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Amphiphilic block copolymer connected through molecular glue and synthesis method and application of copolymer

A technology of amphiphilic block and copolymer, which is applied in the fields of chemical synthesis and biomedicine, and can solve problems such as difficult combination of material libraries and cumbersome synthesis methods

Active Publication Date: 2012-07-11
SHANGHAI JIAO TONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its synthesis method is cumbersome, and it is difficult to obtain a systematic combined material library for screening
So despite a lot of research, only PLA and PEG have real clinical application value.

Method used

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  • Amphiphilic block copolymer connected through molecular glue and synthesis method and application of copolymer
  • Amphiphilic block copolymer connected through molecular glue and synthesis method and application of copolymer
  • Amphiphilic block copolymer connected through molecular glue and synthesis method and application of copolymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Embodiment 1, the synthesis of hydrophilic compound E4

[0087] Described hydrophilic compound E4, its structural formula is as shown in the following formula:

[0088] Wherein, n is any integer from 1 to 300.

[0089] 1.1 When n=3, the synthesis of hydrophilic compound E4

[0090] Its synthetic route diagram is as follows figure 1 Shown:

[0091] (1) Synthesis of E2, under alkaline conditions, take compound E1 and carry out acylation reaction with PEG whose terminal is an amino group, to obtain compound E2;

[0092] The steps are as follows: add 100ml of dichloromethane into a single-necked flask, then add PEG164 (12.0g, 16.0mmol) whose terminal is an amino group, triethylamine (3.34ml, 24.0mmol), E1 (5.53g, 24.0 mmol) and stirred at 0°C for 10 min. React at room temperature (25°C) for 30 minutes. Stop the reaction, wash with water, and dry over anhydrous sodium sulfate to obtain 15.37 g of a reddish-brown liquid. Column chromatographic separation, yield 9...

Embodiment 2

[0133] Embodiment 2, the synthesis of hydrophobic compound P1

[0134] Wherein, R is an alkyl chain. Its synthetic route diagram is as follows figure 2 Shown:

[0135] 2.1 When R is a carbon undecyl chain, the synthesis of the hydrophobic compound P1

[0136] (1) The synthesis of Z2, under the action of a condensing agent, reacts the carboxyl and amino groups in Z1 to obtain Z2.

[0137] The steps are as follows: add 20ml of DMF to a single-necked flask, control the temperature at 0°C, then add compound Z1 (0.36g, 2.0mmol), EDCl (0.95g, 4.8mmol), HOBt (0.65g, 4.8mmol), N2 (2-(triphenylmercapto)ethylamine) (1.91 g, 6.0 mmol). Reaction at room temperature (25°C) for 4h. Stop the reaction, wash with water, and dry over anhydrous sodium sulfate. After separation by column chromatography, 3.7 g of a pale yellow foamy solid was obtained, with a yield of 62%.

[0138] 1 H NMR (CDCl 3 , 400MHz) δ7.17~7.42(m, 31H, ArH), 7.11(d, J=1.2Hz, 2H, ArH), 6.22(t, J=5.6Hz, 2H, -N...

Embodiment 3

[0142] Embodiment 3, the synthesis of hydrophobic compound P2

[0143]

[0144] Among them, R is m is any integer of 1-100.

[0145] The synthetic route of hydrophobic compound P2 is as follows: image 3 Shown:

[0146] Step 1, preparing compound Z4

[0147] (1) Synthesis of Z3, Z2 reacts with succinic anhydride in an organic solvent to obtain Z3.

[0148] Described step is specifically: with CHCl 3 As a solvent, Z2 reacted with succinic anhydride at room temperature, followed by TLC until the reaction was complete. After the reaction, an appropriate amount of water was added, extracted with DCM, the organic phase was washed with water and saturated brine respectively, dried over anhydrous sodium sulfate, the solvent was spun off under reduced pressure, and a white foamy solid product was obtained by column chromatography. The ratio of Z2 (mol) to succinic anhydride (mol) is 1:1.5-2.

[0149] 1 HNMR(d 6 -DMSO, 400MHz) δ10.38(s, 1H, -COOH), 8.60(s, 2H, -NH-), 7...

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Abstract

The invention discloses amphiphilic block copolymer connected through molecular glue and a synthesis method and application of the copolymer, a hydrophilic compound and a hydrophobic compound for synthesizing the copolymer, and preparation methods of the compounds. The copolymer M has a structural formula shown in the specifications. The amphiphilic block copolymer M is prepared by mixing the hydrophilic compound, the hydrophobic compound and an oxidant in a halogenated hydrocarbon solvent. The copolymer M can be used as a medicine transport carrier, and a medicine is poorly soluble in water. Raw materials for synthesizing the compounds are simple and readily available, the synthesis process is the conventional reaction process, reaction conditions are mild, and the compounds can be massively prepared; and a micelle formed by self-assembling the block copolymer can be used for the medicine transport carrier.

Description

technical field [0001] The invention relates to the fields of chemical synthesis and biomedicine, in particular to a novel amphiphilic block copolymer connected by molecular glue, its synthesis method and application. Background technique [0002] Amphiphilic block copolymer micelles are composed of hydrophilic segments and hydrophobic segments, a self-assembled structure formed spontaneously in aqueous solution, with small particle size, narrow particle size distribution, stable structure, wide range of drug loading, It has the characteristics of long residence time in vivo, high drug loading capacity and unique distribution in vivo. [0003] Block copolymer micelles can effectively solubilize insoluble drugs, and can be used as drug carriers for insoluble antineoplastic drugs, antihypertensive drugs, antibacterial drugs, and gene therapy drugs, and have attracted extensive attention. Using it as an anti-tumor drug carrier can not only improve the curative effect, reduce t...

Claims

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Application Information

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IPC IPC(8): C08G65/00C08G65/48C08G63/91C07D285/00C07D417/12C07C323/60C07C319/20C07C323/42C07D249/04A61K31/337A61K31/015A61K31/4745A61K47/34A61K47/22A61K47/20
Inventor 沈玉梅龚兵徐宇虹杨双杨晴来蔡良珍郭勋祥
Owner SHANGHAI JIAO TONG UNIV
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