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Photosensitizer-releasing antibacterial nano micelles and preparation method and application thereof

A technology of nano micelles and photosensitizers, applied in the field of nano biomedical materials, can solve the problems of limited application of vancomycin, low encapsulation efficiency and drug loading rate, and it is difficult for vancomycin to achieve ideal drug efficacy, etc. Degradability, good biocompatibility, and the effect of prolonging circulation time in vivo

Active Publication Date: 2019-07-05
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, biocompatible, degradable mPEG, PCL, and PAE are ideal materials for preparing nanocarriers, Gao Honglin et al., (A charge adaptive nanosystem for prolonged and enhanced invivo antibiotic delivery. Chem Commun (Camb). -6268) used PEG-PCL-PAE to prepare nanoparticles for the delivery of vancomycin for the treatment of dermatitis, but this method uses a double-layer solvent emulsification and evaporation method to load vancomycin, and the encapsulation efficiency and drug loading rate are low, respectively only 45.4% and 9.2%, the low drug loading rate makes it difficult for vancomycin to achieve the desired drug effect
Moreover, with the emergence of drug-resistant bacteria, drug-resistant strains such as vancomycin-resistant Enterococcus and vancomycin-resistant Staphylococcus aureus have gradually emerged, which limits the application of vancomycin
In the above-mentioned public documents, there is no disclosure of preparing antibacterial nanomicelles by embedding photosensitizers in amphiphilic triblock copolymer monomethoxypolyethylene glycol-polycaprolactone-polyβ-amino ester

Method used

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  • Photosensitizer-releasing antibacterial nano micelles and preparation method and application thereof
  • Photosensitizer-releasing antibacterial nano micelles and preparation method and application thereof
  • Photosensitizer-releasing antibacterial nano micelles and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0046] Synthesis of mPEG-PCL-PAE

[0047] The synthesis of mPEG-PCL-PAE includes two parts, one, mPEG-PCL is obtained by ring-opening polymerization (ROP). Among them, mPEG-OH is used as the initiator, stannous isooctanoate (Sn(Oct) 2 ) as a catalyst and ε-CL as a monomer. The specific steps are as follows: weigh mPEG (4.0g, 2.0mmol) and ε-CL (10.0g, 87.8mmol) and dissolve them in 40mL of anhydrous toluene, add a drop of Sn(Oct) 2 , and then freeze the reaction liquid with liquid nitrogen, vacuumize, pass nitrogen, thaw, repeat three times, and exhaust the oxygen. Stir the reaction overnight at 110°C, then remove the solution, and dissolve the crude product in dichloromethane, then add glacial ether ten times the volume of dichloromethane to precipitate to remove impurities, filter and wash the solid product mPEG-PCL Dry in a vacuum oven and store at 4°C for later use. 2. Dissolve mPEG-PCL (1g) and triethylamine (2g) in a 250mL round bottom flask with 10mL of dichlorometha...

Embodiment 2

[0049] Preparation and characterization of mPEG-PCL-PAE-EA micelles Precisely weigh 100mg of mPEG-PCL-PAE and 20mg of escarcin A (EA) into a 25mL round bottom flask, add 15mL of acetone, and dissolve them by ultrasonication. Rotary evaporate at 40°C for about 30min until the acetone is volatilized and a transparent and uniform film is formed. Add 1 mg of D-mannitol, add double distilled water or replace it with 8mL of PBS (pH5.5, 6.5, 7.4), and place in a water bath at 55°C Rotate slowly to hydrate the film. After hydration for 3 hours, use a probe-type ultrasonic instrument to sonicate for 20 minutes (20HZ) in an ice-water bath to obtain drug-loaded nanomicelles ( figure 1 A), use a 0.22 μm filter to remove unencapsulated EA, and freeze-dry the micelles at -80°C for 48 hours in a vacuum to make a freeze-dried powder ( figure 1 B) Store in a refrigerator at 4°C. The micelles made with 5% D-mannitol as a freeze-drying protective agent have good resolubility after freeze-drying...

Embodiment 3

[0052] The preparation process of embodiment 3 is the same as that of embodiment 2, and the difference is that, by weight, photosensitizer scutoclavin B 5 parts, monomethoxy polyethylene glycol-polycaprolactone-poly β-amino ester 5 parts 0.01 part of freeze-dried excipient sucrose; the organic solvent was replaced by dichloromethane; the rotary evaporation temperature was 40°C, and the rotary evaporation was 2h; the hydration temperature was 40°C, and the hydration time was 6h; , the frequency is 20HZ; the freeze-drying condition is -50℃, 48h.

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Abstract

The invention discloses photosensitizer-releasing antibacterial nano micelles and a preparation method and application thereof. The antibacterial nano micelles are formed by embedding a quinone hydrophobic photosensitizer in amphiphilic three-block copolymer which is monomethoxy polyethylene glycol-polycaprolactone-polybeta-amino ester. The antibacterial nano micelles are pH-responsive and can release the photosensitizer in a targeted manner. The nano micelles have good photodynamic antibacterial effect on pathogenic bacteria, especially drug-resistant bacteria, are less prone to causing drugresistance and can gather at positions with lipase-sensitive bacteria and directionally kill the drug-resistant bacteria under illumination. The nano micelles are good in targeting performance, have high biocompatibility and biodegradability and are easy in conversion towards clinical application, high in water solubility, targeting performance and drug cumulativity, remarkable in photodynamic bactericidal effect and good in application prospect.

Description

technical field [0001] The invention belongs to the field of nano-biological medical materials, and relates to an antibacterial nano-micelle releasing a quinone photosensitizer, a preparation method and an application thereof. Background technique [0002] The emergence of drug-resistant bacteria has caused serious health problems and millions of people die every year. The World Health Organization believes that drug-resistant bacteria have become one of the main threats to human health. For example, methicillin-resistant Staphylococcus aureus (MRSA) is a typical opportunistic pathogen frequently isolated from hospital patients. Due to the high infection rate of MRSA, the broad spectrum of drug resistance, and the emergence of multidrug resistance, it is urgent to develop new antibacterial agents to treat MRSA infection. [0003] At present, various antibacterial materials, such as metal ions, antimicrobial peptides, carbon and inorganic nanomaterials, cationic polymers and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K41/00A61K9/107A61K9/19A61K47/34A61P31/04
CPCA61K9/1075A61K9/19A61K47/34A61K41/0057A61P31/04
Inventor 陈双林郭凌媛闫淑珍
Owner NANJING NORMAL UNIVERSITY
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