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Sterilizing material containing protoporphyrin and preparation method and application thereof

A protoporphyrin and reaction technology, applied in the field of protoporphyrin-containing bactericidal materials and their preparation, can solve problems such as insolubility of protoporphyrin in water, and achieve the effects of low risk, good water solubility and mild reaction conditions

Active Publication Date: 2018-08-07
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In view of this, the purpose of the present invention is to overcome the shortcoming that protoporphyrin is insoluble in water, propose a kind of new method that carries out a series of reactions with glycidol having good water solubility to prepare water-soluble protoporphyrin material

Method used

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  • Sterilizing material containing protoporphyrin and preparation method and application thereof
  • Sterilizing material containing protoporphyrin and preparation method and application thereof
  • Sterilizing material containing protoporphyrin and preparation method and application thereof

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preparation example Construction

[0034] 1) Preparation of PPIX-HPG: react after mixing protoporphyrin and glycidol, then dialyze with pure water, and freeze-dry to obtain PPIX-HPG polymer;

[0035] 2) Preparation of PPIX-HPG-OMs: Dissolve the PPIX-HPG polymer in step 1) with pyridine, and at the same time use pyridine as a catalyst, add anhydrous methanesulfonyl chloride dropwise for mesylation, dialyze with ethanol, spin dry to prepare Obtain PPIX-HPG-Oms polymer;

[0036] 3) PPIX-HPG-N 3 Preparation: Dissolve the PPIX-HPG-OMs polymer in step 2) with DMF, react with sodium azide, and obtain PPIX-HPG-N after dialysis with pure water 3 polymer;

[0037] 4) PPIX-HPG-NH 2 Preparation: the PPIX-HPG-N in step 3) 3 The reduction reaction between the polymer and tris(2-carboxyethyl)phosphine hydrochloride reduces the azide group on the polymer to an amino functional group, and obtains PPIX-HPG-NH after water dialysis 2 Sterilizing material.

[0038] In step 1), it is characterized in that: in parts by weight, ...

Embodiment 1

[0044] PPIX-HPG-NH 2 The preparation method of sterilizing material 1, comprises the following steps:

[0045] 1) Preparation of PPIX-HPG: Weigh 90mg of protoporphyrin and 5mL of glycidol, mix and react at 75°C for 36h, then, when the product is cooled to room temperature, put the product into a 3500D dialysis bag and dialyze with deionized water, and the dialysis is completed After filtering with a 0.22 μm pinhole filter, the initial product PPIX-HPG can be obtained;

[0046] 2) Preparation of PPIX-HPG-OMs: Dissolve the PPIX-HPG polymer in step 1) with pyridine, and at the same time use pyridine as a catalyst, add anhydrous methanesulfonyl chloride dropwise for mesylation, react at room temperature for 24h, mol Ratio PPIX-HPG:Ms=1:0.5, dialyzed through ethanol, spin-dried;

[0047] 3) PPIX-HPG-N 3Preparation: Dissolve the PPIX-HPG-OMs polymer in step 2) with DMF, react with sodium azide at 70°C for 36h, the molar ratio is 1:1, wait for the product to cool down to room temp...

Embodiment 2

[0050] PPIX-HPG-NH 2 The preparation method of sterilizing material 2, comprises the following steps:

[0051] 1) Preparation of PPIX-HPG: Weigh 120mg of protoporphyrin and 5mL of glycidol and mix them and react at 85°C for 36h. After the product cools down to room temperature, put the product into a 3500D dialysis bag and dialyze with deionized water. After the dialysis is completed, use The initial product PPIX-HPG can be obtained by filtering through a 0.22 μm pinhole filter;

[0052] 2) Preparation of PPIX-HPG-OMs: Dissolve the PPIX-HPG polymer in step 1) with pyridine, and at the same time use pyridine as a catalyst, add anhydrous methanesulfonyl chloride dropwise for mesylation, react at room temperature for 24h, mol Ratio PPIX-HPG:Ms=1:1.2, dialyzed through ethanol, spin-dried;

[0053] 3) PPIX-HPG-N 3 Preparation: Dissolve the PPIX-HPG-OMs polymer in step 2) with DMF, react with sodium azide at 85°C for 36h, the molar ratio is 1:0.5, wait for the product to cool dow...

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Abstract

The invention relates to a sterilizing material containing protoporphyrin, a preparation method and application thereof. According to the invention, protoporphyrin is mixed with glycidol, then ring-opening reaction is performed at the temperature of 75-100 DEG C, methyl sulfonylation is performed on the mixture and anhydrous methylsufonyl chloride at room temperature by taking pyridine as a reaction solvent and a catalyst, then sodium azide is added to perform nucleophilic substitution, produced PPIX-HPG-N3 polymer generates reduction reaction with tri(2-carboxyethyl) phosphine hydrochloride,so as to reduce an azide group on the polymer to be an amino functional group, and then a PPIX-HPG-NH2 polymer with a sterilization effect is prepared. The sterilizing material prepared by the invention has the advantages of simplified reaction steps, mild reaction conditions, low risk, low-toxic product, and good solubility, and has potential application in the aspect of sterilization.

Description

technical field [0001] The invention belongs to the technical field of polymer material synthesis and preparation, and relates to a protoporphyrin-containing bactericidal material and its preparation method and application. Background technique [0002] In recent years, due to the abuse of antibiotics has led to the emergence and spread of "super bacteria". The so-called "super bacteria" means that these bacteria have multi-drug resistance to current antibiotics, which adds great difficulty to the treatment of clinical wound infections. Therefore, the development of new anti-infection strategies is imminent. Photodynamic antimicrobial therapy is one of the most promising new therapies, which has shown good curative effect on infections caused by bacteria, fungi and viruses, especially for drug-resistant bacterial infections. [0003] Photodynamic therapy is a technology that utilizes the photodynamic effect produced by light and photosensitizers for disease diagnosis and t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00A61P31/04A61P31/10
CPCA61K41/0071A61P31/04A61P31/10C07D487/22
Inventor 徐立群宁玲贵
Owner SOUTHWEST UNIV
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