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Docetaxelpolyoxyethelene-polyoxypropylene-polyoxyethelene compound capable of self-assembling into micelle

A technology of polyoxyethylene and docetaxel, which is applied in the direction of drug combination, medical preparation of non-active ingredients, drug delivery, etc., can solve the problems of reduced sensitivity, tumor drug resistance, rapid release, etc., and achieve simple compound composition , Avoid allergic reactions, easy to operate

Active Publication Date: 2014-09-10
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Docetaxel is used for tumor treatment, and the initial effect is often good, but with the continuation of chemotherapy, the sensitivity of tumor cells to docetaxel decreases, the therapeutic effect is not obvious, and the problem of tumor drug resistance occurs
One of the important reasons is that it is difficult for docetaxel to enter tumor cells, resulting in a low concentration of intracellular docetaxel, and tumor cells develop drug resistance under long-term stimulation of low-dose drugs
Although in the above statement, some scholars encapsulated docetaxel in a nanometer-sized carrier to increase the concentration of the drug entering tumor cells, how to quickly release docetaxel encapsulated in the carrier in tumor cells , has been an intractable problem

Method used

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  • Docetaxelpolyoxyethelene-polyoxypropylene-polyoxyethelene compound capable of self-assembling into micelle
  • Docetaxelpolyoxyethelene-polyoxypropylene-polyoxyethelene compound capable of self-assembling into micelle
  • Docetaxelpolyoxyethelene-polyoxypropylene-polyoxyethelene compound capable of self-assembling into micelle

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Take 50mg of thionyl chloride and 50mg of 3-3’-dithiodipropionic acid and mix them in a water bath at 30℃ for 12 hours. Add 10mg of docetaxel and continue the reaction for 6 hours. Add 0.5ml of triethylamine and 30mg of P85 (purchased from BASF) in a water bath at 25°C for 48 hours. After vacuum drying, dissolve the sample in absolute ethanol, add water for injection ultrasound, and place it in a 3500 Dalton dialysis bag for dialysis to obtain a micelle of compound A .

[0042] Using the different polyoxyethylene-polyoxypropylene-polyoxyethylene block copolymers shown in Table 1, micelles of compounds B, C, F, G, H, J and K can be prepared in the same manner as above .

Embodiment 2

[0044] Take 10mg of docetaxel, 0.5ml of succinic anhydride and 30mg of polyoxyethylene-polyoxypropylene-polyoxyethylene polymer in a water bath at 25°C for 48 hours. After vacuum drying, dissolve the sample in absolute ethanol and add water for injection ultrasound. , Placed in a 3500 Dalton dialysis bag and dialyzed to obtain compound D micelles. Replace different polyoxyethylene-polyoxypropylene-polyoxyethylene polymers according to the table to obtain micelles of compound E and I.

[0045] Table 1 Various docetaxel polyoxyethylene-polyoxypropylene-polyoxyethylene compounds

[0046]

[0047] The particle size was measured with a Malvern particle size analyzer, model ZEW3690. Identify the formation of polyoxyethylene-polyoxypropylene-polyoxyethylene compound of docetaxel by high performance liquid chromatography: chromatographic column: BEH C18 column, mobile phase A is acetonitrile, mobile phase B is water, linear gradient elution , From the beginning to 3 minutes 50% mobile ph...

experiment example

[0060] The beneficial effects of the present invention are described by measuring the half inhibition rate and growth inhibition rate of docetaxel on the drug-resistant human breast cancer cell line MCF-7 / ADM.

[0061] Docetaxel reference substance: Docetaxel injection containing 20mg of docetaxel (trade name Taxotere, produced by French Aventis) is used to solubilize docetaxel with Tween 80 Used for injection.

[0062] Docetaxel micellar reference substance: take 20mg of docetaxel, add 5ml of dichloromethane to dissolve, take polyoxyethylene-polyoxypropylene-polyoxyethylene block copolymer ( F68) 50mg, add 8ml of absolute ethanol to dissolve, mix the two solutions at 50℃, sonicate for 10 minutes, use a rotary evaporator to remove the organic solvent, and dissolve the residue with 5ml of water for injection at 37℃, namely docetaxel Micelles.

[0063] Docetaxel nanoparticle reference substance: take 20mg of docetaxel, add 5ml of absolute ethanol to dissolve, add 200mg of phospholipi...

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Abstract

The invention belongs to the field of pharmaceutical chemistry, and relates to structure modification of an anticancer drug docetaxel, and an unique effect of a new compound in tumor resistance inhibition, specifically to a docetaxelpolyoxyethelene-polyoxypropylene-polyoxyethelene compound capable of self-assembling into a micelle, a preparation method of the compound, and uses of the compound in preparation of drugs for treatment of cancers, wherein the compound is represented by a general formula I.

Description

Technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to the structural modification of the anti-tumor drug docetaxel and the unique effect of new compounds in inhibiting tumor resistance, and specifically relates to a docetaxel polyoxyethylene capable of self-assembly into micelles. Polyoxypropylene-polyoxyethylene compound, its preparation method, and its use in preparing medicine for treating cancer. Background technique [0002] The trade name of Docetaxel (DOCETAXEL) is Docetaxel, and its structure is shown in Structural Formula 1. Docetaxel is a yew drug that promotes the assembly of microtubule dimers into microtubules and prevents depolymerization. The process stabilizes the microtubules and blocks the cells in G2 and M phases, thereby inhibiting the mitosis and proliferation of cancer cells. Docetaxel has a stronger pharmacological effect than paclitaxel. Its intracellular concentration is 3 times higher than paclitaxel, and it st...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/48A61K9/00A61K31/337A61P35/00
Inventor 李亚平肖计生陈伶俐顾王文张志文高瑜
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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