Amphiphilic polymer as well as preparation method and application thereof

A technology of amphiphilic polymers and polymers, applied in the direction of pharmaceutical formulations, medical preparations with non-active ingredients, medical preparations containing active ingredients, etc., can solve problems such as strategies and limitations that have not been developed in modularization

Active Publication Date: 2015-09-09
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 methods that can stimulate the release of antimicrobial agents through bacteria-related (physical, biochemical) factors are still relatively limited, and no general and modular strategies have been developed yet.

Method used

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  • Amphiphilic polymer as well as preparation method and application thereof
  • Amphiphilic polymer as well as preparation method and application thereof
  • Amphiphilic polymer as well as preparation method and application thereof

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preparation example Construction

[0065] The invention also provides a method for preparing the amphiphilic polymer, including:

[0066] A preparation method of amphiphilic polymer, including:

[0067] Polymerizing a polymer having a structure of formula (II) with a monomer having a structure of formula (III) to obtain a polymer having a structure of formula (I);

[0068]

[0069] Among them, M 1 For 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 (111),

[0070]

[0071] Among them, p is from 11 to 445, and q is from 10 to 200;

[0072]

[0073] Among them, m is 1-11;

[0074] M 2 Is formula (202), formula (203) or formula (204),

[0075] Among them, x is 0-19 and y is 0-19;

[0076]

[0077] According to the present invention, the present invention polymerizes the polymer having the structure of formula (II) with the monomer having the structure of formula (III) to obtain the polymer of the structure ...

Embodiment 1

[0095] 1) Preparation of a compound with a structure represented by the hydrophobic monomer formula (III-1) (where m=1, x=0):

[0096]

[0097] Its characteristic is: bacterial esterase can cut off the acetyl group of the end group, and then the 1,6-electron rearrangement of p-hydroxybenzyl alcohol will remove a molecule of carbon dioxide and finally release a primary amine group.

[0098] Preparation method: Dissolve p-hydroxybenzyl alcohol (5.0g, 40mmol) and triethylamine (4.45g, 44mmol) in 120mL of dry dichloromethane, slowly add acetyl chloride (3.14g) while cooling in an ice bath , 40mmol). Stir overnight, filter with suction, concentrate and purify by column to obtain 2.3 g of 4-hydroxymethyl acetophenone ester with a yield of 35%.

[0099] Dissolve 4-hydroxymethyl acetophenate (2.3g, 13.8mmol) and a catalytic amount of dibutyltin dilaurate (50μL) in 80mL of dry dichloromethane. Add methyl slowly while stirring at room temperature. Isocyanoethyl acrylate (3.2 g, 20.8 mmol). ...

Embodiment 2

[0128] 1) Preparation of a compound with a structure represented by the hydrophobic monomer formula (III-2) (where m=1):

[0129]

[0130] It is characterized in that the bacterial nitroreductase enzyme can reduce the terminal nitro group to hydroxylamine or primary amine, followed by 1,6-electron rearrangement to remove a molecule of carbon dioxide, and finally release a primary amine group.

[0131] Preparation method: Dissolve 4-nitrobenzyl alcohol (2.0g, 13.1mmol) and a catalytic amount of dibutyltin dilaurate (60μL) in 100mL of dry dichloromethane, and slowly add methanol dropwise at room temperature and stirring. Isocyanoethyl acrylate (3.1 g, 20.0 mmol). The reaction was finished after 4h, washed with saturated brine, dried with anhydrous magnesium sulfate, concentrated and purified by column chromatography to obtain a white solid, namely the compound of the structure represented by formula (III-2), the yield was 3.6g, and the yield was 90 %.

[0132] The compound of the str...

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Abstract

The invention provides an amphiphilic polymer. The amphiphilic polymer provided by the invention contains both a hydrophilic chain segment and an oleophylic chain segment, enables a prepared polymer to be applied to an antimicrobial drug carrier through M2 with a specific structure, and can carry antimicrobial drugs with different sources, different molecular weights and water affinity degrees, in addition, under the condition of the existence of esterase or nitroreductase, the carrier can be well degraded to respond to the esterase or the nitroreductase.

Description

Technical field [0001] The invention belongs to the field of polymer materials, and particularly relates to an amphiphilic polymer and a preparation method and application thereof. Background technique [0002] Infectious diseases, especially infections caused by pathogenic bacteria, are one of the long-term challenges facing human health (Fauci, A.S., et al. Nature 2004, 430, 242-249). Because it can effectively reduce human morbidity and mortality, antibiotics have become our effective weapon against disease-causing bacteria since the 1940s. However, in the past seventy years, the long-term, large-scale use of antibiotics in medicine and agricultural production, including abuse and misuse in many cases, has caused the gradual accumulation of antibiotics in the natural environment, resulting in resistance genes The enrichment of drug-resistant bacteria accelerates the natural selection process of drug-resistant bacteria, and ultimately leads to the emergence and spread of multi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00A61K47/34A61K47/32A61K45/00A61P31/04
Inventor 刘世勇李亚民
Owner UNIV OF SCI & TECH OF CHINA
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