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New Journal of Chemistry
Page 5 of 7
DOI: 10.1039/C8NJ01793J
Journal Name
ARTICLE
min) and the probe CI (5 μM, 30 min) in turn exhibited different
blue fluorescence (from DAPI channel) for Cys/Hcy (Fig. 5 a1, Fig. 5
b1) and red fluorescence (from TRITC channel) for GSH (Fig. 5c2).
The zebrafish pre-treated with NEM (500 μM, 30 min), and
incubated with CI (5 μM, 30 min) displayed the strong emission in
Cy5 channel (Fig. 5 d3). Thus the zebrafish treated with CI (5 μM)
exhibited strong fluorescence in TRITC channel and weak
fluorescence in Cy5 channel (Fig. 5 e2, e3). The results indicated
that probe CI also has the capacity to image Cys/Hcy and GSH in
zebrafish.
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
This work was financially supported by NSFC (21472067,
21672083), Taishan Scholar Foundation (TS 201511041), and
the startup fund of the University of Jinan (309-10004).
Notes and references
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Fig. 5 One-photon fluorescence imaging of probe CI (5 μM)
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Conclusions
In summary, we have developed a NIR fluorescent probe,
named as CI, for efficiently detecting Cys/Hcy and GSH by
multi-signal fluorescence mode. The probe showed some
advantages, such as fast response, high selectivity and low
cytotoxicity for biological system. The only probe displayed
good fluorescent signal in the near infrared region. The probe
CI could react with Cys/Hcy and GSH via a thiol-halogen SNAr
nucleophilic substitution-rearrangement mechanism. The
conjugated structure of CI was broken and released the
classical TP coumarin dyes. And the two different fluorescent
signals (blue and red) with two different excitation
wavelengths were observed. the new probe could satisfy the
need for imaging with the conversion of NIR to TP modes after
detecting Cys/Hcy and GSH. Importantly, CI could sense
Cys/Hcy and GSH in HeLa cells with OP and TP modes. Thus CI
also achieved the sensing of Cys/Hcy and GSH in zebrafish with
OP modes. The development of the new probe CI may open up
a pathway for the detection of biological thiols, providing
promising tools for revealing the interaction of biological thiols
in various physiological and pathological conditions.
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