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Triple disulfide-bond linked polyethylene glycol-polycaprolactone triblock copolymer as well as preparation method and application thereof

A polycaprolactone and polyethylene glycol technology, applied in the field of polyethylene glycol polycaprolactone triblock polymer and its preparation, can solve problems such as anti-tumor differences, and achieve strong cellular uptake, good stability, good biocompatibility

Active Publication Date: 2016-09-28
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

More notably, the drug-loaded micelles with and without disulfide bonds introduced with different numbers of disulfide bonds showed significant anti-tumor differences in in vivo anti-tumor experiments

Method used

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  • Triple disulfide-bond linked polyethylene glycol-polycaprolactone triblock copolymer as well as preparation method and application thereof
  • Triple disulfide-bond linked polyethylene glycol-polycaprolactone triblock copolymer as well as preparation method and application thereof
  • Triple disulfide-bond linked polyethylene glycol-polycaprolactone triblock copolymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] Embodiment 1 prepares block polymer

[0095] (a) 8 g of methoxypolyethylene glycol and 8.2 g of N,N'-dicyclohexylcarbodiimide were dissolved in 50 mL of anhydrous dichloromethane, and stirred at room temperature for two hours. Then, 7.3 g of 2,2'-dithiodiacetic acid and 4.88 g of 4-dimethylaminopyridine were added to the above solution, and reacted at room temperature for 24 hours. The obtained solution was filtered, and the filtrate was concentrated with a vacuum rotary evaporator. The concentrated solution was dispersed with isopropanol and crystallized at 0°C. The mixture was filtered and recrystallized from dichloromethane-isopropanol to obtain disulfide-linked polyethylene glycol (PEG-SS-PEG).

[0096] (b) 4 g of PEG-SS-PEG and 1.54 g of dithiothreitol were weighed and dissolved in 25 ml of tetrahydrofuran under nitrogen protection. Dissolve 0.027 g of sodium methoxide in 2 ml of methanol. According to the volume ratio of 25:2, the above solution was mixed with...

Embodiment 2

[0106] Embodiment 2 The block polymer of embodiment 1 is prepared into block polymer nanoparticles

[0107] Dissolve 10 mg of triple disulfide bond-linked polyethylene glycol polycaprolactone block polymer in 1 mL of dimethyl sulfoxide. The resulting solution was then added dropwise to 5 mL of double distilled water and stirred for 30 minutes. The mixture was placed in a dialysis bag with a molecular weight cut-off of 3500 Da and dialyzed against double distilled water at room temperature to remove dimethyl sulfoxide to obtain a triple disulfide-linked polyethylene glycol polycaprolactone block polymer Nanoparticles.

[0108] After testing, the polyethylene glycol polycaprolactone block polymer nanoparticles linked by triple disulfide bonds have a regular spherical structure; the particle size is 78±4nm, and the dispersion coefficient is 0.125±0.053.

[0109] figure 1 with figure 2 They are the transmission electron microscope image and the particle size distribution diag...

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Abstract

The invention belongs to the field of macromolecule polymers, in particular to a triple disulfide-bond linked polyethylene glycol-polycaprolactone triblock copolymer as well as a preparation method and application thereof. The weight-average molecular weight of the triblock copolymer is 6000 to 26000 Da; the triblock copolymer is obtained via mutual reaction between activated polyethylene glycol and polycaprolactone which is provided with living functional groups and obtained via ring-opening polymerization. The triblock copolymer is high in biocompatibility and biodegradability and low in toxicity, has the characteristic of intelligent responsive release when being used as an anticancer drug carrier, and also has the advantages of being good in stability, long in circulating time in a body and strong in cell uptake.

Description

technical field [0001] The invention belongs to the field of macromolecular polymers, in particular to a triple-disulfide bond-linked polyethylene glycol polycaprolactone triblock polymer and a preparation method thereof Background technique [0002] Polyethylene glycol (PEG) is a polyether polymer compound with neutral pH, non-toxicity, high water solubility and extremely wide uses. Its repeating unit is oxyethylene, which is linear or branched chain. shape structure. Polyethylene glycol polymer is the polymer with the lowest level of protein and cell absorption among known polymers so far. In vivo, polyethylene glycol can be dissolved in interstitial fluid and can be quickly excreted by the body without any toxic side effects. Because polyethylene glycol is non-toxic and has good biocompatibility, it has been approved by the FDA as a medicinal polymer for intracorporeal injection. Due to the above characteristics, as well as biocompatibility, safety, and almost no foreig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/00C08G63/91A61K9/107A61K47/34
CPCA61K9/1075A61K47/34C08G63/912C08G81/00C08G2230/00
Inventor 吴雁赵彩艳韦宇杰赵宸颖
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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