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A liver-targeted peroxynitrite fluorescent probe, its preparation method and application

A technology of peroxynitrite and fluorescent probes, applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, and material analysis through optical means, which can solve the problems that cannot be studied in depth, probes lack tissue or organ targeting, etc. question

Active Publication Date: 2021-09-14
SHANXI MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the vast majority of probes lack tissue or organ targeting, making it impossible to study ONOO in depth - Relationship to a specific disease and study of its pathogenesis

Method used

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  • A liver-targeted peroxynitrite fluorescent probe, its preparation method and application
  • A liver-targeted peroxynitrite fluorescent probe, its preparation method and application
  • A liver-targeted peroxynitrite fluorescent probe, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A liver-targeted peroxynitrite fluorescent probe

[0037] (1) Synthesis of compound NA-1: Compound 4-bromo-1,8-naphthalic anhydride (5g, 18.05mmol) was dissolved in 150mL of dioxane, stirred until clear, and n-propylamine (1.12g, 19.85 mmol), replaced with nitrogen, and reacted at 110° C. for 8 hours. TLC showed that the reaction was complete, the solvent was spin-dried, and the crude product was separated by column chromatography (petroleum ether: ethyl acetate = 40:1-10:1) to obtain 4 g of a yellow solid. 1 H NMR (400MHz, DMSO-d 6 )δ8.55-8.50 (m, 2H), 8.31 (d, J = 8.0Hz, 1H), 8.31 (d, J = 8.0Hz, 1H), 8.20 (d, J = 8.0Hz, 1H), 7.99 ( t,J=12.0Hz,1H), 4.01(t,J=16.0Hz,2H), 1.69-1.67(m,2H), 0.95(t,J=12.0Hz,3H); 13 C NMR (100MHz, DMSO-d 6 )δ163.1, 132.9, 131.9, 131.7, 131.2, 130.0, 129.5, 128.5, 123.0, 122.2. HRMS: [M+H + ] 318.0131, Calculated: 318.0124;

[0038] (2) Compound NA-1 (2g, 6.29mmol) was dissolved in 50mL of 2-methoxyethanol, 85% hydrazine hydrate (1mL, 12...

Embodiment 2

[0041] Fluorescent probes for different concentrations of ONOO - identification

[0042] Dissolve the fluorescent probe obtained in Example 1 with dimethyl sulfoxide, prepare the probe mother solution, and add different equivalents of ONOO - The solution was incubated at 37° C. for 30 min, diluted with phosphate buffer solution to a concentration of 10 μM to be tested, and then measured by fluorescence spectrum. Such as Figure 6 As shown, the probe was able to respond to 0-14 μM ONOO - Response, and has a good linear relationship at 550nm, the linear regression equation is y=7.48x+0.24, R 2 = 0.9933.

Embodiment 3

[0044] Fluorescent probes are affected by the pH environment

[0045] Dissolve the fluorescent probe obtained in Example 1 with dimethyl sulfoxide, prepare the probe mother solution, and add 10 equivalents of ONOO - , after incubating at 37°C for 30min, dilute it to the test concentration of 10μM with phosphate buffer solution with different pH values, and measure its fluorescence spectrum (λ ex =450nm); according to its fluorescence intensity, evaluate the impact of different pH environments on the fluorescence intensity of the fluorescent probe, the results are as follows Figure 7 shown. The pH values ​​are 4, 5, 6, 7, 8, 9, respectively. Fluorescent probes with ONOO - The fluorescence intensity before and after the treatment was not affected by the pH environment.

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Abstract

The application discloses a liver-targeted peroxynitrite fluorescent probe, its preparation method and application, and belongs to the technical field of chemical and biological materials. Lack of tissue or organ targeting for most probes prevents in-depth study of ONOO ‑ The relationship to a particular disease and the study of its pathogenic mechanisms. The liver-targeted peroxynitrite fluorescent probe of the present application contains the liver-targeted unit ursodeoxycholic acid; the preparation method of the fluorescent probe is by dissolving the compound 4-bromo-1,8-naphthalene dicarboxylic anhydride in Add n-propylamine to dioxane, concentrate the reaction solution, and separate by column chromatography to obtain compound NA-1; then dissolve it in 2-methoxyethanol, add hydrazine hydrate and sodium bicarbonate, and separate by column chromatography to obtain compound NA ‑2; then dissolved in N,N‑dimethylformamide with ursodeoxycholic acid, then added 1‑hydroxybenzotriazole, 1‑ethyl‑(3‑dimethylaminopropyl) Carbodiimide hydrochloride, N,N-diisopropylethylamine, the crude product was subjected to column chromatography to obtain the target compound NA-3.

Description

technical field [0001] The invention belongs to the technical field of chemical and biological materials, and in particular relates to a liver-targeted peroxynitrite fluorescent probe, a preparation method and an application. Background technique [0002] Peroxynitrite (ONOO - ) as an important active oxygen molecule in the organism, participates in important physiological and pathological processes in the organism, mainly composed of nitric oxide (NO) and superoxide free radicals (O 2 .- )synthesis. Highly reactive ONOO - On the one hand, it can react with many biomolecules such as proteins, lipids and NDA, and on the other hand, it can cause oxidative stress toxicity to cells. However, the abnormal concentration of ONOO - Become a key pathogenic factor in many diseases, such as neurodegenerative diseases, ischemia-reperfusion diseases, inflammation and cancer, etc. Therefore, the establishment of an efficient, highly selective ONOO - Detection technology is very imp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J43/00C09K11/06G01N21/64
CPCC07J43/003C09K11/06C09K2211/1011C09K2211/1029G01N21/6428G01N2021/6417
Inventor 马素芳余强李波刘文王浩江李雪任国栋
Owner SHANXI MEDICAL UNIV
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