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Trimethyl cyanine fluorescence probe used for protein labeling and synthetic method thereof

A technology of fluorescent probe and synthesis method, applied in the field of biological macromolecular labeling, can solve problems such as poor water solubility and long linking group, and achieve the effects of small flexibility, improved rigidity, and poor water solubility.

Inactive Publication Date: 2014-07-30
WUHAN INST OF PHYSICS & MATHEMATICS CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The object of the present invention is to provide a kind of trimethylcyanine class fluorescent probe that is used for protein labeling, this probe introduces the compound of indole trimethylcyanine class into hydrophilic sulfonic acid group, improves water solubility ; Reduce the distance between the connection site and the fluorescent group, and improve the rigidity of the probe; thereby solving the problems of poor water solubility and long connection groups of protein fluorescent probes

Method used

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  • Trimethyl cyanine fluorescence probe used for protein labeling and synthetic method thereof
  • Trimethyl cyanine fluorescence probe used for protein labeling and synthetic method thereof
  • Trimethyl cyanine fluorescence probe used for protein labeling and synthetic method thereof

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Embodiment 1

[0038] A method for synthesizing a trimethylcyanine fluorescent probe for protein labeling, the method is carried out in the following steps:

[0039] Take 1 equivalent of the potassium salt of Compound I with R=H and 1.2 equivalents of the sodium salt of Compound II with X=Cl, dissolve them in acetonitrile, add 1.5 equivalents of sodium acetate and 1.5 equivalents of chloroacetic anhydride, and stir at room temperature for 1 hour. The solvent was removed by rotary evaporation, and column chromatography was eluted with methanol: acetone = 1:7 to obtain the corresponding compound III. The resulting 1 equivalent of compound III was reacted with 1.1 equivalent of potassium iodide in a solvent of methanol:chloroform=1:1 at 60°C for 24 hours, filtered, and the solvent was removed by rotary evaporation to obtain the corresponding final product IV. It was confirmed by NMR that it was consistent with the target product.

Embodiment 2

[0041] A method for synthesizing a trimethylcyanine fluorescent probe for protein labeling, the method is carried out in the following steps:

[0042] Take 1 equivalent of the sodium salt of compound I with R=H and 1.2 equivalents of the sodium salt of compound II with X=Br, dissolve them in chloroform, add 2 equivalents of sodium acetate and 2 equivalents of chloroacetic anhydride, and stir at room temperature for 1.2 hours. The solvent was removed by rotary evaporation, and column chromatography was eluted with methanol: acetone = 1:5 to obtain the corresponding compound III. The resulting 1 equivalent of compound III was reacted with 1.5 equivalents of sodium iodide in a solvent of methanol:chloroform=1:2 at 70°C for 20 hours, filtered, and the solvent was removed by rotary evaporation to obtain the corresponding final product IV. NMR showed that it was consistent with the target product.

Embodiment 3

[0044] A method for synthesizing a trimethylcyanine fluorescent probe for protein labeling, the method is carried out in the following steps:

[0045] Take R=-COCH 3 0.7g of potassium salt of compound I and 0.38g of potassium salt of compound II of X=Br are dissolved in 10ml of N,N-dimethylformamide, and 0.43g of chloroacetic anhydride and 0.2g of acetic acid are added sodium, and stirred at room temperature for 1 hour. The solvent was removed by rotary evaporation, and column chromatography was eluted with methanol: acetone = 1:5 to obtain the corresponding compound III. The obtained 0.30 g of compound III was reacted with 1 g of sodium iodide in a solvent of methanol:chloroform=1:1 at 65°C for 24 hours, filtered, and the solvent was removed by rotary evaporation to obtain 0.32 g of the corresponding final product IV. NMR showed that it was consistent with the target product.

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Abstract

The invention relates to a new fluorescence probe used for protein labeling and a synthetic method thereof. The compound is prepared by the condensation of two water soluble indole compounds, by reaction of an iodoacetamide group of the compounds and mercapto groups of proteins, fixed-point fluorescent labeling of the proteins can be realized. The compound has the advantages of good water solubility, high molar absorptivity, longer excitation wavelengths, easy synthesis, mild protein labeling conditions, and the like. The probe can be used for fixed-point fluorescent labeling of the proteins, and has a great help for the study on protein structure, function and dynamics characteristics. Excitation emission wavelength of the probe is in the range of 500-600nm, the probe has a short linking group, can be used for more accurate description on the protein structure, dynamics characteristics and biological functions.

Description

technical field [0001] The present invention relates to biomacromolecule labeling, more specifically to a water-soluble near-infrared fluorescent probe for protein labeling. Background technique [0002] The structure, movement and function of proteins are of great significance to the movement of living organisms. The means of studying protein structure and dynamics include fluorescence spectroscopy, nuclear magnetic resonance, electron microscopy, X-ray crystallography, etc. Fluorescence analysis of protein has the advantages of high sensitivity and simple detection method and has been widely used. The method is to label fluorescent probes at the corresponding sites, and describe the structure, movement and function of proteins by observing their fluorescent properties. [0003] Sanjiachuan cyanine compounds are near-infrared fluorescent dyes, the excitation and emission wavelengths are generally 500-600nm, and the quantum yield is high, which can effectively avoid the ba...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09B23/06G01N21/64C07K1/13C07D209/08
Inventor 顾新华阳雨虹唐淳
Owner WUHAN INST OF PHYSICS & MATHEMATICS CHINESE ACADEMY OF SCI
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