A signal-enhanced near-infrared fluorescent probe and its preparation method and application

A fluorescent probe and signal enhancement technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of inability to avoid tissue self-absorption and self-fluorescence, inability to detect pH in cells and living bodies, and small displacement of stocks and other problems, to avoid tissue self-absorption and self-fluorescence, less damage to cells and living bodies, and less background interference

Active Publication Date: 2019-08-13
SHENZHEN INST OF ADVANCED TECH
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Fluorescent probes are one of the means to effectively detect thiols in the living body. Compared with other detection methods, the use of fluorescent probes for thiol detection has the advantages of high sensitivity and good selectivity, but most of the current pH probes have short wavelengths. , cannot avoid tissue self-absorption and auto-fluorescence, strong background interference, small displacement of some stocks, large overlap between ultraviolet absorption spectrum and fluorescence spectrum, low signal-to-noise ratio, high toxicity, and cannot be used for pH detection of cells and living organisms

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
  • A signal-enhanced near-infrared fluorescent probe and its preparation method and application
  • A signal-enhanced near-infrared fluorescent probe and its preparation method and application
  • A signal-enhanced near-infrared fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] A preparation method of signal-enhanced near-infrared fluorescent probe includes the following steps:

[0060] At room temperature, add cystamine dihydrochloride (81 mg, 0.36 mmol), 1.5 mL methanol, 60 μL triethylamine, and 2 mL acetonitrile to a 25 mL round bottom flask at room temperature. After stirring quickly for about 0.5 hours, the solution becomes transparent and cystamine The dihydrochloride is completely dissolved to obtain the first mixed solution;

[0061] Then put (Abbreviated as Cy.7.Cl, 345.6mg, 0.54mmol) was dissolved in 4mL of acetonitrile to obtain the second mixed solution, and then it was added dropwise to the above-mentioned first mixed solution with a dropping funnel at a rate of about 1 drop / 20s, react at 30°C for 3 hours under nitrogen protection. Spin off the solvent, purify with a silica gel column, dissolve the sample in dichloromethane, load the sample by wet method, use dichloromethane: methanol for gradient elution from 200:1 to 20:1, spin of...

Embodiment 2

[0066] A preparation method of signal-enhanced near-infrared fluorescent probe includes the following steps:

[0067] At room temperature, add cystamine dihydrochloride (81mg, 0.36mmol), 1.5mL methanol, 99.84μL triethylamine (0.72mmol) in a 25mL round bottom flask, then add 2mL DMF, and stir quickly for about 0.5 hours. The solution becomes transparent, cystamine dihydrochloride is completely dissolved, and the first mixed solution is obtained;

[0068] Then put (Abbreviated as Cy.7.Cl, 919.44mg, 1.44mmol) was dissolved in 4mL of DMF to obtain the second mixed solution, which was then added dropwise to the first mixed solution with a dropping funnel at a rate of approximately 1. Drop / 20s, heat, and react at 75°C for 10 hours under nitrogen protection. Spin off the solvent, purify with a silica gel column, dissolve the sample in dichloromethane, load the sample by wet method, use dichloromethane: methanol for gradient elution from 200:1 to 20:1, spin off the solvent, and concentra...

Embodiment 3

[0070] A preparation method of signal-enhanced near-infrared fluorescent probe includes the following steps:

[0071] At room temperature, add cystamine dihydrochloride (81mg, 0.36mmol), 1.5mL methanol, 74.88μL triethylamine (0.54mmol) in a 25mL round-bottom flask, then add 2mL DMF, and stir quickly for about 0.5 hours. The solution becomes transparent, cystamine dihydrochloride is completely dissolved, and the first mixed solution is obtained;

[0072] Then put (Abbreviated as Cy.7.Cl, 919.44mg, 1.44mmol) was dissolved in 4mL of DMF to obtain the second mixed solution, which was then added dropwise to the first mixed solution with a dropping funnel at a rate of approximately 1. Drop / 20s, heat, and react at 40°C for 5 hours under nitrogen protection. Spin off the solvent, purify with a silica gel column, dissolve the sample in dichloromethane, load the sample by wet method, use dichloromethane: methanol for gradient elution from 200:1 to 20:1, spin off the solvent, and concentrat...

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 provides a signal-enhanced type near infrared fluorescence probe, wherein the chemical structural formula is shown as FORMULA (1); in Formula (I), X1 is -S or -Se-, R' is C1-12 alkylene, X2 is -C(CH3)2-, -O-, -S- or Se-; R1 and R2 are independently selected from H atom, C1-18 alkyl or radical groups shown in SO3R5, wherein R5 is C1-18 alkyl or benzyl; R3 and R4 are independently selected from C1-18 alkyl or benzyl; Y is fluorine, chlorine, bromine or iodine. The activating and emitting lights of the probe are located in the near infrared zone; the stocks displacement is big, the background disturbance is few; the probe has high sensitivity and high selectivity for sulfur alcohol; meanwhile, the probe is low in toxicity, small in harm of cell and living body, and very suitable for detecting sulfur alcohol in a biological body. The invention further provides a preparation method of the probe and an application thereof.

Description

Technical field [0001] The invention relates to the technical field of organic probe molecules, in particular to a signal-enhanced near-infrared fluorescent probe and a preparation method and application thereof. Background technique [0002] Thiols (ie, sulfhydryl-containing compounds) play a very important role in life systems. For example, glutathione (GSH) can maintain intracellular redox, intracellular signal conversion, etc., cysteine ​​( Cys) can be used as an extracellular reducing agent and a decisive substrate for protein synthesis. The level of certain thiols is directly related to many diseases (such as psoriasis, liver damage, AIDS) and cancer. Because the role of thiols is very important, the development and research of probes for detecting thiols is of great significance. [0003] Fluorescent probes are one of the effective methods for detecting thiols in the body. Compared with other detection methods, the use of fluorescent probes for thiol detection has the advan...

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 Patents(China)
IPC IPC(8): C07D209/14C09K11/06G01N21/64
CPCC07D209/14C09K11/06C09K2211/1029G01N21/6428
Inventor 蔡林涛孟晓青龚萍张利吕亚琳吴亚运郑明彬盛宗海陈驰
Owner SHENZHEN INST OF ADVANCED TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap