Amphiphilic triblock copolymer with acid sensitivity and preparation method and application thereof

A sensitive, three-block technology, applied in the direction of medical preparations and pharmaceutical formulations of non-active ingredients, can solve the problems of limiting the application of anticancer drugs, poor water solubility, and large toxic and side effects, and achieve high yield and excellent reaction conditions Simple, good product stability

Inactive Publication Date: 2013-02-06
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the current anticancer drugs have the disadvantages of high toxicity and

Method used

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  • Amphiphilic triblock copolymer with acid sensitivity and preparation method and application thereof
  • Amphiphilic triblock copolymer with acid sensitivity and preparation method and application thereof
  • Amphiphilic triblock copolymer with acid sensitivity and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment one: Polyethylene glycol (Cl- α -PEG 135 - α -Cl) synthesis.

[0059] First, through double-terminal hydroxyl-containing polyethylene glycol (HO-PEG 135- OH) and pyridinium p-toluenesulfonate (PPTS) in toluene to remove water by azeotropy, and then use anhydrous dichloromethane as solvent to react with vinyl chloride ethyl ether (CEVE) to prepare terminal dichloroethyl biscondensate Aldehyde polyethylene glycol (Cl- α -PEG 135 - α -Cl). The specific synthesis method is as follows:

[0060] Add polyethylene glycol (6.01 g, 1.0 mmol), pyridinium p-toluenesulfonate (PPTS, 0.5 g, 0.2 mmol) into a 100 mL round bottom flask equipped with a magnetic stirring bar, a drying tube and an atmospheric distillation device and 30 mL of toluene, heated to azeotrope, and distilled out the azeotrope of toluene and water at 110 °C.

[0061] will be loaded with HO-PEG 135 -OH and PPTS round-bottomed flask was cooled to room temperature and added anhydrous dichlorometha...

Embodiment 2

[0063] Embodiment two: the polyethylene glycol (N 3 - α -PEG 135 - α -N 3 )Synthesis.

[0064]In a 50 mL round bottom flask, add Cl- α -PEG 135 - α -Cl (5.03 g, 0.8 mmol), sodium azide (0.57 g, 8 mmol) and 10 mL of dimethylformamide (DMF). The reaction was carried out at 60 °C for 40 h. The reaction system was passed through a basic aluminum oxide column (Al 2 o 3 ) to remove unreacted sodium azide, then use a vacuum oil pump to remove DMF at 50 °C, add 60 mL CH 2 Cl 2 After dilution, wash twice with PBS buffer (10 mL) at pH 10.0, separate the liquids and let stand, collect the organic phase, dry over anhydrous magnesium sulfate, filter, and concentrate the filtrate in ice n-hexane and ice ether (volume ratio 1:1) precipitation, filtration, repeated three times, pumped to dryness, and then placed in a vacuum oven to dry for 24 hours, to obtain polyethylene glycol (N 3 - α -PEG 135 - α -N 3 , 2.48 g), yield 49%.

Embodiment 3

[0065] Example 3: Polycaprolactone (PCL) with an alkynyl group at the single end 30 -C≡C) synthesis method.

[0066] Dry the branched round-bottomed flask with a stirrer in an oven at 120 °C for at least 24 h, then plug it with a glass stopper, connect it to an oil pump through a latex tube, and pump it to room temperature, then introduce high-purity argon gas, and vacuumize, repeat this process three times.

[0067] Using a dry syringe, inject propargyl alcohol (0.12 g, 2.14 mmol), caprolactone (ε-CL) (10.1 g, 86.1 mmol) and stannous octoate [Sn(Oct) 2 ] (430 mg) (calculate the dosage of ε-CL according to the theoretical degree of polymerization; [ε-CL]: [Sn(Oct) 2 ] = 1: 0.04, mass ratio), 25 mL of anhydrous toluene as solvent. After the reaction flask was filled with argon, the reaction was stirred in an oil bath at 90 °C for 4 h.

[0068] After the reaction was finished, the toluene solvent was removed by rotary evaporation, precipitated and filtered in ice anhydrous e...

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Abstract

The invention discloses an amphiphilic triblock copolymer with acid sensitivity and a preparation method and an application thereof. The preparation method comprises the following steps of: modifying polyethylene glycol with a hydroxyl group at the end to enable the structure of polyethylene glycol to contain a diazido ethyl diacetal end group, namely polyethylene glycol contains the diazido ethyl diacetal group at the end; carrying out ring-opening polymerization on cyclic ester monomers by utilizing propargyl alcohol as an initiator and stannous caprylate as a catalyst to obtain biodegradable polyester with alkynyl at the single end; and finally, under the action of a 'click' chemical catalyst and ligand, carrying out 'click' chemical reaction on polyethylene glycol containing the diazido ethyl diacetal group at the end and the biodegradable polyester with alkynyl at the end to obtain the biodegradable amphiphilic triblock copolymer with acid sensitivity. The biodegradable amphiphilic triblock copolymer with acid sensitivity has good biocompatibility, biodegradability and acid sensitivity, and can be used as a drug carrier.

Description

technical field [0001] The invention belongs to the field of biomedical polymer materials, and in particular relates to an acid-sensitive biodegradable amphiphilic triblock copolymer, its preparation method and its application as a drug carrier. Background technique [0002] Globally, more than 7 million people die from cancer every year, and this number is increasing year by year. The treatment of cancer is the biggest test and problem facing mankind in the 21st century. [0003] With the continuous development and progress of science and technology, human beings continue to explore related sciences such as oncology, molecular biology, pharmacy and chemistry, which has made great progress in the research of anti-tumor drugs. Many effective anti-cancer drugs have been used Designed and developed. However, most of the current anticancer drugs have the disadvantages of high toxicity and poor water solubility, which greatly limit the clinical application of anticancer drugs. ...

Claims

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Application Information

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IPC IPC(8): C08G81/00C08G65/48C08G63/08A61K47/34
Inventor 倪沛红王海蓉何金林张明祖李飞陶云锋
Owner SUZHOU UNIV
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