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Preparation of fluorescent probe based on excited-state intramolecular proton transfer and used for detecting monoamine oxidase B

A monoamine oxidase and fluorescent probe technology, applied in material excitation analysis, luminescent materials, fluorescence/phosphorescence, etc., can solve the problems of poor biocompatibility, strong background fluorescence and easy diffusion of fluorescent probes, and achieve good photostability, High sensitivity and good selectivity

Inactive Publication Date: 2019-06-14
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these fluorescent probes for the specific detection of MAO-B have disadvantages such as poor biocompatibility, strong background fluorescence, and easy diffusion.

Method used

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  • Preparation of fluorescent probe based on excited-state intramolecular proton transfer and used for detecting monoamine oxidase B
  • Preparation of fluorescent probe based on excited-state intramolecular proton transfer and used for detecting monoamine oxidase B

Examples

Experimental program
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Effect test

Embodiment 1

[0021] 1) Synthesis of compound HPQ-B0:

[0022] Dissolve 2-(2'-hydroxyphenyl) 4(3H) quinazolinone dye (4 mmol, 1eq), N-Boc-3-aminopropyl bromide (4mmol, 1eq) in 20 mL N, N- Dimethylformamide, then add (0.4 mmol, 0.1eq) anhydrous sodium carbonate and (0.2 mmol, 0.05 eq) sodium iodide to the mixture, stir at room temperature, heat up to 90°C and reflux 12h. Monitor the reaction with a TCL plate. After the reaction is complete, extract with dichloromethane, dry over anhydrous magnesium sulfate, evaporate under reduced pressure, and separate with a silica gel column. The silica gel particle size is 200-300 mesh to obtain the compound HPQ-B0, which is brownish yellow Solid, the eluent is dichloromethane.

[0023] 2) Synthesis of compound HPQ-B1:

[0024] Add 10 ml of trifluoroacetic acid to (2 mmol, 1 eq) of HPQ-B0, and evaporate to dryness to remove the protective group. The residue was purified by a silica gel column with a particle size of 200-300 mesh to obtain the target ...

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Abstract

The invention discloses a preparation method and application of a fluorescent probe based on excited-state intramolecular proton transfer and used for accurately measuring monoamine oxidase B in cells. The probe is connected with N-Boc-3-aminopropyl bromide based on a fluorescent dyestuff 2-(2'-hydroxyphenyl)4(3H)quinazolinone of the excited-state intramolecular proton transfer. The probe disclosed by the invention has the advantages that the disadvantages of poor biocompatibility, strong background fluorescent light, easiness for dispersing and the like of a traditional fluorescent probe fordetecting the monoamine oxidase B are overcome, and the probe also has the advantages of good light stability, strong fluorescent light and the like of the 2-(2'-hydroxyphenyl)4(3H)quinazolinone. Theprobe provides an early-stage monitoring means for health and diseases of nervous systems.

Description

technical field [0001] The present invention relates to the identification of abnormal biological enzyme activity expression levels in cells by small molecule fluorescent probes, more specifically, a fluorescent probe based on excited state intramolecular proton transfer for monoamine oxidase B, an important marker of nervous system diseases detection. Background technique [0002] Monoamine oxidase is an enzyme that catalyzes the oxidative deamination of monoamines. Monoamine oxidase catalyzes the oxidation of biogenic amines to produce the corresponding aldehydes and reactive oxygen species. Monoamine oxidase exists on the mitochondrial outer membrane of cells and is widely distributed in the human body, especially in liver, brain and kidney tissue cells with the highest content. There are two types of monoamine oxidase in the human body, one is monoamine oxidase A and the other is monoamine oxidase B. Although the two enzymes share 70% of the same genetic code, they ha...

Claims

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Application Information

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IPC IPC(8): C07D239/91C09K11/06G01N21/64
Inventor 张喆张晶卫先哲颜梅李增军王平
Owner UNIV OF JINAN
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