An instantaneous near-infrared trimethyl lock based fluorescent probe for biothiols with a large Stokes shift

Using trimethyl lock as a useful mean, a selective and sensitive fluorescent probe was developed for the detection of biothiols with an emission in near infrared spectral region (694 nm) and a large Stokes shift (129 nm). The inserted trimethyl lock between the fluorophore and the sensing group, 2,...

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Bibliographic Details
Published in:Analytica chimica acta 2018-11, Vol.1034, p.168-175
Main Authors: Yang, Lei, Su, Yuanan, Geng, Yani, Qi, Fengpei, Ren, Xiaojie, Zhang, Fan, Song, Xiangzhi
Format: Article
Language:English
Subjects:
Animals
Biothiols
Carbon
Chemical reactions
Extreme values
Fluorescence
Fluorescent Dyes - analysis
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Fluorescent indicators
Fluorescent probe
HeLa Cells
Humans
Infrared Rays
Instantaneous
Linearity
Molecular Structure
MTBE
Nanoscience
Near infrared radiation
Organic chemistry
Organism
Spectrometry, Fluorescence
Spectroscopy, Near-Infrared
Sulfhydryl Compounds - blood
Trimethyl lock
Zebrafish
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Summary:Using trimethyl lock as a useful mean, a selective and sensitive fluorescent probe was developed for the detection of biothiols with an emission in near infrared spectral region (694 nm) and a large Stokes shift (129 nm). The inserted trimethyl lock between the fluorophore and the sensing group, 2, 4-dinitrobenzensulfonate, highly improved the response rate of this probe toward GSH because the unfavorable steric interactions between three methyl groups resulted in an extremely rapid intramolecular lactonization reaction to form a hydrocoumarin. This probe displayed an instantaneous response (within seconds) to GSH at a very low concentration in aqueous medium and the detection limit was as low as 2.5 nM based on S/N = 3. The fluorescence intensity of the solution of probe 1 at 694 nm displayed a good linearity (R = 0.9917) with the concentration of GSH in a range of 0.0–5.0 μM. Importantly, this probe exhibited a good performance in detecting biothiols in serum samples, living cells and organism. A trimethyl lock based fluorescent probe was developed for selective and sensitive detection of biothiols with a near-infrared emission and a large Stokes shift. This probe was successfully applied to detect biothiols in living cells and organism. Particularly, it is the fastest fluorescent probe for GSH detection in aqueous solution. [Display omitted] •An instantaneous trimethyl lock based fluorescent probe 1 is developed for biothiols.•Probe 1 is the fastest one for GSH detection in aqueous medium.•Probe 1 displayed a near-infrared emission (694 nm) and a large Stokes shift (129 nm).•Probe 1 is succesfully used for imaging intracellular biothiols in living cells and organism.
ISSN:0003-2670
1873-4324
DOI:10.1016/j.aca.2018.06.011