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Near-infrared fluorescent probe BODIPY compound and preparation method thereof

A fluorescent probe and near-infrared technology, applied in the field of fluorescent probes, near-infrared fluorescent probes BODIPY compounds and their preparation, can solve the problems of lack of early monitoring AD, high background noise signals, etc., and achieve good application value and steps Simple, mild preparation conditions

Active Publication Date: 2020-07-24
HUAIYIN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these fluorescent probes still have some disadvantages, such as high background noise signal and lack of early detection ability of AD, etc.

Method used

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  • Near-infrared fluorescent probe BODIPY compound and preparation method thereof
  • Near-infrared fluorescent probe BODIPY compound and preparation method thereof
  • Near-infrared fluorescent probe BODIPY compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Dissolve fluorobodipyrrole fluorescent dye (0.54mmol), 4-N,N-diphenylaminobenzaldehyde (1.08mmol), p-toluenesulfonamide (0.01mmol) in toluene (25mL) and piperidine (1mL) Place the mixed solution in a round-bottomed flask equipped with a Dean-Stark apparatus, heat to reflux at 142°C until all the solvent is collected by the Dean-Stark apparatus, then add toluene (25mL) and piperidine (1mL) to the reaction medium , continue heating to reflux at 142°C until all solvents are collected by the Dean-Stark apparatus, repeat the process of adding toluene (25mL) and piperidine (1mL) and heating to reflux for a total of 4 times, this process is tracked by TLC, after the raw materials are completely reacted, the column layer After the solvent was distilled off under reduced pressure, a black solid product was obtained, and the compound was obtained by NMR 1 HNMR spectrum, mass spectrum TOF MS EI + To characterize, 1 H NMR (300MHz, DMSO-D 6 ): δ=7.54(d, J=8.8Hz, 2H), 7.18(d, J=8....

Embodiment 2

[0034] Dissolve fluorobodipyrrole fluorescent dye (0.54mmol), benzaldehyde (0.54mmol), p-toluenesulfonamide (0.01mmol) in a mixed solution of toluene (25mL) and piperidine (1mL), and place in a Dean- In the round bottom flask of the Stark apparatus, heat to reflux until all the solvents are collected by the Dean-Stark apparatus, then add toluene (25mL) and piperidine (1mL) to the reaction medium, and continue to heat at reflux at 142°C until all the solvents are collected by the Dean-Stark apparatus. -Collection by Stark device, repeated addition of toluene (25mL) and piperidine (1mL) and heating to reflux for a total of 2 times, this process was tracked by TLC, after the reaction of the raw materials was complete, column chromatography, after the solvent was distilled off under reduced pressure, a black solid was obtained The product, the compound by NMR 1 H NMR spectrum, mass spectrum MS EI + To characterize, 1 H NMR (300MHz, DMSO-D 6 ):δ=7.33-7.60(m,15H),6.67-6.99(m,4H),...

Embodiment 3

[0036] Dissolve fluorobodipyrrole fluorescent dye (0.54mmol), acetaldehyde (1.62mmol), p-toluenesulfonamide (0.01mmol) in a mixed solution of toluene (25mL) and piperidine (1mL), and place in a Dean- In the round-bottomed flask of the Stark apparatus, heat to reflux at 140°C until all the solvents are collected by the Dean-Stark apparatus, then add toluene (25mL) and piperidine (1mL) to the reaction medium, and continue to heat to reflux at 142°C until all the solvents are Collected by Dean-Stark device, repeat adding toluene (25mL) and piperidine (1mL) and heating to reflux for a total of 2 times, this process is tracked by TLC, after the raw material reaction is complete, column chromatography, after vacuum distillation to remove the solvent, to obtain Black solid product, the compound by NMR 1 H NMR spectrum, mass spectrum MS EI + To characterize, 1 H NMR (300MHz, DMSO-D 6 ):δ=7.33-7.37(m,5H),6.27-6.41(m,4H),6.02(s,2H),2.19(s,6H),2.01(s,6H); MS EI + :376.2.

[0037] Ap...

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Abstract

The invention discloses a near-infrared fluorescent probe BODIPY compound and a preparation method thereof. The BODIPY compound is synthesized through a Knoevenagel condensation reaction of a boron dipyrromethene (BODIPY) fluorescent dye and an aldehyde compound. The maximum absorption wavelength and the maximum emission wavelength in trichloromethane are in a near-infrared region. Diphenylalaninedipeptide serving as the minimum unit of a beta-amyloid protein recognition core can be self-assembled into nanofibers, the BODIPY compound can be combined with the diphenylalanine dipeptide fibers,and the basic morphology of the diphenylalanine dipeptide fibers can be subjected to fluorescence imaging. Besides, beta-amyloid protein entanglement is used as one of main reasons of Alzheimer's disease, and the BODIPY compound can be combined with diphenylalanine dipeptide in beta-amyloid protein to achieve the purpose of early diagnosis of Alzheimer's disease.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a near-infrared fluorescent probe BODIPY compound and a preparation method thereof, which belongs to the content of fluorescent probes and can be used as a diphenylalanine dipeptide response in β-amyloid protein Fluorescent probes have potential application value in the early diagnosis of Alzheimer's disease. Background technique [0002] Alzheimer's disease (AD) is a neurodegenerative disease, mainly manifested by clinical symptoms such as memory loss, spatial recognition impairment and cognitive function loss. According to the "World Alzheimer's Disease Report 2018", there are about 50 million Alzheimer's patients in the world in 2018, and there will be about 100 million Alzheimer's patients by 2050. Currently, the most effective way to treat AD is Drug treatment, unfortunately, only 6 drugs have passed the US Food and Drug Administration (FDA) for clinica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06C09B23/04G01N21/64
CPCC07F5/022C09K11/06C09B23/04G01N21/6486C09K2211/1055
Inventor 权莉魏言春柳森杨忠美潘长江
Owner HUAIYIN INSTITUTE OF TECHNOLOGY