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A kind of quinazoline fluorescent probe and its preparation method and application

A fluorescent probe, quinazoline technology, applied in the field of biomedicine, can solve the problems of large autofluorescence background interference, high price and popularization, affecting the detection effect, etc., achieves important application value, avoids autofluorescence interference, and has good affinity. Effect

Active Publication Date: 2021-04-16
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nuclide imaging can detect diseases through molecular and cellular changes. For example, tumors can be detected by nuclide imaging before causing changes in tissue structure, but there are also problems such as low spatial resolution, insufficient structural information, high price and difficult to popularize, etc. question
The spatial resolution of fluorescent probe imaging is higher than that of nuclide imaging, which can solve these problems well, but the autofluorescence in vivo is concentrated at 300-600nm, and the autofluorescence reaching 650nm is rarely , while the emission wavelength of general fluorescent probes is 300-650nm, therefore, the background interference of autofluorescence in organisms is relatively large, which seriously affects the detection effect

Method used

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  • A kind of quinazoline fluorescent probe and its preparation method and application
  • A kind of quinazoline fluorescent probe and its preparation method and application
  • A kind of quinazoline fluorescent probe and its preparation method and application

Examples

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Effect test

Embodiment 1

[0050] The embodiment of the present application provides the synthesis method of quinazoline fluorescent probe, and the specific steps are as follows:

[0051] According to the synthetic route of reactant 1 Synthetic Reactant 1:

[0052] 4.3g, 31.35mmol of (N,N-Dimethyl-m-aminophenol) was added to a mixed solution of 25ml of concentrated hydrochloric acid and 10ml of water, the temperature was kept at -5°C, and 20ml of sodium nitrite (2.18g, 31.60mmol) aqueous solution was added slowly, mechanically Stir for 2h, let it stand, and filter with suction to obtain a brown-yellow solid. The crude product is washed with 50ml of saturated sodium acetate solution to obtain reactant 1 (4.20g, 81%) of dark red solid powder, and the structural formula of reactant 1 is

[0053] According to the synthetic route of reactant 2 Synthetic Reactant 2:

[0054] 4.12g, 19.90mmol of (α-bromonaphthalene) and 4.65g, 40.02mmol of (1,6-hexanediamine) was added to 40ml of ethylene glycol ...

Embodiment 2

[0067] In the embodiment of the present application, the product 1 is subjected to spectral determination, and the specific steps are as follows:

[0068] The product 1 prepared in Example 1 was made into different concentrations (respectively 200 μM, 100 μM, 50 μM, 25 μM, 12.5 μM and 0 μM) and dissolved in ethyl acetate, tetrahydrofuran, ethanol, methanol, acetonitrile, 1,4-bis In oxane, water or DMEM, use a microplate reader to scan the absorption spectrum at all wavelengths to find the maximum absorption wavelength, then use the maximum absorption wavelength as the excitation wavelength, and measure the maximum emission wavelength. The results are as follows Figure 3-4 as shown, image 3 It is the absorption spectrum figure of the product 1 of the embodiment of the present application in different solvents, Figure 4 It is the emission spectrum diagram of the product 1 in the embodiment of the present application in different solvents. It can be seen that the maximum emis...

Embodiment 3

[0070] In the embodiment of the present application, the product 1 was subjected to a cytotoxicity experiment, and the specific steps were as follows:

[0071] In this experiment, the thiazolium blue MTT method was used to evaluate the toxicity of product 1 to cells by the survival rate of cells. BV2 cells were divided into 5×10 4 Seed in a 96-well plate at a density of / ml, add 100 μL of cell solution to each well, and after 24 hours, the cells adhered to the wall, and the supernatant was sucked away, and the product 1 was dissolved in DMEM, and the concentration was divided into 200 μM, 100 μM, 50 μM, 25 μM, Incubate at 5 μM and 3 μM, add 100 μL of DMEM solution of product 1 to each well, absorb the supernatant after 24 hours, add 100 μL of MTT solution (500 μg / ml) to each well, continue to incubate for 4 hours, and measure the concentration at 570 nm on a microplate reader. OD value. Cell survival rate=(OD experimental group-OD blank group) / (OD control group-OD blank grou...

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Abstract

The application belongs to the technical field of biomedicine, and in particular relates to a quinazoline fluorescent probe and its preparation method and application. The application provides a quinazoline fluorescent probe whose chemical formula is shown in formula I, wherein, R 1 selected from H or Cl; R 2 Selected from fluorescent molecules; n is an integer of 2‑8. The present application provides a quinazoline fluorescent probe and its preparation method and application, which can eliminate the interference of the autofluorescence of the organism, and efficiently and accurately detect the TSPO content in the organism.

Description

technical field [0001] The application belongs to the technical field of biomedicine, and in particular relates to a quinazoline fluorescent probe and its preparation method and application. Background technique [0002] Studies have shown that neuroinflammation runs through the entire pathogenesis of neurodegenerative diseases. Under normal physiological conditions, neuroinflammation contributes to the repair of nervous system damage, but when the inflammatory response is excessive, it will cause cell damage and accelerate neurodegeneration. exacerbation of the disease. Neuroinflammation in the brain is closely related to degenerative diseases of the central nervous system. [0003] Mitochondrial 18kDa Translocation Molecule Protein (TSPO) is the peripheral benzodiazepine receptor transporter. It is a hydrophobic protein with a molecular weight of 18kDa. It is widely distributed in the mitochondrial outer membrane of peripheral tissues and participates in a large number of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14C07D405/12C07D413/12C07D417/12C07F5/02C09K11/06G01N21/64
CPCC07D403/14C07D405/12C07D413/12C07D417/12C07F5/022C09K11/06C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1051C09K2211/1088G01N21/6486
Inventor 周渭臧小豪刘起发胡蒙蒙李尤胡锦荣
Owner GUANGDONG UNIV OF TECH
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