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Fluorescent probe for detecting peroxynitrite, and preparation and application of fluorescent probe

A nitroso peroxide, fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as poor specificity, inability to apply in vivo detection, etc., and achieve good stability and good biofilm. The effect of permeability and detection of high signal-to-noise ratio

Inactive Publication Date: 2015-09-09
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This detection method has two problems, such as poor specificity and inapplicability to live detection.

Method used

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  • Fluorescent probe for detecting peroxynitrite, and preparation and application of fluorescent probe
  • Fluorescent probe for detecting peroxynitrite, and preparation and application of fluorescent probe
  • Fluorescent probe for detecting peroxynitrite, and preparation and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of fluorescent probe molecule Ia-1

[0042] 1g of o-aminothiophenol (8 mmol) and o-hydroxybenzaldehyde (8 mmol) were stirred in 8 mL of methanol for two hours at room temperature, and filtered by suction to obtain a white solid 2-(2,3-dihydrobenzo[d ]thiazol-2-yl)phenol. That is, 1a-1 was obtained with a yield of 50%. 1 H NMR (500 MHz, DMSO) δ9.85 (s,1H), 7.4 (d,1H), 7.1(t,1H), 6.95(d,1H), 6.75-6.85(m,3H), 6.65(d ,2H), 6.55(t,1H), 6.45(s,1H).

[0043] .

Embodiment 2

[0044] Embodiment 2: the preparation of fluorescent probe molecule Ib-1

[0045]o-Aminothiophenol (0.5g, 3.6mmol) and o-Hydroxybenzaldehyde (0.438g, 3.5mmol) were dissolved in 5mL of methanol solution, 37% hydrogen peroxide (15.75mmol) was added dropwise under ice-cooling and then Then add 37% hydrochloric acid (9.2 mmol) dropwise, react at room temperature for two hours and filter with suction, recrystallize from ethanol to obtain intermediate 2-(benzo[d]thiazol-2-yl)phenol II-1, yield 70 %; Intermediate II-1 (0.5g, 2 mmol) was first dissolved by stirring with 20 ml of anhydrous dichloromethane, replaced with nitrogen, and first added dropwise pyridine solution (328 μL, 4 mmol) to the reaction solution under ice bath, Then trifluoromethanesulfonic anhydride (0.863 g, 3 mmol) was slowly added dropwise to the reaction solution at a uniform speed, and stirred at room temperature for 3-4 hours. After the reaction was completed, it was extracted with ethyl acetate, dried over anh...

Embodiment 3

[0047] Embodiment 3: the preparation of fluorescent probe molecule Ib-2

[0048] Intermediate 2-(Benzo[d]thiazol-2-yl)phenyl triflate (0.25 g, 0.7 mmol) and 4-((tert-butyldimethylsilyl)oxy) -3-Methoxyaniline (0.25 g, 0.8 mmol), palladium acetate (3% mmol), BINAP (4.5% mmol) and cesium carbonate (1.4 mmol) were dissolved in 4 mL of toluene and reacted at 80 °C for 16 Hours, suction filtration, column chromatography purification. The key intermediate of yellow 2-(benzo[d]thiazol-2-yl)-N-phenylaniline was obtained with a yield of 80%; the intermediate was N-methylated and dehydroxylated to obtain the probe molecule 1b -2, yield 65%. 1 H NMR (500 MHz, DMSO) δ10.4 (s, 1H), 8.15 (d, 1H), 8.05 (d, 1H), 7.8 (d, 1H), 7.55 (t, 1H), 7.45 (t, 1H ), 7.3(m, 2H), 7.0 (3, 1H), 6.85 (3, 1H), 6.7(d, 1H), 6.5 (dd, 1H) ,3.85 (s, 3H), 3.8 (s, 3H) .

[0049] .

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Abstract

The invention provides a fluorescent probe for detecting peroxynitrite. The probe has a general structure formula Ia or Ib. The probe is prepared by: (1) stirring R4-substituted o-aminothiophenol or R4-substituted o-aminophenol and R1 / R2-substituted benzaldehyde in a methanol solution at a room temperature for two hours to obtain Ia; and (2) performing oxidative condensation of R4-substituted o-aminothiophenol or o-aminophenol and R2-substituted o-hydroxybenzaldehyde to obtain a benzothiazole or benzoxazole intermediate, coupling triflate converted by the phenolic hydroxyl group of the intermediate and R3-substituted p-hydroxybenzene tert-butyldimethylsilylester / p-aminobenzene tert-butyldimethylsilylester, and performing methylation of aniline nitrogen atoms and hydroxy elimination of silylester protecting group to obtain Ib. The fluorescent probe provided in the invention can have fast specific reaction with peroxynitrite to generate a product with strong fluorescence, so that specific detection of peroxynitrite is realized. The general structure formula of the probe in the invention is shown in the description.

Description

technical field [0001] The invention belongs to the field of biological detection, and relates to a fluorescent probe for detecting peroxynitroso and its preparation method and application. Background technique [0002] Peroxynitroso is a member of the reactive nitrogen family and one of the products of nitrification stress in organisms. It is synthesized in vivo from nitric oxide free radicals and superoxide anions. Due to its strong oxidative properties and strong nucleophilicity, peroxynitroso can react with many biomolecules in the body, including proteins, metalloenzymes, lipids, nucleic acids, etc., causing oxidative damage in the body and eventually leading to cell apoptosis. In fact, peroxynitroso is widely considered to be the culprit of the cytotoxicity of nitric oxide free radicals and superoxide anions, and is involved in the occurrence and development of cardiovascular diseases, neurodegenerative diseases and other diseases. On the other hand, peroxynitroso has...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D277/66G01N21/64
CPCY02P20/55
Inventor 李新陶蓉蓉韩峰胡有洪胡永洲程娟
Owner ZHEJIANG UNIV
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