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Antitumor drug based on PGA-RB (Polyglutamic Acid-Rose Bengal) bound compound and preparation method and application of antitumor drug

A technology of tetrachlorotetraiodofluorescein and anti-tumor drugs, which is applied in the direction of anti-tumor drugs, drug combinations, pharmaceutical formulations, etc., can solve the problems such as no reports of tetrachlorotetraiodofluorescein sodium drug polymers, and achieve in vivo time The effect of long circulation, good water solubility, and long blood circulation time

Inactive Publication Date: 2015-04-08
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there is no report on the drug polymer obtained by reforming tetrachlorotetraiodofluorescein sodium

Method used

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  • Antitumor drug based on PGA-RB (Polyglutamic Acid-Rose Bengal) bound compound and preparation method and application of antitumor drug
  • Antitumor drug based on PGA-RB (Polyglutamic Acid-Rose Bengal) bound compound and preparation method and application of antitumor drug
  • Antitumor drug based on PGA-RB (Polyglutamic Acid-Rose Bengal) bound compound and preparation method and application of antitumor drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Preparation of antitumor drugs based on polyglutamic acid and tetrachlorotetraiodofluorescein bond

[0038] (1) Synthesis of tetrachlorotetraiodofluorescein-ethylamine (reaction principle sees figure 1 ):

[0039] ①Dissolve sodium tetrachlorotetraiodofluorescein (1.05g, 1.03mmol) and 2-bromoethylamine hydrobromide (0.45g, 2.20mmol) in 20mL of anhydrous DMF, and react in an oil bath at 80°C for 6h;

[0040] ② After the reaction is completed, evaporate the DMF to dryness under reduced pressure, add 50 mL of anhydrous ether, centrifuge, and wash three times;

[0041] ③Add 50mL water, centrifuge and wash 3 times;

[0042] ④Recrystallize in 10mL of methanol, filter and drain to obtain tetrachlorotetraiodofluorescein-ethylamine.

[0043] tetrachlorotetraiodofluorescein-ethylamine 1 H NMR (DMSO-d 6 ) characterization see figure 2 .

[0044](2) Synthesis of polyglutamic acid and tetrachlorotetraiodofluorescein bond (reaction principle see image 3 ):

[0045...

Embodiment 2

[0050] Example 2 Cytotoxicity measurement

[0051] Taking the polyglutamic acid and tetrachlorotetraiodofluorescein bond (hereinafter referred to as the bond) prepared in Example 1 as an example, the MTT (3-(4,5- Dimethylthiazole-2)-2,5-diphenyltetrazolium bromide) method was used to detect the cytotoxicity of the conjugate to cancer cell Bcap-37. Specific steps are as follows:

[0052] The Bcap-37 cells were respectively treated with the bond (final concentrations were 0.8mg / mL, 0.27mg / mL, 0.089mg / mL, 0.030mg / mL, 0.0099mg / mL, 0.0033mg / mL, 0.00037mg / mL, 0.00012mg / mL) (lighting experiment group and non-lighting experiment group), equal concentration of sodium tetrachlorotetraiodofluorescein (RB light group, RB non-light group), and equal concentration of linear polyglutamic acid (PGA group) After 3 hours, light was applied to the light experiment group and the RB light group for 1 hour (fluorescent lamp, with a wavelength of 500-600 nm) (the non-light experiment group, the RB...

Embodiment 3

[0054] Example 3 Blood Clearance Speed ​​Test

[0055] Taking the polyglutamic acid and tetrachlorotetraiodofluorescein bonded compound prepared in Example 1 as an example, inject the same medicine (10 mg / kg) containing the equivalent of tetrachlorotetraiodofluorescein sodium to the tail vein of mice, and regularly take Blood, every 0.05ml of blood is precipitated with 0.95ml of acetonitrile, centrifuged to get the supernatant, and utilizes the fluorescence linear relationship (564nm excitation, 596nm emission) of the drug in an organic solvent to measure the drug concentration in the plasma. The results are as follows: Figure 8 shown. It can be seen that the in vivo circulation time of polyglutamic acid and tetrachlorotetraiodofluorescein-bonded nanoparticles prepared in Example 1 is longer than that of the small-molecule drug of tetrachlorotetraiodofluorescein sodium.

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Abstract

The invention discloses an antitumor drug based on a PGA-RB (Polyglutamic Acid-Rose Bengal) bound compound and a preparation method and application of the antitumor drug. The structural formula of the antitumor drug is shown as Formula I, wherein the bonding rate of RB is 5-30 percent. According to the invention, RB is modified to obtain an RB derivative, the RB derivative is bound with PGA to obtain the antitumor drug, the antitumor drug can be self-assembled in a water solution into nanometer particles of 100-200 nm, and the nanometer particles have the advantages of high stability, good biocompatibility, long in-vivo circulation time, obviously enhanced toxicity to cancer cells under light, and the like; and the preparation method has simple steps and is convenient to operate.

Description

technical field [0001] The invention belongs to the field of pharmacy, and in particular relates to an antitumor drug based on a bonded polyglutamic acid and tetrachlorotetraiodofluorescein, and a preparation method and application thereof. Background technique [0002] Malignant tumor is a disease that seriously endangers human health, and its incidence is increasing year by year. According to data from the Cancer Prevention and Control Office of the Ministry of Health, in the past 20 years, one out of every four to five deaths in China has died of cancer, which has become the number one killer threatening national health. There are about 2.6 million cancer cases and 1.8 million deaths in my country every year. [0003] Surgery and chemotherapy are currently the main methods for treating tumors. They all exist the big shortcoming to bodily injury. As a new treatment method, photodynamic therapy injects a specific photosensitizer into the body, and the photosensitizer wil...

Claims

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Application Information

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IPC IPC(8): A61K41/00A61K47/48A61K9/14A61P35/00
Inventor 唐建斌王天宇刘祥瑞申有青
Owner ZHEJIANG UNIV
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