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Organic compound and application thereof

A technology for organic compounds and organisms, applied in the field of fluorescent probes for ratiometric detection of monoamine oxidase, can solve the problems of poor positioning of mitochondria, inability to effectively avoid biological autofluorescence interference, and lack of positioning groups

Active Publication Date: 2018-02-23
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the probe can only detect MAO-A in the ultraviolet region before the reaction, which cannot effectively avoid the interference of biological autofluorescence. At the same time, ultraviolet light has a great photobleaching effect on organisms and is easy to damage biological samples.
Not only that, the probe does not have a positioning group and cannot be well positioned to the mitochondria. Therefore, it is of great significance to develop a fluorescent probe with good selectivity that can be linked to detect MAO in biological systems in the near-infrared region.

Method used

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  • Organic compound and application thereof
  • Organic compound and application thereof
  • Organic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of organic compound of formula I based on cyanine:

[0028] (1) Preparation of Compound 1

[0029] Under the protection of argon, (4-bromobutyl)triphenylphosphine bromide (14.35g, 30mmol) and sodium azide (3.9g, 60mmol) were dissolved in 50mL DMF. Stir overnight at 90°C. The color of the solution ranges from colorless to light yellow to red. The reaction flask was cooled to room temperature, and 50 mL of dichloromethane was added until a large amount of precipitation occurred. Filter and collect the filtrate. The collected filtrate was extracted with ethyl acetate and water 1:1 (v / v), and the organic phase was collected and rotary evaporated. Put the product after rotary evaporation into a round bottom flask, install a reflux device, stir, add about 7.5 ml of dichloromethane to make it completely dissolved, heat to a solution temperature of about 40°C, and reflux. reflow. When the solution boiled slightly, ethyl acetate was added to make the solution w...

Embodiment 2

[0043] The prepared formula I compound is used as a probe to detect MAO in cells, tissues and organs, simulating physiological conditions, and the following experiments are all carried out under the condition of pH=7.4 (HEPES buffer solution, concentration is 40mM), the probe The concentration was 10 μM.

[0044] The ultraviolet response of the compound of formula I prepared above to MAO:

[0045] pH was controlled with HEPES buffer solution. Add the compound of formula I to a 10mL colorimetric tube to ensure its final concentration is 10μM, then add 40mM HEPES, then add MAO, add 10mL of ultrapure water to make the concentration of MAO respectively 0μgmL -1 , 1 μg mL -1 , 2 μg mL -1 , 3 μg mL -1 , 4 μg mL -1 , 5 μg mL -1 , 6 μg mL -1 , 7 μg mL -1 , 8 μg mL -1 , 9 μg mL -1 , 10 μg mL -1 . Shake the solution well and equilibrate for 100 minutes, then add the above working solution into a cuvette to measure the ultraviolet absorption spectrum. The changes of UV absor...

Embodiment 3

[0048] The fluorescence response of the compound of formula I to MAO:

[0049] pH was controlled with HEPES buffer solution. Add the compound of formula I to a 10mL colorimetric tube to ensure its final concentration is 10μM, then add 40mM HEPES, then add MAO, add 10mL of ultrapure water to make the concentration of MAO respectively 0μgmL -1 , 1 μg mL -1 , 2 μg mL -1 , 3 μg mL -1 , 4 μg mL -1 , 5 μg mL -1 , 6 μg mL -1 , 7 μg mL -1 , 8 μg mL -1 , 9 μg mL -1 , 10 μg mL -1 . Shake the solution evenly and equilibrate for 100 minutes, then add the above working solution into the fluorescence dish to measure the fluorescence spectrum. The changes of the fluorescence spectrum before and after the detection of MAO are as follows: figure 2 shown. The compound of formula I can be used to realize the detection of MAO in organisms.

[0050] Depend on figure 2 Indicates the change of fluorescence intensity of the system with the change of MAO concentration, indicating that...

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Abstract

The invention relates to a ratio-based monoamine oxidase (MAO) detection fluorescent probe, and particularly relates to an organic compound and application thereof. The compound is as shown in a structural formula I. The compound as the fluorescent probe is used in ratio-detection of MAO on an outer membrane of mitochondrion. The compound is used for detecting MAO based on ratio. When MAO exists,corresponding fluorescent wavelength displaces obviously, so as to be used for MAO detection, interference of an external detection condition is greatly reduced, and the detection accuracy is improved. According to the compound used as the fluorescent probe detecting MAO based on ratio, when MAO exists, ultraviolent absorption changes obviously, and an ultraviolent spectrophotometer and naked eyescan be used for detecting. The compound can be used as a fluorescent probe to detect MAO levels in and out of cells, thereby having biomedical significance in deep research of a manner of catalyzingmonoamine substance through MAO in organisms as well as kinetic mechanisms of production and accumulation of catalyzed products, particularly the physiological action of MAO in the organism and the impact of catalyzed products on life health of the organisms.

Description

technical field [0001] The invention relates to a fluorescent probe for ratiometric detection of monoamine oxidase (MAO), in particular to an organic compound and its application. Background technique [0002] Monoamine oxidase (monoamine oxidase, MAO, EC1.4.3.4) is an oxidoreductase located on the outer mitochondrial membrane, which catalyzes the oxidation of amines produced in vivo under the synergistic action of FAD coenzyme, including neurotransmitters dopamine, norepinephrine (NE), serotonin (5-HT), tyramine, phenylethylamine (PEA) and neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyrimidine (MPTP), etc., To maintain the amine balance in the organism. Due to being edited by different genes, MAO is divided into two subtypes: MAO-A and MAO-B, which differ in their substrate or inhibitor selectivity, cell distribution, and immune specificity. The enzyme is mainly distributed in the brain and liver of vertebrates. When the content of MAO in the brain is abnormal, it can...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6558C09K11/06G01N21/64
CPCC07F9/65583C09K11/06C09K2211/1029C09K2211/1059C09K2211/1096G01N21/6402G01N21/6428G01N21/6486
Inventor 陈令新王蕊王猛于法标
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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