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Cyclic polycaprolactone-polyethylene glycol amphiphilic block copolymer and its preparation and application

A technology of amphiphilic block and polycaprolactone, which is applied in the direction of medical preparations and pharmaceutical formulations of non-active ingredients, can solve the problem of non-existence of amphiphilic block copolymers, and achieve low cytotoxicity, good The effect of drug loading capacity

Active Publication Date: 2020-08-04
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 amphiphilic block copolymer and its preparation and application
  • Cyclic polycaprolactone-polyethylene glycol amphiphilic block copolymer and its preparation and application
  • Cyclic polycaprolactone-polyethylene glycol amphiphilic block copolymer and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The preparation of embodiment 1 alkyne acid anhydride

[0045] In the following examples of the present invention, the synthetic route of the used alkynoic anhydride is as follows:

[0046]

[0047] The specific operation is as follows:

[0048]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). 6.0 g (107.0 mmol) of propynyl alcohol was dissolved in 10 mL of dry DCM, which was slowly added dropwise to the above suspension solution, protected by argon, and stirred at 25°C for 36 h. After the reaction, add 50mL DCM to dilute, 10% NaHSO 4 Wash three times with aqueous solution (3×20 mL), 10% NaHCO 3 Wash three times with aqueous solution (3 x 20 mL). Take the organic phase with anhydrous Na 2 SO 4 Dry, filter with suction, and rotary evaporate to obtain a white solid powder (compound 1 in the figure above, 10.0 g, yield: 68.9%).

[0049] 8.0 g (51.3 mmol) of compoun...

Embodiment 2

[0050] Example 2 Preparation of Small Molecules Endcapped by Azide Groups at Both Ends (hereinafter referred to as Double Azide Capped Small Molecules)

[0051] In the following examples of the present invention, the synthesis route of the double-headed azide-terminated small molecule used is as follows:

[0052]

[0053] The specific operation is as follows:

[0054] 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 was finished, cool to room temperature, add 300mL DCM to dilute, wash with water to remove DMF. Take the DCM phase with anhydrous Na 2 SO 4 Dry, filter with suction, and rotary evaporate to obtain a white waxy solid, which is a double-headed azide-terminated small molecule (compound 3 in the figure above, 3.7 g, yield: 86.4%). NMR characterization: 1 H NMR (300MHz, DMSO-d 6 ,δ,ppm):5.22(d,2H),3.77(m,2H),3....

Embodiment 3

[0055] The preparation of embodiment 3c-PCL-2alkynyl

[0056] The synthesis steps are as follows:

[0057] (1) Synthesis of l-PCL-2OH

[0058] Add a stirring bar to the 5mL ampoule, heat it under vacuum on the double row tube, fill it with argon to cool three times, and put it into the glove box. 4.0 mL (36.0 mmol) ε-CL (ε-caprolactone) and 40.0 μL (0.7 mmol) initiator ethylene glycol were added to the ampoule. Then add 80.0μL (0.8mol / L) catalyst Sn(Oct) 2 of toluene solution. Seal it with a rubber tube, and stir and react at 100°C for 2h. After the reaction, take it out from the glove box, cool it immediately, add THF to dissolve, 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%). H NMR spectrum ( 1 H NMR) measurement result: M n,NMR =4900g / mol; Size exclusion chromatography (SEC) measurement result: M n,SEC = 8300g / mol,

[0059] (...

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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, and also has good drug penetration Sex, because PCL is often used as a controlled release carrier for drugs. PCL is a strong hydrophobic group, which generally makes it grafted or block-connected with another hydrophilic segment, such as polyisopropylacrylamide (PNIPAM), dextran and polyethylene glycol (PEG), etc. , thus forming an amphiphilic copolymer. It can not only improve the hydrophilicity of aliphatic polyester, but also increase the degradation rate of PCL. Through the self-assembly of amphiphilic copolymers to form assemblies such as micelles or vesicles, the entrapme...

Claims

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Application Information

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Patent Type & Authority Patents(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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