Preparation method of supra-molecular polymer compound micelle based on hydrogen bonds

A technology of supramolecular polymers and composite micelles, which is applied in the field of preparation of supramolecular polymer composite micelles, can solve problems such as strong crystallinity, poor hydrophilicity, and long biodegradation cycle, and achieve mild preparation conditions and easy operation Effect

Active Publication Date: 2018-10-12
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to its poor hydrophilicity, long biodegradation cycle, and strong crystallinity, its wide application in the field of biomedicine is limited.

Method used

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  • Preparation method of supra-molecular polymer compound micelle based on hydrogen bonds
  • Preparation method of supra-molecular polymer compound micelle based on hydrogen bonds
  • Preparation method of supra-molecular polymer compound micelle based on hydrogen bonds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Example 1. Preparation of supramolecular polymer PCL1-DAT...U-PDEA composite micelles based on hydrogen bonds.

[0061] (1) Synthesis of terminal diaminotriazine polycaprolactone (PCL1-DAT) segment

[0062] 1. Synthesis of DAT by click reaction

[0063] Weigh 2.743g (0.02mol) 2,4-diamino-6-vinyl-s-triazine, 0.256g (0.001mol) benzoin dimethyl ether (DMPA), 2.8mL (0.04mol) mercaptoethanol and 70mLN, N-dimethylformamide was placed in a 100mL round bottom flask, stirred at room temperature, and reacted under 365nm ultraviolet light irradiation for 1h after the solid was fully dissolved. After the reaction was completed, it was filtered, and the filtrate was removed by rotary evaporation to obtain a solid. The resulting solid was washed with a mixed solution of 80 mL of acetone and absolute ethanol (1:1), and filtered with suction. Repeat the above operation twice to obtain a white powder. After vacuum drying at 25°C for 24 hours, it is ready for use. The qualitative anal...

Embodiment 2

[0101] Embodiment 2, preparation of supramolecular polymer PCL2-DAT...U-PDEA composite micelles based on hydrogen bond

[0102] The preparation method of the present embodiment 2 is the same as the preparation method of the embodiment 1, and the PCL2-DAT...U-PDEA composite micelle solution with a concentration of 0.5 mg / mL is prepared, the only difference is that the diaminotriazine-terminated polycaprolactone ( The synthetic method of PCL2-DAT) segment, concrete steps are as follows:

[0103] Weigh 0.172g (0.8mmol) DAT, 3.648g (32mmol) caprolactone and 0.007g (0.016mmol) stannous octoate in a 50mL round bottom flask, vacuumize and ventilate nitrogen for six times, under nitrogen protection, 120°C The reaction was stirred for 24h. After the reaction was completed, the reaction mixture was cooled to room temperature. The obtained solid was dissolved in 3 mL of dichloromethane, and the obtained solution was slowly added dropwise to 20 mL (0° C.) ether to precipitate, left to s...

Embodiment 3

[0108] Embodiment 3, preparation of supramolecular polymer PCL3-DAT...U-PDEA composite micelles based on hydrogen bond

[0109] The preparation method of this embodiment 3 is the same as the preparation method of embodiment 1, and the PCL3-DAT...U-PDEA composite micelle solution with a concentration of 0.5 mg / mL is obtained, the only difference is that the diaminotriazine-terminated polycaprolactone ( The synthetic method of PCL3-DAT) segment, concrete steps are as follows:

[0110] Weigh 0.172g (0.8mmol) DAT, 5.472g (48mmol) caprolactone and 0.007g (0.016mmol) stannous octoate in 50mL in a 50mL round-bottomed flask, vacuumize and ventilate nitrogen repeatedly six times, under nitrogen protection, The reaction was stirred at 120°C for 24h. After the reaction was completed, the reaction mixture was cooled to room temperature. The obtained solid was dissolved in 3 mL of dichloromethane, and the obtained solution was slowly added dropwise to 20 mL (0° C.) ether to precipitate, le...

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Abstract

The present invention belongs to the technical field of chemical synthesis and particularly relates to a preparation method of a supra-molecular polymer compound micelle based on hydrogen bonds. A hydrophobic diaminotriazine-terminated polycaprolactone (PCL-DAT) chain segment and a hydrophilic uracil-terminated poly N,N-diethylacrylamide (U-PDEA) chain segment are synthezed; and then the novel supra-molecular polymer PCL-DAT...U-PDEA micelle with temperature sensitivity and pH sensitivity is constructed by triple hydrogen bonds between DAT and U. The novel supra-molecular copolymer micelle with amphiphilic, temperature-sensitive and pH-sensitive properties is prepared by interacting hydrophobic and hydrophilic chain segments with temperature sensitivity and pH sensitivity through the solidtriple hydrogen bonds. The novel self-assembled micelle has fast and controllable release properties.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for preparing supramolecular polymer composite micelles based on hydrogen bonds. Background technique [0002] Compared with conventional polymers linked by covalent bonds, supramolecular polymers based on non-covalent bond interactions are more sensitive to external stimuli. In various non-covalent bond interactions, hydrogen bonds are very sensitive to pH changes. sensitive. In living organisms, multiple hydrogen bond interactions occur in base pairs in DNA or RNA, such as adenine and uracil (A-U), adenine and thymine (A-T), guanine and cytosine (G-C) . At present, Wang Dali et al. have synthesized PEG-U...A-PCL, a supramolecular polymer micelle bound by double hydrogen bonds, but the micelles are only amphiphilic and pH sensitive, and are bound by double hydrogen bonds. Combined, not strong enough. [0003] Poly(N,N-diethylacrylamide) (PDEA)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/02C08G63/08C08G63/85C08G63/87C08F120/54C08F2/38C08F8/30
CPCC08F2/38C08F8/30C08F120/54C08G63/08C08G63/823C08G63/87C08G81/027
Inventor 吴秋华杨辰薛菲张国林刘学矣杰宋溪明
Owner LIAONING UNIVERSITY
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