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Reduction-responsive viologen molecule, polypeptide-viologen derivative, preparation method and application

A derivative, responsive technology, applied in the field of biomedicine, can solve problems such as deficiency

Pending Publication Date: 2022-08-02
HENAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Therefore, introducing responsive molecules into antimicrobial peptide molecules is expected to solve the toxic and side effects of synthetic antimicrobial peptides and achieve efficient antibacterial and antitumor properties, but such responsive molecules are currently lacking.

Method used

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  • Reduction-responsive viologen molecule, polypeptide-viologen derivative, preparation method and application
  • Reduction-responsive viologen molecule, polypeptide-viologen derivative, preparation method and application
  • Reduction-responsive viologen molecule, polypeptide-viologen derivative, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] A method for synthesizing a reduction-responsive viologen molecule, comprising the following steps:

[0074] (1)C n V + Synthesis:

[0075] ① Dissolve 200 mg of 4,4'-bipyridine in 10 ml of dichloromethane, pass nitrogen to remove oxygen, add 80 μL of methyl iodide dropwise under nitrogen atmosphere, and react in the dark for 24 hours at room temperature; after the reaction is completed, filter and collect the filtered cake, washed three times with dichloromethane, and dried in vacuo to give a pale yellow solid C 1 V + ;

[0076] ② Dissolve 200 mg of 4,4'-bipyridine in 10 ml of dichloromethane solution, pass nitrogen to remove oxygen, add 120 μL of n-bromopropane dropwise under nitrogen atmosphere, and react at room temperature in the dark for 24 hours; filter and collect the filter cake , washed three times with dichloromethane, and dried in vacuo to give a yellow solid C 3 V + ;

[0077] ③ Dissolve 200 mg of 4,4'-bipyridine in 15 ml of anhydrous acetonitrile so...

Embodiment 2

[0081] A preparation method of a polypeptide-viologen derivative, comprising the following steps:

[0082] (1) Dissolve 40mg polypeptide molecule Pep in 10mL deionized water, and add 20mg C n V 2+ Mal, dissolved, mixed, and reacted at room temperature for 24 hours; the specific sequence of the polypeptide molecule Pep is NH 2 -C-VAQLEVKVAQLESK-VSKLESK-VSSLESK-COOH;

[0083] (2) the mixed solution obtained in (1) is placed in a dialysis bag, the dialysis bag has a molecular weight cut-off of 3500, and the dialysis bag is put into ultrapure water for dialysis, fresh dialysate is replaced every 2 hours, and dialysis is performed for 24 hours;

[0084] (3) After the dialysis, freeze-dry the solution in the dialysis bag to finally obtain a white loose powder, which is the polypeptide-viologen derivative Pep-C n V 2+ (n=1,3,5).

[0085] Determination of C by 1H NMR 1 V 2+ The molecular structure of Mal, as figure 1 shown; the use of infrared spectroscopy to determine the pol...

Embodiment 3

[0086] Example 3 to the polypeptide-viologen derivative Pep-C prepared in Example 2 n V 2+ Conduct reduction responsiveness studies

[0087] 1. Ultraviolet absorption spectroscopy to study reduction responsiveness

[0088] Prepare 0.1mol of Pep-Cn V 2+ The aqueous solution was measured by adding Na at room temperature 2 S 2 O 3 Before and after UV absorption spectrum (200nm-500nm), among which, Pep-C n V 2+ with Na 2 S 2 O 3 The mass ratio is 1:9. like image 3 shown, in Na 2 S 2 O 3 Before adding, a characteristic absorption peak appeared at 260 nm; by contrast, adding Na 2 S 2 O 3 After that, the characteristic peak at 260nm disappeared, which proved that the polypeptide-bauhinia derivative had good reduction responsiveness.

[0089] 2. Fluorescence spectroscopy to study reduction responsiveness

[0090] Prepare 0.1mol of Pep-C n V 2+ The aqueous solution was measured by adding Na at room temperature 2 S 2 O 3 Fluorescence spectrum before and after (4...

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Abstract

The invention belongs to the technical field of biological medicine, and particularly relates to a viologen molecule with reduction response performance, a polypeptide-viologen derivative, a preparation method and application. The viologen molecular structure is CnV2 + Mal, and n is equal to 1, 3 or 5; v < 2 + > represents a viologen molecule in an ionic state, and Mal represents maleimide; and dissolving polypeptide molecules Pep and CnV2 + Mal in deionized water, dissolving and uniformly mixing, dialyzing the solution obtained after the normal-temperature reaction is finished in a dialysis bag with the cutoff molecular weight of 3500 for more than 24 hours, and drying the solution in the dialysis bag to obtain the polypeptide-viologen derivative. The selective adsorption effect on the surfaces of tumor cells is achieved through the charged performance of polypeptide, meanwhile, the damage effect on cell membranes is achieved through the hydrophobicity of viologen molecules under the effect of a reducing agent, and therefore the tumor cells are dead, and the anti-tumor potential is achieved; therefore, the viologen molecule and the polypeptide-viologen derivative provided by the invention have good application prospects in antibacterial and anti-tumor aspects.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to a viologen molecule with reduction response performance, a polypeptide-viologen derivative, a preparation method and an application. Background technique [0002] Diseases caused by microbial infections are becoming more and more serious, and the human mortality rate is increasing year by year. At that time, infectious diseases have become an important type of disease that threatens public safety and health. In 1928, the emergence of artemisinin successfully fought infectious diseases. Subsequently, various antibiotics such as erythromycin and streptomycin appeared in clinical application. So far, mankind has entered the era of antibiotics. However, the widespread application of antibiotics also brings its drug resistance problem, which leads to the ineffectiveness of the treatment of bacterial infections, and bacterial infections have once again become a threat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/04C07D498/10C07D498/14C07D519/00A61K31/553A61P35/00A61P35/02A61P19/08A61P29/00A61P37/02A61P25/00A61P3/00A61P11/00A61P9/00
CPCC07D498/04C07D498/10C07D498/14C07D519/00A61P35/00A61P35/02A61P19/08A61P29/00A61P37/02A61P25/00A61P3/00A61P11/00A61P9/00Y02A50/30
Inventor 王斯佳李圆圆孙月王飞燕
Owner HENAN UNIV OF CHINESE MEDICINE
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