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A high drug loaded polymer nanoparticle based on a dimer prodrug structure and a preparing method thereof

A high drug-loading, polymer technology, applied in the directions of polymer compounds inactive ingredients, drug combinations, pharmaceutical formulations, etc., can solve problems such as hidden dangers of human safety, increase drug loading, uniform particle size distribution, and improve target cells. The effect of specific lethal ability

Inactive Publication Date: 2018-11-16
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In order to achieve the effective drug concentration of the target tissue and target cells, traditional nanoparticles will inevitably introduce a large amount of carrier materials during the drug delivery process, which has the disadvantage of causing potential safety hazards to the human body.

Method used

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  • A high drug loaded polymer nanoparticle based on a dimer prodrug structure and a preparing method thereof
  • A high drug loaded polymer nanoparticle based on a dimer prodrug structure and a preparing method thereof
  • A high drug loaded polymer nanoparticle based on a dimer prodrug structure and a preparing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of sulfur-containing dimer camptothecin prodrug, its preparation method is as follows figure 1 shown, including the following steps:

[0035] (1) Compound 1 (2g, 11.9mmol) and imidazole (2.02g, 29.7mmol) were dissolved in 10ml of anhydrous DMF, and tert-butyldimethylsilane (4.5g, 29.7mmol) was dissolved in 5ml of anhydrous DMF, Slowly add in an ice bath, return the reaction solution to room temperature and stir overnight, confirm the completion of the reaction by TLC plate, suspend the reaction solution to dryness, separate and purify the product by column chromatography to obtain compound 2;

[0036] (2) Compound 4 (9.45g, 100mmol) was dissolved in 150ml aqueous solution and NaN was added 3 (9.75g, 150mmol) was heated to reflux for 22h, the product was extracted 3 times with dichloromethane, dried over anhydrous magnesium sulfate, and suspended to dry to obtain a colorless oily compound 5;

[0037] (3) Compound 5 (1.13g, 11.2mmol) was dis...

Embodiment 2

[0041] Embodiment 2: Synthesis of NT peptide modified prodrug-polyethylene glycol amphiphilic polymer and non-modified prodrug-polyethylene glycol amphiphilic polymer, its preparation method is as follows figure 2 shown

[0042] 1) Synthesis of prodrug-polyethylene glycol amphiphilic polymer

[0043] (1) NaH (7.2mg, 0.3mmol) was slowly added to mPEG in an ice bath 5000 (500mg, 0.1mmol) in 10ml of anhydrous THF solution. After 1h, propargyl bromide (35.7mg, 0.3mmol) was slowly added to the reaction solution and stirred overnight. After the reaction was detected by TLC, 30ml of methanol was added to terminate the reaction. Added dropwise to glacial ether to obtain a white precipitate of alkynylated PEG 5000 ;

[0044] (2) Sulfur-containing dimer prodrug CPTD (12mg, 0.01mmol), alkynylated PEG 5000 (50mg, 0.01 mmol), CuBr (2mg), PMDTA (2μl) were dissolved in 2ml of DMF solution, reacted at room temperature for 24h, the product was dialyzed in EDTA solution for 1d, and then lyo...

Embodiment 3

[0048] Embodiment 3: Preparation of NT peptide modified highly drug-loaded dimer prodrug polymer nanoparticles (NT-CPTD NPs)

[0049] (1) The sulfur-containing dimer camptothecin prodrug CPTD, the drug-containing amphiphilic polymer material CPTD-PEG 5000 and NT-peptide-modified drug-containing amphiphilic polymer material NT-PEG 5000 -CPTD was respectively dissolved in DMF to prepare a stock solution with a mass concentration of 10 mg / ml;

[0050] (2) Pipette 10μl CPTD stock solution, 4μl CPTD-PEG 5000 stock solution and 1 μl NT-PEG 5000 - CPTD stock solution mixed evenly;

[0051] (3) The above-mentioned mixed solution is dropped into 1ml of high-speed stirred deionized water (rotating speed 6000rpm), and the highly drug-loaded dimer prodrug polymer nanoparticles (NT- CPTD NPs). The nanoparticle is a spherical particle with an obvious core-shell structure, and the inner core is a dense prodrug aggregate. The nanoparticle particle size distribution is uniform, and the a...

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Abstract

The invention belongs to the field of medicinal preparation, and relates to a high drug loaded polymer nanoparticle and a preparing method thereof based on a dimer prodrug structure. A high drug loaded polymer nanoparticle preparation is prepared from a sulfur containing dimer camptothecin prodrug, a prodrug-polyethylene glycol amphiphilic polymeric material and the prodrug-polyethylene glycol amphiphilic polymeric material modified by polypeptide to prepare a sulfur containing dimer prodrug high drug loaded polymer nanometer administration system. Amphiphilic polymeric material is synthetizedby directly chemically bonding the sulfur containing dimer camptothecin prodrug with hydrophilic PEG, through a dimer special structure and a drug-cover-drug strategy, and the high drug loaded polymer nanoparticle is prepared. A disulfide bond is introduced in synthetizing the dimer prodrug, the stability of a carrier can be effectively improved, controllability releasing of a drug in a target cell can be realized, breast cancer targeting of the nanoparticle is improved, accumulation of the drug is increased, and the antineoplastic curative effect of the drug is improved.

Description

technical field [0001] The invention belongs to the field of pharmaceutical preparations, in particular to a method for preparing high drug-loaded polymer nanoparticles based on dimer prodrug structure, especially the preparation of hydrophobic drug high drug-load polymer nanoparticles based on dimer structure method Background technique [0002] In recent years, research on nano drug delivery system for tumor drug delivery system has been frequently reported. Studies have shown that compared with traditional chemotherapy, nano drug delivery systems can effectively change the pharmacokinetic properties of drugs, effectively deliver drugs to tumor tissues or cells through passive targeting or active targeting strategies, reduce adverse reactions, and improve the efficacy of chemotherapy drugs. the therapeutic effect. Common nanoparticles are mainly loaded with drugs through physical encapsulation and covalent modification, but practice shows that the drug loading of the two...

Claims

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Application Information

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IPC IPC(8): A61K47/64A61K47/60A61K47/55A61K31/4745A61K9/51A61K47/42A61K47/10A61P35/00
CPCA61K9/5146A61K9/5169A61K31/4745
Inventor 蒋晨贺曦程建军蔡恺珉
Owner FUDAN UNIV
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