Multi-functional-group polyethylene oxide-b-aliphatic polyester block copolymers, preparing method thereof and applications thereof

A technology of aliphatic polyester and ethylene oxide, which is applied in pharmaceutical formulations, medical preparations of inactive ingredients, etc., can solve the problems of functional groups affecting polymerization, restricting promotion and application, and difficulty in monomer synthesis, and achieves the reaction conditions. Controllable, easy-to-operate, and easy-to-quantify effects

Active Publication Date: 2014-07-23
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the synthesis route is simple, there are many problems in the actual reaction process, such as difficulty in monomer synthesis, low

Method used

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  • Multi-functional-group polyethylene oxide-b-aliphatic polyester block copolymers, preparing method thereof and applications thereof
  • Multi-functional-group polyethylene oxide-b-aliphatic polyester block copolymers, preparing method thereof and applications thereof
  • Multi-functional-group polyethylene oxide-b-aliphatic polyester block copolymers, preparing method thereof and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0051] Example 1: Synthesis of poly(ethylene oxide-co-epichlorohydrin) random copolymer P(EO-co-ECH)

[0052] Add 3.0g of ethylene oxide and 0.7g of epichlorohydrin into the reaction flask at about 0℃, add 25mL of dichloromethane, and then add 1.0M potassium triisobutyl oxide in tetrahydrofuran solution 0.75mL, triisobutyl aluminum Catalyst 1.5mL. After 4 hours of reaction, the temperature was raised to room temperature and the reaction was continued for 24 hours. The above operations ensure that the reaction system is anhydrous and oxygen-free. The reaction was terminated by adding 200 μL of ethanol. Most of the solvent was removed by rotary evaporation and then precipitated in 200 mL of ice methanol to obtain 3.2 g of poly(ethylene oxide-co-epichlorohydrin) product with a yield of 86%. Its molecular weight is measured by gel permeation chromatography (see Figure 7 ), the chemical structure is confirmed by proton nuclear magnetic resonance spectroscopy. The number average m...

Example Embodiment

[0053] Example 2: Synthesis of P (EO-co-Glycidyl Azide)

[0054] Dissolve 2.0 g of a poly(ethylene oxide-co-epichlorohydrin) random copolymer with a number average molecular weight of 5000 (the molar ratio of ethylene oxide to epichlorohydrin is 9 / 1) in 15 mL of nitrogen , Nitrogen-dimethylformamide (DMF), add sodium azide (NaN 3 ) 2.0g, refluxed at 100°C for 48 hours under argon protection. After cooling to room temperature, the precipitate was removed by centrifugation, and the supernatant was precipitated in 200 mL of ice ether. The product was vacuum-dried to remove the organic solvent and dissolved in 10 mL of deionized water, and transferred to a dialysis bag with a molecular weight cut-off of 3500 Da for dialysis for 48 hours. The water was changed every 8 hours. After the dialysis was completed, it was freeze-dried to remove moisture to obtain 1.6 g of P (EO-co-Glycidyl Azide) product with a yield of 80%. Its molecular weight is measured by gel permeation chromatography...

Example Embodiment

[0055] Example 3: Synthesis of amphiphilic block copolymer containing P (EO-co-Glycidyl Azide) block

[0056] (1) Synthesis of PCL-b-P (EO-co-Glycidyl Azide)

[0057] Put 2.0g of P(EO-co-Glycidyl Azide) prepared in Example 2 (wherein the ratio of ethylene oxide to azido propylene oxide is 9 / 1) in the reaction flask, and repeatedly remove the reaction system. Sn(Oct) with a concentration of 0.982mol / L is added sequentially after oxygen 2 5.0 μL of toluene solution, 2.0 g of caprolactone, and 12 mL of toluene. The closed reaction system was reacted at 110° C. for 48 hours and then cooled to room temperature, and precipitated in 300 mL of glacial ether to obtain 3.6 g of PCL-b-P (EO-co-Glycidyl Azide) block copolymer with a yield of 90%. Its molecular weight is measured by gel permeation chromatography (see Picture 9 ), the chemical structure is confirmed by proton NMR spectroscopy (see Picture 10 ).

[0058] After measurement, the obtained PCL-bP (EO-co-Glycidyl Azide) has a number...

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Abstract

The invention discloses aliphatic polyester-b-poly(ethylene oxide-co-propylene epoxide) amphipathy block copolymers side hydrophilic chains of which are provided with different functional groups, and a preparing method of the copolymers. The functional groups comprise halogen, azido, amino, carboxyl, and other groups. P(EO-co-ECH) is synthesized under mild reaction conditions through a controllable anionic coordinate polymerization method. A random copolymer (P(EO-co-Glycidyl Azide)) side chains of which is provided with the azido is obtained by azidation of the halogen on the P(EO-co-ECH). An amphipathy block copolymer the side hydrophilic chains of which are functionalized is obtained by subjecting the P(EO-co-Glycidyl Azide) and an aliphatic ester monomer to ring opening polymerization. Through reduction and click chemistry reactions, the azido of the block copolymer is converted, so as to obtain a series of amphipathy block copolymers the side hydrophilic chains of which are provided with the different functional groups such as amino and carboxyl are obtained.

Description

technical field [0001] The invention relates to a multifunctional polyethylene oxide-b-aliphatic polyester block copolymer and its preparation method and application. Background technique [0002] In the field of drug controlled release, the micellar drug-loading system formed by amphiphilic polymers has unique advantages due to its core-shell structure: 1) The hydrophobic core of the micelles can increase the solubility of the drug while protecting the activity of the drug; 2) The core-shell structure of the micelles can be regulated by controlling the chemical structure of the polymer, so as to achieve the purpose of controlling drug release; 3) The nanometer size of the micelles enables them to stay at the tumor site and thus have a passive targeting effect. (Xiao, L. et a1. Role of cellular uptake in the reversal of multidrug resistance by PEG-b-PLA polymeric micelles. Biomaterials2011, 32, 5148.) [0003] Aliphatic polyester-b-polyethylene oxide amphiphilic block copol...

Claims

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Application Information

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IPC IPC(8): C08G63/08C08G65/325C08G65/24C08G65/333C08G65/332A61K47/34
Inventor 刘俊杰喻青松甘志华
Owner INST OF CHEM CHINESE ACAD OF SCI
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