A core-shell structured chitosan-based nano-prodrug that co-loads doxorubicin and platinum drugs and its preparation method and application

A technology of platinum-based drugs and core-shell structure, which is applied in the direction of drug combinations, pharmaceutical formulas, and medical preparations of non-active ingredients. Clear, simple effect of drug loading

Active Publication Date: 2021-09-07
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, chitosan itself is insoluble in water, which greatly limits its application range.

Method used

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  • A core-shell structured chitosan-based nano-prodrug that co-loads doxorubicin and platinum drugs and its preparation method and application
  • A core-shell structured chitosan-based nano-prodrug that co-loads doxorubicin and platinum drugs and its preparation method and application
  • A core-shell structured chitosan-based nano-prodrug that co-loads doxorubicin and platinum drugs and its preparation method and application

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preparation example Construction

[0043]A preparation method of a core-shell structured chitosan-based nano-prodrug co-loaded with doxorubicin and platinum drugs of the present invention is as follows: firstly, 3,3'-dithiodipropionyl Hydrazine is bonded to chitosan derivatives to obtain hydrazide chitosan derivatives. At the same time, doxorubicin is linked to 3,3'-dithiodipropionyl hydrazide through a hydrazone bond to obtain hydrazide doxorubicin Then the aqueous solution of hydrazidated chitosan derivatives, hydrazidated doxorubicin and platinum drugs is mixed evenly, and the core-shell structure type chitosan-based nano-prodrug is obtained through the self-assembly process, which specifically includes the following steps:

[0044] (1) Preparation of hydrazidated chitosan derivatives: Aldehydated furan solution is added dropwise to water-soluble chitosan solution, aldehyde groups and amino groups undergo a Schiff base reaction, and are reduced by sodium cyanoborohydride to form Furanated chitosan derivative...

Embodiment 1

[0066] (1) Preparation of hydrazidated hydroxyethyl chitosan: 3-(2-furyl) acrolein solution with a mass concentration of 0.33% was added dropwise to 1.0% hydroxyethyl chitosan (MW = 170kDa) solution and mix well, the molar ratio of 3-(2-furyl) acrolein to amino group in hydroxyethyl chitosan is 10:8, at 30℃ and N 2 React under the atmosphere for 12h, then add the sodium cyanoborohydride solution with a mass concentration of 0.6%. The amount of sodium cyanoborohydride is 1.3 times the number of Schiff base bonds. 2 The reduction reaction was continued for 12 hours under the atmosphere to form a furanated hydroxyethyl chitosan crude product, which was dialyzed in deionized water for 72 hours with a dialysis bag with a molecular weight cut-off of 3500 Da and then freeze-dried to obtain furanated hydroxyethyl chitosan;

[0067] Be that the mass concentration of 1.0% maleimide caproic acid solution is 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide solution and 0.57mmol mass concent...

Embodiment 2

[0079] (1) Preparation of hydrazidated hydroxyethyl chitosan: 3-(2-furyl) acrolein solution with a mass concentration of 0.33% was added dropwise to 1.0% hydroxyethyl chitosan (MW = 200kDa) solution and mix well, the molar ratio of 3-(2-furyl) acrolein to amino group in hydroxyethyl chitosan is 10:1, at 30 ℃ and N 2 React under the atmosphere for 12h, then add a sodium cyanoborohydride solution with a mass concentration of 0.6%, the amount of sodium cyanoborohydride is 1.1 times the number of Schiff base bonds, at 20 ° C and N 2 The reduction reaction was continued for 1 h under the atmosphere to form a furanated hydroxyethyl chitosan crude product, which was dialyzed in deionized water for 72 h with a dialysis bag with a molecular weight cut-off of 3500 Da and then freeze-dried to obtain furanated hydroxyethyl chitosan;

[0080] Be that the mass concentration of 1.0% maleimide caproic acid solution is 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide solution and 0.57mmol mass c...

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Abstract

A core-shell structured chitosan-based nano-prodrug that co-loads doxorubicin and platinum drugs and its preparation method and application. First, 3,3'-dithiodipropionyl hydrazide is synthesized by Diels-Alder reaction Bonding to chitosan derivatives to obtain hydrazide chitosan derivatives; at the same time, doxorubicin is connected to 3,3'-dithiodipropionyl hydrazide through a hydrazone bond to obtain hydrazide doxorubicin; Then, the aqueous solution of the hydrazidated chitosan derivative and the hydrazidated doxorubicin is uniformly mixed with the platinum drug solution, and a core-shell structured chitosan-based nanometer prodrug is formed through a self-assembly process. The particle size of the nano-prodrug can be adjusted in the range of 100‑200nm, and it has dual stimulation responsiveness to glutathione and pH. The occurrence of drug-like phenomenon can be used for combined chemotherapy of various tumors, improving anti-tumor effect and reducing toxic and side effects.

Description

technical field [0001] The invention belongs to the field of biological materials, and in particular relates to a core-shell structured chitosan-based nano-prodrug that co-loads doxorubicin and platinum drugs, and a preparation method and application thereof. Background technique [0002] Cancer is the second leading cause of death in the world. According to a report released by the World Health Organization in September 2019, 1 / 5 men and 1 / 6 women will suffer from cancer in their lifetime, and 1 / 8 men and 1 / 11 women will die of cancer. Chemotherapy is an important means of cancer treatment, and platinum-based antineoplastic drugs play a pivotal role in chemotherapy. Cisplatin has been proven to be one of the most effective anti-tumor drugs since it was approved by the US Food and Drug Administration for clinical use in 1978 as the first generation of platinum-based anti-tumor drugs. However, platinum-based drugs still have some shortcomings in the treatment of tumors, suc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08A61K47/61A61K47/69A61K31/704A61K33/243A61K31/555A61P35/00
CPCA61K31/704A61K33/24A61K47/36A61P35/00C08B37/003
Inventor 钱军民王亚萍胥伟军侯光晖
Owner XI AN JIAOTONG UNIV
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