Ursolic acid-aspirin conjugate and application thereof in preparing drugs for preventing tumor metastasis

A technology for aspirin and tumor metastasis, applied in ursolic acid-aspirin conjugates and its application fields, can solve the problems of lack of selectivity, toxic and side effects of chemotherapy drugs, and reduce the efficacy of drugs, and achieve the effect of preventing and treating lung metastasis

Inactive Publication Date: 2015-12-02
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most chemotherapeutic drugs lack selectivity and are widely distributed in the body, which can easily cause toxic side effects, cause patients intolerance, and reduce the efficacy of drugs

Method used

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  • Ursolic acid-aspirin conjugate and application thereof in preparing drugs for preventing tumor metastasis
  • Ursolic acid-aspirin conjugate and application thereof in preparing drugs for preventing tumor metastasis
  • Ursolic acid-aspirin conjugate and application thereof in preparing drugs for preventing tumor metastasis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] At room temperature, 0.5g of acetylsalicylic acid (aspirin) was dissolved in 20mL of dry dichloromethane, 2mL of oxalyl chloride was added, magnetically stirred for 10h, and the gas and solvent were evaporated under reduced pressure. Add 20mL of dichloromethane to the reaction bottle again, add dropwise to 20mL1v / 1v pyridine:dichloromethane mixed solution dissolved with 1.27g ursolic acid and 0.1eqDMAP through the constant pressure funnel, and continue stirring for 8-10h after the dropwise addition is completed . After the reaction was complete, dichloromethane was distilled off under reduced pressure. Add 100mL water to the reaction bottle to precipitate the product, filter it with suction, wash the filter cake with 500mL water until neutral, dry it in vacuum, and get ASP-UA by column chromatography.

[0030] Properties: white powder; yield: 70.51%; product characterization data are as follows: 1HNMR (500MHz, CDCl3) δ10.52 (s, 1H), 7.93 (dd, J=8.0, 1.6Hz, 1H), 7.55–7....

Embodiment 2

[0034] After digesting mouse breast cancer cells MCF-7 in the logarithmic growth phase, the cell density was adjusted to 1×10 5 cells / mL, seeded in a 96-well plate, 100 μl per well, placed at 37°C, 5% CO 2 Cultivate in the incubator for 24 hours; remove the old medium, add the medium for the test drug to dilute the stock solution of the test drug, set different concentrations, 100 μl per well, and set up a blank control group, and set 5 replicates in each group. hole. After 24 hours of drug action, discard the drug-containing medium, add 100 μl of blood-free phenol red-free 1640 medium to each well, then add 100 μl of 0.5 mg / ml MTT solution, and continue incubation for 4 hours, then terminate the culture; carefully aspirate and discard 96 Add 100 μl DSMO to each well of the supernatant of the well plate, shake for 10 minutes, measure the light absorption value (OD value) of each well on a microplate reader at a wavelength of 570 nm, and calculate the cell survival rate (%) = ...

Embodiment 3

[0037] The fibronectin FN (fibronectin) stored at -20°C was placed in a 37°C water bath until it was completely melted, and the serum-free culture medium was used to prepare the FN working solution with a concentration of 10 μg / ml. Use 100 μL / well FN working solution to completely cover the 96-well plate, leave it at room temperature overnight, and gently suck off the liquid. Take MCF-7 cells in the logarithmic growth phase and make a single cell suspension with a cell concentration of 5×10 5 / ml, mixed with different concentrations of drugs (0, 5, 10, 15, 20 μ M), inoculated in FN-coated 96-well plates. 37℃,5%CO 2 After incubation for 2 hours, wash lightly with PBS 3 times, add 100 μl of MTT culture solution after drying, continue to incubate for 4 hours, discard the supernatant, add 100 μl DMSO, and detect the OD value at 570 nm with an enzyme-linked detector after dissolution. Adhesion inhibition rate (%)=(1-average OD value of medication group / average OD value of blank c...

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Abstract

The invention relates to a ursolic acid-aspirin conjugate shown in a formula (I) and application thereof in preparing drugs for preventing tumor metastasis. In vivo experiments verify that the ursolic acid-aspirin conjugate provided by the invention has a remarkable inhibitory effect on adhesion, migration, invasion and the like of tumor cells. in vivo animal experiments verify that the ursolic acid-aspirin conjugate can be used for reducing experimental pulmonary metastasis of 4T1 breast cancer of a rat and showing a relatively good tumor metastasis resisting effect. The ursolic acid-aspirin conjugate provided by the invention can be applied to preventive drugs for tumor metastasis, thereby providing novel selection for developing new drugs for tumor metastasis and preventing postoperative retransfer of malignant tumors. The formula (I) is shown in the description.

Description

technical field [0001] The invention relates to an ursolic acid-aspirin conjugate and its application, in particular to an ursolic acid-aspirin conjugate and its application in the preparation of drugs for preventing and treating tumor metastasis. Background technique [0002] Malignant tumors are one of the major diseases that seriously endanger human health. Most of the deaths of cancer patients are caused by late metastasis of malignant tumors. Tumor metastasis (Cancer metastasis) refers to the process of tumor cells dissociated from the primary tumor, infiltrating into surrounding tissues, invading into the circulatory system, and then metastasizing in vivo, and adhering and infiltrating with endothelial cells to form metastases. Tumor metastasis is one of the main reasons for tumor refractory and recurrence, and also a key factor leading to the death of tumor patients. Clinical diagnosis results show that more than 60% of newly diagnosed cancer patients have metastasiz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61K31/616A61P35/04
Inventor 邵敬伟汤乔刘亚军杨祥
Owner FUZHOU UNIV
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