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Beta-cyclodextrin-adriamycin prodrug molecule with pH responsiveness and preparation method thereof

A technology of cyclodextrin and doxorubicin, which is applied in the field of β-cyclodextrin-doxorubicin prodrug molecule and its preparation, can solve the problem of damage to normal human cells, achieve good water solubility and biocompatibility, The effect of fast speed and mild reaction conditions

Inactive Publication Date: 2019-09-27
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Doxorubicin (DOX) is a broad-spectrum antineoplastic drug that can kill a variety of tumors and tumor cells of various growth cycles, but it also has certain toxicity and will inevitably damage human normal cells.

Method used

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  • Beta-cyclodextrin-adriamycin prodrug molecule with pH responsiveness and preparation method thereof
  • Beta-cyclodextrin-adriamycin prodrug molecule with pH responsiveness and preparation method thereof
  • Beta-cyclodextrin-adriamycin prodrug molecule with pH responsiveness and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 1) Synthesis of 6-esterified β-cyclodextrin

[0043] Weigh 117.2 mg of mono-6-deoxy-6-propargylamine-β-cyclodextrin and 25.8 mg of ethyl azide bromoacetate respectively, add 1.5 mL of dry N, N-dimethylformamide as a solvent, and Fully dissolved under stirring conditions. Then 9.3 mg of tris(triphenylphosphine)copper bromide was added, and nitrogen gas was introduced for 15 minutes. The system was sealed and the reaction was stirred at 60 °C for 24 h. After the reaction was completed, the resulting mixed solution was precipitated in 150 mL of cold acetone, and the solid product was filtered out. After the solid product was vacuum-dried at room temperature for 1-2 days, it was dissolved in N,N-dimethylformamide, precipitated in 150 mL of cold acetone, and the solid product was filtered out, and the dissolution-precipitation process was repeated twice to obtain the product , that is, β-cyclodextrin esterified at the 6-position;

[0044] 2) Synthesis of β-cyclodextrin w...

Embodiment 2

[0049] 1) Synthesis of 6-esterified β-cyclodextrin

[0050] Weigh 117.2 mg of mono-6-deoxy-6-propargylamine-β-cyclodextrin and 38.7 mg of ethyl azide bromoacetate respectively, add 1.5 mL of dry N, N-dimethylformamide as a solvent, and Fully dissolved under stirring conditions. Then 9.3 mg of tris(triphenylphosphine)copper bromide was added, and nitrogen gas was introduced for 15 minutes. The system was sealed and the reaction was stirred at 70 °C for 18 h. After the reaction was completed, the resulting mixed solution was precipitated in 150 mL of cold acetone, and the solid product was filtered out. After the solid product was vacuum-dried at room temperature for 1-2 days, it was dissolved in N,N-dimethylformamide, precipitated in 150 mL of cold acetone, and the solid product was filtered out, and the dissolution-precipitation process was repeated twice to obtain the product , that is, the 6-esterified β-cyclodextrin.

[0051] 2) Synthesis of β-cyclodextrin with 6-position...

Embodiment 3

[0056] 1) Synthesis of 6-esterified β-cyclodextrin

[0057] Weigh 117.2 mg of mono-6-deoxy-6-propargylamine-β-cyclodextrin and 51.6 mg of ethyl azide bromoacetate respectively, add 2 mL of dry N, N-dimethylformamide as a solvent, and stir under magnetic force fully dissolved under the conditions. Then 9.3 mg of tris(triphenylphosphine)copper bromide was added, and nitrogen gas was introduced for 15 minutes. The system was sealed and the reaction was stirred at 65 °C for 20 h. After the reaction was completed, the resulting mixed solution was precipitated in 150 mL of cold acetone, and the solid product was filtered out. After the solid product was vacuum-dried at room temperature for 1-2 days, it was dissolved in N,N-dimethylformamide, precipitated in 150 mL of cold acetone, and the solid product was filtered out, and the dissolution-precipitation process was repeated twice to obtain the product , that is, the 6-esterified β-cyclodextrin.

[0058] 2) Synthesis of β-cyclode...

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Abstract

The invention discloses beta-cyclodextrin-adriamycin prodrug molecule with pH responsiveness and a preparation method thereof, and belongs to the field of chemical synthesis. The beta-cyclodextrin-adriamycin prodrug molecule adopts the structural formula that beta-cyclodextrin in a beta-cyclodextrin-adriamycin prodrug molecule skeleton is connected with adriamycin through a dynamic chemical covalent bond-acylhydrazone bond, solves the problem of low drug loading capacity or undefined drug loading capacity, has good water solubility and biocompatibility, realizes controlled release of DOX since the acylhydrazone bond is subjected to hydrolysis to be reduced under the stimulation of tumor cell acid environment, and is beneficial to the promotion of accurate and effective treatment of tumor. The preparation method comprises the following steps: firstly, synthesizing single 6-esterified beta-cyclodextrin; secondly, synthesizing single 6-hydrazided beta-cyclodextrin; and thirdly, synthesizing the beta-cyclodextrin-adriamycin prodrug molecule.

Description

technical field [0001] The invention belongs to the field of chemical drug synthesis, in particular to a pH-responsive beta-cyclodextrin-doxorubicin prodrug molecule and a preparation method thereof. Background technique [0002] Doxorubicin (DOX) is a broad-spectrum antineoplastic drug that can kill a variety of tumors and tumor cells of various growth cycles, but it also has certain toxicity and will inevitably damage human normal cells. . In order to improve the solubility, biocompatibility, physiological activity and reduce the toxic and side effects of DOX, various methods have been used to carry DOX. Cyclodextrin has good biocompatibility and water solubility, and will not cause immune reactions in the physiological environment of the human body. The effective combination of cyclodextrin and DOX is conducive to improving the biological activity of DOX in the human body. [0003] The stimuli-responsive prodrug system has designable structure and function, targeting an...

Claims

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Application Information

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IPC IPC(8): A61K47/61A61K31/704A61P35/00C08B37/16
CPCA61K31/704A61K47/61A61P35/00C08B37/0012
Inventor 白阳刘彩萍安娜杨靖
Owner SHAANXI UNIV OF SCI & TECH
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