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A betulinic acid prodrug micelle with dual response to reduction and near-infrared light, preparation method and application

A dual-response, near-infrared light technology, applied in the field of medicine, can solve the problems of fast systemic clearance, poor water solubility, non-selective cytotoxicity, etc., and achieve the effect of reducing the use of excipients, improving safety, and increasing drug loading.

Active Publication Date: 2021-06-08
CHANGZHOU VOCATIONAL INST OF ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Although betulinic acid has a wide range of anticancer activities, there are still some obvious defects, such as poor water solubility, rapid systemic clearance, non-selective cytotoxicity, and weak in vitro activity, which greatly limit the application of BA in the field of antitumor. treatment effect

Method used

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  • A betulinic acid prodrug micelle with dual response to reduction and near-infrared light, preparation method and application
  • A betulinic acid prodrug micelle with dual response to reduction and near-infrared light, preparation method and application
  • A betulinic acid prodrug micelle with dual response to reduction and near-infrared light, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Preparation of polymer 1 (mPEG 2K -SS-BA Ploymers), the reaction process is referring to the above formula 5:

[0065] H1: To synthesize the compound Link SS, dissolve bromoacetic acid (2.00g, 14.39mmol) in 10mL tetrahydrofuran (THF), add N-hydroxysuccinimide (NHS) (1.84g, 15.83mmol), stir to dissolve Under nitrogen protection, lower the temperature to 0°C; weigh dicyclohexylcarbodiimide (DCC) (3.07g, 15.83mmol) and dissolve it in 10mL THF, add it dropwise to the above reaction solution, and control the rate of addition to ensure that the temperature does not exceed 5 ℃, after dropping, stir at room temperature for 6h; Stir overnight, TLC monitors the complete conversion of raw materials (developing solvent, n-hexane:ethyl acetate=3:1), the reaction solution is filtered, a small amount of THF rinses the filter cake, concentrates the filtrate, and column chromatography (developing solvent, n-hexane:ethyl acetate=3:1) Ester=4:1), to obtain off-white solid compound Link ...

Embodiment 2

[0070] Preparation of polymer 1 (mPEG 5K -SS-BAPloymers), the method of operation is the same as in Example 1, the difference is that in step H3, methoxypolyethylene glycol succinimide ester (mPEG) with a molecular weight of 5000 is used 5K -NHS) to replace 2000 methoxypolyethylene glycol succinimide ester (mPEG 2K -NHS), to obtain white solid polymer 1 (mPEG 5K -SS-BA Ploymers) (2.24g).

Embodiment 3

[0072] Preparation of polymer 1 (mPEG 10K -SS-BAPloymers), the method of operation is the same as in Example 1, the difference is that in step H3, methoxypolyethylene glycol succinimide ester (mPEG) with a molecular weight of 10000 is used 10K -NHS) to replace methoxypolyethylene glycol succinimide ester (mPEG) with a molecular weight of 2000 2K -NHS), to obtain white solid polymer 1 (mPEG 10K -SS-BAPloymers) (1.24g).

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Abstract

The invention discloses a betulinic acid prodrug micelle with dual responses of reduction and near-infrared light, a preparation method and an application. Large and highly hydrophobic, the design uses its skeleton itself as the hydrophobic end of the micelles, omitting the design of polymer fragments with hydrophobic ends, which not only further increases the drug loading of the betulinic acid skeleton, but also reduces the amount of excipients. Use to further improve the safety of the drug-loading system (micelle); strong targeting of tumor cell tissue; long circulation time in the body fluid environment, that is, to avoid fast clearance in the body and prolong the actual drug effect time; As an anti-tumor agent, it can work synergistically with photothermal therapy to kill tumor cells; the preparation method of the betulinic acid prodrug micelle is simple, which ensures the preparation and implementation feasibility of the betulinic acid prodrug micelle, and provides the anti-tumor effect of betulinic acid The field of disease treatment lays the groundwork.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a betulinic acid prodrug micelle with dual responses of reduction and near-infrared light, a preparation method and application. Background technique [0002] Betulinic acid (English name: Betulinic acid, BA for short), also known as betulinic acid, is a lupine-type pentacyclic triterpenoid compound derived from plants such as white birch, jujube seed, rosemary, and prunella vulgaris. See formula 1 for its structural general formula. Betulin, a hydroxyl derivative of betulinic acid, has the highest content in birch bark, up to 10% to 35%, and can be used to prepare betulinic acid in large quantities. Betulinic acid is a white crystal with a melting point of 295-298°C and a molecular formula of C 30 h 48 o 3 , there are 5 rings in the molecular structure, A, B, C, D, E, containing two main functional groups of the 3-position hydroxyl group and the 28-position carboxyl group. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/60A61K31/56A61K41/00A61K47/59A61K9/107C08G65/334C08G65/333A61P35/00
CPCA61K9/1075A61K31/56A61K41/0052A61K47/59A61K47/60A61P35/00C08G65/33396C08G65/3348A61K2300/00
Inventor 周海平张云然张娟娟刘雨贤
Owner CHANGZHOU VOCATIONAL INST OF ENG
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