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Cyclic polycaprolactone-polyethylene glycol amphipathic block copolymer and preparation and applications

An amphiphilic block and polycaprolactone technology is applied in the directions of non-active ingredients such as medical preparations and pharmaceutical formulations, which can solve the problem of the absence of amphiphilic block copolymers, and achieve low cytotoxicity and good The effect of drug-carrying capacity

Active Publication Date: 2017-11-24
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the current copolymers of polycaprolactone and hydrophilic segment are all linear structures, and there is no amphiphilic block copolymer containing cyclic polycaprolactone

Method used

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  • Cyclic polycaprolactone-polyethylene glycol amphipathic block copolymer and preparation and applications
  • Cyclic polycaprolactone-polyethylene glycol amphipathic block copolymer and preparation and applications
  • Cyclic polycaprolactone-polyethylene glycol amphipathic block copolymer and preparation and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 Preparation of acetylenic anhydride

[0048] In the following examples of the present invention, the synthetic route of the acetylenic anhydride used is as follows:

[0049]

[0050] The specific operations are as follows:

[0051] 9.3 g (93.0 mmol) of succinic anhydride and 2.6 g (21.4 mmol) of 4-dimethylaminopyridine (DMAP) were dissolved in 20 mL of dry dichloromethane (DCM). 6.0g (107.0mmol) of propynol was dissolved in 10mL of dry DCM, slowly added dropwise to the above suspension solution, protected by argon, and stirred at 25°C for 36h. After the reaction, add 50mL DCM to dilute, 10% NaHSO 4 Wash three times with aqueous solution (3×20mL), 10% NaHCO 3 Wash with aqueous solution three times (3×20 mL). Use anhydrous Na for organic phase 2 SO 4 Drying, filtering with suction, and rotary evaporation to obtain a white solid powder (Compound 1, 10.0 g in the above figure, yield: 68.9%).

[0052] 8.0 g (51.3 mmol) of compound 1 was dissolved in 40 mL of dry DCM, and...

Embodiment 2

[0053] Example 2 Preparation of small molecules terminated with azide groups at both ends (hereinafter referred to as double-headed azide-terminated small molecules)

[0054] In the following embodiments of the present invention, the synthetic route of the double-headed azide-terminated small molecule used is as follows:

[0055]

[0056] The specific operations are as follows:

[0057] Mix 3.0g (14.8mmol) 1,4-butanediol diglycidyl ether, 4.8g (78.0mmol) NaN 3 And 4g (74.0mmol) NH 4 Cl was added to 30 mL of DMF solvent, and the reaction was stirred at 50°C for 24 h. After the reaction is over, cool to room temperature, add 300 mL DCM for dilution, and wash with water to remove DMF. Use anhydrous Na for the DCM phase 2 SO 4 Drying, suction filtration, and rotary evaporation to obtain a white waxy solid, which is a double-headed azide-terminated small molecule (compound 3 in the above figure, 3.7 g, yield: 86.4%). NMR characterization: 1 H NMR(300MHz, DMSO-d 6 ,δ,ppm):5.22(d,2H),3.77...

Embodiment 3

[0058] Preparation of Example 3c-PCL-2alkynyl

[0059] The synthesis steps are as follows:

[0060] (1) Synthesis of l-PCL-2OH

[0061] Add a stir bar to a 5 mL ampoule, apply vacuum heating on the double-row tube, fill it with argon and cool it three times, and put it in the glove box. Add 4.0 mL (36.0 mmol) ε-CL (ε-caprolactone) and 40.0 μL (0.7 mmol) of initiator ethylene glycol into the ampoule. Then add 80.0μL (0.8mol / L) catalyst Sn(Oct) 2 In toluene. Seal with a rubber tube, stir and react at 100°C for 2h. After the reaction is over, take it out of the glove box, cool it immediately, add THF to dissolve it, precipitate with ice anhydrous ether, filter with suction, and dry the filter cake in a vacuum oven at 25°C overnight to obtain a white powder, which is l-PCL-2OH (2.9g , Yield: 70.4%). NMR spectrum ( 1 H NMR) measurement result: M n,NMR =4900g / mol; SEC measurement result: M n,SEC =8300g / mol,

[0062] (2) Synthesis of l-PCL-2alkynyl

[0063] Add 0.5g (0.1mmol) of l-PC...

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Abstract

The invention relates to a cyclic polycaprolactone-polyethylene glycol amphipathic block copolymer, the structural formula of which is as shown in the specification, wherein n is equal to 10-100, and m is equal to 20-200. The invention further discloses a preparation method of the cyclic polycaprolactone-polyethylene glycol amphipathic block copolymer. The preparation method comprises the following steps: mixing cyclic polycaprolactone with two ends terminated by alkynyl, with polyethylene glycol with one end terminated by azide group, and reacting by adopting a CuAAC method to obtain the cyclic polycaprolactone-polyethylene glycol amphipathic block copolymer. The invention further discloses applications of the cyclic polycaprolactone-polyethylene glycol amphipathic block copolymer as a drug carrier. The block copolymer contains cyclic PCL, has different amphipathic chain segment rations, and can entrap drugs by utilizing the topological structure of cyclic PCL.

Description

Technical field [0001] The invention relates to the field of polymer synthesis, in particular to a cyclic polycaprolactone-polyethylene glycol amphiphilic block copolymer and its preparation and application. Background technique [0002] Polycaprolactone (PCL) has five non-polar methylene groups and one polar ester group. This special structure makes it have good biocompatibility and degradability, in addition to good drug penetration Because PCL is often used as a controlled release carrier of drugs. PCL is a strong hydrophobic group, which is generally grafted or block connected to another hydrophilic segment, such as polyisopropylacrylamide (PNIPAM), dextran and polyethylene glycol (PEG), etc. , Thereby forming an amphiphilic copolymer. It can not only improve the hydrophilicity of aliphatic polyester, but also increase the degradation rate of PCL. By self-assembling the amphiphilic copolymer to form assemblies such as micelles or vesicles, the encapsulation and controlled ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/00C08G63/91C08G63/08A61K47/34
CPCA61K47/34C08G63/08C08G63/912C08G81/00
Inventor 张正彪陈未朱秀林朱健周年琛张伟潘向强
Owner SUZHOU UNIV
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