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A kind of bodipy-containing bactericidal material and its preparation method and application

A BODIPY-N3 reaction technology, which is applied in the direction of luminescent materials, preparation of sugar derivatives, chemical instruments and methods, etc., can solve the problem of BODIPY being insoluble in water, etc., and achieve the effect of simple reaction steps, low risk and good water solubility

Active Publication Date: 2020-06-23
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 object of the present invention is to overcome the shortcoming that BODIPY is insoluble in water, provide a kind of BODIPY-containing bactericidal material and its preparation method and application

Method used

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  • A kind of bodipy-containing bactericidal material and its preparation method and application
  • A kind of bodipy-containing bactericidal material and its preparation method and application
  • A kind of bodipy-containing bactericidal material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of BODIPY-Mal-I multifunctional sterilizing material 1:

[0040] 1) BODIPY-N 3 Preparation: Weigh 350mg BODIPY-Br, dissolve it with 8mL DMF, and react with sodium azide at 70°C for 12h at a molar ratio of 1:1. Then, when the product is cooled to room temperature, add ethyl acetate for extraction, and then saturated Wash with ammonium chloride, dry with anhydrous sodium sulfate, spin dry under reduced pressure to obtain BODIPY-N 3 ;

[0041] 2) Preparation of BODIPY-Mal: Combine BODIPY-N in step 1) 3 Dissolve in DMF and add acetylenized maltoheptaose (Mal7-alkyne) at the same time. Under anaerobic conditions, the "click reaction" is carried out under the catalysis of CuCl / PMDETA complex, and the reaction temperature is 40℃ for 24h, molar ratio BODIPY-N 3 :Mal7-alkyne=1:0.8, after the reaction, put the product into a 500D dialysis bag, dialyzed with deionized water, filtered with a 0.22μm pinhole filter, and lyophilized;

[0042] 3) Preparation of BODIPY-Mal-I: Diss...

Embodiment 2

[0044] Preparation of BODIPY-Mal-I multifunctional sterilizing material 2:

[0045] 1) BODIPY-N 3 Preparation: Weigh 380mg BODIPY-Br, dissolve it with 10mL DMF, and react with sodium azide at 60°C for 24h with a molar ratio of 1:1.5. Then, when the product is cooled to room temperature, add ethyl acetate for extraction, and then saturated Wash with ammonium chloride, dry with anhydrous sodium sulfate, spin dry under reduced pressure to obtain BODIPY-N 3 ;

[0046] 2) Preparation of BODIPY-Mal: Combine BODIPY-N in step 1) 3 Dissolve in DMF, and add acetylenized maltoheptaose (Mal7-alkyne) at the same time. Under anaerobic conditions, the "click reaction" is carried out under the catalysis of CuCl / PMDETA complex. The reaction temperature is 50℃ for 24h, molar ratio BODIPY-N 3 :Mal7-alkyne=1:1, after the reaction is over, put the product into a 500D dialysis bag, dialyzed with deionized water, filter with a 0.22μm pinhole filter and freeze-dry;

[0047] 3) Preparation of BODIPY-Mal-I: ...

Embodiment 3

[0049] Preparation of BODIPY-Mal-I multifunctional sterilization material 3:

[0050] 1) BODIPY-N 3 Preparation: Weigh 400mg BODIPY-Br, dissolve it with 10mL DMF, and react with sodium azide at 50℃ for 36h with a molar ratio of 1:2. Then, when the product drops to room temperature, add ethyl acetate for extraction, and then saturated Wash with ammonium chloride, dry with anhydrous sodium sulfate, spin dry under reduced pressure to obtain BODIPY-N 3 ;

[0051] 2) Preparation of BODIPY-Mal: Combine BODIPY-N in step 1) 3 Dissolve in DMF, add acetylenized maltoheptaose (Mal7-alkyne) at the same time, under anaerobic conditions, carry out "click reaction" under the catalysis of CuCl / PMDETA complex, and react at 60℃ for 24h, molar ratio BODIPY-N 3 :Mal7-alkyne=0.8:1, after the reaction is over, put the product into a 500D dialysis bag, dialyzed with deionized water, filter with a 0.22μm pinhole filter and freeze-dry;

[0052] 3) Preparation of BODIPY-Mal-I: Dissolve BODIPY-Mal in water in...

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Abstract

The invention discloses a BODIPY-containing bactericidal material and a preparation method and application thereof. The preparation method comprises that BODIPY-Br and sodium azide undergo a reactionto produce BODIPY-N3, BODIPY-N3 and acetylated maltoheptaose undergo a reaction under the catalytic action of a CuCl / PMDETA complex to produce BODIPY-Mal, and the BODIPY-Mal, iodic acid and iodine undergo an iodination reaction to produce the BODIPY-Mal-I bactericidal material. The BODIPY-Mal-I bactericidal material has good water solubility and completely retains the properties of BODIPY. The photodynamic power generated by BODIPY-Mal-I can effectively inactivate yeast cells and especially kill gram-positive bacteria. The preparation method has the advantages of simple processes, mild reaction conditions, low risk and low toxicity.

Description

Technical field [0001] The invention belongs to the field of antibacterial materials, and relates to a BODIPY-containing sterilization material and a preparation method and application thereof. Background technique [0002] In recent years, the abuse of antibiotics has led to the emergence and spread of "super bacteria". The so-called "super bacteria" refers to the multi-drug resistance of these bacteria to current antibiotics, which adds great difficulty to the treatment of clinical trauma infections. Therefore, the development of new anti-infection strategies is extremely urgent. Photodynamic antibacterial therapy is one of the most promising new therapies. It has shown a good effect on infections caused by bacteria, fungi and viruses, especially infections caused by resistant bacteria. [0003] Photodynamic therapy is a technology that uses the photodynamic effects of light and photosensitizers to diagnose and treat diseases. The mechanism of photodynamic antibacterial action...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/26C07H1/00C09K11/06A61K41/00A61P31/04A61P31/10
CPCA61K41/0057A61P31/04A61P31/10C07H1/00C07H15/26C09K11/06C09K2211/1055C09K2211/1059C09K2211/1088
Inventor 徐立群郝杰宁玲贵王浩哲程艳芳
Owner SOUTHWEST UNIV
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