Porphyrin-chrysin compounds and anti-tumor activity thereof

A technology of porphyrin and compound, which is applied in the field of porphyrin-chrysin complex, can solve the problems of poor water solubility, easy metabolism and inactivation, and achieve the effect of broadening the scope and reducing the side effects of killing

Active Publication Date: 2019-06-21
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its poor water solubility, intestinal absorption

Method used

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  • Porphyrin-chrysin compounds and anti-tumor activity thereof
  • Porphyrin-chrysin compounds and anti-tumor activity thereof
  • Porphyrin-chrysin compounds and anti-tumor activity thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Synthesis of porphyrin-chrysin complex

[0038] .

[0039] Add 2 (110.1 mg) / 3 (118.1 mg) / 4 (101.8 mg), (0.15 mmol) to a 100 mL three-necked flask, add an appropriate amount of baked potassium carbonate and potassium iodide as a catalyst, and then add 40 mL of DMF As a solvent, the reaction was stirred and refluxed at 80°C (65°C, 4). After 30 min, chrysin derivatives 1a (1b, 1c, 1d, 1e) (0.18 mmol) were added, and the reflux reaction was continued for about 8 h. The reaction was monitored by TLC until the raw material point remained unchanged. Pour the cooled reaction solution into a separatory funnel, extract the reaction product with dichloromethane solvent, and wash with water several times to remove impurities such as DMF solvent, potassium carbonate, and potassium iodide. After removing water from the organic solvent, the solvent was spin-dried by a rotary evaporator, and the remaining solid was separated and purified by silica gel column chromatograph...

Embodiment 2

[0054] Example 2 MTT colorimetric assay for in vitro anti-tumor cell activity

[0055] Cell inoculation: Digest gastric cancer cell MGC-803 and cervical cancer cell Hela cultured in monolayer with 0.25% trypsin, respectively, and use 10% concentration of calf serum (containing 1×10 5 U·L -1 Penicillin and 1×10 5 U·L -1 Streptomycin) RPMI-1640 culture medium to culture cells in 96-well culture plate at 5×10 per well 3 A cell suspension was inoculated with a volume of 150 µL per well. Only the same amount of culture medium was added to the blank group. And add a blank PBS solution to the outermost circle of the inoculation plate. Culture cells: transfer the seeded 96-well plate to 37 ℃, 5% CO 2 The incubator continued to cultivate for about 48 h until the cell monolayer covered the bottom of the well.

[0056] Carefully suck off the supernatant in the wells of the 96-well plate with a pipette gun, and add 150 μL of the compound solution to be tested prepared in advance ...

Embodiment 3

[0063] Example 3 Cell cycle distribution experiment

[0064] Dosing: Hela cells were seeded on a 6-well plate at about 100,000 cells per well, and placed in an incubator for 24 hours. With the drug (4a) concentration gradient of 0 (Control), 20, 40, and 60 μM, set up 2 auxiliary wells for each concentration, add the drug, and continue to cultivate for 48 h. After the first 4 hours, the orifice plates with 4 concentrations were taken out, and the 12 W LED purple light was used to continuously irradiate for 10 min at a distance of 20 cm from the 6-well plate, and then put into the incubator to continue culturing.

[0065] Fixation: Aspirate the drug-containing medium and wash with PBS, digest the cells with trypsin, centrifuge the cell suspension, and wash three times with PBS. Add 1 mL of 70% ethanol at 4 °C to each sample, resuspend the cells, cover the lid, and place in a 4 °C environment for 12 h.

[0066] Staining: After 12 h, centrifuge and wash twice in the same way. A...

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Abstract

The invention synthesizes novel porphyrin-chrysin derivatives. Porphyrin molecules are used as a carrier, the tumor tissue aggregation effect of the porphyrin molecules is used, meanwhile, the property that the porphyrin molecules can produce singlet oxygen to kill tumor cells is used and combined with natural anti-tumor activity of chrysin, so that the novel anti-tumor compounds are obtained, anda new direction is provided for research on anti-tumor drugs.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of porphyrin-chrysin complexes, a preparation method and uses thereof. Background technique [0002] In modern society, the incidence of cancer is getting higher and higher, and the mortality rate is always high. Traditional chemotherapy drugs non-specifically block cell division and cause cell death. While killing cancer cells, they also destroy the growth of normal human cells, causing many toxic and side effects. [0003] Photodynamic therapy is a new technology that began to be applied to tumor treatment in the late 1970s, but it has developed rapidly and has been approved by the relevant departments of the United States, Britain, Germany, Japan and many other countries to enter clinical application. So far, this therapy has been successfully used to treat a variety of malignant tumors. [0004] The basic elements of photodynamic therapy can be divided into: photo...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61P35/00A61K31/352A61K31/409A61K47/54
Inventor 刘运美刘鼎张奇志李洋杨静刘振华何军
Owner NANHUA UNIV
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