a releasable so 2 Polymers, their preparation methods and applications, and nanomicelles

A polymer, SO2 technology, applied in the direction of drug combination, sulfur/selenium/tellurium active ingredients, emulsion delivery, etc., can solve the problem that the effect of cancer treatment has not been studied, and achieve the improvement of active oxygen level and obvious killing effect. Effect

Active Publication Date: 2020-07-28
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the release of SO 2 The polymer has not been reported, and its therapeutic effect on cancer has not been studied

Method used

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  • a releasable so <sub>2</sub> Polymers, their preparation methods and applications, and nanomicelles
  • a releasable so <sub>2</sub> Polymers, their preparation methods and applications, and nanomicelles
  • a releasable so <sub>2</sub> Polymers, their preparation methods and applications, and nanomicelles

Examples

Experimental program
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Effect test

preparation example Construction

[0043] The present invention provides a SO described in the technical solution 2 The preparation method of polymer, comprises the following steps:

[0044]In the presence of a catalyst and a solvent, the polyethylene glycol monomethyl ether-poly(γ-propargyl-glutamic acid ester) block copolymer having the structure of formula II and the 3-azidopropene having the structure of formula III The base-2,4-dinitrobenzenesulfonamide is reacted by click chemistry to obtain SO with the structure of formula I 2 polymer;

[0045]

[0046] In formula II, 10≤m≤450; 5≤n≤100;

[0047]

[0048] In the present invention, in order to distinguish it from the catalyst in the following technical scheme, the polyethylene glycol monomethyl ether-poly(γ-propargyl-glutamic acid ester) block copolymer with formula II structure and the The catalyst adopted by the 3-azidopropyl-2,4-dinitrobenzenesulfonamide with the structure of formula III through the click chemical reaction is named as the first...

Embodiment 1

[0073] Embodiment 1: the synthesis of 3-azidopropylamine

[0074] Weigh 8.8 g of 3-chloropropylamine hydrochloride and 13.3 g of sodium azide, and add 200 mL of water into the reaction flask. The reaction was stirred at 80°C overnight, and the resulting mixture was adjusted to pH 11 with potassium hydroxide, and then extracted three times with 100 ml of ether. The organic phase was collected and dried over anhydrous magnesium sulfate, and the diethyl ether was removed by rotary evaporation to obtain 3-azidopropylamine as a light yellow oily product.

Embodiment 2

[0075] Embodiment 2: the synthesis of 3-azidopropyl group-2,4-dinitrobenzenesulfonamide with formula III structure

[0076] Weigh 2.0 g of 3-azidopropylamine prepared in Example 1, and dissolve 3.3 g of sodium bicarbonate in 20 ml of anhydrous THF. Weigh 5.5 g of dinitrobenzenesulfonyl chloride, dissolve it in 20 mL of anhydrous THF, slowly add it dropwise and stir in an ice bath, react for 24 hours, acidify the pH value to 1 with hydrochloric acid, and then extract three times with 50 mL of dichloromethane , the organic phase was collected and dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain the yellow-brown product 3-azidopropyl-2,4-dinitrobenzenesulfonamide.

[0077] The 3-azidopropyl-2,4-dinitrobenzenesulfonamide obtained above is detected, figure 2 The proton nuclear magnetic resonance spectrum of the 3-azidopropyl-2,4-dinitrobenzenesulfonamide prepared in Example 2 of the present invention; the results show that the 3-...

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Abstract

The present invention provides a releasable SO 2 The polymer, its preparation method and its application and nano micelles, the polymer has the structure of formula I. The polymer material has amphiphilicity, and in the environment where cysteine ​​or glutathione exists, the dinitrobenzenesulfonamide group in the structure of formula I responds to the sulfhydryl group and undergoes a rearrangement reaction to release SO 2 ; The material self-assembles in aqueous solution to form nanomicelles. The releasable SO provided by the present invention 2 The polymer has good water dispersibility, can be endocytosed by cells, and releases SO under the action of intracellular glutathione 2 , increase the level of reactive oxygen species in cancer cells, and then show a significant killing effect on cancer cells. Releasable SO 2 The polymer nanoparticles were able to reduce the cancer cell survival rate to 11±1%, and the hydrodynamic radius of the nanoparticles was 29±0.1nm.

Description

technical field [0001] The invention relates to the technical field of new polymer materials, in particular to a releasable SO 2 Polymers, their preparation methods and their applications, and nanomicelles. Background technique [0002] Many cancer cells typically produce more intracellular reactive oxygen species (ROS) than normal cells. A certain concentration of ROS can stimulate the occurrence, proliferation and even drug resistance of cancer cells. Correspondingly, in order to maintain the normal metabolism and proliferation of cells under such a high ROS concentration, that is, cancer cells in a state of high oxidative stress, they usually derive a corresponding strength of antioxidant system, including higher concentrations of glutathione and anti-oxidative stress. oxidase, etc. Once this intracellular redox balance is disrupted, it will lead to necrosis or apoptosis of cancer cells. Therefore, by disrupting this redox balance in tumor cells, cancer cells can be e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/48C08G69/40A61K33/04A61K9/107A61P35/00
CPCA61K9/1075A61K33/04C08G69/40C08G69/48
Inventor 肖春生沈伟陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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