Journal
ANALYTICAL CHEMISTRY
Volume 92, Issue 2, Pages 2316-2322Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.analchem.9b05204
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Funding
- National Natural Science Foundation of China [21435005, 21605139, 21627808, 21721003, 21974132]
- Key Research Program of Frontier Sciences, CAS [QYZDY-SSW-SLH019]
- Youth Innovation Promotion Association, CAS [2018258]
- Open Project of State Key Laboratory of Supramolecular Structure and Materials [sklssm2019023]
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Analyte-responsive chromo-fluorogenic reactions under accessible conditions are important for designing small-molecule spectroscopic probes. We describe a series of newly constructed motifs based on the chromo-fluorogenic reaction between catechol derivatives (typically hydroxytyrosol, dopamine, and levodopa) and naphthoresorcin (NR) in aqueous solution under ambient conditions. The weakly absorptive and fluorogenic catechols/NR was converted to products having visible absorption and bright fluorescence within several minutes. The chromo-fluorophores produced from this reaction had a maximum absorbance at 458 nm and emission at 480 nm with high fluorescence quantum yields (30-84%). Inspired by the tyrosinase-catalyzed hydroxylation of monophenols to catechols, the tyrosinase-enabled chromo-fluorogenic reaction was verified by using monophenol (typically tyrosol) as the substrate. In this regard, a dual-readout tyrosinase activity assay was developed by virtue of the in situ turn-on optical signals. Furthermore, a test of tyrosinase inhibition, by using a common inhibitor kojic acid, demonstrated the potential of the chromo-fluorogenic reaction for developing other tyrosinase related assays and signal transduction.
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