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Porphyrin tetraazacyclo-based light-controlled pyroptosis material as well as preparation method and application thereof

A technology of tetranitroheterocycles and nitrogen heterocycles, which is applied in the field of light-controlled pyroptotic materials and its preparation, can solve the problems of short excitation wavelength, high light source energy, and small penetration of photopyrotic materials, and achieve rapid Effects of light-controlled pyroptotic properties, good biocompatibility, and cheap and easy-to-obtain raw materials

Pending Publication Date: 2022-04-08
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application of pyroptosis in photodynamic therapy has not been reported, which is mainly limited by the short excitation wavelength of photopyretic materials, the high energy of the light source itself, and poor penetration, which makes it difficult to penetrate biological body skin
[0003] Aiming at the problems of short laser wavelength (ultraviolet region) and low penetrability of existing light-controlled cell pyroptosis materials, and the energy of the light source itself is relatively large, long-term irradiation will cause certain damage to cells or organisms, etc.

Method used

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  • Porphyrin tetraazacyclo-based light-controlled pyroptosis material as well as preparation method and application thereof
  • Porphyrin tetraazacyclo-based light-controlled pyroptosis material as well as preparation method and application thereof
  • Porphyrin tetraazacyclo-based light-controlled pyroptosis material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1, the synthesis of photopyrotic material

[0029] Below with X=I, Z=Zn is a typical molecule, and its synthetic route is shown in the following formula:

[0030]

[0031] Specific steps are as follows:

[0032] (1) Preparation of compound 1

[0033] First, dissolve 0.4g of zinc acetate in 3mL of methanol solution, dissolve 0.8g of 5,10,15,20-tetrakis(4-pyridyl)porphyrin in 150mL of chloroform solution, mix the two, heat to reflux and Stir the reaction for 30 minutes; after the reaction, wait until the temperature drops to room temperature, extract at least twice with deionized water, collect the organic phase solution, add a large amount of anhydrous sodium sulfate to it to absorb excess water; filter to obtain the supernatant, and spin evaporate the organic phase solution. Solvent, to obtain a dark brown solid is compound 1;

[0034] (2) Preparation of compound 2

[0035] Compound 1 was dissolved in a mixed solution of an appropriate amount of meth...

Embodiment 2

[0039] Example 2, the difference between molecules before and after demethylation

[0040] Take compound 1 and compound 2 respectively, and use the complete culture solution to prepare the concentration of 10 -5 M's solution. A total of three groups of Hela cells were set up, wherein the first group of cells was directly cultured with complete culture medium for 12 h, as the blank control of the first two groups, the second group and the third group of cells were co-cultured with compound 1 and compound 2 solutions for 12 h respectively, and the three groups All culture conditions of the cells were the same. The morphological changes of the three groups of cells under 640nm laser irradiation were observed by laser confocal and compared. It can be seen that after 10 minutes of laser irradiation, the cells of the second group shrank significantly compared with the cells of the first group ( figure 2 ), which is a typical phenomenon of apoptosis, indicating that compound 1 ha...

Embodiment 3

[0041] Example 3, multi-wavelength photo-induced pyroptosis

[0042] Take compound 2 by 10 -5 M concentration was added to Hela cells for culture, and the morphological changes of cells under different wavelength lasers were observed by confocal laser. In the initial state, the cells have a normal irregular shape. With the change of the wavelength of the laser confocal laser (405nm, 488nm, 561nm, 640nm), it can be seen that under the laser of each wavelength, the phenomenon of "bubbling" on the cell surface can be observed after 1 minute, that is, it will start to occur. pyroptosis ( image 3 ). This shows that the material synthesized in the present invention can realize multi-wavelength photopyrotoxicity from ultraviolet light to visible light.

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Abstract

The invention belongs to the technical field of chemical biological materials, and particularly relates to a porphyrin tetraazacyclo-based light-operated pyroptosis material as well as a preparation method and application thereof. The light-controlled pyroptosis material provided by the invention is a porphyrin tetraazacyclo positive ion salt and a related metal complex material thereof, and has a rapid multi-band light-controlled pyroptosis property, the action wavelength can be maximally adjusted to a visible light range of 640nm, the damage of a light source to cells or organisms is greatly reduced, and meanwhile, the light penetrability is also enhanced; the feasibility is provided for the light-operated pyroptosis technology in the field of tumor treatment. The light-controlled pyroptosis material provided by the invention takes an aqueous solution as an environment, so that the light-controlled pyroptosis material is good in biocompatibility and non-toxic; the raw materials are cheap and easy to obtain, synthesis is simple, 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 light-controlled cell pyroptosis material and a preparation method and application thereof. Background technique [0002] As a new type of programmed cell death, pyroptosis is involved in many diseases, so the study of pyroptosis is particularly important. At the same time, since the generation of pyroptosis will activate the immune system in the body and cause a large area of ​​immune response, the application of pyroptosis in tumor treatment has gradually become a new research hotspot. However, the application of pyroptosis in photodynamic therapy has not been reported, which is mainly limited by the short excitation wavelength of photopyretic materials, the high energy of the light source itself, and poor penetration, which makes it difficult to penetrate biological body skin. [0003] Aiming at the existing light-controlled cell pyropt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C09K11/06A61K41/00A61P35/00G01N21/64
Inventor 朱亮亮周璐璐姚先先杨武利
Owner FUDAN UNIV
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