Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Organic compound based on gallocyanine and application thereof

An organic compound and catalytic reaction technology, applied in the field of fluorescent probes, can solve the problems that the external environment cannot simultaneously detect reactive oxygen species, reactive oxygen species cells, and biological damage cannot be fed back in time

Active Publication Date: 2018-02-23
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
View PDF4 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the probe can only detect MAO-B in the visible light region, there is a certain interference from the external environment, and it cannot detect the active oxygen species when MAO-B catalyzes monoamines at the same time. Therefore, the active oxygen species can damage cells and organisms. Can't give feedback in time

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Organic compound based on gallocyanine and application thereof
  • Organic compound based on gallocyanine and application thereof
  • Organic compound based on gallocyanine 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), the organic phase was collected, and rotary evaporated. Put the product after rotary evaporation into a round-bottomed flask, install a reflux device, stir, add about 7.5 ml of dichloromethane to dissolve it completely, heat the solution to a temperature of about 40°C, and reflux. When the solution boiled slightly, ethyl acetate was added to make the solution white crystal...

Embodiment 2

[0051] The prepared compound of formula I was used as a probe in cells, tissues and organs to detect MAO-B and the reactive oxygen species produced by its catalysis, simulating physiological conditions, and the following experiments were all carried out under the condition of pH=7.4 (HEPES buffer solution, the concentration is 40 mM), and the concentration of the probe is 10 μM.

[0052] The ultraviolet response of the compound of formula I prepared above to MAO-B and the active oxygen species produced by its catalysis:

[0053]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-B, add 10mL of ultrapure water to make the concentration of MAO-B 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 ...

Embodiment 3

[0056] The fluorescence response of the compound of formula I to MAO-B and the reactive oxygen species produced by its catalysis:

[0057] 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-B, add 10mL of ultrapure water to make the concentration of MAO-B 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-B are as follows: figure 2 shown. The compound of formula I can be used to realize the detection of MAO-B and the active oxygen species produced by its catalysis in organisms.

[0058] Depend on figure ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a fluorescence probe, in particular to an organic compound based on gallocyanine and application thereof. The structural formula of the organic compound based on the gallocyanine is shown in a first formula, and the compound is used for carrying out linkage detection on a mitochondrial outer membrane. The compound can be taken as the fluorescence probe for detecting MAO-Blevels in and out of cells so as to have an important biomedicine meaning on deeply researching the kinetic mechanisms of the way of MAO-B for catalyzing monoamine substances in a living body, and theproduction and accumulation process of catalysate and especially have an important biomedicine meaning on the physiological action of MAO-B in the living body and the influence of the catalysate to the living body. The formula is shown in the specification.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a cyanine-based organic compound and its application. Background technique [0002] The full name of monoamine oxidase (monoamine oxidase, MAO, EC1.4.3.4) is monoamine-oxygen oxidoreductase, which is a flavoenzyme located on the outer mitochondrial membrane. Amines, oxidative deamination to generate reactive oxygen species, including the neurotransmitters dopamine, norepinephrine (NE), serotonin (5-HT), tyramine, phenylethylamine (PEA), and the neurotoxin 1-methyl-4- Phenyl-1,2,3,6-tetrahydropyrimidine (MPTP), etc. According to its substrate or inhibitor selectivity, cell distribution, immune specificity, etc., it is divided into two subtypes: MAO-A and MAO-B. MAO is widely distributed in various organs in the body, especially in secretory glands, brain, liver, kidney and small intestine. MAO-A and MAO-B maintain the steady state of biogenic amines, including primary amines, secondary am...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6558C09K11/06G01N21/64
CPCC07F9/65583C09K11/06C09K2211/1029C09K2211/1059C09K2211/1096G01N21/6402G01N21/6428G01N21/6486
Inventor 于法标王蕊陈令新韩潇玥
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com