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Specifically marked capsaicin fluorescent probe and synthetic method and application thereof

A technology of fluorescent probe and synthesis method, which is applied in the field of capsaicin fluorescent probe and its synthesis, can solve the problems of inability to visualize the dynamic research of TRPV1 channel, lack of fluorescence characteristics, etc., and achieves long excitation wavelength, mild labeling, and good fat solubility. Effect

Active Publication Date: 2016-02-03
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main TRPV1 endogenous ligand is known to be capsaicin, which itself does not have fluorescent properties, and there is currently no capsaicin-like fluorescent ligand, so it is impossible to visualize and dynamically study the activation and inactivation of TRPV1 channels and other gating processes

Method used

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  • Specifically marked capsaicin fluorescent probe and synthetic method and application thereof
  • Specifically marked capsaicin fluorescent probe and synthetic method and application thereof
  • Specifically marked capsaicin fluorescent probe and synthetic method and application thereof

Examples

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Embodiment 1

[0047]Take 1 equivalent of compound I and 1 equivalent of R=(CH 2 ) 5 Compound II, dissolved in DMF, was added with 1 equivalent of HOBT, 1 equivalent of DCC, and 0.1 equivalent of DMAP, and stirred at room temperature for 24 hours. The organic solvent was removed, and column chromatography was eluted with dichloromethane:methanol=10:1 to obtain the corresponding compound III. It was confirmed by nuclear magnetic spectrum that it was consistent with the target product, and its hydrogen nuclear magnetic resonance spectrum was assigned as follows: 1 HNMR (500MHz, DMSO-d 6 ): δ9.54(s,1H),8.81(s,1H),8.50(t,1H,J=6Hz),8.16(t,1H,J=6Hz),6.79(d,1H,J=1.5Hz ),6.68(d,1H,J=8Hz),6.62(dd,1H,J=8Hz,J=2Hz),6.39(d,1H,J=9Hz),4.13(d,2H,J=5.5Hz) ,3.72(s,3H),3.44(s,2H),2.13(t,2H,J=7.5Hz),1.68(dt,2H),1.57(dt,2H),1.36(d,2H,J=6Hz ). The fluorescence excitation wavelength of the compound in methanol solvent is 466nm, and the emission wavelength is 528nm. In biological activity assays, the compoun...

Embodiment 2

[0049] Take 1 equivalent of compound I and 1 equivalent of R=(CH 2 ) 11 Compound II, dissolved in DMF, was added with 1 equivalent of HOBT, 1 equivalent of DCC, and 0.1 equivalent of DMAP, and stirred at room temperature for 24 hours. The organic solvent was removed, and column chromatography was eluted with dichloromethane:methanol=10:1 to obtain the corresponding compound III. It was confirmed by nuclear magnetic spectrum that it was consistent with the target product, and its hydrogen nuclear magnetic resonance spectrum was assigned as follows: 1 HNMR (500MHz, DMSO-d 6 )δ9.54(s,1H),8.80(s,1H),8.51(d,1H,J=8.5Hz),8.14(t,1H,J=6Hz),6.79(d,1H,J=2Hz) ,6.68(d,1H,J=8Hz),6.62(dd,1H,J=8Hz,J=2Hz),6.40(d,1H,J=9Hz),4.13(d,2H,J=6Hz),3.72 (s,3H),3.45(s,2H),2.09(t,2H,J=7Hz),1.67(dt,2H),1.49(m,2H),1.36(m,2H),1.26(m,12H ). The fluorescence excitation wavelength of the compound in methanol solvent is 467nm, and the emission wavelength is 528nm. In the biological activity test, the comp...

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Abstract

The invention relates to a specifically marked capsaicin fluorescent probe and a synthetic method and application thereof, which belong to the technical field of biology. Firstly, the invention discloses the specifically marked capsaicin fluorescent probe, and the structural formula (III) is as follows, wherein R=(CH2)2, (CH2)3, (CH2)4, (CH2)5, (CH2)6, (CH2)7, (CH2)8, (CH2)9, (CH2)10 or (CH2)11, the excitation wavelength is between 450 and 480 nm, and the emission wavelength is between 510 and 540 nm. The compound provided by the invention has the advantages of good lipid solubility, long excitation wavelength, simplicity and convenience in synthesis, mild markers and the like, and especially, a good tool is provided for the research on comformational change in a membrane protein gating process due to the difference of the fluorescence intensity of the compound in liposoluble and hydrosoluble environments.

Description

technical field [0001] The invention belongs to the field of biotechnology, and relates to a specifically labeled capsaicin fluorescent probe and its synthesis method and application. 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. Among them, the fluorescent detection method of protein has the advantages of flexible labeling method, high sensitivity, and simple detection method, and has been widely used. However, currently only a few institutions in the world have the ability to use fluorescently labeled ligand probes to study the dynamic process of ion channel structure and function. The needle is still functional. Subsequently, by detecting the binding and dissociation effects between the probe and the receptor mem...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D271/12G01N21/64
Inventor 余沛霖宋珍臻罗建红杨巍
Owner ZHEJIANG UNIV
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