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Selenium-containing photosensitizer as well as preparation method and application thereof

A photosensitizer and reaction technology, applied in the field of biomedicine, can solve the problem of no improvement of tumor metabolism characteristics, and achieve the effect of no drug resistance, significant effect, and no antibiotics

Inactive Publication Date: 2018-06-15
THE THIRD XIANGYA HOSPITAL OF CENT SOUTH UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] How to fight against tumor growth has become a current research hotspot, but there are still some problems, such as patent, application number: CN201611022732.6, publication number: CN106632195A, a research method of Vitex vitae anti-tumor compound, which mentioned The method of extracting anti-tumor compounds in Vitex vitae does not combine the specific metabolic characteristics of tumors to improve the accuracy of the compounds' action on tumors

Method used

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  • Selenium-containing photosensitizer as well as preparation method and application thereof
  • Selenium-containing photosensitizer as well as preparation method and application thereof
  • Selenium-containing photosensitizer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: the synthesis of photosensitizer EtNBSe-PDT

[0038] The synthetic method of EtNBSe-PDT comprises the following steps:

[0039] (1) Acetic acid and α, β-tetrahydropyrrolecarboxylic acid acetic acid are dissolved in 95% ethanol to obtain intermediate product A, and the reaction process is as follows:

[0040]

[0041] The molar ratio of acetic acid to α, β-tetrahydropyrrolecarboxylic acid acetic acid is 1:1-1.5, and the reaction temperature is 50-70°C.

[0042] (2) Will And the intermediate product A that step (1) obtains obtains intermediate product B in the benzene-containing organic solvent sealed heating reaction 6-12 hour, and reaction temperature is about 200 ℃, and its reaction process is as follows:

[0043]

[0044] (3) intermediate product B obtained by step (2) and Heat and stir in aniline, gradually add sodium hydroxide to adjust the pH to 6.5-7.2, react for 5-7 hours, sequentially extract with petroleum ether, ethyl acetate, n-butanol...

Embodiment 2

[0048] Example 2 EtNBSe-PDT causes apoptosis in epithelial cancer Example

[0049] Annexin V is a reagent for detecting cell apoptosis. In normal cells, phosphatidylserine is only distributed on the inner side of the lipid bilayer of the cell membrane. In the early stage of cell apoptosis, the membrane phosphatidylserine (PS) is turned from the inner side of the lipid membrane to outside. Therefore, Annexin V is a sensitive indicator for detecting early cell apoptosis. PI (propidium iodide) is a nuclear staining reagent that can stain DNA. Although PI cannot pass through the living cell membrane, it can pass through the damaged cell membrane and stain the nucleus. Therefore, the combination of Annexin V and PI can stain live and dead cells at the same time. According to flow cytogram analysis, under the action of EtNBSe-PDT, the number of apoptotic cells increased significantly compared with the blank group, which proved that EtNBSe-PDT can induce tumor cell apoptosis to ach...

Embodiment 3

[0055] Example 3 EtNBSe-PDT Induces Cell Apoptosis and Endoplasmic Reticulum Stress Example

[0056] The ASK / JNK signaling pathway is one of the three important signals in the endoplasmic reticulum stress. Activating the ASK / JNK signal can significantly promote the generation of endoplasmic reticulum stress in cells, and increase the expression of GADD153 and GRP78, indicating that the endoplasmic reticulum stress Excited. Caspase-3 is an important indicator of cell apoptosis, and the increase of Caspase-3 expression is an important symbol of cell apoptosis. According to the fluorescent results of immune cells, under the action of EtNBSe-PDT, the expression of Caspase-3 and Bcl-2 changed accordingly, indicating that the apoptosis increased; according to the results of Western Blot, under the action of EtNBSe-PDT, ASK / JNK Signal-related proteins change accordingly, ASK / JNK signaling is activated, and ER stress occurs. It shows that EtNBSe-PDT can obviously activate ASK / JNK si...

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Abstract

The invention discloses a selenium-containing photosensitizer as well as a preparation method and application thereof. A novel selenium-containing photosensitizer with an anti-tumor angiogenesis effect is synthesized for a first time. The selenium-containing photosensitizer can be applied to treatment on skin scale cancer and is remarkable in effect, the dosage of the selenium-containing photosensitizer is far lower than that of 5-ALA in the market, in addition is free of antibiotics, free of drug resistance and small in side effect, and is safe and non-toxic and economic and practical; in addition, because of the limited light penetration function and other factors, a tumor treatment effect can be achieved even for tumor tissue without light dynamic response through tumor angiogenesis inhibition.

Description

technical field [0001] The invention relates to a selenium-containing photosensitizer and its preparation method and application, belonging to the field of biomedicine. Background technique [0002] Epithelial cancer is a kind of skin cancer, and its main features are: it starts as a blemish-like raised mass, with a hard base, a rough surface like a cauliflower, visible telangiectasia, and spike-like cutin at the top. [0003] Photodynamic therapy (PDT) is a new non-invasive or minimally invasive treatment technology that combines light, photosensitizers and oxygen molecules in tissues to selectively destroy diseased tissues through photodynamic reactions to achieve therapeutic purposes. PDT is an emerging medical discipline that is researching and developing the treatment of tumors and other benign diseases. It is another new tumor therapy after traditional tumor therapies such as surgery, radiotherapy, chemotherapy and immunotherapy. It is based on the difference in the c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H1/00C07H19/04A61K41/00A61P35/00
CPCA61K41/0057C07H1/00C07H19/04
Inventor 黄进华康健王臻宋相志陈静郭爱元杨盛波刘波黄芳刘怀政吕侣柳岸赵海福王乙宇刘香贺
Owner THE THIRD XIANGYA HOSPITAL OF CENT SOUTH UNIV
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