: Arnaboldi, Serena, Benincori, Tiziana, Cirilli, Roberto, Grecchi, Sara, Santagostini, Laura, Sannicolò, Francesco, Mussini, Patrizia R.
Format: Article
Language:English
Subjects:
Amino acids
Amino compounds
Analytical Chemistry
Biochemistry
Catecholamines
Characterization and Evaluation of Materials
Chemical properties
Chemical Sensing Systems
Chemistry
Chemistry and Materials Science
Chirality
Chromatography
Electrodes
Enantiomers
Epinephrine
Equipment and supplies
Esters
Feature Article
Food Science
Laboratory Medicine
Methods
Molecular structure
Monitoring/Environmental Analysis
Observations
Oligomers
Oxidation
Phenols
Tyrosine
Voltammetry
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Summary:“Inherently chiral” thiophene-based electroactive oligomer films have recently been shown to exhibit outstanding chirality manifestations. One of the most exciting among them is an unprecedented enantioselection ability as electrode surfaces. In fact, in preliminary chiral voltammetry experiments, the new electrodes have been shown to both discriminate the enantiomers of chiral probes (either enantiopure or in a mixture, in terms of large differences in peak potentials) and quantify them (in terms of linear dynamic ranges in peak currents), without the need for preliminary separation steps. Such ability has now been tested on a series of chiral DOPA-related molecules, from phenolic amino acid tyrosine (together with its methyl ester) to catecholic amino acid DOPA (together with its methyl ester), to catecholamine epinephrine (adrenaline). The wide-range enantioselectivity of the new inherently chiral electrode surfaces is fully confirmed, as large peak potential differences are obtained for probe enantiomers of the whole series working in common aqueous buffers. Moreover, interesting modulating effects on enantiodiscrimination can be observed as a function of both molecular structure and pH. Graphical abstract Inherently chiral thiophene-based electrodes at work with pharmaceutically relevant probes
ISSN:1618-2642
1618-2650
DOI:10.1007/s00216-016-9852-x