Preparation method of polyamino acid segmented copolymer and polyamino acid segmented copolymer hydrogel

A technology of block copolymer and polyamino acid, which is applied in the directions of non-active ingredient medical preparations, pharmaceutical formulations, aerosol delivery, etc., can solve the problem of ineffective enhancement of cancer cell endocytosis, and achieve good biocompatibility Sexuality and biodegradability, enhanced endocytosis effect

Active Publication Date: 2013-03-13
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
View PDF2 Cites 13 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no reductive difference between most tumor tissues and normal tissues, so the polyethylene glycol in the micelles is not easy to fall off, and cannot effectively enhance the endocytosis of the carrier by cancer cells

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of polyamino acid segmented copolymer and polyamino acid segmented copolymer hydrogel
  • Preparation method of polyamino acid segmented copolymer and polyamino acid segmented copolymer hydrogel
  • Preparation method of polyamino acid segmented copolymer and polyamino acid segmented copolymer hydrogel

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0034] The embodiment of the present invention discloses a preparation method of a polyamino acid block copolymer, comprising the following steps:

[0035] reacting the compound represented by formula (I), L-cystine-N-endocarboxylic anhydride and amino acid-N-endocarboxylic anhydride in an organic solvent to obtain a polyamino acid block copolymer;

[0036]

[0037] Wherein R is hydrogen or methyl, preferably methyl;

[0038] The number average molecular weight of the compound represented by formula (I) is 500-30000.

[0039] The present invention uses the compound represented by formula (I), L-cystine-N-internal carboxylic acid anhydride and amino acid-N-internal carboxylic anhydride as raw materials to prepare the polyamino acid block copolymer. Under the initiation of the compound represented by formula (I), L-cystine-N-endocarboxylic anhydride and amino acid-N-endocarboxylic anhydride undergo ring-opening polymerization, wherein L-cystine-N-endocarboxylic anhydride Th...

Embodiment 1

[0061] Weigh 30g of N-(2-hydroxyethyl)phthalimide and 300ml of toluene to remove water azeotropically, then slowly add 0.285g of p-toluenesulfonic acid and 15.3ml of 2-methanol Oxypropylene. React in an ice bath for 1h. Then azeotrope with toluene to remove water for 3h, after cooling to room temperature, add 36ml triethylamine to terminate the reaction, and add 9ml acetic anhydride to neutralize unreacted N-(2-hydroxyethyl)phthalimide. The resulting product was recrystallized three times with 50ml of ethyl acetate, then refluxed for 12h in 6M sodium hydroxide solution, and extracted three times with 50ml of chloroform and isopropanol mixed solution with a volume ratio of 1:1 after cooling to room temperature. The phase was dried overnight with anhydrous magnesium sulfate, and the solvent was removed by a rotary evaporator to obtain an acid-sensitive diethylamino ketal, that is, a compound represented by formula (II), with a yield of 68.2%.

Embodiment 2~6

[0063] Weigh 20g of polyethylene glycol monomethyl ether with number average molecular weight of 1000 (0.02mol), 2000 (0.01mol), 5000 (0.004mol), 10000 (0.002mol) and 20000 (0.001mol) respectively, put into 5 In a dry reaction flask with a branch, add 100mL pyridine respectively, then add 30.02g (0.3mol), 15.01g (0.15mol), 6.01g (0.06mol), 3.02g (0.03mol) and 1.50g ( 0.0015mol) succinic anhydride, reacted 72h at 25 DEG C. After the reaction was completed, it was neutralized with 100ml of saturated sodium bicarbonate solution, washed three times with 50ml of ethyl acetate, extracted three times with 50ml of chloroform, dried, concentrated, and settled to finally obtain the compound shown in formula (III). The compound represented by the formula (III) was analyzed by nuclear magnetic resonance, and its number average molecular weight was calculated. See Table 1 for the results.

[0064] The number-average molecular weight and the productive rate of the compound shown in the for...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
degree of polymerizationaaaaaaaaaa
degree of polymerizationaaaaaaaaaa
degree of polymerizationaaaaaaaaaa
Login to view more

Abstract

The invention provides a preparation method of a polyamino acid segmented copolymer, which comprises the steps of: carrying out reaction on a compound shown by formula (I), L-cystine-N-inner carboxylic acid anhydride and amino acid-N-inner carboxylic acid anhydride in an organic solvent to obtain the polyamino acid segmented copolymer, wherein the number-average molecular weight of the compound shown by formula (I) is 500-30000. The invention further provides a polyamino acid segmented copolymer hydrogel which comprises the polyamino acid segmented copolymer obtained by the method and an aqueous medium. The amino acid-N-inner carboxylic acid anhydride provided by the invention has pH sensitivity and reductive sensitivity, and is beneficial for enhancing endocytosis of cancer cells when the amino acid-N-inner carboxylic acid anhydride is used as a carrier so as to release entrapped medicine effectively. In addition, the polyamino acid segmented copolymer hydrogel obtained by the invention has good biocompatibility and biodegradability.

Description

technical field [0001] The invention relates to the field of polymer drug carriers, in particular to a preparation method of a polyamino acid block copolymer and a polyamino acid block copolymer hydrogel. Background technique [0002] Malignant tumors are becoming one of the most serious diseases threatening human health. The difference between tumor tissue and normal tissue lies in the low pH value of its microenvironment, while the internal environment of tumor cells is characterized by low oxygen, low sugar, low pH value and high glutathione concentration. [0003] At present, the commonly used clinical cancer treatment methods include chemotherapy, radiotherapy and surgery. Among them, chemotherapy is the most commonly used and important treatment approach. However, clinically used antineoplastic drugs still face problems such as poor water solubility and stability, and large toxic and side effects on normal tissues. In order to solve these problems, drugs can be comb...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/40C08J3/075C08L77/00A61K47/34A61K9/06
Inventor 丁建勋石丰华庄秀丽陈莉陈学思
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap