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Near-infrared fluorescent probe based on basic dye as well as preparation method and application of near-infrared fluorescent probe

A technology of fluorescent probes and basic dyes, applied in fluorescence/phosphorescence, chemical instruments and methods, analytical materials, etc., to achieve the effects of obvious detection signal, simple synthesis, and simple detection means

Active Publication Date: 2021-06-11
SHANXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But abnormal concentrations of GSH can lead to diseases such as cancer, Alzheimer's and cardiovascular diseases

Method used

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  • Near-infrared fluorescent probe based on basic dye as well as preparation method and application of near-infrared fluorescent probe
  • Near-infrared fluorescent probe based on basic dye as well as preparation method and application of near-infrared fluorescent probe
  • Near-infrared fluorescent probe based on basic dye as well as preparation method and application of near-infrared fluorescent probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1L1

[0035] Synthesis and characterization of embodiment 1L1, L2

[0036] Dissolve p-hydroxybenzyl alcohol (5mmol, 620.6mg) in 15mL of dichloromethane, stir in an ice-water bath for 5min, then add triethylamine (15mmol, 2mL), stir for 30min, then add dropwise 2 , 4-dinitrobenzenesulfonyl chloride (5mmol, 1333mg), stirred and reacted overnight, TLC detected the reaction process, extracted three times with 50mL saturated sodium chloride solution, extracted three times with 50mL dichloromethane solution, dried over anhydrous sodium sulfate The organic phase was purified by column with petroleum ether / ethyl acetate=3:1 to obtain the pure product 4-(hydroxymethyl)phenyl 2,4-dinitrobenzenesulfonate (3.86mmol, 1367.5mg), the yield 77.2%.

[0037] 4-(Hydroxymethyl)phenyl 2,4-dinitrobenzenesulfonate (0.6mmol, 212.4mg), 3,7-bis(diethylamino)-10H-phenoxazine-10-carbonyl chloride (0.5mmol, 194.1mg), sodium carbonate (Na 2 CO 3 , 1.5mmol, 160mg) and 4-dimethylaminopyridine (DMAP, 0.5mmol, 6...

Embodiment 2

[0040] Prepare pH=7 phosphate buffer solution (10mM, containing 10% absolute ethanol) system solution, dissolve L1 and L2 in DMSO to prepare 2mM preparation solution, and prepare 20mM glutathione (GSH) solution; take 1900μL of The reaction system solution, 2 μL L1 (L2) DMSO solution, and 100 μL GSH solution were added to a fluorescence cuvette, and the fluorescence scanning was performed in a water bath at 37 °C. Increased strength. Fluorescence emission map see Figure 7 , Figure 8 .

Embodiment 3

[0042] Prepare PBS buffer solution with pH=7.4 and concentration of 10mM, prepare 2μM DMSO solution of L1 and L2; add 10μL DMSO solution of L1 and L2 to 2mL PBS solution to make its concentration 10μM; add this solution to HepG-2 In the cells, after incubation at 37°C for 30min, confocal imaging showed strong red fluorescence under the fluorescence imager; see Figure 9 .

[0043] HepG-2 cells were incubated with 2 mL of 50 μM NEM (GSH inhibitor) solution for 30 min, washed three times with 2 mL of PBS, then incubated with 2 mL of 10 μM probe L1 (L2) for 30 min, washed three times with 2 mL of PBS, and added with 2 mL of PBS solution for confocal imaging. Reduced red fluorescence intensity; see Figure 9 .

[0044] HepG-2 cells were incubated with 2mL of 50μM NEM (GSH inhibitor) solution for 30min, washed three times with 2mL PBS, then incubated with 2mL 200μM, 1mM GSHee for 30min, washed three times with 2mL PBS, incubated in L1 for 30min, washed three times with 2mL PBS, ...

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Abstract

The invention provides a near-infrared fluorescent probe based on basic dye as well as a preparation method and application of the near-infrared fluorescent probe. The compound name of the probe is 4-(((2,4-dinitrophenyl)sulfonyl)oxy)benzyl3,7-bis(diethylamino)-10H-phenoxazine-10-carboxylate, or 4-(((2,4-dinitrophenyl)sulfonyl)oxy)benzyl3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate; and the probes are respectively named as L1 and L2. The invention further provides an application of the near-infrared fluorescent probe L1 or L2 based on the basic dye in GSH detection, that is, in a phosphoric acid buffer solution pH=7:ethanol / 9:1 (v / v) system, the content of GSH is quantitatively detected through a fluorospectro photometer, and the detection method is high in sensitivity and simple and convenient.

Description

technical field [0001] The invention relates to the detection of basic dyes and GSH, in particular to a basic dye-based near-infrared fluorescent probe and a preparation method thereof, as well as the application of the probe in detecting GSH content. Background technique [0002] Glutathione (GSH) plays an important role in regulating the redox balance of life, maintaining the normal life activities of organisms and preventing diseases. But abnormal concentrations of GSH can lead to diseases such as cancer, Alzheimer's and cardiovascular disease. Therefore, accurately tracking the level changes of these active molecules is the premise of in-depth understanding of cell function, and also reveals the essence of cell life activity rules. Near-infrared fluorescent probes (650-900nm) have attracted the attention of researchers because of their high signal-to-noise ratio, strong penetration depth and high imaging resolution. Among them, the basic dye near-infrared fluorescent c...

Claims

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Application Information

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IPC IPC(8): C07D265/38C07D279/30C09K11/06G01N21/64
CPCC07D265/38C07D279/30C09K11/06G01N21/6428G01N21/6447C09K2211/1014C09K2211/1033C09K2211/1037
Inventor 温莹龙志清阴彩霞霍方俊
Owner SHANXI UNIV
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