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A kind of ethidium bromide derivative and its preparation and application in antitumor

A technology of ethidium bromide and derivatives, which is applied in the field of medicine, can solve the problems of tumor treatment failure, poor selectivity, and inability to effectively reach the action target, so as to reduce the level of reduced glutathione and increase the level of oxidative free radicals. Level and effect of large medical application value

Active Publication Date: 2019-04-09
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these anti-tumor drugs have poor selectivity for tumor treatment, resulting in relatively large toxic and side effects during treatment.
Moreover, these therapeutic drugs cannot effectively reach the target, resulting in lower therapeutic effect
In order to improve the therapeutic effect on tumors, the method of increasing the dosage is usually adopted, which further leads to multidrug resistance of tumor cells, and finally leads to the failure of tumor treatment.

Method used

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  • A kind of ethidium bromide derivative and its preparation and application in antitumor
  • A kind of ethidium bromide derivative and its preparation and application in antitumor
  • A kind of ethidium bromide derivative and its preparation and application in antitumor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of Antitumor Drug Compound 1:

[0038]

[0039] (1) EB (230 mg) was dissolved in 50 mL of a mixed solvent of trifluoroacetic acid / acetonitrile / dichloromethane with a volume ratio of 0.01:1:4. The mixture was protected with nitrogen and stirred at 0°C for 10 minutes.

[0040] (2) Sodium nitrite (150 mg) was added to the mixture obtained in step (1), and the mixture was kept at 0°C and stirred for 5 minutes.

[0041] (3) Add sulfamic acid (200mg) into the reaction solution obtained in step (2), and keep stirring at 0°C for 10 minutes.

[0042] (4) Dissolve N,N-diethylaniline (200 μL) in 2 mL of trifluoroacetic acid / acetonitrile / dichloromethane mixed solvent with a volume ratio of 0.01:1:4, and add it to the reaction solution obtained in step (3) , kept stirring at 0°C for 60 minutes.

[0043] (5) After the reaction, the reaction solution obtained in step (4) was diluted with dichloromethane, washed with water three times, and the organic phase was collected...

Embodiment 2

[0048] Synthesis of antitumor drug compound 2:

[0049]

[0050] (1) EB (230 mg) was dissolved in 50 mL of a mixed solvent of trifluoroacetic acid / acetonitrile / dichloromethane with a volume ratio of 0.01:1:4. The mixture was protected with nitrogen and stirred at 0°C for 5 minutes.

[0051] (2) Sodium nitrite (150 mg) was added to the mixture obtained in step (1), and the mixture was kept at 0° C. and stirred for 10 minutes.

[0052] (3) Add sulfamic acid (200mg) into the reaction solution obtained in step (2), keep stirring at 0°C for 5 minutes.

[0053](4) Dissolve N,N-bis(2-chloroethyl)aniline (200 μL) in 2 mL of trifluoroacetic acid / acetonitrile / dichloromethane mixed solvent with a volume ratio of 0.01:1:4, and add to step (3 ) in the resulting reaction solution, kept stirring at 0°C for 60 minutes.

[0054] (5) After the reaction, the reaction solution obtained in step (4) was diluted with dichloromethane, washed with water three times, and the organic phase was coll...

Embodiment 3

[0059] Breast cancer cells (4T1 cells) and African green monkey kidney cells (COS7 cells) were divided into 1 × 10 5 Cells / well were seeded into confocal small dishes and cultured in 1 mL RPMI-1640 medium at 37°C. After 24 hours, the anti-tumor compound 2 was dissolved in the medium, and 1 mL of the medium containing the anti-tumor compound 2 (20 μmol / L) was added to the breast cancer cells and Vero cells. After culturing for 2 hours, the medium containing the anti-tumor compound 2 was aspirated, the cells were washed three times with PBS buffer solution, and the nuclei were labeled with Hoechst 33342, and then the fluorescence intensity of the anti-tumor compound 2 in the cells was observed with a confocal laser microscope.

[0060] The result is as image 3 As shown, compared with the African green monkey kidney cells, the anti-tumor compound 2 has a better enrichment effect on breast cancer cells, indicating that the anti-tumor compound 2 has a good targeted enrichment eff...

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Abstract

The invention discloses an ethidium bromide derivative as well as preparation and application in tumor resistance and belongs to the technical field of medicines. The ethidium bromide derivative disclosed by the invention has the following structural general formula, wherein R is H or halogen elements. The ethidium bromide derivative disclosed by the invention can realize targeted enrichment of tumor cells, has a mitochondrial targeting effect, has an excellent selective inhibition effect on the tumor cells and can be used for preparing antitumor medicines. The preparation of the ethidium bromide derivative disclosed by the invention is simple and efficient and has extremely high medical application value. The structural formula is as shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to an ethidium bromide derivative and its preparation and application in antitumor. Background technique [0002] Tumor is a major disease that threatens human health, and targeted tumor therapy is a major topic in the fields of clinical medicine, biomedicine and life science research. Drug therapy is an effective method to inhibit tumor growth and improve the quality of life of patients, and is widely used in clinical cancer treatment. Traditional antineoplastic drugs include doxorubicin, paclitaxel, cisplatin, camptothecin, etc. However, these anti-tumor drugs have poor selectivity for tumor treatment, thus causing relatively large toxic and side effects during the treatment process. Moreover, these therapeutic drugs cannot effectively reach the target, resulting in a lower therapeutic effect. In order to improve the therapeutic effect on tumors, the method of incr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/12A61K31/473A61P35/00
CPCC07D221/12
Inventor 张先正李仕颖成红曾旋
Owner WUHAN UNIV
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