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A biodegradable and sugar-responsive Y-shaped polymer drug delivery material and its preparation

A sugar-responsive, polymer technology is applied in the field of polymer drug delivery materials and their preparation to achieve the effects of being beneficial to human metabolism, good biocompatibility and biodegradability

Active Publication Date: 2015-12-23
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to solve the problem of the existing sugar-responsive drug delivery materials. Polyethylene glycol monomethyl ether at the double hydroxyl end is used as the hydrophilic segment, polylactic acid is the biodegradable hydrophobic segment, and poly(2-phenylboronic acid ester- Polymer drug delivery material with 5-methyl-1,3-dioxane) acrylate as sugar-responsive hydrophobic segment and preparation method thereof

Method used

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  • A biodegradable and sugar-responsive Y-shaped polymer drug delivery material and its preparation
  • A biodegradable and sugar-responsive Y-shaped polymer drug delivery material and its preparation
  • A biodegradable and sugar-responsive Y-shaped polymer drug delivery material and its preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 1) The raw material phenylboronic acid (8.0g, 65.6mmol) and trimethylolethane (7.9g, 67.5mmol) were dissolved in toluene (100mL) and refluxed at 140°C for 5h. After the reaction, the reaction solution was concentrated, and then vacuum-dried to obtain compound II.

[0033]

[0034] 2) N 2 Under protection, the above compound II (10.0g, 54.4mmol) and triethylamine (4.9g, 54.24mmol) were dissolved in 40mL of dichloromethane, and added to the above solution in an ice bath (0-4°C) A dichloromethane solution of acryloyl chloride (5.4 g, 66.1 mmol) was slowly added dropwise and reacted for 11 hours; after the reaction was terminated, the reaction solution was crudely purified, then the reaction solution was concentrated, and separated and purified by column chromatography to obtain compound III; 1 HNMR (400MHz, CDCl 3 ), δ (ppm): 1.04 (s, 3H, -CH 3 ), δ (ppm): 3.86 (d, J=12Hz, 2H, -BOCH 2 (CCH 3 )), 4.06 (d, J=8Hz, 2H, -BO-CH 2 (CCH 2 CH 3 )), 5.85 (d, J=12Hz, 1H, -...

example 2

[0047] 1) Same as step 1 of embodiment 1)

[0048] 2) Same as step 2 of Example 1)

[0049] 3) Same as Step 3 of Example 1)

[0050] 4) Same as Step 4 of Example 1)

[0051] 5) in N 2 Under protection, add 250mg (0.05mmol) initiator V-1, 1.1mg (0.005mmol) copper bromide, 14mg (0.1mmol) cuprous bromide, 17.8mg (0.1mmol) pentylenediethylene to the reaction device Triamine and 2.0g (7.7mmol) of compound III were dissolved in 2.1mL of anisole and reacted for 18 hours under nitrogen protection at 90°C. The reaction solution was concentrated and precipitated in ether / n-hexane to obtain product I-2 .

[0052]

[0053] Where n=44, r=10, m=39

example 3

[0055] 1) Same as step 1 of Example 1)

[0056] 2) Same as step 2 of Example 1)

[0057] 3) Same as Step 3 of Example 1)

[0058] 4) Same as Step 4 of Example 1)

[0059] 5) in N 2 Under protection, add 250mg (0.05mmol) initiator V-1, 1.1mg (0.005mmol) copper bromide, 14mg (0.1mmol) cuprous bromide, 17.8mg (0.1mmol) pentylenediethylene to the reaction device Triamine and 1.5g (5.8mmol) of compound III were dissolved in 2.1mL of anisole and reacted for 18 hours under nitrogen protection at 90°C. The reaction solution was concentrated and precipitated in ether / n-hexane to obtain product I-3 .

[0060]

[0061] In the formula, n=44, r=10, m=25.

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Abstract

The invention provides a biodegradable and sugar responsive Y type polymer drug delivery material and preparation, which belongs to the field of biological materials. The structural formula of the compound is obtained by the following steps of firstly preparing a compound III, and then, preparing a compound V, and reacting the compound III with the compound V under conditions of cuprous bromide, copper bromide and divinyl pentamethylene triamine. The material provided by the invention has glucose responsive self-discipline insulin release ability and has selectivity on glucose concentration.

Description

technical field [0001] The invention belongs to the field of biomaterials, and specifically relates to poly(2-phenylboronic acid ester-5-methyl-1, 3-dioxane) acrylate is a sugar-responsive hydrophobic segment polymer drug delivery material and a preparation method thereof. Background technique [0002] Nano drug delivery systems are increasingly replacing traditional drug delivery routes, which can not only improve the solubility of hydrophobic drugs, but also protect some natural macromolecules from the damage of the human physiological environment. In the nanotechnology of drug delivery, polymer nanomicelles are widely used in the research and application of drug delivery, they overcome the shortcomings of poor water solubility of drugs, and help drugs cross physiological barriers to improve the bioavailability of drugs, thereby , essentially altering the distribution of the drug in the body. In addition, the polymer micelles reduce drug toxicity and have slow-release an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F293/00C08F230/06C08G65/48C08G63/08A61K47/34A61P3/10
Inventor 杨晶赵丽源
Owner BEIJING UNIV OF CHEM TECH
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