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-N=N- dinitrogen bond bridged A[beta] inhibitor fluorescent probe and preparation method thereof

A technology of β-inhibitors and fluorescent probes, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as weak selectivity, poor fluorescence emission performance, and low sensitivity

Pending Publication Date: 2021-11-09
HUAIYIN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the fluorescent probes for AD detection in the prior art have the problems of poor fluorescence emission performance, low sensitivity, weak selectivity, and poor biocompatibility, which greatly limit their application range, and can only be used for monitoring but cannot be used effectively. intervene

Method used

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  • -N=N- dinitrogen bond bridged A[beta] inhibitor fluorescent probe and preparation method thereof
  • -N=N- dinitrogen bond bridged A[beta] inhibitor fluorescent probe and preparation method thereof
  • -N=N- dinitrogen bond bridged A[beta] inhibitor fluorescent probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Dissolve the Aβ inhibitor kaempferol (0.3mmol), DCC (0.02mmol), and DMAP (0.02mmol) in chloroform, add azobenzene-4,4-dicarboxylic acid (0.3mmol), stir at 70°C for 3h, The solvent was removed by vacuum rotary evaporation at 25°C, and the crude product was purified by chromatographic column to obtain the product K-L N＝N , the compound by NMR 1 H NMR spectrum for characterization, 1 H NMR (300MHz, DMSO-D 6 ):δ=12.71(s,1H),9.55(s,1H),8.38-8.39(m,4H),8.06-8.12(m,4H),7.77(d,J=8.8Hz,1H),7.60( d,J=8.8Hz,1H),7.30-7.37(m,2H),6.91-7.18(m,5H),6.24(d,J=8.8Hz,1H),4.59(s,2H),3.83-3.87 (m,6H).

[0034] K-L N＝N (0.5mmol), DCC (0.01mmol), DMAP (0.01mmol) were dissolved in chloroform, NB (0.5mmol) was added, stirred at 70°C for 3h, the solvent was removed by rotary evaporation at 30°C, purified by column chromatography, and a black solid product was obtained NB-N=N-K, the compound is obtained by NMR 1 H NMR spectrum for characterization, 1 H NMR (300MHz, DMSO-D 6):δ=9.55(s,1H),8...

Embodiment 2

[0036] Dissolve Aβ inhibitor curcumin (0.1mmol), DCC (0.01mmol), DMAP (0.01mmol) in chloroform, add azobenzene-4,4-dicarboxylic acid (0.1mmol), stir at 80°C for 2h, 50 °C vacuum rotary evaporation to remove the solvent, column chromatography to obtain the product C-L N＝N , the compound by NMR 1 H NMR spectrum for characterization, 1 H NMR (300MHz, DMSO-D 6 ):δ=12.71(s,1H),9.55(s,1H),8.38-8.39(m,4H),8.06-8.12(m,4H),7.77(d,J=8.8Hz,1H),7.60( d,J=8.8Hz,1H),7.30-7.37(m,2H),6.91-7.18(m,5H),6.24(d,J=8.8Hz,1H),4.59(s,2H),3.83-3.87 (m,6H).

[0037] Change C-L N＝N (0.2mmol), DCC (0.01mmol), DMAP (0.01mmol) were dissolved in chloroform, NB (0.2mmol) was added, stirred at 60°C for 5h, the solvent was removed by rotary evaporation at 30°C, and purified by column chromatography to obtain a black solid product NB-N=N-C, the compound is passed nuclear magnetic 1 H NMR spectrum for characterization, 1 H NMR (300MHz, DMSO-D 6 ):δ=9.55(s,1H),8.39(d,J=4.4Hz,2H),8.22(d,J=4.4Hz,2H),8.02-8....

