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A fluorescent probe capable of simultaneously detecting β-amyloid deposition plaques and peroxynitrite, its preparation method and application

A technology of peroxynitrite and amyloid, applied in chemical instruments and methods, fluorescence/phosphorescence, material analysis through optical means, etc., can solve the problem of few small molecule fluorescent probes, achieve good staining effect, The effect is simple and easy to promote

Active Publication Date: 2021-10-01
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the inventors have found that Aβ deposition plaques and ONOO can be detected simultaneously - There are very few small molecule fluorescent probes

Method used

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  • A fluorescent probe capable of simultaneously detecting β-amyloid deposition plaques and peroxynitrite, its preparation method and application
  • A fluorescent probe capable of simultaneously detecting β-amyloid deposition plaques and peroxynitrite, its preparation method and application
  • A fluorescent probe capable of simultaneously detecting β-amyloid deposition plaques and peroxynitrite, its preparation method and application

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preparation example Construction

[0052] The preparation method of above-mentioned fluorescent probe, comprises the steps:

[0053] The reaction equation is:

[0054]

[0055] 1) dissolving compound 1 in glacial acetic acid, and adding diethyl ketomalonate therein and stirring evenly to obtain a mixed solution;

[0056] 2) After reacting the mixed solution in 1) for a set time and temperature, it is ready.

[0057] In some embodiments, in step 1), the ratio of compound 1 to diethyl ketomalonate is 1:1-3 to synthesize the target probe BTNPO.

[0058] In some embodiments, in step 2), the reaction temperature is 30-118° C., and the reaction time is 8-18 hours, so as to improve the reaction efficiency.

[0059] In some embodiments, in step 2), the reaction temperature is 90-118° C., and the reaction time is 12-15 hours, so that higher reaction rate and yield can be obtained.

[0060] In some embodiments, step 2) also includes the steps of spinning the reaction product solution to dryness and purifying, so as...

Embodiment 1

[0071] Embodiment 1: the synthesis of fluorescent probe

[0072] Compound 1 (274 mg, 1 mmol) was dissolved in 3 mL of glacial acetic acid, and the above mixture was heated to reflux. Then, a solution of diethyl ketomalonate (348 mg, 2 mmol) in glacial acetic acid (2 mL) was added dropwise to the above mixed solution, and reacted for 15 h. After the reaction was completed, the reaction solution was cooled to room temperature, concentrated and spin-dried to dry the solvent, and the solid was subjected to column chromatography (eluents were dichloromethane:methanol:triethylamine=100:1:1, V / V / V) The product solids were obtained in 324 mg (yield 65%), respectively.

[0073] Mass Spectrometry and NMR Characterization:

[0074] BTNPO: HRMS (ESI): calculated for C 22 h 15 N 2 o 4 S - (M-H) - 403.0747, found 403.0747.

[0075] 1 H NMR (400MHz, DMSO-d 6 )δ10.92(s,1H),8.69(s,1H),8.22(t,J=8.3Hz,2H),8.17(d,J=8.0Hz,1H),8.09(d,J=8.1Hz, 1H), 7.96(d, J=8.8Hz, 1H), 7.57(t, J=7.6Hz, ...

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Abstract

The present invention relates to a preparation method and application of a fluorescent probe capable of simultaneously detecting β-amyloid deposition plaques and peroxynitrite. ‑Benzothiazole derivatives as fluorophores with substituted lactam functional groups as ONOO ‑ Reactive recognition groups, except with ONOO ‑ In addition to fast response, the probe itself can also bind to Aβ deposition plaques with high sensitivity and good selectivity. It can be used as an excellent imaging tool for the detection of Aβ deposition plaques and ONOO in living cells and AD model mice ‑ simultaneous detection.

Description

technical field [0001] The invention belongs to the technical field of fluorescence imaging detection, and in particular relates to a fluorescent probe capable of simultaneously detecting beta amyloid deposition plaques and peroxynitrite, a preparation method and application thereof. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Current studies have shown that the deposition of plaques formed by the aggregation of β-amyloid (Aβ) is one of the key factors leading to the decline of cognitive function. Neurotoxicity in Aβ-deposited plaques can alter mitochondrial calcium homeostasis, induce inflammation, and increase reactive oxygen species (ROS) production. Studies have ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04C09K11/06G01N21/64
CPCC07D417/04C09K11/06C09K2211/1029C09K2211/1037G01N21/6428G01N21/6486G01N2021/6439
Inventor 唐波解希雷刘光照王栩张建焦晓云
Owner SHANDONG NORMAL UNIV