Amphiphilic polysaccharide derivative containing cholesterol and phytolectin group as well as preparation method and application of amphiphilic polysaccharide derivative

A technology of amphiphilic polysaccharides and plant lectins, applied in the field of amphiphilic polysaccharide derivatives and their preparation, can solve the problems of difficult subcutaneous or intravenous injection, large size, etc., and achieve the effect of intelligent release of therapeutic drugs

Active Publication Date: 2019-06-14
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, it has been reported in the literature that the concanavalin A system with glucose responsiveness is mainly hydrogel and microsphere (Yin R.X. et al, Carbohydrate Polymers, 2014, 103, 369-376, patent CN201710612832.2), however, these systems Difficult to achieve subcutaneous or intravenous administration due to large size

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  • Amphiphilic polysaccharide derivative containing cholesterol and phytolectin group as well as preparation method and application of amphiphilic polysaccharide derivative
  • Amphiphilic polysaccharide derivative containing cholesterol and phytolectin group as well as preparation method and application of amphiphilic polysaccharide derivative
  • Amphiphilic polysaccharide derivative containing cholesterol and phytolectin group as well as preparation method and application of amphiphilic polysaccharide derivative

Examples

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Effect test

Embodiment 1

[0075] 1. Synthesis of amphipathic amylose derivatives containing cholesterol and lectin groups

[0076] (1) Weigh 0.1 g of carboxylated amylose derivatives, dissolve in 20 ml of dimethyl sulfoxide, stir and dissolve in an oil bath at 15° C. for 2 hours;

[0077] (2) Weigh 0.2 g of cholesterol in 10 ml of ethanol, slowly add it dropwise to the solution of step (1), then weigh 0.5 g of DCC and 1.1 g of DMAP, dissolve it in 100 ml of organic solvent, and slowly add it dropwise to step (1) ) solution, continue to stir and react in an oil bath at 15°C for 1 hour;

[0078] (3) After the above reaction was completed, 1 mL of acetone was added dropwise to the reaction solution to precipitate amphipathic amylose derivatives containing cholesterol, and the precipitate was collected by centrifugation (5000 rpm, 5 min). Dissolve the precipitate in 20 mL of ethanol, add 1-20 mL of acetone dropwise to precipitate amphipathic amylose derivatives containing cholesterol, centrifuge (5000 rpm...

Embodiment 2

[0099] 1. Synthesis of amphiphilic glycogen derivatives containing cholesterol and lectin groups

[0100] (1) Weigh 0.3 g of carboxylated glycogen derivatives, dissolve in 15 ml of acetonitrile, stir and dissolve in an oil bath at 40° C. for 5 hours;

[0101] (2) Weigh 0.2 g of cholesterol in 10 ml of acetone, slowly add it dropwise to the solution of step (1), then weigh 1.0 g of DCC and 1.0 g of DMAP, dissolve it in 100 ml of acetone, and slowly add dropwise to the solution of step (1) solution, the stirring reaction was continued for 5 hours.

[0102] (3) After the above reaction was completed, 1 mL of acetone was added dropwise to the reaction solution to precipitate amphiphilic glycogen derivatives containing cholesterol, and the precipitate was collected by centrifugation (5000 rpm, 5 min). Dissolve the precipitate in 20 mL of ethanol, add 1-20 mL of acetone dropwise to precipitate amphiphilic glycogen derivatives containing cholesterol, centrifuge (5000 rpm, 5 min), an...

Embodiment 3

[0115] 1. Synthesis of amphiphilic guar gum derivatives containing cholesterol and lectin groups

[0116] (1) Weigh 0.5 g of carboxylated guar gum derivatives, dissolve in 15 ml of formamide, stir and dissolve in an oil bath at 20° C. for 20 hours;

[0117] (2) Weigh 0.5 gram of cholesterol in 15 milliliters of dimethylformamide, slowly add it dropwise to the solution of step (1), then weigh 0.5 gram of DCC and 1.5 gram of DMAP and dissolve in 100 milliliters of dimethylformamide, Slowly added dropwise to the solution of step (1), and continued to stir and react for 20 hours.

[0118] (3) After the above reaction was completed, 1 mL of isopropanone was added dropwise to the reaction solution to precipitate amphiphilic glycogen derivatives containing cholesterol, and the precipitate was collected by centrifugation (5000 rpm, 5 min). Dissolve the precipitate in 20 mL of dimethylformamide, add 1-20 mL of isopropyl ketone dropwise to precipitate amphiphilic glycogen derivatives c...

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Abstract

The invention discloses an amphiphilic polysaccharide derivative containing cholesterol and phytolectin group as well as a preparation method and application of the amphiphilic polysaccharide derivative. According to the invention, firstly, an amphiphilic polysaccharide derivative containing cholesterol and a phytolectin group is synthesized; and further an insulin-loaded amphiphilic polysaccharide derivative nanoparticle with glucose responsiveness is synthesized. The capability of combining free glucose molecules in the surrounding environment of the phytolectin group in the nanoparticle ishigher than that of combining glucose groups on polysaccharide chains, so that the chain segments of the amphiphilic polysaccharide derivative become loose, the size of the nanoparticles is increased,insulin is released, and intelligent regulation and control are realized. The preparation conditions of the amphiphilic polysaccharide derivative and the nanoparticle are mild, the used raw materialsare safe, and the activity of specific binding of phytolectin to glucose molecules and the structural stability and biological activity of insulin are maintained. The amphiphilic nanoparticle for intelligently regulating and controlling insulin release prepared by the invention is expected to be used as an insulin delivery carrier, and can intelligently regulate and control insulin release according to the change of the blood glucose level in the body of a diabetes patient, so that the amphiphilic nanoparticle has a certain application prospect in the aspect of diabetes treatment.

Description

technical field [0001] The invention relates to the technical field of biomedical polymer materials, more specifically, to an amphiphilic polysaccharide derivative containing cholesterol and plant lectin groups and its preparation method and application. Background technique [0002] Diabetes is a serious fatal disease, which is mainly caused by the disorder of blood sugar regulation in the body. The current treatment mainly relies on subcutaneous injection of insulin multiple times a day. The disadvantages of this method are hypoglycemia, syncope, etc. complication. [0003] The glucose-responsive system that can intelligently regulate the release of insulin according to the blood sugar level of diabetic patients will hopefully become a new type of smart material for the treatment of diabetes (Webber M.J.et al., Journal of DrugTargeting, 2015, 23:651-655). The technology is to make smart materials that respond to changes in blood sugar levels. [0004] Some glucose-respon...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B33/00C08B37/00C08B37/02A61K38/28A61K9/14A61K47/42A61P3/10
Inventor 杨立群林坤华易菊珍李春龙毛旭宏江桂生
Owner SUN YAT SEN UNIV
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