Acid-sensitive amphipathic compound, and preparation method and application thereof

An amphiphilic compound and acid-sensitive technology, which is applied in the field of acid-sensitive amphiphilic compounds and their preparation, and can solve the problems of being easily rejected by the human body, poor in biocompatibility, and affected by patient recovery.

Active Publication Date: 2019-04-02
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current amphiphilic micelles have poor biocompatibility and are easily rejected by the human body, thus affecting the recovery of patients.

Method used

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  • Acid-sensitive amphipathic compound, and preparation method and application thereof
  • Acid-sensitive amphipathic compound, and preparation method and application thereof
  • Acid-sensitive amphipathic compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] A preparation method of an acid-sensitive amphiphilic compound, comprising the following steps:

[0043] Step 1: Put 0.001 mol of 1,4-butanediol and 10 ml of chloroform into reaction vessel A, and stir at 200 rad / min for 15 min at 20°C to form mixed solution A;

[0044] Step 2: put 0.0011mol of itaconic anhydride and 10ml of chloroform into reaction vessel B and mix evenly, and stir at 25°C for 15min at a speed of 200rad / min to form a mixed solution B;

[0045] Step 3: Pour the mixed solution B into the mixed solution A, and stir at a speed of 300rad / min for 20min at 25°C; raise the temperature of the solution to 60°C, and start at a speed of 1600rad / min Reaction, the reaction time is 16h;

[0046] Step 4: After the reaction in Step 3 is complete, dry at 35°C and 0.09Mpa for 10 minutes to obtain a crude product; the crude product is separated by silica gel column chromatography (developing agent is ethyl acetate) to obtain pure product A;

[0047] Step 5: Put the pure...

Embodiment 2

[0052] A preparation method of an acid-sensitive amphiphilic compound, comprising the following steps:

[0053] Step 1: Put 0.001 mol of 1,4-butanediol and 10 ml of chloroform into reaction vessel A, and stir at 200 rad / min for 15 min at 20°C to form mixed solution A;

[0054] Step 2: put 0.0009mol of itaconic anhydride and 10ml of chloroform into reaction vessel B and mix evenly, and stir at 25°C for 15min at a speed of 200rad / min to form a mixed solution B;

[0055] Step 3: Pour the mixed solution B into the mixed solution A, and stir at a speed of 300rad / min for 20min at 25°C; raise the temperature of the solution to 70°C, and start at a speed of 1500rad / min Reaction, the reaction time is 15h;

[0056] Step 4: After the reaction in Step 3 is complete, dry at 35°C and 0.09Mpa for 10 minutes to obtain a crude product; the crude product is separated by silica gel column chromatography (developing agent is ethyl acetate) to obtain pure product A;

[0057] Step 5: Put the pure...

Embodiment 3

[0062] A preparation method of an acid-sensitive amphiphilic compound, comprising the following steps:

[0063] Step 1: Put 0.0009 mol of 1,4-butanediol and 10 ml of chloroform into reaction vessel A, and stir at 200 rad / min for 15 min at 20°C to form mixed solution A;

[0064] Step 2: Put 0.001 mol of itaconic anhydride and 10 ml of chloroform into reaction vessel B and mix evenly, and stir at 200 rad / min for 15 min at 25° C. to form mixed solution B;

[0065] Step 3: Pour mixed solution B into mixed solution A, and stir at 300rad / min for 20min at 25°C; raise the temperature of the solution to 55°C, and start at 1600rad / min Reaction, the reaction time is 14h;

[0066] Step 4: After the reaction in Step 3 is complete, dry at 35°C and 0.09Mpa for 10 minutes to obtain a crude product; the crude product is separated by silica gel column chromatography (developing agent is ethyl acetate) to obtain pure product A;

[0067] Step 5: Put the pure product A obtained in Step 4, 10ml o...

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Abstract

The invention discloses an acid-sensitive amphipathic compound, and a preparation method and an application thereof. The method includes two steps of reactions, wherein itaconic anhydride, 1,4-butanediol and vinyl isooctyl ether are raw materials and chloroform is a solvent; in the first reaction step, the itaconic anhydride and 1,4-butanediol are reacted to form a pure product A; in the second reaction step, the pure product A and the vinyl isooctyl ether are reacted, under catalytic effect of a catalyst, p-toluenesulfonic acid, to finally prepare the acid-sensitive amphipathic compound, yield being more than 90%. Two terminals of the compound are respectively oleophylic and hydrophilic, so that the compound is amphipathic and can be self-assembled in water to form nano-micelle. The nano-micelle of the acid-sensitive amphipathic compound is good in biocompatibility, is basically toxic-free and is free of influence on body health and rejection by human body; meanwhile, the compound canbe degraded under acidic conditions, so that the compound is suitable for being used as a target carrier for anticancer drugs.

Description

technical field [0001] The invention relates to the field of organic synthesis, and more specifically relates to an acid-sensitive amphiphilic compound and its preparation method and application. Background technique [0002] Cancer is one of the major public health problems in the world. The International Agency for Research on Cancer (IARC), located in Lyon, France, estimates based on the socioeconomic development trends of 184 countries that the number of new cancer cases in the world will increase from 2008 to From 12.7 million to 22.2 million in 2030, deaths will increase from 7.6 million in 2008 to 13.1 million in 2030. However, the current clinical application of anticancer drugs has constraints such as excessive toxicity and poor water solubility, which have a great impact on the rehabilitation of cancer patients. [0003] In recent years, research on micellar drug carriers has risen rapidly, because of its controllable structure, high drug loading and loading rate,...

Claims

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Application Information

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IPC IPC(8): C07C67/29C07C69/593A61K9/107A61K47/14A61P35/00
CPCA61K9/1075A61K47/14A61P35/00C07C67/08C07C67/29C07C69/593
Inventor 李钟玉卢成洁易明李大爱
Owner WENZHOU UNIVERSITY
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