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Fluorescence probe and preparation method and application thereof

A technology of fluorescent probes and detection reagents, which is applied in the field of preparation of fluorescent probes for distinguishing normal cells and cancer cells, can solve the problems of expensive instruments, short excitation wavelengths, complicated pretreatment processes, etc., and achieves strong light stability, good The effect of solubility

Active Publication Date: 2018-03-13
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Fluorescent probes have the advantages of high sensitivity, good selectivity, real-time in situ and visualized nondestructive testing, and can also overcome the shortcomings of traditional methods such as complicated sample pretreatment, expensive instruments, and inability to visualize in situ in real time. , fluorescent probes have been widely used in the field of molecular biological detection
However, so far, commercial kits for the detection of γ-glutaminyl transferase on the market use coumarin as a fluorescent group. This fluorescent probe needs to be excited by single photons, with short excitation wavelength and tissue penetration. Low power, difficult for in vivo tumor imaging applications
Especially based on targeting overexpressed γ-glutamine transferase, fluorescent probes to distinguish normal cells from mixed cultured cancer cells have not been reported in the literature

Method used

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  • Fluorescence probe and preparation method and application thereof

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preparation example Construction

[0061] On the other hand, the present invention provides a method for preparing the fluorescent probe having the structure of formula I of the present invention, and the method includes the following steps:

[0062] (1) Compound 1 is prepared by reacting compound 1 with malononitrile in a molar ratio of 1:2~1:4;

[0063]

[0064] (2) Compound 5 is prepared by reacting compound 3 with compound 4 in a molar ratio of 1:1 to 1:2;

[0065]

[0066] (3) Compound 5 is prepared by reacting compound 5 with manganese dioxide in a molar ratio of 1:5~1:10;

[0067]

[0068] (4) Compound 7 is prepared by reacting compound 2 with compound 6 in a molar ratio of 1:1 to 1:2;

[0069]

[0070] (5) The compound of formula I is prepared by reacting compound 7 with trifluoroacetic acid in a molar ratio of 1:50 to 1:200;

[0071]

[0072] In specific embodiments, the above-mentioned fluorescent probe of the present invention can be prepared by the following method:

[0073] (1) Using 10ml of ethanol as the rea...

Embodiment 1

[0090] The solubility test of fluorescent probe in PBS (10mM pH 7.4) buffer solution.

[0091] Prepare the mother liquor of the fluorescent probe with dimethyl sulfoxide solvent in a volumetric flask. Then use a micro-injector to sample and prepare solutions with concentrations of 0, 5, 10, 15, 20, 25, 30, 40, 50, 60, and 80 μM, and scan them with an ultraviolet-visible absorption spectrometer to obtain the following Figure 1a UV-Vis absorption spectrum. Take the absorption intensity (Abs) at the position of the maximum absorption peak as the ordinate and the concentration as the abscissa ( Figure 1b ). It is found that as the concentration continues to increase, the concentration and absorption intensity show a strong linear relationship (R 2 = 0.9999), indicating that the fluorescent probe of the present invention has good solubility in PBS (10 mM pH 7.4) buffer solution.

Embodiment 2

[0093] Investigate the ultraviolet-visible absorption and fluorescence emission experiments of fluorescent probes in common different solvents.

[0094] 5μM fluorescent probe was added to dichloromethane (DCM), ethyl acetate (EA), acetonitrile (ACN), methanol (MeOH), ethanol (EtOH), dimethyl sulfoxide (DMSO), dimethyl methyl Scan the UV-visible absorption spectra of amide (DMF) and PBS (10 mM pH 7.4) buffer solutions ( Figure 2a ) And fluorescence spectrum ( Figure 2b ). In most solvents, the position of the absorption peak of the probe is basically unchanged, only the absorption peak in DMF has a significant blue shift. The fluorescent probe emits the strongest in DMSO solution.

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Abstract

Disclosed are a fluorescence probe and a preparation method an application thereof. The fluorescence probe is of a structure as shown in the formula I, which is a long-wavelength fluorescence probe with excellent two-photon performance and designed on the basis of intramolecular Charge Transfer (TCT) mechanism. By means of gamma-transglutaminase which is in over-expression on the surface of targeted cancel cells, recognition sites are cut off by enzyme selectively, strong electron-donating groups are then released, and thus long-wavelength fluorescent light is strengthened. The fluorescence probe has excellent solubility and high light stability, is free of influence from acidity and basicity, is featured by double-photon laser, and the like. Besides, the fluorescence probe realizes confocal fluorescence imaging selectively to cancel cells.

Description

Technical field [0001] The invention belongs to the field of fine chemicals, and relates to a preparation method and application of a fluorescent probe for distinguishing normal cells from cancer cells. Background technique [0002] With the deterioration of the living environment and the increase of life pressure, the number of humans suffering from cancer is showing a trend of rapid increase. According to statistics, there were 14.1 million new cancer patients worldwide in 2015, and the death toll was as high as 8.2 million. It is estimated that new cases will increase by 70% in the next 20 years. Due to the delay of diagnosis and the lack of effective personalized treatment plans, the inefficiency of treatment for cancer patients is as high as 75%. For an ordinary family, it often brings a catastrophic blow. Although the government invests a large amount of research funding every year in the hope of conquering the treatment of cancer. But for now, through the "early detecti...

Claims

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Application Information

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IPC IPC(8): C07D307/68C09K11/06G01N21/64
CPCC07B2200/07C07D307/68C09K11/06C09K2211/1007C09K2211/1088G01N21/64
Inventor 彭孝军李海东姚起超樊江莉杜健军
Owner DALIAN UNIV OF TECH
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