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Near-infrared fluorescent probe for identifying glutathione and its preparation and application

A fluorescent probe, glutathione technology, applied in the direction of fluorescence/phosphorescence, luminescent materials, chemical instruments and methods, etc., can solve the problems of inability to selectively identify glutathione, lack of specificity, etc., and achieve good real-time tracking and quantification, high sensitivity and specificity, low photon absorption effect

Active Publication Date: 2020-08-28
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The recognition groups of the existing probes for GSH imaging all contain a sulfonate structure, which can be combined with cysteine ​​(Cys), homocysteine ​​(Hcy), glutathione in biological systems (GSH) The sulfhydryl groups in the three structures react to produce a fluorescent response, so there is a lack of specificity, and it is impossible to selectively recognize glutathione to detect the content of GSH in the organism

Method used

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  • Near-infrared fluorescent probe for identifying glutathione and its preparation and application
  • Near-infrared fluorescent probe for identifying glutathione and its preparation and application
  • Near-infrared fluorescent probe for identifying glutathione and its preparation and application

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preparation example Construction

[0049] The preparation method of the above-mentioned probe, in general, can use 2,3,3-trimethyl-3H-indole, cyclohexanone as the starting material, through methyl substitution, and N,N-dimethyl formaldehyde Amide condensation, and then the two undergo Aldol condensation reaction to obtain cyanine dyes, and finally react cyanine dyes with anilines to obtain near-infrared fluorescent probes containing Schiff base structures. For any one of the above preparation methods, the solvent can be selected from: acetonitrile, methanol, N,N-dimethylformamide, water, ethyl acetate, petroleum ether; the reaction temperature can be selected arbitrarily within the range of 25°C-100°C .

[0050] Of course, it is also possible to directly use commercially available cyanine dyes as raw materials and directly react them with anilines to obtain near-infrared fluorescent probes containing Schiff base structures.

[0051] The on-off near-infrared fluorescent probe of the present invention can be use...

Embodiment 1

[0054] In the present invention, the on-off near-infrared fluorescent probe HCG that can be used for glutathione detection in living cells and living bodies (such as mice) has a synthetic route as shown in the following reaction formula:

[0055]

[0056] 2,3,3-trimethyl-3H-indole and cyclohexanone can be used as starting materials, and the on-off near-infrared fluorescent probe HCG can be obtained through 4-step reaction; the preparation process is simple and the operation steps Less, strong maneuverability. Concrete reaction step can be as follows:

[0057][1] Add 2,3,3-trimethyl 3H indole (1g, 6.28mmol) and methyl iodide (1.2g, 8.45mmol) solution to acetonitrile, and reflux in an oil bath at 100°C for 12h. The reaction was monitored by thin layer chromatography (TLC). After the reaction was completed, the mixture was cooled to room temperature. The solvent was evaporated under reduced pressure, and the crude product was precipitated and filtered to obtain a pink solid...

Embodiment 2

[0062] About the fluorescent response of the on-off near-infrared fluorescent probe HCG to glutathione (GSH):

[0063] The final concentration of fixed HCG was 10 μM, the final concentration of GSH was (0, 10, 20, 40, 60, 80, 100, 200, 500, 1000 μM), reacted at 37 ° C for 15 minutes, and measured the concentration curve. The results showed that: the fluorescence intensity value with time or GSH The concentration increases, and has a good linear relationship. The calculated detection limit is 0.25 μM, indicating that the off-off near-infrared fluorescent probe can quantitatively detect GSH under the physiological condition of pH=7.4. At the same time, it is found that the probe itself has only a short wave peak (450nm), and after reacting with glutathione, it shows as a long emission peak (653nm) (such as figure 1 a to d in), indicating that the probe has on-off optical properties.

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Abstract

The invention belongs to the technical field of biological fluorescence analysis, and discloses a near-infrared fluorescent probe used for identifying glutathione as well as a preparation and application of the probe. The probe includes a structure represented by a chemical structural formula shown in the specification, wherein R1, R2 are independently selected from halogen atoms, (CH2)nR3, (CH2)mOR4, NO2, CN, NH2, CONHNH2, COOR5 or (CH2CH2O)pR6. According to the probe provided by the invention, the design of a key chemical structure of the probe is improved, a Schiff base structure is used asa recognition group, a hemicyanine structure is used as a fluorophore, the novel recognition group can specifically react with the glutathione to avoid interference of cysteine and homocysteine, andthe obtained turn-on near-infrared fluorescent probe can quantitatively detect the glutathione in biological samples in a more sensitive manner.

Description

technical field [0001] The invention belongs to the technical field of bioluminescent analysis, and more specifically relates to a near-infrared fluorescent probe for identifying glutathione and its preparation and application. The near-infrared fluorescent probe is an on-off near-infrared fluorescent probe. The needle uses a new recognition group to specifically recognize glutathione, can quickly recognize glutathione, and can detect glutathione in aqueous solution, living cells and mice. Background technique [0002] Intracellular biothiols mainly include reduced glutathione (GSH), cysteine ​​(Cys), homocysteine ​​(Hcy), etc. They play important roles in many biological processes. Notably, glutathione is widely distributed in organisms and can be used as a biomarker of intracellular biothiols. According to literature reports, glutathione (GSH) can improve the body's immunity and anti-aging ability in physiological processes, and is a good physiological antioxidant. Howe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/14C09K11/06G01N21/64
CPCC07D209/14C09K11/06C09K2211/1014C09K2211/1029G01N21/6428
Inventor 张玉聂刚王凯平汪会玲郑子明崔政吴止境
Owner HUAZHONG UNIV OF SCI & TECH
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