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Fluorescent dye based on aggregation-induced luminescence near-infrared, large Stokes shift, and photostability, and its preparation method and application

A technology of aggregation-induced luminescence and fluorescent dyes, applied in the field of mitochondrial fluorescent labeling, fluorescent dyes and their preparation, can solve the problems of failing to provide mitochondrial number, shape, prone to photobleaching, and difficult long-term tracer of mitochondria

Active Publication Date: 2020-08-07
EAST CHINA UNIV OF SCI & TECH +1
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] However, the emission wavelength of the existing mitochondrial fluorescent labeling dyes is relatively short (mainly in the range of 400-600nm), the Stokes shift is small, and the photostability is poor, resulting in large background fluorescence interference during imaging, and it is prone to photobleaching. It is difficult to achieve long-term tracking of mitochondria (Proc.Natl.Acad.Sci., 1980, 77, 990; J.Am.Chem.Soc., 2013, 135, 62); in particular, most commercial mitochondria-targeted fluorescent probes Due to its own aggregation-caused quenching (ACQ) phenomenon, needles cannot provide real information about the number, shape and movement of mitochondria, which further limits their real-time imaging and display of mitochondria in aqueous environments. trace

Method used

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  • Fluorescent dye based on aggregation-induced luminescence near-infrared, large Stokes shift, and photostability, and its preparation method and application
  • Fluorescent dye based on aggregation-induced luminescence near-infrared, large Stokes shift, and photostability, and its preparation method and application
  • Fluorescent dye based on aggregation-induced luminescence near-infrared, large Stokes shift, and photostability, and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] (1) Synthesis of Dye I-1:

[0047]

[0048] In a 50mL round bottom flask, add 2-(1-dodecyl-2,6-lutidine-4(1H)-ylidene) malononitrile (350mg, 1.03mmol, compound V-1) , ethanol (20mL), (2-(2-formylphenoxy)ethyl)triphenylphosphine bromide (1.52g, 3.09mmol, compound VI-1), triethylamine 1.0mL, under the protection of argon , Reflux reaction 1h. Cool, remove the solvent by rotary evaporation under reduced pressure, and perform column chromatography (DCM:EA:MeOH=4:3:2, v / v / v) to obtain 630 mg of solid (dye I-1), with a yield of 47.6%.

[0049] 1 H NMR (400MHz, DMSO-d 6 ,ppm): δ7.84(m,24H,phenyl-H),7.63-7.59(m,6H,phenyl-H),7.38-7.30(m,4H,phenyl-H),7.15(t,J=10.2 Hz, 4H, phenyl-H), 7.03-7.01 (d, J = 8.0Hz, 2H, alkene-H), 7.17 (t, J = 15.0Hz, 2H, alkene-H), 6.48-6.44 (d, J =16.0Hz, 2H, alkene-H), 4.05-3.96(m, 6H, -CH 2 -),3.66(t,J=14.8Hz,4H,-CH 2 -),1.43-1.26(m,20H,-CH 2 -),0.88(t,J=8.0Hz,3H,-CH 3 ).

[0050] Mass spectrometry(ESI-MS,m / z):[M-2Br] 2+ calcd for C 76 ...

Embodiment 2

[0082] Absorption and Fluorescence Spectra of Dye I-7 in Aggregated State

[0083] The dye I-7 prepared in Example 1 was dissolved in analytically pure dimethyl sulfoxide to make 1.0 × 10 -2 stock solution of M. Then, 2 mL of a THF / water mixed solvent having a tetrahydrofuran (THF) content of 99% was prepared. Take 2 μL of the above stock solution and add it to the prepared THF / water mixed solvent, mix well and transfer to an optical quartz cuvette (10×10 mm) to test its absorption and fluorescence spectra. Such as figure 1 As shown, the dye I-7 exhibits a broad absorption peak at 350-650nm, and the maximum absorption wavelength is located at 520nm; with 520nm as the excitation wavelength, the maximum emission peak of the dye I-7 is located at about 685nm and is located in the near-infrared region. The Kex shift reaches 165nm; and the aggregation of the dye I-7 in the mixed solvent leads to the enhancement of its fluorescence, which has typical fluorescence enhancement char...

Embodiment 3

[0085] Dye I-7 photostability test

[0086] Photostability is one of the important performance indicators for evaluating dyes in practical applications such as long-term imaging. We evaluated the photostability of the dye by continuously illuminating the dye and then monitoring its fluorescence intensity, and selected the commercial dye Mitotracker Green as a reference dye. Such as figure 2 As shown, as the illumination time increases, the fluorescence intensity of Mitotracker Green decreases sharply. When the illumination time is about 6 minutes, Mitotracker Green produces serious photobleaching, indicating that its photostability is poor; however, under the same illumination conditions, the fluorescence intensity of dye I-7 Slowly decreased, when the light time reached 15min, its fluorescence intensity was 75% of the initial fluorescence intensity, indicating that the dye I-7 has excellent photostability.

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Abstract

The invention provides an aggregation-induced emission-based near-infrared, large-Stokes-shift and stably luminescent fluorescent dye and a preparation method thereof. The aggregation-induced emission-based near-infrared, large-Stokes-shift and stably luminescent fluorescent dye has a structure shown as the formula I. besides, the invention also provides application of the aggregation-induced emission-based near-infrared, large-Stokes-shift and stably luminescent fluorescent dye to mitochondria fluorescence labelling. The aggregation-induced emission-based near-infrared, large-Stokes-shift andstably luminescent fluorescent dye has the advantages of near-infrared emission, large Stokes shift, high luminescent stability, low cytotoxicity, good water solubility and the like and can achieve long-term tracking and three-dimensional visual imaging of mitochondria.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and specifically relates to a fluorescent dye based on aggregation-induced luminescence near-infrared, large Stokes shift, and photostability, a preparation method thereof, and an application of mitochondrial fluorescent labeling. Background technique [0002] Mitochondria is an organelle with a double-membrane structure that exists in most eukaryotic cells. It is the main place for cells to perform aerobic respiration. It provides energy for cell metabolism through oxidative phosphorylation, and is called the "energy factory" of cells. ". Mitochondria exhibit different shapes in different types of cells, sometimes linear, sometimes granular, and their shape will change with different metabolic conditions, developmental stages, and environmental stimuli, and can also undergo division and fusion processes. To adapt to normal physiological functions in cells. Relevant studies have shown th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/10C09K11/06G01N21/64
CPCC09B23/107C09K11/06C09K2211/1007C09K2211/1029G01N21/6486
Inventor 朱为宏郭志前张杰顾开智徐益升叶红华
Owner EAST CHINA UNIV OF SCI & TECH
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