ABA type triblock biodegradable polyurethane with amino side chains and preparation method and uses thereof

A biodegradable, triblock technology is applied in the field of ABA type triblock biodegradable polyurethane and its preparation, which can solve the problems of wide molecular weight distribution index, uncontrollable molecular weight of biodegradable polyurethane, and complex self-assembly.

Inactive Publication Date: 2014-01-08
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The purpose of the present invention is to provide a kind of ABA type triblock biodegradable polyurethane with amino group in side chain and its Preparation method and use

Method used

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  • ABA type triblock biodegradable polyurethane with amino side chains and preparation method and uses thereof
  • ABA type triblock biodegradable polyurethane with amino side chains and preparation method and uses thereof
  • ABA type triblock biodegradable polyurethane with amino side chains and preparation method and uses thereof

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preparation example Construction

[0071] The present invention also provides a method for preparing an ABA-type triblock biodegradable polyurethane with amino groups in the side chain. When R is a protecting group for amino groups, the steps for preparing the structure shown in formula I' include:

[0072] Add aliphatic diisocyanate, glycol with amino group protection and polyethylene glycol alkyl ether into the reaction vessel, then add the reaction solvent and catalyst, stir and mix evenly, and react at 60-90°C for 1-8 hours , that is, the ABA-type three-block biodegradable polyurethane (PU-NHR) with amino groups in the side chain of the structure of formula Ⅰ' is obtained;

[0073]

[0074] In formula I', R' is the protecting group of amino group, R 1 for C 1 ~C 12 the alkyl group, R 2 It is aliphatic diisocyanate OCN-R 2 -Skeleton part of NCO group excluding NCO group, R 3 It is a dihydric alcohol HO-R with an amino group 3 (NHR)-OH does not count the skeleton part of OH and NHR groups, x=10-500, ...

Embodiment 1

[0123] Example 1 One-step preparation of ABA triblock biodegradable polyurethane (PU-NHR) with amino groups in the side chain of formula Ⅰ'

[0124] 2,2-bis(benzyloxycarbonylaminomethyl)-1,3-propanediol (0.05mol, 9.95g), lysine diisocyanate (0.1mol, 22.6g) and polyethylene glycol monomethyl ether (Mn , 2kg / mol) (0.1mol, 200.0g) into a dry 5L reactor, add 2000ml of dioxane, stir to dissolve, add 0.04g of stannous octoate, nitrogen protection, 60 ℃, react for 3h, the product precipitates in ether , the product was collected and dried to obtain PU-NHR.

[0125] Polyethylene glycol monomethyl ether of different molecular weights, other types of diols and isocyanates with protective amino groups are used to carry out the above synthesis at different catalyst dosages and different reaction temperatures, and the raw material ratio is listed in Table 1:

[0126] Table 1 Conditions for the one-step preparation of ABA triblock biodegradable polyurethane (PU-NHR) with amino groups in th...

Embodiment 2

[0128] Example 2 Two-step preparation of ABA triblock biodegradable polyurethane (PU-NHR) with amino groups in the side chain of formula Ⅰ'

[0129] Put 2,2-bis(tert-butoxycarbonylaminomethyl)-1,3-propanediol (0.005mol, 0.995g) and HDI (0.01mol, 1.68g) in a dry 50ml reaction flask, add 10ml of anhydrous After tetrahydrofuran is completely dissolved, add 0.1g stannous octoate, under nitrogen atmosphere, 70°C, react for 0.5 hours, and add polyethylene glycol monomethyl ether (Mn, 5kg / mol) (0.01mol, 20.0g) into 100ml Anhydrous tetrahydrofuran solution was added to the reaction solution, reacted at 70°C for 1 hour, the product was precipitated in 500ml of glacial ether, filtered, and dried to obtain the white powder product PU-NHR.

[0130] The infrared spectrogram and nuclear magnetic spectrogram of the PU-NHR that embodiment 2 obtains are respectively figure 1 The A curve in and figure 2 shown, from figure 1 and figure 2 It can be seen that the successful synthesis of the ...

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Abstract

The invention provides ABA type triblock biodegradable polyurethane with amino side chains and a preparation method and uses thereof, belongs to the field of biomedical materials and solves the problem that the existing biodegradable polyurethane has molecular weight uncontrollable, wide molecular distribution index and complexity in self-assembly. The ABA type triblock biodegradable polyurethane with amino side chains is shown as in a structural formula I or II. The ABA type triblock biodegradable polyurethane is controllable in polymer molecular weight and wide in molecular weight distribution and can serve as a drug carrier; drug molecules, target molecules or fluorescence molecules are grafted to active side groups of the polyurethane by means of physical encapsulation or chemical bonding, so that a carrier drug system having one or multiple of functions such as being untargeted, being targeted, pH sensitivity, photosensitivity, enzyme sensitivity and fluorescence probing is constructed.

Description

technical field [0001] The invention belongs to the field of biomedical materials, and in particular relates to an ABA type triblock biodegradable polyurethane with amino groups in the side chain, a preparation method and application thereof. Background technique [0002] As a killer of human health, cancer is always threatening human life. "2012 China Cancer Registration Annual Report" released: "6 people are diagnosed with cancer every minute in the country, 8550 people become cancer patients every day, and one person dies of cancer in every seven to eight people." "The situation of cancer incidence in the country is severe." , the morbidity and mortality rates continue to rise, with about 3.5 million new cancer cases and 2.5 million cancer deaths per year." In 2009, the cancers with the highest incidence in China were lung cancer, gastric cancer, colorectal cancer, liver cancer and Esophageal cancer, the most deadly cancer type is lung cancer, followed by liver cancer, g...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/83C08G18/66C08G18/48C08G18/32A61K47/48
CPCA61K47/34A61K47/59A61K49/0054C08G18/283C08G18/3296C08G18/83C08G18/831C08G69/08C08G69/48C08G2230/00
Inventor 杨立新景遐斌谢志刚黄宇彬柳时王伟奇胡秀丽郑勇辉
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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