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Thioketal bond connected pegylated Ce6 material as well as preparation method and application thereof

A technology of PEGylation and polyethylene glycol carboxyl group is applied in the field of PEGylated Ce6 material and its preparation, which can solve problems such as the limitation of wide applicability of nanoparticles, achieve good biocompatibility and degradability, The effect of enhanced uptake, great potential for clinical application

Inactive Publication Date: 2020-07-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the broad applicability of tumor microenvironment-responsive nanoparticles is limited due to the heterogeneity of tumors, the pH value of the tumor microenvironment, and the differences in the dynamic expression of enzymes at different stages in different types of tumors or in different parts of the same tumor.

Method used

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  • Thioketal bond connected pegylated Ce6 material as well as preparation method and application thereof
  • Thioketal bond connected pegylated Ce6 material as well as preparation method and application thereof
  • Thioketal bond connected pegylated Ce6 material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Embodiment 1, mPEG 45 -Synthesis and Characterization of TK-Ce6 and PLA

[0075] 1. Pegylated Ce6 materials linked by thioketal bonds (mPEG 45 -TK-Ce6) and polylactic acid (PLA) synthesis

[0076] mPEG 45 -TK-Ce6 consists of 2,2'-(propane-2,2-diylbis(sulfadiyl))bis(ethanol-1-amine) and mPEG 45 -COOH, Ce6 can be obtained through condensation reaction.

[0077] PLA is obtained by using stannous isooctanoate as a catalyst, and 10-hydroxydecanoic acid triggers the ring-opening polymerization of L-lactide.

[0078] Synthetic route such as figure 1 shown.

[0079] Preparation and pretreatment of required components

[0080] 1. Synthesis of PEGylated Ce6 materials linked by thioketal bonds

[0081] (1) Cysteamine hydrochloride (11.36g, 100mmol) and anhydrous acetone (15.6g, 270mmol) were mixed and dissolved in 4 mL of chloroform, and dry hydrogen chloride was introduced to saturate the solution and stirred at room temperature for 8 hours. After the reaction, the white...

Embodiment 2

[0091] Example 2, Preparation and Application of Photoinduced ROS Responsive Nanoparticles

[0092] 1. Preparation of nanoparticles encapsulating Pt(IV) prodrugs (TCNP Pt )

[0093] The above mPEG 45 -TK-Ce6 (5.0 mg), PLA (5.0 mg) and Pt(IV) (0.5 mg) were dissolved in dimethyl sulfoxide (DMSO, 1.0 mL), and then added dropwise to ultrapure water (10.0 mL) Stir for 2 hours. This solution was dialyzed with ultrapure water for 24 hours, and filtered with a 0.45 μm filter membrane to obtain the nanoparticles (abbreviated as TCNP) of the encapsulated Pt (IV) prodrug Pt ) solution. Similarly, fluorescein isothiocyanate (FITC)-labeled Pt(IV) prodrug-encapsulated nanoparticles (abbreviated as FITC TCNP Pt ) solution.

[0094] 2. Generation of ROS in vitro

[0095] The above TCNP Pt solution (2mL), free Ce6 solution ([Ce6]=10μg / mL, 2mL), 50mM p-nitrosodimethylaniline (RNO, 100μL) and 100mM imidazole (100μL) in 20 mM phosphate buffer (pH 7.4 ) and mixed at 0.05W / cm 2 660 nm la...

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Abstract

The invention discloses a thioketal bond connected pegylated Ce6 material as well as a preparation method and application thereof. The method comprises the following steps: saturating a mixture of cysteamine hydrochloride and acetone with hydrogen chloride, and performing reaction to obtain diamine containing thioketal bonds; performing reaction on methoxy polyethylene glycol carboxyl, dicyclohexylcarbodiimide and N-hydroxysuccinimide, and dropwise adding a polyethylene glycol solution into a diamine solution containing thioketal for reaction to obtain mPEG-TK-NH2; dissolving chlorin e6, dicyclohexylcarbodiimide and N-hydroxysuccinimide in a solvent for reaction; and adding the activated Ce6 solution into the mPEG-TK-NH2 solution, and carrying out a stirring reaction to obtain the thioketal bond connected pegylated Ce6 material. The thioketal bond connected pegylated Ce6 material has biocompatibility and degradability, and can enhance the uptake of drug-loaded particles by cells, so that the drug concentration in the cells is improved, tumor cells are killed, and the chemotherapy effect is improved.

Description

technical field [0001] The invention relates to the field of functional materials, in particular to a thioketal bond-linked PEGylated Ce6 material and its preparation method and application. Background technique [0002] Modification of polyethylene glycol (PEG) on the surface of anti-tumor nanocarriers, namely PEGylation, is currently the most widely used strategy to prevent protein adsorption and avoid rapid blood circulation clearance, which can prolong blood circulation time by enhancing permeability The Enhanced permeability and retention effect (EPR) effect is enriched in tumor tissue, which can reduce the toxic and side effects of drugs. PEGylated nanomedicines including liposomal doxorubicin and paclitaxel in the form of polyethylene glycol-polylactic acid micelles Already approved for the treatment of malignancies, an increasing number of PEGylated nanomedicines have entered clinical trials. [0003] Modification with PEG improves the tumor enrichment of nanopa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/334C08G65/333A61K9/51A61K47/34A61K47/22A61K33/243A61P35/00
CPCA61K9/5146A61K9/5153A61K33/243A61K41/0042A61P35/00C08G65/33396C08G65/3348
Inventor 杨显珠张正海曹紫洋
Owner SOUTH CHINA UNIV OF TECH
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