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A fluorescent probe, synthesis method and application for detecting peroxynitrite anion

A technology of peroxynitroso group and synthesis method is applied in the field of synthesizing and detecting fluorescent probes of peroxynitrite anion, which can solve the problems of interference, low selectivity and small Stoke shift, and achieve accurate detection and selection. High-performance, easy-to-synthesize effects

Active Publication Date: 2020-07-03
GUANGZHOU YUEWANG AGRI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for in vivo ONOO - detection, these fluorescent substances not only have small Stoke shifts, but also easily combine with other oxides such as OH, OCl - Response; especially the small Stoke displacement, which is more susceptible to the interference of the organism itself, which is not conducive to ONOO - accurate detection of
[0005] Document CN107488189A discloses the self-assembly of diphenol compound and 2-formyl phenylboronic acid and its application as a fluorescent probe for the quantitative detection of free radical hypochlorous acid and peroxynitroso, but this method does not Involves and solves the problems of small stoke shift and low selectivity of fluorescent probes

Method used

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  • A fluorescent probe, synthesis method and application for detecting peroxynitrite anion
  • A fluorescent probe, synthesis method and application for detecting peroxynitrite anion
  • A fluorescent probe, synthesis method and application for detecting peroxynitrite anion

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] About the synthetic method of fluorescent probe, comprise following experimental steps:

[0034] (1) 2-Hydroxybenzaldehyde (122mg, 1mmol) and triethylamine (200mg, 2mmol) were dissolved in dry 10mL tetrahydrofuran, and diphenylphosphinic chloride (236.5mg, 1mmol) was added dropwise under stirring, at room temperature Down reaction 12 hours;

[0035] (2) After the reaction is completed, evaporate under reduced pressure to obtain the crude product, and then use silica gel column chromatography, wherein the volume ratio of ethyl acetate and sherwood oil in the silica gel column chromatography is 1:4 to obtain a white intermediate product (232mg, Productive rate 72%), the synthetic reaction equation of this intermediate product is as figure 1 shown;

[0036] (3) Dissolve the white intermediate product (322mg, 1mmol) and hydrazine hydrate (50mg, 1mmol) in 10mL ethanol, the reaction mixture is heated, stirred, and refluxed for 2 hours. After the reaction solution is cooled...

Embodiment 2

[0041] About testing fluorescent probe detection ONOO - effect, the experimental steps are:

[0042](1) Dissolving the fluorescent probe in N,N-dimethylformamide (DMF) to prepare a 1mmol / L probe solution;

[0043] (2) Take the probe solution and add DMF and PBS (pH = 7.4) buffer solution to form a 10 μM solution (organic phase: PBS aqueous phase = 1:99, V / V), and test the changes in the ultraviolet absorption spectrum and fluorescence emission spectrum Condition.

[0044] The changes in the UV absorption spectrum are as follows: Figure 5 As shown, where the fluorescent probe was added to ONOO - The UV-Vis absorption spectrum curve is (a), without ONOO - The UV-visible absorption spectrum curve is (b). From Figure 5 It can be seen from the figure that when ONOO is not added - In the case of , the probe has no absorption peak at 400nm, while adding ONOO - Afterwards, the probe has an obvious absorption peak at 400nm, indicating that this fluorescent probe has a strong ...

Embodiment 3

[0047] In order to test the Stoke shift value of the fluorescent probe of the present invention, the following experiment is now done.

[0048] (1) Synthesis of ONOO by autoxidation of hydroxylamine in alkaline medium - : Vigorously stir the mixed solution containing 0.01mol / L hydroxylamine, 0.5mol / LNaOH and 0.001mol / L EDTA under aerobic conditions for about 3 hours, then use MnO 2 Powder filtration mixture to remove H 2 o 2 , The filtered mixture can be used for experiments immediately or stored at -18°C. Among them, ONOO can be detected at 302nm by UV-Vis spectrophotometer - concentration.

[0049] (2) Dissolve the fluorescent probe in N,N-dimethylformamide (DMF) to prepare a 1mmol / L probe solution, add the probe solution to DMF and PBS (pH=7.4) buffer, and prepare into a 10uM (organic phase: PBS aqueous phase = 1:99, V / V) solution; then add 45uM ONOO - The reaction solution was delayed for 10 seconds, and its luminous intensity was continuously measured for 10 seconds...

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Abstract

The invention discloses a fluorescent probe for detecting peroxynitrite anions, and a synthesis method and applications thereof. The structural formula of the fluorescent probe is shown in the description. The Stoke shift of the fluorescent probe is 120 nm. The range of absorption wavelength is 450-476 nm. The fluorescent probe is used to carry out quantitative detection on peroxynitrite anions. According to the synthesis method, 2-hydroxyl benzaldehyde and triethylamine are dissolved by tetrahydrofuran, then diphenyl phosphinyl chloride is added to carry out reactions; after reactions, the reaction products are processed to obtain an intermediate; the intermediate and hydrazine hydrate are dissolved by an organic solvent, and then the solution is processed to obtain the fluorescent probe.The provided fluorescent probe has high selectivity, and can generate a large Stoke shift when ONOO- is detected by the fluorescent probe, and the ONOO- detection precision is improved.

Description

technical field [0001] The invention relates to the field of applied biology, in particular to a fluorescent probe for detecting peroxynitrite anions, a synthesis method and application. Background technique [0002] Peroxynitrite anion (ONOO - ) is considered to be one of the most important anions in the human body by excess nitric oxide (NO) and oxygen free radicals (.O 2- ) reaction, it is not only a strong oxidant, but also a nitrating agent, which can react with macromolecular substances such as nucleic acid, protein, and lipid in human cells, making cell metabolism difficult and causing the body to consume a large amount of energy, thus causing a series of Biological pathological processes such as tumors, arteriosclerosis, body inflammation, retinal damage, etc. In recent years, there has been a lot of research on ONOO in the medical field. - detection studies, but since ONOO - Strong oxidizing property, very unstable in the body, this is ONOO - detection is incon...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/32C09K11/06G01N21/64
CPCC07F9/3229C07F9/3282C09K11/06C09K2211/1007C09K2211/1014G01N21/6428G01N2021/6432
Inventor 申有名唐裕才张春香张向阳丁祥周诗彪靳俊玲黄小兵
Owner GUANGZHOU YUEWANG AGRI CO LTD
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