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GSH/ROS double-sensitive polymer capable of being completely degraded, and preparation method and application thereof

A completely degradable, polymer technology, applied in the field of GSH/ROS dual-sensitive polymer and its preparation, can solve the problems of the tumor microenvironment cannot achieve rapid response, the carrier material cannot be completely degraded, and the single redox sensitivity can achieve rapid response. and large release, convenient application, good in vivo stability

Active Publication Date: 2020-02-04
THE SEVENTH AFFILIATED HOSPITAL SUN YAT SEN UNIV SHENZHEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, many redox-responsive drug delivery platforms have been developed based on the tumor-specific microenvironment, but there are still problems such as the carrier material cannot be completely degraded into harmless substances, and a single redox-sensitive ability cannot achieve rapid response to the complex tumor microenvironment, etc. problem, needs to be further improved

Method used

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  • GSH/ROS double-sensitive polymer capable of being completely degraded, and preparation method and application thereof
  • GSH/ROS double-sensitive polymer capable of being completely degraded, and preparation method and application thereof
  • GSH/ROS double-sensitive polymer capable of being completely degraded, and preparation method and application thereof

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Effect test

Embodiment 1

[0056] The synthesis of the fully degradable GSH / ROS double sensitive polydisulfide amide polymer Cys-0E of embodiment 1

[0057] The synthesis of GSH / ROS double sensitive polymer Cys-0E comprises the following steps:

[0058] (1) L-cystine dimethyl ester dihydrochloride ((L-Cys-OMe) 2 2HCl) dehydrochlorination treatment: L-cystine dimethyl ester dihydrochloride (5g, 14.66mmol) was placed in a conical flask, dissolved in 20mL saturated sodium carbonate solution and stirred at room temperature for 20min; after the reaction, The above solution was extracted with dichloromethane and repeated 3 times; the extract was dried with a certain amount of anhydrous sodium sulfate for 3 hours, and finally rotary evaporated to obtain a yellow oily dehydrochlorination product with a yield of 54.96%;

[0059] (2) Synthesis of Cys-0E: put the dehydrochlorination acid product (5.33g, 19.88mmol) into a 100mL round-bottomed flask and add a certain amount of chloroform to dissolve it, and slowly ...

Embodiment 2

[0060] The synthesis of the fully degradable GSH / ROS double sensitive polydisulfide amide polymer Cys-0E of embodiment 2

[0061] 1, the synthesis of GSH / ROS double sensitive polymer Cys-0E, comprises the following steps:

[0062] (1) L-cystine dimethyl ester dihydrochloride ((L-Cys-OMe) 22HCl) dehydrochlorination treatment: L-cystine dimethyl ester dihydrochloride (5g, 14.66mmol) was placed in a conical flask, dissolved in 30mL saturated sodium carbonate solution and stirred at room temperature for 30min; after the reaction, The above solution was extracted with dichloromethane and repeated 3 times; the extract was dried with a certain amount of anhydrous sodium sulfate for 5 hours, and finally rotary evaporated to obtain a yellow oily dehydrochlorination product with a yield of 56.86%;

[0063] (2) Synthesis of Cys-0E: put the dehydrochlorination acid product (5.33g, 19.88mmol) into a 100mL round-bottomed flask and add a certain amount of chloroform to dissolve it, and slow...

Embodiment 3

[0064] The synthesis of the fully degradable GSH / ROS double sensitive polydisulfide amide polymer Cys-0E of embodiment 3

[0065] 1, the synthesis of GSH / ROS double sensitive polymer Cys-0E, comprises the following steps:

[0066] (1) L-cystine ethyl ester dihydrochloride dehydrochlorination treatment: L-cystine ethyl ester dihydrochloride (14.66mmol) was placed in a conical flask, dissolved in 30mL saturated sodium bicarbonate solution and Stir at room temperature for 30 min; after the reaction, extract the above solution with dichloromethane and repeat 3 times; dry the extract with a certain amount of anhydrous sodium sulfate for 4 h, and finally rotary evaporate to obtain a yellow oily dehydrochlorination product with a yield of 53.69 %;

[0067] (2) Synthesis of Cys-0E: put the dehydrochlorination acid product (5.33g, 19.88mmol) into a 100mL round bottom flask and add a certain amount of dichloromethane to dissolve it, slowly drop it into In the oxalyl chloride solution ...

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Abstract

The invention discloses a GSH / ROS double-sensitive polymer capable of being completely degraded, and a preparation method and an application thereof. Natural cystine ester containing a disulfide bondand oxalyl chloride, which are used as raw materials, are ued to synthesize a novel carrier material polymer Cys-0E with an oxalate-like bond and the disulfide bond, and the polymer material can be successfully assembled to form a targeted delivery nano-system for efficiently loading various hydrophilic and hydrophobic drugs. Drug-loaded nano-particles constructed by a nano-precipitation technology have remarkable GSH / ROS dual responsiveness, and have the advantages of small particle size, high drug loading capacity, good in-vivo stability and specific tumor targeting; and complete degradationof the carrier and rapid and large-scale release of the entrapped drug are realized under the action of a tumor redox environment, so efficient inhibition of tumors in vitro and vivo is achieved. TheGSH / ROS double-sensitive polymer has the advantags of simplicity in synthesis, convenience in application, greenness, environmental friendliness, and promising application in the field of biologicaldrugs.

Description

technical field [0001] The invention belongs to the technical fields of functional polymer materials and biomedicine. More specifically, it relates to a fully degradable GSH / ROS dual-sensitive polymer and its preparation method and application. Background technique [0002] Cancer, also known as malignant tumor, is a disease that seriously endangers human life and health. Given the high morbidity and mortality of cancer, it has been given increasing attention. At present, the common treatment methods for cancer mainly include surgery, radiotherapy, chemotherapy and biological therapy, and these methods are usually used in combination for tumor treatment in clinic. According to statistics, 1 / 3 of cancer patients undergo surgery and radiotherapy, and 2 / 3 undergo chemotherapy. Therefore, chemotherapy, as an adjuvant therapy to surgery or radiotherapy, plays an important role in combined therapy. However, the systemic administration of chemotherapy and the hydrophobicity of ...

Claims

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Application Information

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IPC IPC(8): C08G69/42A61K9/51A61K47/34A61K31/337A61P35/00
CPCC08G69/42A61K9/5146A61K31/337A61P35/00
Inventor 康洋吴钧李丹丹张铷和
Owner THE SEVENTH AFFILIATED HOSPITAL SUN YAT SEN UNIV SHENZHEN
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