Fosfomycin chitosan hybrid salt and preparation method thereof

A technology of fosfomycin and chitosan, applied in the field of fosfomycin-chitosan hybrid salt and preparation thereof, can solve the problem of low antibacterial broad-spectrum and the like, and achieve the effect of excellent biological activity

Active Publication Date: 2020-06-30
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In view of this, the present invention aims to propose a kind of fosfomycin chitosan hybrid salt, to

Method used

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  • Fosfomycin chitosan hybrid salt and preparation method thereof
  • Fosfomycin chitosan hybrid salt and preparation method thereof
  • Fosfomycin chitosan hybrid salt and preparation method thereof

Examples

Experimental program
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Embodiment 1

[0038] A kind of fosfomycin-chitosan hybrid salt, specifically prepares by following method:

[0039] 1) Dissolve 0.578g of sodium hydroxide in 5mL of purified water, add 2.2g of left phosphorus and right ammonium salt, stir well, release α-phenylethylamine, let it stand for stratification, separate liquid, and collect fosfomycin sodium solution in the water layer ;

[0040] 2) At -10°C, mix fosfomycin sodium solution in 1) with 20mL of cation exchange resin (model: D001 macroporous strongly acidic styrene-based cation exchange resin), and add an appropriate amount of ethanol to avoid solution under low temperature. Freeze, and then perform ion exchange for 20 minutes. After the ion exchange is completed, elute twice with pre-cooled ethanol, 25 mL each time, to obtain fosfomycin solution;

[0041] 3) Select 6.6 g of non-water-soluble chitosan with a molecular weight in the range of 183837 to 292614 to fully stir and mix with the fosfomycin solution in step 2), and carry out a...

Embodiment 2

[0043] A kind of fosfomycin-chitosan hybrid salt, specifically prepares by following method:

[0044] 1) Dissolve 2.89g of sodium hydroxide in 25mL of purified water, add 1.1g of left phosphorus and right ammonium salt, stir well, release α-phenylethylamine, let stand to separate layers, separate liquids, and collect fosfomycin sodium solution in the water layer ;

[0045] 2) At -10°C, mix the fosfomycin sodium solution in 1) with 50mL of cation exchange resin (model: D001 macroporous strongly acidic styrene-based cation exchange resin), and add an appropriate amount of ethanol to avoid solution under low temperature. Freezing, then, ion exchange for 10 minutes, after the ion exchange is completed, elute with pre-cooled ethanol twice, 25 mL each time, to obtain fosfomycin solution;

[0046] 3) Select 6.6g of chitosan oligosaccharide with molecular weight less than 1000, dissolve in 30mL of purified water, mix with 100mL of strong basic anion exchange resin (chlorine type 717 ...

Embodiment 3

[0052] A kind of fosfomycin-chitosan hybrid salt, specifically prepares by following method:

[0053] 1) Dissolve 2.89g of sodium hydroxide in 25mL of purified water, add 1.1g of left phosphorus and right ammonium salt, stir well, release α-phenylethylamine, let stand to separate layers, separate liquids, and collect fosfomycin sodium solution in the water layer ;

[0054] 2) At -10°C, mix the fosfomycin sodium solution in 1) with 50mL of cation exchange resin (model: D001 macroporous strongly acidic styrene-based cation exchange resin), and add an appropriate amount of ethanol to avoid solution under low temperature. Freezing, then, ion exchange for 10 minutes, after the ion exchange is completed, elute with pre-cooled ethanol twice, 25 mL each time, to obtain fosfomycin solution;

[0055] 3) Select 6.6g of glucosamine hydrochloride, dissolve in 30mL of purified water, mix with 100mL of strong basic anion exchange resin (chlorine type 717 strong basic anion exchange resin), ...

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Abstract

The invention provides a fosfomycin chitosan hybrid salt and a preparation method thereof; the fosfomycin chitosan hybrid salt is obtained by salifying two hydroxyl groups of fosfomycin and amino groups on chitosan molecules with the same chain, or salifying two hydroxyl groups of fosfomycin and amino groups on different chitosan chains. The preparation method of the fosfomycin chitosan hybrid salt provided by the invention comprises the steps: by taking phosphonomycin (R)-1-phenethylamine salt as an initial raw material, dissociating fosfomycin sodium by virtue of a sodium hydroxide solution,preparing a fosfomycin acid solution by virtue of cation exchange, carrying out a reaction with chitosan with different molecular weights, and refining, so as to obtain the fosfomycin chitosan hybridsalt. According to the preparation process disclosed by the invention, the fosfomycin chitosan hybrid salts with different molecular weight segment grades can be obtained, the hybrid salts can have different water solubility according to different molecular weights of chitosan, the biological activity is excellent, and the fosfomycin chitosan hybrid salts can be used for antibacterial treatment in different ways.

Description

technical field [0001] The invention relates to the technical field of medicine synthesis, in particular to a fosfomycin-chitosan hybrid salt and a preparation method thereof. Background technique [0002] Fosfomycin is a broad-spectrum antibacterial drug, its molecular structure is similar to phosphoenolpyruvate, it was originally isolated from Streptomyces fradicle, and it is effective against Gram-positive and negative bacteria. It has high antibacterial activity against Staphylococcus, Escherichia coli, Serratia and Shigella, etc. It also has certain antibacterial activity against Pseudomonas aeruginosa, Proteus, Aerobacter, Klebsiella pneumoniae, Streptococcus and some anaerobic bacteria effect, but are worse than penicillins and cephalosporins. Bacteria do not produce cross-resistance to this product and other antibiotics. [0003] Fosfomycin has a unique antibacterial mechanism. It can be covalently bound to uracil-acetylglucosamine diphosphate transferase (MurA), a...

Claims

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Application Information

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IPC IPC(8): C07F9/655C08B37/08A61K31/665A61K31/722A61P31/04
CPCC07F9/65505C08B37/003A61K31/665A61K31/722A61P31/04A61K2300/00Y02A50/30
Inventor 祝宏李爽李丽姜志炜李雪方世通
Owner WUHAN INSTITUTE OF TECHNOLOGY
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