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Fluorescent probe for detecting peroxynitrite ions, preparation method and applications thereof

A technology of peroxynitrite and fluorescent probes, which is applied in the field of analytical chemistry, can solve the problems of difficult measurement of peroxynitrite ions, short lifetime of peroxynitrite ions, and low steady-state concentration, and achieve good fluorescence The effect of emission spectrum characteristics, easy promotion, and low preparation cost

Inactive Publication Date: 2020-04-07
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The lifetime of peroxynitrite ion in living organisms is very short, resulting in usually very low steady-state concentration, and the short lifetime and low concentration mean that the determination of peroxynitrite ion is very difficult

Method used

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  • Fluorescent probe for detecting peroxynitrite ions, preparation method and applications thereof
  • Fluorescent probe for detecting peroxynitrite ions, preparation method and applications thereof
  • Fluorescent probe for detecting peroxynitrite ions, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Synthesis of Fluorescent Probes

[0035] (1) Add β-alanine (600 mg, 6.7 mmol) to distilled water (4 mL), add NaOH aqueous solution (2 M, 3.4 mL), then add p-toluenesulfonyl chloride (1.83 g, 9.6 mmol), and react The mixture was stirred at 35°C. Add 1M NaOH aqueous solution to keep the pH value at 9. After the alkali is completely consumed, stir at 35°C for one hour, filter to remove unreacted p-toluenesulfonyl chloride, and use 5 M HCl aqueous solution at 0°C Acidify the reaction mixture to make pH=2, and the precipitated white precipitate is filtered, washed with cold water, dissolved in dichloromethane solvent, and purified by column chromatography (petroleum ether:ethyl acetate=5:1), which is compound 1. 1 H NMR spectrum such as figure 1 :

[0036] ;

[0037] (2) Dissolve 4-diethylaminoketoacid (940 mg, 3 mmol), m-hydroxyphenylpiperazine (534.7 mg, 3 mmol) in 5 mL CH 3 In COOF, heated at reflux at 90 °C for 12 h, the reaction mixture was concentrated...

Embodiment 2

[0043] Example 2 Responses of fluorescent probes to different concentrations of peroxynitrite ions

[0044] Prepare the fluorescent probe obtained in Example 1 as a mother solution (containing 10% acetonitrile), add the same volume of solutions containing peroxynitrite ions at different concentrations, and use water as a blank (0 μM) to make the probe concentration 5 μM, for fluorescence detection (λ ex=540nm); Calculate the fluorescence intensity in each system; Evaluate the response performance of the probe to peroxynitrite ion, such as Figure 4 (A) shows: the probe can respond to peroxynitrite ion at a concentration of 5-200 μM; analyze the linear relationship between the fluorescence intensity at 581 nm and the concentration of peroxynitrite ion at 5-50 μM, as shown in Figure 4 (B) As shown: within this concentration range, the linear relationship between fluorescence intensity and peroxynitrite ion concentration is good, and the linear regression equation is y=24.34x-4...

Embodiment 3

[0045] Example 3 Response time of fluorescent probes to peroxynitrite ions

[0046] Prepare the fluorescent probe obtained in Example 1 as a mother solution (containing 10% acetonitrile), and add a solution containing peroxynitrite ions so that the concentration of the probe is 5 μM, and the concentration of peroxynitrite ions is 100 μM , fluorescence detection is performed every 5s (λ ex =540 nm) for a total of 10 min; calculate the fluorescence intensity in each system; evaluate the response speed of the probe to peroxynitrite ion, as Figure 5 Shown: join ONOO - After that, the response time is less than 5 s, indicating that the probe is ONOO - Very responsive.

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Abstract

The invention provides a fluorescent probe for detecting peroxynitrite ions. The fluorescent probe provided by the invention has high specificity, is not interfered by other components in a corresponding peroxynitrite ion detection process, can be used for real-time determination of peroxynitrite ions in living cells, amd has wide application prospect. The fluorescent probe for detecting the peroxynitrite ions in cells is high in sensitivity and good in fluorescence emission spectrum characteristic, wherein the peroxynitrite ions in cells are determined by drawing a standard curve, so that thepurpose of rapid and accurate detection of the peroxynitrite ions in the cells can be achieved.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a fluorescent probe for detecting peroxynitrite ions and an application thereof. Background technique [0002] In addition to normal physiological functions, nitric oxide is also related to some cell and tissue damage. Available evidence indicates that the product of the reaction of nitric oxide with superoxide anion is peroxynitrite ion (ONOO-). On the one hand, peroxynitrite ion can play an auxiliary regulatory role in the body's immune system. On the other hand, peroxynitrite ion is a strong oxidizing and potent cytotoxic substance, which is the cause of pathological effects of nitric oxide, which can cause DNA damage, enzyme inhibition, cell death and bacterial poisoning and can cause a range of diseases. At present, it has been found that peroxynitrite ion exists in septic shock, ischemia-reperfusion injury, atherosclerosis, diabetes, Alzheimer's ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06G01N21/6428G01N21/6458C09K2211/1033C09K2211/1044
Inventor 林伟英孙亚茹董宝利卢雅如
Owner UNIV OF JINAN
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