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Oxidation response type nano-micelle, and preparation method and application thereof

A nano-micelle, responsive technology, applied in the field of molecular medical nano-materials, can solve the problems of tumor necrosis, lack of deep soft tissue penetration ability, low toxicity and side effects, etc., to achieve prolonged residence time, highly space-time controlled drug release effect, damage reduction effect

Active Publication Date: 2021-11-26
ZHONGNAN HOSPITAL OF WUHAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Photodynamic therapy (PDT) is a method that stimulates photosensitizers to generate reactive oxygen species (ROS) by near-infrared light irradiation, leading to tumor necrosis. Due to its high selectivity and low toxicity and side effects, it has been widely studied, but it does not have the ability to penetrate deep soft tissues. Limits application to deep tumor treatment

Method used

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  • Oxidation response type nano-micelle, and preparation method and application thereof
  • Oxidation response type nano-micelle, and preparation method and application thereof
  • Oxidation response type nano-micelle, and preparation method and application thereof

Examples

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Embodiment 1

[0045] Embodiment 1: In a specific embodiment of the present invention, a method for preparing oxidation-responsive nanomicelles provided in this embodiment includes the following steps:

[0046] 1) Add 3-mercaptopropionic acid (5.2g, 49.1mmol) into anhydrous acetone (5.8g, 98.2mmol), react in dry hydrogen chloride gas, stir and react at room temperature for 4h, then place the product crystals at -20°C Freeze, wash with n-hexane and ultrapure water in sequence after freezing, and then freeze-dry to obtain dicarboxylic acid white powder COOH-TK-COOH containing sulfur ketal TK bond.

[0047] 2) Under nitrogen, disperse COOH-TK-COOH (252.1mg, 1mmol), dicyclohexylcarbodiimide (61.8mg, 0.3mmol), 4-dimethylaminopyridine (61.1mg, 0.5mol) in In 10ml anhydrous dichloromethane (DCM), obtain reaction system; Polyethylene glycol monomethyl ether mPEG 2000 (1g, 0.5mmol) was dispersed in 10ml of anhydrous anhydrous dichloromethane (DCM), and then added dropwise to the above reaction system...

Embodiment 2

[0052] Example 2: The method for preparing oxidation-responsive nanomicelles and the application of nanomicelles provided in this example are basically the same as those in Example 1, except that:

[0053] In step 1), the stirred reaction was carried out in dry hydrogen chloride gas for 6 hours; the freezing temperature was -60°C; the weight ratio of 3-mercaptopropionic acid to anhydrous acetone was 6.2g:6.8g.

[0054] In step 2), the stirring reaction time in an ice bath is 4 hours; the reaction time at room temperature is 24 hours; the dicarboxylic acid product COOH-TK-COOH, dicyclohexylcarbodia The dosage ratio of amine, 4-dimethylaminopyridine and anhydrous dichloromethane is 260mg:68mg:66mg:1ml; polyethylene glycol monomethyl ether mPEG 200 The dosage ratio of anhydrous dichloromethane is 1.2g: 11ml.

[0055] In step 3), the dosage ratio of hydrophobic drug molecule (doxorubicin hydrochloride), organic solvent, and anhydrous triethylamine is 70mg: 12ml: 18ul; the stirrin...

Embodiment 3

[0057] Example 3: The method for preparing oxidation-responsive nanomicelles and the application of nanomicelles provided in this example are basically the same as in Example 1, except that:

[0058] In step 1), the stirred reaction was carried out in dry hydrogen chloride gas for 5 hours; the freezing temperature was -50°C; the weight ratio of 3-mercaptopropionic acid to anhydrous acetone was 5.8g:6.1g.

[0059] In step 2), the stirring reaction time in an ice bath is 4 hours; the reaction time at room temperature is 36 hours; the dicarboxylic acid product COOH-TK-COOH, dicyclohexylcarbodia The dosage ratio of amine, 4-dimethylaminopyridine and anhydrous dichloromethane is 295mg:90mg:70mg:14ml; polyethylene glycol monomethyl ether mPEG 200 The dosage ratio of anhydrous dichloromethane is 1.5g: 16ml.

[0060] In step 3), the dosage ratio of hydrophobic drug molecule (doxorubicin hydrochloride), organic solvent, and anhydrous triethylamine is 80mg: 13ml: 19ul; the stirring tim...

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Abstract

The invention discloses an oxidation response type nano-micelle, and a preparation method and application thereof. The oxidation response type nano-micelle is an amphiphilic active oxygen response type nano-drug delivery system, which is constructed by bonding a hydrophobic anti-tumour drug adriamycin and polyethylene glycol monomethyl ether through an oxidation response thioketal bond; an active oxygen response group in the nano-micelle is one of compounds sensitive to hydroxyl radicals, singlet oxygen or active oxygen; and the active oxygen sensitive compound is a thioketal group. The nano-micelle in the invention can generate a large amount of active oxygen and stimulate thioketal bond breakage under the sonodynamic effect, so that the nano-micelle releases the anti-tumour drug adriamycin; the adriamycin directly acts on tumour tissues; furthermore, damage to surrounding healthy tissues is greatly reduced; combined treatment of sonodynamic and chemotherapy is achieved; effective enrichment and time-space controlled release of the medicine at a tumour part are realized; and an effective anti-tumour effect is achieved.

Description

technical field [0001] The invention relates to the technical field of molecular medicine nanomaterials, in particular to an oxidation-responsive nanomicelle and its preparation method and application. Background technique [0002] With the development of nanotechnology, nanoparticles with volume effect, surface effect, quantum size effect and macroscopic quantum tunneling effect have been widely used to construct drug delivery system (DDS). Due to the rich blood vessels in the tumor tissue and the defect of lymphatic return, the tumor tissue has a high permeability retention effect (ERP), polymer nanoparticles can be effectively enriched and delayed in the tumor part, and small molecule chemotherapy drugs can freely pass through the vascular wall of normal tissue tumor tissue , the nano-drug delivery system DDS is beneficial to achieve high permeability and retention effect ERP, increase the drug concentration in tumor tissue, reduce the frequency of administration and syst...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/107A61K47/60A61K47/54A61K41/00A61K31/704A61P35/00B82Y5/00B82Y40/00
CPCA61K9/1075A61K47/60A61K47/54A61K41/0033A61K31/704A61P35/00B82Y5/00B82Y40/00A61K2300/00
Inventor 邓凯廖星男周军吴波龙清云黄世文
Owner ZHONGNAN HOSPITAL OF WUHAN UNIV
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