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Polyarylthiopyridine positive ion salt light-controlled cell pyroptosis material as well as preparation method and application of polyarylthiopyridine positive ion salt light-controlled cell pyroptosis material

A technology of arylthiopyridine and ylthiopyridine, which is applied in the field of polyarylthiopyridine positive ion salt light-controlled pyroptosis materials and its preparation, can solve the problem of unreachable pyroptosis and uncontrollable pyroptosis process and other issues, to achieve the effects of easy large-scale commercialization, good biocompatibility, and cheap and easy-to-obtain raw materials

Active Publication Date: 2021-02-09
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are mainly two ways to achieve pyroptosis: PAMP (pathogen associated molecular patterns) and DAMP (damage associated molecular patterns), but these two methods cannot achieve fixed-point and timing cell pyroptosis, and there are certain limitations in operation. , and the whole process of pyroptosis is uncontrollable

Method used

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  • Polyarylthiopyridine positive ion salt light-controlled cell pyroptosis material as well as preparation method and application of polyarylthiopyridine positive ion salt light-controlled cell pyroptosis material
  • Polyarylthiopyridine positive ion salt light-controlled cell pyroptosis material as well as preparation method and application of polyarylthiopyridine positive ion salt light-controlled cell pyroptosis material
  • Polyarylthiopyridine positive ion salt light-controlled cell pyroptosis material as well as preparation method and application of polyarylthiopyridine positive ion salt light-controlled cell pyroptosis material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1 (synthesis of photoluminescence material)

[0031] The synthesis of compound 1, the specific steps are as follows:

[0032] Add 12 mmol of ethyl 4-mercaptobenzoate, 1 mmol of hexachlorobenzene into 20 mL of DMF solvent, and simultaneously add 24 mmol of K 2 CO 3 , reacted at 60°C for 60 hours under a nitrogen atmosphere, and stopped the reaction; when cooled to room temperature, 100 mL of distilled water was added to produce a yellow precipitate, which was purified by column chromatography after filtration, and the eluent was ethyl acetate and petroleum ether (1:3 ) to obtain compound 1 with a yield of 72%.

[0033] The synthesis of compound 2, the specific steps are as follows:

[0034] Add 20 mL of THF to 1 mmol of compound 1 to dissolve it, then add 20 mL of 1.5 M sodium hydroxide aqueous solution, and react at room temperature for 24 hours; after the reaction, add 30 mL of 2 M hydrochloric acid to precipitate an orange-yellow precipitate; After filt...

Embodiment 2

[0042] Example 2 (macromolecule binding luminescent phenomenon)

[0043] Take the solution of the concentration obtained in step 3, dilute it 10 times with deionization, take 3 mL in a cuvette, detect the emission peak in the wavelength range of 385 nm ~ 600 nm, and obtain the absorption spectrum under 365 nm light as figure 1 As shown in the gray curve of the emission spectrum, the solution emits almost no light. Take 1 mL of the diluted solution, add 0.5 mg of DNA aqueous solution dropwise to it continuously, place the mixed solution in a cuvette, use 365 nm as the excitation wavelength, and detect the emission spectrum between 385 nm and 600 nm. The maximum emission wavelength was obtained at 535 nm, and the luminous intensity increased significantly with the increase of DNA content ( figure 2 ).

Embodiment 3

[0044] Example 3 (specific markers)

[0045] The solution with the concentration obtained in step 3 was diluted 100 times, and the standard mitochondrial fluorescent probe was added to Hela cells containing 10 μM for culture, and laser confocal imaging was used. The cultured cells were illuminated and imaged. At this time, it can be seen that the position of the compound 4 solution in the cell is completely consistent with the position of the mitochondria, indicating that the compound 4 can specifically reach the mitochondria of the cell ( figure 2 ).

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Abstract

The invention belongs to the technical field of organic light-emitting materials, and particularly relates to a polyarylthiopyridine positive ion salt light-controlled cell pyroptosis material as wellas a preparation method and application of the polyarylthiopyridine positive ion salt light-controlled cell pyroptosis material. The polyarylthiopyridine positive ion salt material provided by the invention has no luminescence phenomenon and no AIE characteristic, but has strong phosphorescence phenomenon after being combined with biomacromolecules such as DNA, BSA, HS and the like; after the material enters cells, under the irradiation of 405nm ultraviolet light, the cells can quickly generate a cell pyroptosis phenomenon, namely, the material shows the characteristic of light-controlled cell pyroptosis; and as a light-controlled cell pyroptosis material, the light-controlled cell pyroptosis material can specifically reach cell mitochondria after entering cells, mark the mitochondria andaccurately display the position of the cell mitochondria, so that the light-controlled cell pyroptosis material can be applied to biological cell imaging. The light-controlled cell pyroptosis material takes an aqueous solution as an environment, so that the light-controlled cell pyroptosis material is good in biocompatibility and non-toxic; and synthesis is simple, raw materials are cheap and easy to obtain, and large-scale commercialization is easy.

Description

technical field [0001] The invention belongs to the technical field of organic light-emitting materials, and in particular relates to a polyarylthiopyridinium positive ion salt light-controlled pyroptosis material and its preparation method and application. Background technique [0002] Pyroptosis is a new type of cell death, and its mechanism and process are still not completely clear. Usually, pyroptosis is accompanied by a strong intracellular inflammatory response due to the activation of inflammasome NLRP3. An appropriate amount of inflammatory response is beneficial for the body to clean up internal inflammatory factors and repair damaged tissues. At present, there are mainly two methods to achieve pyroptosis: PAMP (pathogen associated molecular patterns) and DAMP (damage associated molecular patterns), but these two methods cannot achieve fixed-point and timing cell pyroptosis, and there are certain limitations in operation. , and the whole process of pyroptosis is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/75C09K11/06G01N21/63
CPCC07D213/75C09K11/06G01N21/63C09K2211/1014C09K2211/1029
Inventor 朱亮亮周璐璐
Owner FUDAN UNIV