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Enzyme-responsive polymer as well as preparation method and applications thereof

A polymer and enzyme-responsive technology, applied in the field of enzyme-responsive polymers and their preparation, can solve rare and other problems

Active Publication Date: 2015-08-12
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing polymersomes that can respond to bacterial enzymes are concentrated on some common enzymes, such as esterases, proteases, etc.; however, specific enzymes that can target pathogenic bacteria, such as penicillin G that can degrade penicillin G Amidase (English, A.R., et al.Proc.Soc.Exp.Biol.Med.1960,104,547-549) and β-lactam antibiotics (penicillins, cephalosporins, carbapenems) degrading -Lactamase (the parentheses themselves are fine, because the English words must be connected on one line when inputting, the space between the system words is automatically shrunk) (Bush K., et al.Antimicrob.Agents Chemother.1995,39 ,1211-1233), etc., the polymersome system for responsive drug delivery is still rare

Method used

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  • Enzyme-responsive polymer as well as preparation method and applications thereof
  • Enzyme-responsive polymer as well as preparation method and applications thereof
  • Enzyme-responsive polymer as well as preparation method and applications thereof

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preparation example Construction

[0086] The present invention also provides a method for preparing an enzyme-responsive polymer, comprising:

[0087] A method for preparing an enzyme-responsive polymer, comprising:

[0088] polymerizing the polymer with the structure of formula (II) and the monomer with the structure of formula (III-1) to obtain the polymer with the structure of formula (I-1);

[0089]

[0090] Among them, M 1 Formula (101), formula (102), formula (103), formula (104), formula (105), formula (106), formula (107), formula (108), formula (109), formula (110) and one or more of formula (111),

[0091]

[0092] Among them, m is 11-445, q is 10-200;

[0093]

[0094] Among them, y is 1 to 11;

[0095] z is 1~6;

[0096] R is H or C1-C8 alkyl;

[0097] Among them, x is 10-200; R 1 for H or

[0098] According to the present invention, the present invention polymerizes the polymer with the structure of formula (II) and the monomer with the structure of formula (III-1) to obtain t...

Embodiment 1

[0131] 1) Prepare the compound of the structure shown in the hydrophobic monomer formula (III-1) (wherein, R=CH 3 ,p=1,q=1):

[0132]

[0133] Dissolve p-aminobenzyl alcohol (1.0g, 8mmol) and p-dimethylaminopyridine (2.6g, 21.3mmol) in 100mL of dry dichloromethane, and slowly add phenylacetyl chloride (3.2 g, 21 mmol). The reaction was stirred overnight, washed three times with 1M aqueous sodium hydroxide solution, dried, concentrated, and purified by column chromatography, and the product was subjected to amination reaction at 80°C with a large excess of ethylenediamine to finally obtain N-(4-(hydroxy Methyl)phenyl)-2-phenylacetamide (1.2 g, ~90% yield). Dissolve N-(4-(hydroxymethyl)phenyl)-2-phenylacetamide (1.2 g, 5 mmol) and a catalytic amount of dibutyltin dilaurate (20 μL) in 50 mL of dry dichloromethane at room temperature . Isocyanoethyl methacrylate (1.2 g, 7.5 mmol) was slowly added dropwise with stirring. After 4 hours, the reaction was completed, washed with...

Embodiment 2

[0156] 1) Prepare the compound of the structure shown in the hydrophobic monomer formula (III-2) (wherein, R=CH 3 ,y=1,z=1):

[0157]

[0158] 4-aminobenzyl alcohol (5.0g, 40mmol) and phenyl chloroformate (5mL, 42mmol) were reacted in tetrahydrofuran and aqueous sodium bicarbonate solution and purified by column chromatography to obtain product 9.1g with a yield of 93%.

[0159] The above product (1.0 g, 4.1 mmol) and a catalytic amount of dibutyltin dilaurate (20 μL) were dissolved in 50 mL of dry dichloromethane, and isocyanoethyl methacrylate ( 0.96g, 6.2mmol), after 4h, the reaction was terminated, washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated and purified by column chromatography to obtain a white solid, the compound 1.5 of the structure shown in the target product formula (III-2) g, the productive rate is 90%.

[0160] The compound of the structure shown in formula (III-2) is detected by nuclear magnetic resonance, the results can...

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Abstract

The invention provides an enzyme-responsive polymer. The enzyme-responsive polymer provided by the invention simultaneously contains a hydrophilic chain segment and an oleophylic chain segment; and through a specific structure containing M2, a prepared enzyme-responsive polymer is applied to anti-bacterial drug carriers, so that the carriers not only can carry anti-bacterial drugs which are different in sources, molecular weight and hydrophilic-hydrophobic properties, but also can be degraded well in the presence of beta-lactamase or penicillin G amidase, and therefore, the carriers are beta-lactamase or penicillin G amidase responsive carriers.

Description

technical field [0001] The invention belongs to the field of polymer materials, and in particular relates to an enzyme-responsive polymer and its preparation method and application. Background technique [0002] Beginning with the synthesis of Prontocil in the 1930s and 1940s, the clinical use of penicillin, and the discovery of streptomycin, antibiotics have become our reliable and powerful weapons against infectious diseases, thereby effectively reducing human morbidity. rate and case fatality rate (Fauci, A.S., et al. N. Engl. J. Med. 2012, 366, 454-461); however, at the same time, some "cunning" pathogenic bacteria, through genetic mutation (de novo gene mutation) and horizontal gene transfer (horizontal gene transfer), such as methicillin-resistant Staphylococcus aureus (MRSA) and carbapenem-resistant Enterobacteriaceae (CRE); worse, drug resistance Accumulation of genes in bacterial plasmids and chromosomes leads to the emergence of multi-drug resistant bacteria (Levy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00C08F220/36C08F120/36C08F120/54C08F120/34C08F120/06C08F120/38C08F112/14C08F126/06C08G65/48A61K47/32
Inventor 刘世勇李亚民
Owner UNIV OF SCI & TECH OF CHINA