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Fluorescent compound having affinity with A[beta] plaque, preparation method and applications thereof

A fluorescent compound and affinity technology, which is applied in the field of specific molecular recognition diagnostic reagents, can solve problems such as radiation damage, and achieve the effects of low cost, low background fluorescence interference, and strong penetrating power

Active Publication Date: 2017-11-07
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the past few years, many radioactive Aβ molecular probes have entered the clinical trial stage, and related PET imaging reagents have been launched. However, the application of radioactive imaging methods is also limited by some factors, such as the radiation emitted by radioactive imaging agents. The human body has certain radiation damage, and medical institutions need to be equipped with cyclotrons for the production of radionuclides, and radioactive imaging agents need to be marked and prepared by professional technicians, etc.

Method used

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  • Fluorescent compound having affinity with A[beta] plaque, preparation method and applications thereof
  • Fluorescent compound having affinity with A[beta] plaque, preparation method and applications thereof
  • Fluorescent compound having affinity with A[beta] plaque, preparation method and applications thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0042] The synthesis of a kind of fluorescent compound (I) of the present embodiment, concrete synthetic steps are as follows:

[0043] (1) Synthesis of Intermediate 1

[0044] Stir 4.77g of 2,3,3-trimethylindole (30mmol) and 3.22ml of iodomethane (7.08g, 50mmol) in 60ml of ethanol, seal the pressure vessel, and react at 80°C for 12h. After the reaction was completed, cooled to room temperature, the solid was precipitated, filtered with suction, and 7.7 g of the precipitated solid was obtained, namely Intermediate 1;

[0045] (2) Synthesis of Intermediate 2

[0046] Mix 17.5ml of DMF (16.54g, 225mmol) and 18ml of dichloromethane evenly, in an ice bath and under the protection of nitrogen, slowly add 15ml of phosphorus oxychloride (24.68g, 160mmol) drop by drop, stir for 20-40min, then add 4.6ml of cyclohexanone (4.37g, 45mmol), raised the temperature to 80°C for 4h under reflux, cooled to room temperature, slowly poured the reaction solution into ice water, precipitated solid,...

Embodiment 2

[0058] The synthesis of a kind of fluorescent compound (I) of the present embodiment, concrete synthetic steps are as follows:

[0059] (1) Synthesis of Intermediate 1

[0060] Stir 4.77g of 2,3,3-trimethylindole (30mmol) and 3.22ml of iodomethane (7.08g, 50mmol) in 60ml of ethanol, seal the pressure vessel, and react at 80°C for 12h. After the reaction was completed, cooled to room temperature, the solid was precipitated, filtered with suction, and 7.7 g of the precipitated solid was obtained, namely Intermediate 1;

[0061] (2) Synthesis of Intermediate 2

[0062] Mix 17.5ml of DMF (16.54g, 225mmol) and 18ml of dichloromethane evenly, in an ice bath and under the protection of nitrogen, slowly add 15ml of phosphorus oxychloride (24.68g, 160mmol) drop by drop, stir for 20-40min, then add 4.6ml of cyclohexanone (4.37g, 45mmol), raised the temperature to 80°C for 4h under reflux, cooled to room temperature, slowly poured the reaction solution into ice water, precipitated soli...

Embodiment 3

[0070] The synthesis of a kind of fluorescent compound (I) of the present embodiment, concrete synthetic steps are as follows:

[0071] (1) Synthesis of Intermediate 1

[0072] Stir 4.77g of 2,3,3-trimethylindole (30mmol) and 3.22ml of iodomethane (7.08g, 50mmol) in 60ml of ethanol, seal the pressure vessel, and react at 80°C for 12h. After the reaction was completed, cooled to room temperature, the solid was precipitated, filtered with suction, and 7.7 g of the precipitated solid was obtained, namely Intermediate 1;

[0073] (2) Synthesis of Intermediate 2

[0074] Mix 17.5ml of DMF (16.54g, 225mmol) and 18ml of dichloromethane evenly, in an ice bath and under the protection of nitrogen, slowly add 15ml of phosphorus oxychloride (24.68g, 160mmol) drop by drop, stir for 20-40min, then add 4.6ml of cyclohexanone (4.37g, 45mmol), raised the temperature to 80°C for 4h under reflux, cooled to room temperature, slowly poured the reaction solution into ice water, precipitated soli...

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PUM

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Abstract

The present invention belongs to the field of specific molecular recognition diagnosis reagents, and discloses a fluorescent compound having affinity with A[beta] plaque, a preparation method and applications thereof, wherein the fluorescent compound has a structure general formula represented by a formula (I), and R is a malononitrile substituent or cyanoethyl acetate substituent. According to the present invention, the fluorescent compound has good fluorescent property, wherein the emission wavelength reaches the near infrared region; and the obtained fluorescent compound shows the affinity with A[beta] plaques in the in vitro experiment, can be successfully used for the near infrared fluorescence imaging of A[beta] plaques, and has advantages of safety, no radioactivity, low cost, low background fluorescence interference, strong penetrating in biological tissues, and the like. The formula (I) is defined in the specification.

Description

technical field [0001] The invention belongs to the field of specific molecular recognition diagnostic reagents, and in particular relates to a fluorescent compound having affinity with Aβ plaques and its preparation and application. Background technique [0002] Alzheimer's disease (AD) is a neurodegenerative disease. According to the latest survey data in 2016, there are currently more than 47 million AD patients worldwide. However, China has entered into an aging society ahead of schedule. The survey shows that there are more than 8 million AD patients in my country, ranking first in the world, and the number of patients is increasing at a rate of more than 300,000 per year. AD not only seriously affects the health of the elderly, but also brings a heavy burden to the society and family. At present, the clinically available drugs for the treatment of AD cannot delay, terminate or reverse the development of AD, and can only partially improve the clinical symptoms. Moreo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D209/24A61K49/00A61P25/28A61P9/00
Inventor 颜金武张雷朱佳莹李晶
Owner SOUTH CHINA UNIV OF TECH
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