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Highly Selective and Sensitive 2‐(2′‐Hydroxyphenyl)benzothiazole‐Based Turn‐On Fluorescent Probes for Detecting and Imaging Bisulfite in Living Cells
Author(s) -
Wang ShaoJing,
Li Jin,
Gao Ying,
Guo Yuan
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700626
Subject(s) - benzothiazole , chemistry , moiety , fluorescence , intramolecular force , stokes shift , photochemistry , bisulfite , selectivity , stereochemistry , organic chemistry , catalysis , biochemistry , physics , gene expression , quantum mechanics , dna methylation , gene
Bisulfite (HSO 3 − ) is one of the main forms of sulfur dioxide in physiological systems. Two 2‐(2′‐hydroxyphenyl)benzothiazole‐derived fluorescent probes bearing a nitroolefin moiety were designed based on the intramolecular charge transfer (ICT) effect and excited‐state intramolecular proton transfer (ESIPT) mechanism to afford a fluorescent turn‐on response specifically in the present of HSO 3 − ions. Owing to the remarkable ICT effect from hydroxy group to the nitro group, the probes exhibit extremely weak fluorescence. Upon the conjugate addition reaction with HSO 3 − at the nitroolefin moiety of the probes, the ICT character is weakened and the absorption spectra of the products are blueshifted. A pronounced fluorescence enhancement based on ESIPT was also observed. The two probes exhibited good sensitivity, high selectivity and an excellent anti‐interference properties of their large Stokes shifts, indicating that the probes are highly suitable for biological systems. Furthermore, they were successfully applied to the imaging of HSO 3 − in living cells.