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Preparation method of supramolecular polymer composite micelles based on hydrogen bond

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

Active Publication Date: 2021-06-18
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 supramolecular polymer composite micelles based on hydrogen bond
  • Preparation method of supramolecular polymer composite micelles based on hydrogen bond
  • Preparation method of supramolecular polymer composite micelles based on hydrogen bond

Examples

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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, ...

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Abstract

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. The present invention synthesizes a hydrophobic terminal diaminotriazine polycaprolactone (PCL-DAT) segment and a hydrophilic terminal uracil poly-N,N-diethylacrylamide (U-PDEA) segment, and then passes the DAT The triple hydrogen bond between U and U constructs a novel supramolecular polymer PCL-DAT...U-PDEA micelles with temperature sensitivity and pH sensitivity, and the present invention adopts hydrophobic and hydrophilic and temperature-sensitive The novel supramolecular copolymer micelles with amphiphilicity, temperature sensitivity and pH sensitivity are prepared through the strong triple hydrogen bond interaction, and the novel supramolecular copolymer micelles with fast and controllable release properties Self-assembled micelles.

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 Patents(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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