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A kind of random copolymer based on natural cholesterol, preparation method and application thereof

A technology of random copolymer and cholesterol, which is applied in the directions of drug combination, pharmaceutical formula, medical preparation of inactive ingredients, etc., and achieves the effect of good application prospect, simple and efficient synthesis method and low cost.

Active Publication Date: 2022-06-28
SHANGHAI TENTH PEOPLES HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • A kind of random copolymer based on natural cholesterol, preparation method and application thereof
  • A kind of random copolymer based on natural cholesterol, preparation method and application thereof
  • A kind of random copolymer based on natural cholesterol, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Example 1 Synthesis based on natural cholesterol random copolymer P1 (PDMAEMA18-PMChol16)

[0029] Dodecyl mercaptan DDMAT (109.4 mg, 0.3 mmol), azobisisobutyronitrile (16.4 mg, 0.1 mmol), cholesterol-6C-methacrylic acid monomer were added to a dry Schlenk reaction tube with a pre-stirred bar. (3.33 g, 6 mmol), DMAEMA monomer (0.91 g, 6 mmol) and 20 mL of freshly distilled toluene were subjected to three cycles of liquid nitrogen freezing-evacuating-melting through nitrogen circulation to remove residual oxygen in the reaction tube. The reaction tube was immersed in an oil bath pre-heated to 80°C for 12 hours, the reaction was concentrated and dropped into petroleum ether for precipitation, and the polymer was purified by twice methanol-cyclohexane repeated dissolution-precipitation method, and finally obtained after vacuum drying. Based on the natural cholesterol random copolymer P1, the product was 2.26 g as a light yellow powder, and the yield was 82%.

[0030] Chem...

Embodiment 2

[0032] Example 2 Synthesis based on natural cholesterol random copolymer P2 (PDMAEMA30-PMChol16)

[0033] Dodecyl mercaptan DDMAT (109.4 mg, 0.3 mmol), azobisisobutyronitrile (16.4 mg, 0.1 mmol), cholesterol-6C-methacrylic acid monomer were added to a dry Schlenk reaction tube with a stirring bar. (3.33 g, 6 mmol), DMAEMA monomer (1.81 g, 12 mmol) and 20 mL of freshly distilled toluene were subjected to three cycles of liquid nitrogen freezing-evacuating-melting through nitrogen circulation to remove residual oxygen in the reaction tube. The reaction tube was immersed in an oil bath pre-heated to 80 °C for 10 h, the reaction was concentrated and the droplets were deposited into cyclohexane for precipitation, and the polymer was purified by the method of repeated dissolution and precipitation of acetone-n-hexane twice, and finally obtained after vacuum drying. Based on the natural cholesterol random copolymer P2, the product was 2.11 g as a light yellow powder, and the yield wa...

Embodiment 3

[0036] Example 3 Synthesis based on natural cholesterol random copolymer P3 (PDMAEMA43-PMChol16)

[0037] Dodecyl mercaptan DDMAT (109.4 mg, 0.3 mmol), azobisisobutyronitrile (16.4 mg, 0.1 mmol), cholesterol-6C-methacrylic acid monomer were added to a dry Schlenk reaction tube with a stirring bar. (3.33 g, 6 mmol), DMAEMA monomer (2.41 g, 18 mmol) and 20 mL of freshly distilled toluene were subjected to three cycles of liquid nitrogen freezing-evacuating-melting through nitrogen circulation to remove residual oxygen in the reaction tube. The reaction tube was immersed in an oil bath pre-heated to 80 °C for 12 hours, the reaction was concentrated and dropped into n-hexane for precipitation, and the polymer was purified by the method of repeated dissolution and precipitation of acetonitrile-n-hexane twice. The natural cholesterol random copolymer P3 was 1.98 g of a light yellow powdery product with a yield of 72%.

[0038] Chemical structure of polymer P3

[0039]

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Abstract

The present invention relates to a kind of random copolymer based on natural cholesterol, preparation method and application thereof. The hydrophobic block in the random copolymer is derived from biocompatible natural steroidal compound cholesterol, and then combined with polymethacrylic acid N, N-dimethylaminoethyl ester (PDMAEMA) is obtained by cationic ring-opening polymerization and adding functionalized amines. Its molecular structure based on natural cholesterol random copolymer of the present invention is amphiphilic, has the advantage that molecular weight and hydrophilic-hydrophobic ratio can be regulated, copolymer has obviously higher isotropy and non-liquid crystal, and known PDMAEMA Compared with it, it has better hydrophobic properties. And the layer-by-layer material can be prepared layer by layer by solvent coating method. The preparation method provided by the invention has the advantages of simplicity, high efficiency, and easy availability of raw materials, and is expected to be practically applied in medical tissue engineering as a low-cost, high biocompatibility bioremediation material.

Description

technical field [0001] The invention relates to the field of interface biomaterials and biomedicine technologies oriented to novel natural cholesterol random copolymers, in particular to a class of natural cholesterol random copolymers, a preparation method and applications thereof. Background technique [0002] Research and development of biocompatible interface biomaterials has become one of the most popular research topics in the interdisciplinary fields of life science and materials science. Under normal physiological conditions, cells / tissues have specific microenvironments to maintain their related functions. Under pathological conditions, tissue defects or lesions will lead to microenvironmental damage and abnormal physiological signals. Interface biomaterials can simulate the cell / tissue microenvironment and reconstruct its composition and morphology. Studying the mechanical response and signal transduction of cells at the interface of biomaterials can guide the repa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F220/34C08F220/40A61K47/34A61P31/04A61P31/10A61P35/00A61L27/16
CPCC08F220/34A61K47/34A61P31/04A61P31/10A61P35/00A61L27/16C08L33/14C08F220/40
Inventor 盛瑞隆史向阳李茂全王昭
Owner SHANGHAI TENTH PEOPLES HOSPITAL
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