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Fluorescent probe for rapidly responding to hydrogen peroxide as well as preparation method and application thereof

A fluorescent probe and fast-response technology, applied in chemical instruments and methods, fluorescence/phosphorescence, and material analysis by optical means, can solve the problem of long response time, high reactivity, and steady-state concentration of probes and hydrogen peroxide Low-level problems, to achieve the effect of good dyeing effect, simple synthesis steps, and high dyeing efficiency

Inactive Publication Date: 2016-04-13
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the common problem of fluorescent probes used to detect hydrogen peroxide is that the response time between the probe and hydrogen peroxide is long, and the detection of the true concentration of hydrogen peroxide in a specific area of ​​the cell cannot be realized.
Under normal circumstances, the steady-state concentration is extremely low, the reactivity is high, and the existence of various oxides and antioxidants in the organism brings certain difficulties to the determination of hydrogen peroxide.
Therefore, designing and synthesizing fluorescent probes with good selectivity, fast response, high sensitivity and biocompatibility to detect the real concentration of hydrogen peroxide in living cells is one of the challenging frontier topics in the development of life chemistry, especially Is it very challenging to design and synthesize fluorescent probes with high selectivity and fast response

Method used

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  • Fluorescent probe for rapidly responding to hydrogen peroxide as well as preparation method and application thereof
  • Fluorescent probe for rapidly responding to hydrogen peroxide as well as preparation method and application thereof
  • Fluorescent probe for rapidly responding to hydrogen peroxide as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Under the protection of argon, the compound TPE-Br (0.982g, 2mmol) and diboronic acid pinacol ester (1.27g, 5mmol) were dissolved in anhydrous DMF20mL, and anhydrous potassium acetate (1.374g, 14mmol) and pd( dppf)Cl 2 (0.08g, 0.11mmol, react at 85°C for 24h. After the reaction, cool to room temperature, extract the mixture with dichloromethane and water, dry the organic phase with anhydrous magnesium sulfate overnight. Redissolve with dichloromethane, column Chromatographic separation (eluent: petroleum ether: ethyl acetate 15:1, V / V) gave 0.67 g (57%) of a milky white solid.

Embodiment 2

[0040] Under the protection of argon, the compound TPE-Br (1mmol) and diboronic acid pinacol ester (5mmol) were dissolved in anhydrous DMF 20mL, anhydrous sodium carbonate (8mmol) and tetrakistriphenylphosphopalladium (0.11mmol) were added, Reaction at 100°C for 20h. After the reaction was completed, it was cooled to room temperature, the mixture was extracted with dichloromethane and water, and the organic phase was dried overnight with anhydrous magnesium sulfate. It was redissolved with dichloromethane and separated by column chromatography (petroleum ether: ethyl acetate 15:1, V / V) to obtain 0.67 g (57%) of a milky white solid.

Embodiment 3

[0042] Under the protection of argon, the compound TPE-Br (2mmol) and diboronic acid pinacol ester (6mmol) were dissolved in anhydrous DMF 20mL, and anhydrous cesium carbonate (15mmol) and ferrocenetriphenylphosphorous palladium chloride ( 0.11 mmol), reacted at 75°C for 35h. After the reaction was completed, it was cooled to room temperature, the mixture was extracted with dichloromethane and water, and the organic phase was dried overnight with anhydrous magnesium sulfate. It was redissolved with dichloromethane and separated by column chromatography (petroleum ether: ethyl acetate 15:1, V / V) to obtain 0.67 g (57%) of a milky white solid.

[0043] NMR and mass spectrometry characterization:

[0044] 1 HNMR (300MHz, CDCl 3 ,δ):7.54(d,J=1.5Hz,2H),7.51(d,J=1.5Hz,2H),7.06-7.10(m,6H),7.05-6.99(m,8H),1.32(s, 24H)

[0045] 13 CNMR (100MHz, CDCl 3 ,δ):146.80,146.62,143.61,143.45,141.34,134.23,134.14,131.41,130.76,127.79,127.66,126.62,126.55,83.78,24.99

[0046] 11 BNMR (400...

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Abstract

The invention discloses a fluorescent probe for rapidly responding to hydrogen peroxide as well as a preparation method and application thereof. The structural formula of the fluorescent probe is shown in the specification. A raw material TPE-Br and bis(pinacolato)diboron are dissolved in a solvent, a reaction is carried out under a heating condition with a catalyst, the probe is obtained, and the probe is named TPE-BO. The probe molecule has an aggregation-induced emission property, and response time between the fluorescent probe and hydrogen peroxide is effectively reduced by 10 minutes. The dyeing effect for living cells is good, the dyeing time is short, and the dyeing efficiency is high. The synthesis steps are relatively simple, the yield is high and purification is easy.

Description

technical field [0001] The invention specifically relates to a fluorescent probe that responds quickly to hydrogen peroxide, a preparation method and application thereof, which have the advantages of fast response speed, high selectivity and the like. Background technique [0002] Hydrogen peroxide is an important class of reactive oxygen species, which plays an important role in cell signaling as a second messenger and as a marker of oxidative stress in the aging of organisms and various diseases. Hydrogen peroxide produced during biological metabolism is necessary for life activities, such as activation of immune cells, vascular remodeling in mammals, closure of stomata and root growth in plants, etc. But the excessive production of hydrogen peroxide can lead to the accumulation of oxidative damage, which can cause aging and a series of diseases, such as cardiovascular disease, diabetes, cancer. Therefore, the detection of hydrogen peroxide in vivo is of great significanc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F5/02G01N21/64
CPCC09K11/06C07F5/025C09K2211/1007C09K2211/1096G01N21/6428
Inventor 张卫刘伟李平唐波
Owner SHANDONG NORMAL UNIV
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