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Folic acid modified tellurium bond bridged polyethylene glycol-poly(epsilon-caprolactone) segmented copolymer as well as preparation method and application thereof

A technology of block copolymer and polyethylene glycol, which is applied in the field of polyethylene glycol-polyblock copolymer drug delivery system and nano-drug delivery system, which can solve the problem of low responsiveness and insufficient responsiveness of nano-delivery system and other problems, to achieve the effect of simple and controllable synthesis method, which is conducive to repetition and improves the therapeutic effect

Pending Publication Date: 2020-06-09
TIANJIN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, common redox-responsive bridging chemical bonds, such as disulfide bonds, diselenide bonds, are insufficiently responsive to this concentration of GSH, making the nano-delivery system less responsive.

Method used

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  • Folic acid modified tellurium bond bridged polyethylene glycol-poly(epsilon-caprolactone) segmented copolymer as well as preparation method and application thereof
  • Folic acid modified tellurium bond bridged polyethylene glycol-poly(epsilon-caprolactone) segmented copolymer as well as preparation method and application thereof
  • Folic acid modified tellurium bond bridged polyethylene glycol-poly(epsilon-caprolactone) segmented copolymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Example 1: Synthesis of folic acid modified ditellurium bond bridged polyethylene glycol-poly(ε-caprolactone) block copolymer

[0088] The chemical structure and synthetic route of folic acid modified ditellurium bond bridged polyethylene glycol-poly(ε-caprolactone) block copolymer are shown in the appendix figure 1 shown.

[0089] Folate-modified ditellurium bond-bridged polyethylene glycol-poly(ε-caprolactone) block copolymers with different molecular weights are polyethylene glycol derivatives with ditellurium bonds and folic acid groups at the end groups and terminal groups For carboxyl poly (ε-caprolactone) coupled. The specific experimental steps of synthesis are as follows:

[0090] At 25°C, completely dissolve FA-PEG-TeTe-OH, PCL-COOH, dicyclohexylcarbodiimide and 4-dimethylaminopyridine in anhydrous dichloromethane according to the ratio in Table 2, and react for 24 hours . After the reaction, by-products were removed by filtration, precipitated three times...

Embodiment 2

[0098] Embodiment 2: nanoparticle preparation

[0099] Amphiphilic polyethylene glycol-poly(ε-caprolactone), based on the hydrophobic-hydrophobic interaction in aqueous solution, can obtain "core-shell" micellar structure nanoparticles in water by optimizing the preparation method under specific conditions . In its hydrophobic core, hydrophobic drug molecules can be entrapped to obtain a nano drug delivery system. In this example, the nanoprecipitation method was used to prepare the following nanoparticles.

[0100] 1) Preparation of unloaded nanoparticles with FA-PEG 113 -TeTe-PCL 50 As an example, the specific method is: FA-PEG with a mass of 10mg 113 -TeTe-PCL 50 Dissolve in 200 μL of DMSO, slowly drop the above oil phase into 5 mL of stirred ultrapure water, continue to stir for 30 minutes after the dropwise addition, transfer to a dialysis bag with a molecular weight cut-off of 3500, and use ultrapure water for dialysis for 24 hours at 3000 rpm Empty nanoparticles w...

Embodiment 3

[0102] Example 3: DOX release assay of ditellurium bond bridged targeted nano-delivery system under different conditions

[0103] This embodiment selects mPEG 113 -b-PCL 52 、FA-PEG 113 -b-PCL 46 and FA-PEG 113 -TeTe-PCL 50 Preparation of drug-loaded nanoparticles, respectively named as NP DOX , F-NP DOX and F-TeNP DOX . Dilute the nanoparticle solution to 2 mL (10 mg / mL) with a pH 7.40 buffer solution containing glutathione, transfer to a dialysis tube with a molecular weight cut-off of 3500, immerse in 15 mL of buffer solution, and process on a shaking table at 37 ° C and 60 rpm . At different time intervals, take 100 μL of the buffer solution outside the dialysis bag, and detect the DOX content in the solution by high performance liquid chromatography. The results are shown in Figure 5 .

[0104] Depend on Figure 5 As shown, for NPs without ditellurium bonds DOX , F-NP DOX The release behavior of DOX is basically the same no matter whether glutathione is adde...

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Abstract

The invention relates to a folic acid modified tellurium bond bridged polyethylene glycol-poly(epsilon-caprolactone) segmented copolymer as well as a preparation method and an application thereof. Thesegmented copolymer can be used as a nano delivery system for horizontally delivering small molecular hydrophobic chemotherapeutic drugs in vivo. The bridged block polymer can actively target tumor tissues and promote tumor cell uptake; and specific degradation occurs under the stimulation of glutathione in tumor cells, so that the nanoparticle structure is changed, the intracellular drug releasespeed is increased, and the tumor cell killing function is enhanced.

Description

technical field [0001] The invention relates to the field of nano drug delivery system, in particular to the field of drug delivery system of polyethylene glycol-poly(ε-caprolactone) block copolymer modified by targeted bridge. Background technique [0002] The nano-drug delivery system has a unique size, which can improve the stability of the drug in vivo and avoid the rapid clearance of the drug in the blood; in addition, the nano-drug delivery system can take advantage of the enhanced permeability and retention effect of tumor blood vessels. , EPR effect) changes the distribution of drugs in vivo, passively enhances the drug focus enrichment, reduces the dosage and side effects. Due to the great potential in tumor treatment, nano-drug delivery system has long been a hot spot in the research field, especially drug excipients and their preparations based on amphiphilic block polymers, some of which have been approved for clinical use. huge economic benefits. These amphiph...

Claims

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Application Information

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IPC IPC(8): C08G81/00A61K47/34A61K9/51
CPCC08G81/00A61K47/34A61K9/5146
Inventor 于春水孙春阳庞泽堃周佳妍
Owner TIANJIN MEDICAL UNIV
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