Signal-enhanced type near infrared fluorescence probe, preparation method thereof 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: 2017-07-07
SHENZHEN INST OF ADVANCED TECH
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  • 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

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  • Signal-enhanced type near infrared fluorescence probe, preparation method thereof and application
  • Signal-enhanced type near infrared fluorescence probe, preparation method thereof and application
  • Signal-enhanced type near infrared fluorescence probe, preparation method thereof and application

Examples

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Embodiment 1

[0059] A method for preparing a signal-enhanced near-infrared fluorescent probe, comprising the following steps:

[0060] At room temperature, add cystamine dihydrochloride (81mg, 0.36mmol), 1.5mL methanol, 60μL triethylamine, and then add 2mL acetonitrile into a 25mL round-bottomed flask. After stirring rapidly for about 0.5 hours, the solution becomes transparent and cystamine The dihydrochloride is all 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, which was then added dropwise to the above first mixed solution with a dropping funnel at a rate of about 1 drop / 20s, and reacted at 30°C for 3 hours under the protection of nitrogen. Spin off the solvent, purify with a silica gel column, dissolve the sample in dichloromethane, apply the wet method, use dichloromethane:methanol as the eluent for gradient elution from 200:1 to 20:1, spin off th...

Embodiment 2

[0066] A method for preparing a signal-enhanced near-infrared fluorescent probe, comprising the following steps:

[0067] At room temperature, add cystamine dihydrochloride (81mg, 0.36mmol), 1.5mL methanol, 99.84μL triethylamine (0.72mmol) into a 25mL round bottom flask, then add 2mL of DMF, and stir rapidly for about 0.5 hours, Solution becomes transparent, and cystamine dihydrochloride is all dissolved, obtains the first mixed solution;

[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 above-mentioned first mixed solution with a dropping funnel at a rate of about 1 drop / 20s, heat, and react at 75°C for 10 hours under the protection of nitrogen. Spin off the solvent, purify with a silica gel column, dissolve the sample in dichloromethane, apply the wet method, use dichloromethane:methanol as the eluent for gradient elution from 200:1 to 20:1, spin off the solv...

Embodiment 3

[0070] A method for preparing a signal-enhanced near-infrared fluorescent probe, comprising the following steps:

[0071] At room temperature, add cystamine dihydrochloride (81mg, 0.36mmol), 1.5mL methanol, 74.88μL triethylamine (0.54mmol) into a 25mL round bottom flask, then add 2mL of DMF, and stir rapidly for about 0.5 hours, Solution becomes transparent, and cystamine dihydrochloride is all dissolved, obtains the first mixed solution;

[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 above-mentioned first mixed solution with a dropping funnel at a rate of about 1 drop / 20s, heat, and react at 40°C for 5 hours under the protection of nitrogen. Spin off the solvent, purify with a silica gel column, dissolve the sample in dichloromethane, apply the wet method, use dichloromethane:methanol as the eluent for gradient elution from 200:1 to 20:1, spin off the solve...

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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 its preparation method and application. Background technique [0002] Thiols (that is, compounds containing sulfhydryl groups) play a very important role in living systems, for example, glutathione (GSH) can maintain intracellular redox, intracellular signal conversion, etc., cysteine ​​( Cys) can be used as an extracellular reducing agent, a decisive substrate for protein synthesis, etc. The level of certain thiols is directly related to many diseases (such as psoriasis, liver damage, AIDS) and cancer. Since the role of thiols is very important, it is of great significance to develop and study probes for detecting thiols. [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...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/14G01N21/64
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
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