3,5-Dihydroxybenzoic Acid-Based Selective Dopamine Detection via Subsititution-Enhanced Kinetics Differences

The selective recognition of dopamine (DA) over other neurotransmitter analogues is difficult due to the similar molecular structure and chemical reactivity. In this study, substitution-regulated chemical reactivity of the sensing substrate is utilized to explore a novel DA detection probe with sati...

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Bibliographic Details
Published in:Analytical chemistry (Washington) 2023-10, Vol.95 (40), p.14944-14953
Main Authors: Liu, Yang, Cheng, Junqi, Lu, Fengniu, Li, Shuo, Ma, Zhiyong, Du, Yi, Yuan, Zhiqin, Lu, Chao
Format: Article
Language:English
Subjects:
Biological properties
Biological samples
Cerebrospinal fluid
Chemical reactions
Dihydroxybenzoic acid
Dopamine
Fluorescence
Kinetics
Logic circuits
Molecular structure
Reaction kinetics
Recognition
Resorcinol
Substitution reactions
Substrates
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Summary:The selective recognition of dopamine (DA) over other neurotransmitter analogues is difficult due to the similar molecular structure and chemical reactivity. In this study, substitution-regulated chemical reactivity of the sensing substrate is utilized to explore a novel DA detection probe with satisfying selectivity. As a case study, 3,5-dihydroxybenzoic acid (DHBA, carboxy-substituted resorcinol)-based probes have been explored for selective and ratiometric DA sensing. The carboxy substitution benefits the stabilization of the carbanion intermediate and the azamonardine product, which enhances the reaction kinetics and thermodynamics and subsequently facilitates selective DA recognition over other analogues and interferents. By exploring DHBA emission as the internal reference, ratiometric fluorescence variation is realized, which contributes to sensitive DA analysis. With the combination of logic gate and fluorometric analysis, DA detection in both low and high concentrations can be readily achieved. In addition, the DA analysis in biological samples and the enzymatic transformation of DA analogues in cerebrospinal fluid samples are achieved by the proposed DHBA probe.
ISSN:0003-2700
1520-6882
DOI:10.1021/acs.analchem.3c02313