Embodiment 3

[0039] Dissolve the Aβ inhibitors resveratrol (0.3mmol), DCC (0.03mmol), and DMAP (0.03mmol) in chloroform, add azobenzene-4,4-dicarboxylic acid (0.3mmol), and stir at 70°C for 6h , 50 ° C vacuum rotary evaporation to remove the solvent, chromatographic column separation and purification, to obtain the product R-L N＝N , the compound by NMR 1 H NMR spectrum for characterization, 1 H NMR (300MHz, DMSO-D 6 ):δ=12.71(s,1H),9.07(s,2H),8.38-8.39(m,4H),8.06-8.12(m,4H),7.81(d,J=4.4Hz,2H),7.41( d, J=4.4Hz, 2H), 6.56(s, 2H), 6.38(s, 2H), 6.12(s, 1H).

[0040] R-L N＝N (1mmol), DCC (0.03mmol), DMAP (0.03mmol) were dissolved in chloroform, NB (1mmol) was added, stirred at 80°C for 10h, the solvent was removed by rotary evaporation at 40°C, purified by column chromatography, and the black solid product NB- N=N-R, the compound is passed by NMR 1 H NMR spectrum for characterization, 1 H NMR (300MHz, DMSO-D 6 ):δ=9.07(s,2H),8.39(d,J=4.4Hz,2H),8.22(d,J=4.4Hz,2H),8.02-8.06(m,4H),7.77-7.8...

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Abstract

The invention provides a -N=N- dinitrogen bond bridged A[beta] inhibitor fluorescent probe and a preparation method thereof. An A[beta] inhibitor (M) and DCC / DMAP are dissolved in chloroform according to the molar ratio of 1:0.1-1 / 0.1-1, 1-1.3 equivalent weight of dinitrogen bond-containing (M:M) Linker is added, stirring is performed for 1-6 h at the temperature of 50-100 DEG C, vacuum rotary evaporation is performed to remove a solvent, separation and purification are performed by adopting a chromatographic column, and a solid product M-LN=N is obtained; and NB and M-LN=N are dissolved in chloroform according to a molar ratio of 1:(1-3), 0.1-1 equivalent (M:M) of a catalyst B is added, stirring is performed at 60-70 DEG C for 1-12 hours, vacuum rotary evaporation is conducted at 25-60 DEG C to remove a solvent, separating and purifying are conducted by adopting a chromatographic column, and a final product NB-N=N-M is obtained after the reaction is finished. The -N=N- dinitrogen bond is used as a reaction active site, and multiple functions can be organically combined on the basis of a single function of an original system after introduction. In the project, the BODIPY and the A[beta] inhibitor are connected through the -N=N- dinitrogen bond to obtain the fluorescent probe in which the -N=N- dinitrogen bond is bridged with the A beta inhibitor, so that the BODIPY and the A[beta] inhibitor synergistically exert the functions of monitoring and inhibiting beta-amyloid protein in real time, thereby achieving the purpose of early diagnosis and treatment of Alzheimer's disease.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a fluorescent probe (NB-N=N-M) of an -N=N-double nitrogen bond bridge-linked Aβ inhibitor and a preparation method thereof. Background technique [0002] Alzheimer's disease (AD) is a lethal neurodegenerative disease with gradual deterioration of cognitive function. September 21, 2020 is the seventh Alzheimer's Day in the world. According to the report of the United States, the number of people who died of Alzheimer's disease has greatly increased. Since 2010, Alzheimer's disease has become The sixth leading cause of death in the United States, Alzheimer's or other dementias account for one in three seniors. According to the current medical level, there is no good treatment plan for Alzheimer's disease, and the progress of its drug development is full of difficulties, and the early diagnosis of Alzheimer's disease is also a big challenge. The cases of Alzh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02A61K49/00A61K47/54A61K31/352A61K31/12A61K31/05A61P25/28C09K11/06G01N21/64
CPCC07F5/022C09K11/06A61K49/0021A61K47/542A61K31/352A61K31/12A61K31/05A61P25/28G01N21/6428C09K2211/1055C09K2211/1007C09K2211/1014C09K2211/1088
Inventor 赵应时权莉林岳宾宋钦涌岳江涛
Owner HUAIYIN INSTITUTE OF TECHNOLOGY
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