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Amphiphilic peptide dendrimer for photodynamic/NO synergistic biofilm infection resistance and wound healing promotion and preparation method and application thereof

A dendritic polypeptide and anti-biofilm technology, applied in the field of medical bio-nanomaterials, can solve the problems of L-Arg being easily degraded, few antibiotics with broad-spectrum antibacterial activity, and poor controllability

Active Publication Date: 2021-09-10
温州医科大学附属口腔医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are many problems in the use of antibiotics: 1) the lack of blood vessels in the abscess and the dense wall of the cyst seriously hinder the antibiotics from entering the affected area; 2) the existing antibiotics rarely have broad-spectrum antibacterial activity, especially against drug-resistant pathogens. Antibacterial effect, and the more adverse effect is that the appearance of biofilm also plays a role in protecting bacteria against the host's immune system and improving drug resistance; 3) The overuse and abuse of antibiotics will cause many side effects, such as flora imbalance and decreased immune function
Most of the current research is to physically wrap L-Arg in inorganic or organic nano / micro particles to achieve the controllable delivery of NO, but these delivery systems also face many problems, such as 1) L-Arg loading is limited; 2) Hydrophilic L-Arg is easily degraded during delivery; 3) Only relying on iNOS or low concentration of ROS in diseased tissues to trigger L-Arg to generate NO also has problems such as poor controllability

Method used

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  • Amphiphilic peptide dendrimer for photodynamic/NO synergistic biofilm infection resistance and wound healing promotion and preparation method and application thereof
  • Amphiphilic peptide dendrimer for photodynamic/NO synergistic biofilm infection resistance and wound healing promotion and preparation method and application thereof
  • Amphiphilic peptide dendrimer for photodynamic/NO synergistic biofilm infection resistance and wound healing promotion and preparation method and application thereof

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preparation example Construction

[0069] The present invention also provides a method for preparing a light-responsive amphiphilic dendritic polypeptide used for photodynamic / NO synergistically resisting biofilm infection and promoting wound healing, comprising:

[0070] Centered on Boc-Lys(Boc)-OH, NH was grafted by divergent method 2 -Lys-OMe, for the synthesis of four generations of lysine dendrimer peptides (synthetic pathways such as figure 1 shown), and then Boc-Arg(Pbf)-OH was loaded onto the dendritic end of the fourth-generation lysine dendritic polypeptide by chemical grafting to obtain an arginine-rich dendritic polypeptide (synthetic path as shown in figure 2 shown).

[0071] Stearic acid is grafted to the tail end of the arginine-rich dendritic polypeptide through ethylenediamine, and forms a hydrophobic inner core to obtain the arginine-rich amphiphilic dendritic polypeptide Arg-ADP (synthetic path such as image 3 , 4 shown).

[0072] Ce6 was loaded into the hydrophobic core of Arg-ADP to o...

Embodiment 1

[0090] (1) Four-generation lysine NH protected by methyl ester 2 -Synthesis of Lys(G4)-OMe

[0091] Accurately weighed NH 2 -Lys-OMe (5g, 21.4mmol), Boc-Lys(Boc)-OH (17.8g, 51.4mmol), HOBT (7.0g, 51.4mmol) and HBTU (19.5g, 51.4mmol) were added to 100mL branch tube in a pear shaped bottle. then in N 2 Under protection, 100 mL of anhydrous DMSO was added, and 28.4 mL of DIPEA was added at 0° C., and then reacted at 25° C. for 48 h. After the reaction was finished, a large amount of chloroform was added, washed with saturated NaHCO3, HCl (1M), and NaCl several times successively, and the supernatant was collected, dried with anhydrous MgSO4, and then evaporated under reduced pressure to obtain the crude product. Boc-Lys(G2)-OMe was obtained after purification by column chromatography (methanol:dichloromethane=1:20). Finally, it was added to a mixed solution of trifluoroacetic acid (10 times the equivalent of Boc group) and chloroform (1:1 mixed with trifluoroacetic acid) in ...

Embodiment 2

[0103] The preparation process of steps (1)-(4) is the same as in Example 1 to obtain Arg-ADP.

[0104] (5) Synthesis of Ce6@Arg-ADP

[0105] First, weigh 0.2 mg of Ce6 and 10 mg of Arg-ADP and place them in a centrifuge tube, add 1 mL of DMSO, mix well, then add the mixture dropwise to 10 mL of deionized water to form a micellar suspension. Stirred at room temperature in the dark for 24 h. Then, the aqueous solution was placed in a dialysis bag (1000 Da), and slowly stirred in deionized water for 48 h, and then freeze-dried for 36 h to obtain the final product Ce6@Arg-ADP-2%.

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Abstract

The invention provides a photoresponse amphiphilic peptide dendrimer for photodynamic / NO synergistic biofilm infection resistance and wound healing promotion, the photoresponse amphiphilic peptide dendrimer has a hydrophilic end and a hydrophobic end, the hydrophilic end is a fourth-generation lysine peptide dendrimer, and the dendritic end is loaded with an NO donor material; and the hydrophobic end is stearic acid, and is grafted to the tail end of the fourth-generation lysine peptide dendrimer through ethylenediamine, a hydrophobic core is formed at the tail end of the fourth-generation lysine peptide dendrimer, and a photosensitizer is loaded in the hydrophobic core. The invention also provides a preparation method and application of the photoresponse amphiphilic peptide dendrimer for photodynamic / NO synergistic biofilm infection resistance and wound healing promotion. The photoresponse amphiphilic peptide dendrimer can permeate the bacterial biofilm, induces H2(subscript)O2(subscript) generated by the photosensitizer to quickly oxidize arginine to release a large amount of NO, singlet oxygen is generated in the photochemical process at the same time, and the combination of photodynamic therapy and NO gas therapy is achieved, so as to realize synergistic anti-bacteria and biofilm ablation.

Description

technical field [0001] The present invention relates to the technical field of medical bio-nanomaterials, especially dendritic polypeptides, in particular to an amphiphilic dendritic polypeptide for photodynamic / NO synergistic anti-biofilm infection and wound healing promotion and its preparation method and use . Background technique [0002] Staphylococcus aureus is a common food-borne pathogenic microorganism that widely exists in the natural environment. Under appropriate conditions, it can produce enterotoxin and cause food poisoning. Reports of food poisoning caused by Staphylococcus aureus emerge in endlessly. Food poisoning caused by Staphylococcus aureus accounts for about 25% of food-borne microbial food poisoning incidents. Microbial pathogens seriously endanger human life and health. [0003] Staphylococcus aureus tends to form biofilms with sticky multicellular communities in tissues, and the antibiotics commonly used in the treatment process have slow penetrat...

Claims

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Application Information

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IPC IPC(8): A61K41/00A61K33/00A61K47/64A61P31/04A61P17/02
CPCA61K41/0071A61K33/00A61K47/641A61P31/04A61P17/02A61K2300/00Y02A50/30
Inventor 蔡晓军祝精武陈俊鹏杨超
Owner 温州医科大学附属口腔医院
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