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Organic compound based on cyanine and application of organic compound

A technology for organic compounds and organisms, applied in the field of detection of monoamine oxidase, which can solve the problems of damage to biological samples, inability to effectively avoid biological autofluorescence interference, and large photobleaching effect of organisms.

Active Publication Date: 2018-04-13
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.

Method used

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  • Organic compound based on cyanine and application of organic compound
  • Organic compound based on cyanine and application of organic compound
  • Organic compound based on cyanine and application of organic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of organic compound of formula I based on cyanine:

[0029] (1) Preparation of Compound 1

[0030] 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. When the solution boiled slightly, ethyl acetate was added to make the solution white crys...

Embodiment 2

[0052] The prepared compound of formula I is used as a probe to detect MAO-A in cells, tissues and organs, and to simulate physiological conditions. The following experiments are all carried out under pH=7.4 conditions (HEPES buffer solution, concentration is 40mM), The probe concentration was 10 μM.

[0053] The ultraviolet response of the compound formula I prepared above to MAO-A:

[0054] 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-A, add 10mL of ultrapure water to make the concentration of MAO-A respectively 0μg mL -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 and equilibrate for 60 minutes, then add the above working solution into the cuvette to measure the ultraviolet absorption spectrum. The changes of the ultravio...

Embodiment 3

[0058] The fluorescence response of the compound of formula I to MAO-A:

[0059] 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-A, add 10mL of ultrapure water to make the concentration of MAO-A respectively 0μg mL -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 60 minutes, then add the above working solution into the fluorescence dish to measure the fluorescence spectrum. The changes of fluorescence spectrum before and after detection of MAO-A are as follows: figure 2 shown. The compound of formula I can be used to realize the detection of MAO-A in organisms.

[0060] Depend on figure 2 Indicates the change of fluorescence intensity of the system with the change of MAO-A concentration, indicating th...

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Abstract

The invention relates to detection of monoamine oxidase, and specifically relates to an organic compound based on cyanine and an application of the organic compound. The organic compound is shown in astructural formula I, and the compound is used as a fluorescent probe for ratio detection of monoamine oxidase A (MAO-A) on mitochondrial outer membranes. According to the compound used as the fluorescent probe for the ratio detection of the MAO-A, in the presence of the MAO-A, a response group is used as a substrate of the MAO-A; and under the action of an FAD coenzyme, methylamino is oxidized to form an aldehyde group under catalysis of the MAO-A, beta-elimination is carried out on a propionaldehyde part, and CO2 is released spontaneously, so that a fluorescent group is released. The organic compound disclosed by the invention is used for the ratio detection of the MAO-A, and in the presence of the MAO-A, obvious displacement of the corresponding fluorescence wavelength occurs, so thatthe organic compound can be used for the detection of the MAO-A, the interference of external detection conditions can be greatly reduced, and the detection precision is improved. According to the compound used as the fluorescent probe for the ratio detection of the MAO-A, when the MAO-A exists, the ultraviolet absorption changes obviously, and an ultraviolet spectrophotometer and naked eyes can be simultaneously used for detection.

Description

technical field [0001] The invention relates to the detection of monoamine oxidase, in particular to a cyanine-based organic compound and its application. Background technique [0002] Monoamine oxidase (monoamine oxidase, MAO, EC1.4.3.4) is a flavin enzyme located on the outer mitochondrial membrane, which catalyzes the oxidation of amines produced in vivo under the synergistic action of FAD coenzymes, including neurotransmitters dopamine, norepinephrine (NE), serotonin (5-HT), tyramine, phenylethylamine (PEA) and neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyrimidine (MPTP), etc. 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. MAO-A and MAO-B maintain the steady state of biogenic amines, including primary amines, secondary amines, tertiary amines, and some long-chain diamines. The amines mainly oxidized by MAO-A are: 5-hydroxy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6558C09K11/06G01N21/33G01N21/64
CPCC07F9/65583C09K11/06C09K2211/1059G01N21/33G01N21/6428G01N21/6486
Inventor 于法标王蕊郭晓艳陈令新
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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