Carbonate polymer with disulfur five-membered ring functional group on side chain and application thereof

A carbonate polymer and functional group technology, applied in the field of medical materials, can solve the problems of cumbersome preparation process and achieve the effects of simple preparation, excellent biodegradability, and simplified operation steps

Active Publication Date: 2014-09-10
BRIGHTGENE BIO MEDICAL TECH (SUZHOU) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In addition, in the prior art, in the process of ring-opening polymerization, the active group in the monomeric structure of the cyclocarbonate is easy to react, so when the functional cyclocarbonate polymer is prepared from the monomer, it needs to be protected and deprotected. steps, which makes the preparation process cumbersome

Method used

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  • Carbonate polymer with disulfur five-membered ring functional group on side chain and application thereof
  • Carbonate polymer with disulfur five-membered ring functional group on side chain and application thereof
  • Carbonate polymer with disulfur five-membered ring functional group on side chain and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1 Synthesis of a cyclic carbonate monomer (CDC) containing a disulfide five-membered ring functional group

[0053]

[0054] 1. Sodium hydrosulfide monohydrate (28.25g, 381.7mmol) was dissolved in 400mL N,N-dimethylformamide (DMF), heated at 50°C until completely dissolved, and dibromoneopentyl glycol (20g, 76.4mmol), reacted for 48 hours. The reactant was distilled off under reduced pressure to remove the solvent DMF, then diluted with 200mL distilled water, extracted four times with 250mL ethyl acetate, and finally the organic phase was rotary evaporated to obtain yellow viscous compound A, yield: 70%;

[0055] 2. Compound A dissolved in 400 mL of tetrahydrofuran (THF) was placed in the air for 24 hours, and the intermolecular sulfhydryl groups were oxidized into sulfur-sulfur bonds to obtain Compound B, with a yield of >98%;

[0056] 3. Under nitrogen protection, compound B (11.7 g, 70.5 mmol) was dissolved in dried THF (150 mL), and stirred until complet...

Embodiment 2

[0057] Example 2 Synthesis of carbonate polymer PEG5k-P (CDC2.5k-co-CL3.9k) containing disulfide five-membered ring functional groups in two-block side chains

[0058] Under a nitrogen atmosphere, 0.28g (1.46mmol) of CDC monomer and 0.4g (3.51mmol) of caprolactone (ε-CL) were dissolved in 3mL of dichloromethane and added to the sealed reactor, and then polystyrene with a molecular weight of 5000 was added. Ethylene glycol 0.5g (0.1mmol) and the dichloromethane solution (0.1mol / L) of the catalyzer bis(bistrimethylsilyl)amine zinc of 0.1mol / L, then seal the reactor well, transfer out the glove box , placed in a 40°C oil bath to react for 1 day, terminate the reaction with glacial acetic acid, precipitate in glacial ether, and finally filter and vacuum-dry to obtain a carbonate polymer PEG5k- P(CDC2.5k-co-CL3.9k).

[0059]

[0060] In the formula, m=113.6, x=34.2, y=13.0, n=47.2.

[0061] attached figure 1 is the NMR spectrum of the above polymer. 1 H NMR (400MHz, CDCl 3 ...

Embodiment 3

[0062] Example 3 Synthesis of Carbonate Polymer PEG5k-b-PCDC2.8k Containing Disulfide Five-membered Ring Functional Groups in Two Block Side Chains

[0063] Under nitrogen atmosphere, add 0.3g (1.56mmol) of CDC monomer, 2mL of dichloromethane into the sealed reactor, then add 0.5g (0.1mmol) of polyethylene glycol with a molecular weight of 5000 and 1mL of catalyst bis(bistri Methylsilyl) amine zinc dichloromethane solution (0.1mol / L), then seal the reactor well, transfer it out of the glove box, put it into a 40°C oil bath and react for 1 day, terminate the reaction with glacial acetic acid, and Precipitate in diethyl ether, and finally filter and vacuum-dry to obtain a carbonate polymer PEG5k-b-PCDC2.8k containing a disulfide five-membered ring functional group in the side chain of the product.

[0064] 1 H NMR (400MHz, CDCl 3 ): 3.08 (s, -CCH 2 ), 3.30 (m, -OCH 3 ), 4.05(s, -CH 2 OCOCHCH 2 -), 4.07(s, -OCH 2 CCH 2 O-), 4.31 (m, -CCH 2 ).

[0065]

[0066] In the...

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Abstract

The invention discloses a carbonate polymer with a disulfur five-membered ring functional group on a side chain and an application thereof. The polymer is obtained by active ring opening polymerization from a cyclic carbonate monomer containing the disulfur five-membered ring functional group; the polymer is controllable in molecular weight, narrower in weight molecular distribution and free from protecting and deprotecting process. The polymer obtained by active ring opening polymerization of the cyclic carbonate monomer has biodegradability and can be used for controlling a drug release system; a reduction-sensitive reversible crosslinking nano medicine carrier targeting tumor supports long circulation in vivo but is highly enriched in tumor cells and is quickly crosslinked to release medicine in cells so as to efficiently kill the tumor cells with specificity. Meanwhile, the carbonate polymer has an application prospect in aspects such as tissue engineering scaffolds and biochip coatings and the like.

Description

technical field [0001] The invention relates to a biodegradable polymer material and its application, in particular to a carbonate polymer with a disulfide five-membered ring functional group in its side chain and its application, belonging to the field of medical materials. Background technique [0002] Biodegradable polymers have very unique properties. For example, they usually have good biocompatibility and can be degraded in vivo. The degradation products can be absorbed by the human body or excreted through the normal physiological channels of the human body, and are widely used in biomedical applications. Various fields, such as surgical sutures, bone fixation devices, biological tissue engineering scaffold materials, and drug controlled release carriers, etc. Among them, synthetic biodegradable polymers have attracted special attention because of their low immunogenicity and their properties, such as degradation and mechanical properties, can be easily controlled. S...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/64C08G64/30C08G64/18A61K47/34A61L27/18A61P35/00
CPCA61K31/704A61K47/34A61P35/00C08G63/64C08G64/025C08G64/183C08G64/30C08G64/18C08L69/00C08L2203/02C09D169/00
Inventor 孟凤华邹艳钟志远
Owner BRIGHTGENE BIO MEDICAL TECH (SUZHOU) CO LTD
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