Cyclodextrin drug inclusion compound as well as preparation method and application thereof

A cyclodextrin and drug technology, applied in the field of cyclodextrin drug inclusion compound and its preparation, can solve the problems of low permeability of intestinal epithelial cells and low bioavailability of insulin

Active Publication Date: 2021-05-07
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, oral delivery of insulin faces many difficulties, such as enzymatic degradation in the gastrointestinal tract and low permeability of intestinal epithelial cells, which lead to low bioavailability of insulin

Method used

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  • Cyclodextrin drug inclusion compound as well as preparation method and application thereof
  • Cyclodextrin drug inclusion compound as well as preparation method and application thereof
  • Cyclodextrin drug inclusion compound as well as preparation method and application thereof

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preparation example Construction

[0025] In order to solve the above problems, the present invention provides a cyclodextrin drug inclusion complex that can not only prevent insulin from being destroyed in the digestive tract, but also prolong the residence time of insulin, thereby improving the absorption efficiency of insulin and its preparation method.

[0026] Specifically, the present invention provides a cyclodextrin graft copolymer for inclusion of insulin in the first aspect, wherein, the cyclodextrin graft copolymer comprises: cyclodextrin as a parent skeleton and graft Sulfhydryl-containing amino acids and guanidine-containing amino acids branched on the parent backbone. The cyclodextrin graft copolymer can be used as a host molecule to form a host-guest inclusion complex with insulin as a guest molecule.

[0027] In some preferred embodiments, the cyclodextrins include but are not limited to α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin, hydroxypropyl-β-cyclodextrin, hydroxypropyl-γ - Cyclodextrin...

Embodiment 1

[0056] Synthesis of Product A

[0057] Weigh 880mg EDC, 530mg NHS, and 150mg thiol-containing amino acids respectively. In a round-bottomed flask, dissolve the mercapto-containing amino acid in the first reaction solvent, then add EDC and NHS and mix well, and stir and activate at room temperature for 3 h. After the reaction was completed, 257 mg of cyclodextrin was added, and stirring was continued at room temperature for 24 h. After the reaction, the mixture was freeze-dried, and acetone was added to sonicate for 0.5 h, and the acetone was removed by filtration to obtain product A.

[0058] When synthesizing product A, the amino acid containing thiol used is N-acetyl-L-cysteine, and the first reaction solvent is distilled water; the cyclodextrin is hydroxypropyl-β-cyclodextrin with a molecular weight of 1399; The molar ratio of amino acid containing thiol to the first catalyst is 1:5; the molar ratio of EDC to NHS is 1:1; the molar ratio of amino acid containing mercapto t...

Embodiment 2

[0066] Synthesis of Product A

[0067] Weigh 880mg EDC, 530mg NHS, and 150mg thiol-containing amino acids respectively. In a round-bottomed flask, dissolve the mercapto-containing amino acid in the first reaction solvent, then add EDC and NHS and mix well, and stir and activate at room temperature for 3 h. After the reaction was completed, 290 mg of cyclodextrin was added, and stirring was continued at room temperature for 24 h. After the reaction, the mixture was freeze-dried, and acetone was added to sonicate for 0.5 h, and the acetone was removed by filtration to obtain product A.

[0068] When synthesizing product A, the amino acid containing thiol used is N-acetyl-L-cysteine, and the first reaction solvent is distilled water; the cyclodextrin is hydroxypropyl-γ-cyclodextrin with a molecular weight of 1580; The molar ratio of mercapto amino acid to the first catalyst is 1:5; the molar ratio of EDC to NHS is 1:1; and the molar ratio of amino acid containing mercapto to cy...

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Abstract

The invention relates to a cyclodextrin drug inclusion compound as well as a preparation method and application thereof. Specifically, the invention relates to a cyclodextrin grafted copolymer for inclusion of drugs, and the cyclodextrin grafted copolymer comprises cyclodextrin as a matrix skeleton, and sulfydryl-containing amino acid and guanidyl-containing amino acid grafted on the matrix skeleton. The invention also relates to a preparation method of the cyclodextrin grafted copolymer and application of the cyclodextrin grafted copolymer in inclusion drugs, especially insulin and other drugs. The cyclodextrin grafted copolymer can effectively protect enzymatic degradation of drugs such as insulin, and improve mucosal adhesion and membrane permeability of insulin.

Description

technical field [0001] The invention relates to the technical field of polymer materials and pharmaceutical preparations, in particular to a cyclodextrin drug inclusion compound and its preparation method and application. Background technique [0002] Diabetes is a chronic disease that can be attributed to insufficient secretion of insulin. Insulin is secreted by pancreatic beta cells and has the ability to regulate blood glucose levels. At present, subcutaneous injection of insulin is still a common method for the treatment of diabetes. However, frequent subcutaneous injections bring a lot of physical pain to patients, and may lead to allergic reactions, hypoglycemia and insulin resistance. Over the past few decades, researchers have developed various alternative drug delivery systems, such as oral, nasal, pulmonary, rectal, and transdermal delivery of insulin. Among them, oral administration is considered to be the most ideal way of administration because of its good pa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/69A61K47/54A61K38/28A61P3/10
CPCA61K47/6951A61K47/542A61P3/10A61K38/28
Inventor 孙少平李思怡
Owner HEILONGJIANG UNIV
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