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Synthesis method of poly-benzyl L-glutamate/ethyl polyphosphate block copolymer

A technology of amino-terminated polyethylphosphate and ethylpolyphosphate, which is applied in the direction of pharmaceutical formulations, medical preparations of non-active ingredients, etc., can solve the problems of poor solubility of polyamino acids, achieve improved water solubility, increase cycle time, and better The effect of applying the foreground

Active Publication Date: 2012-10-17
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is in order to overcome the shortcoming that polyamino acid has poor solubility in water, make amphiphilic block copolymer with hydrophobic polyamino acid and hydrophilic polyphosphate ethyl ester, thereby obtain energy by changing the content of each chain segment Solubility Controlled Block Copolymers

Method used

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  • Synthesis method of poly-benzyl L-glutamate/ethyl polyphosphate block copolymer
  • Synthesis method of poly-benzyl L-glutamate/ethyl polyphosphate block copolymer
  • Synthesis method of poly-benzyl L-glutamate/ethyl polyphosphate block copolymer

Examples

Experimental program
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Embodiment 1

[0027] Example 1 Poly L-glutamic acid-benzyl ester / polyethyl phosphate (PBLG1- b -PEEP) block copolymer synthesis

[0028] (1) Amino-terminated ethyl polyphosphate (H 2 N-PEEP) synthesis

[0029] 1. Synthesis of cyclic ethyl phosphate (EEP)

[0030] Add 274.66g (2mol) of phosphorus trichloride and 250mL of anhydrous dichloromethane into a 500mL three-necked flask, and slowly add 124.14g (2mol) of anhydrous ethylene glycol dropwise. 123.2 g of colorless liquid was obtained as 2-chloro-1, 3, 2-dioxaphospholane (49% yield, 42-45°C / 1600 Pa).

[0031] Add 200 mL of toluene solution containing 123.2 g of 2-chloro-1, 3, 2-dioxaphospholane into a 250 mL round bottom flask, and pass O at 40 °C 2 Reaction 48h. Toluene was removed by rotary evaporation, and 77.9 g of colorless liquid was obtained by distillation under reduced pressure, which was 2-chloro-2-oxo-1, 3, 2-dioxaphospholane (yield: 56 %, 88-90 °C / 107 Pa ).

[0032] Dissolve 77.9g (0.55 mol) of 2-chloro-2-oxo-1,3,2-dioxa...

Embodiment 2

[0052] Example 2 Poly L-glutamic acid-benzyl ester / polyethyl phosphate (PBLG2- b -PEEP) block copolymer synthesis

[0053] Weigh 0.2g (1.0mmol) H 2 N-PEEP and 0.6 g BLG-NCA (20.2 mmol) were dissolved in 3 mL (46 mmol) and 40 mL (0.621 mol) CH 2 Cl 2 , and then placed in a three-necked flask for mixing, and stirred at room temperature for 26h. After the reaction was completed, the reaction mixture was added dropwise to 300 mL of ether to precipitate, left to stand at 2° C. for 14 h, and filtered. Repeat the above precipitation operation once, filter, and vacuum-dry the precipitate at 30°C to constant weight to obtain the product PBLG2- b -PEEP, yield 34%. The product was confirmed by infrared spectroscopy, nuclear magnetic resonance and gel permeation chromatography.

Embodiment 3

[0054] Example 3 Poly L-glutamic acid-benzyl ester / polyethyl phosphate (PBLG3- b -PEEP) block copolymer synthesis

[0055] Weigh 0.2g (1.0mmol) H 2 N-PEEP and 0.9 g BLG-NCA (30.3 mmol) were dissolved in 3 mL (46 mmol) and 60 mL (0.932 mol) CH 2 Cl 2 , and then placed in a three-necked flask for mixing, and stirred at room temperature for 28 hours. After the reaction was completed, the reaction mixture was added dropwise to 350 mL of diethyl ether to precipitate, left to stand at 2° C. for 16 h, and then filtered. The above precipitation operation was repeated once, filtered, and the precipitate was vacuum-dried at 30°C until constant weight to obtain the product with a yield of 27%. The product was confirmed by infrared spectroscopy, nuclear magnetic resonance and gel permeation chromatography.

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Abstract

The invention relates to a synthesis method of a poly-benzyl L-glutamate / ethyl polyphosphate block copolymer. The technical scheme is as follows: the synthesis method comprises the following steps: respectively dissolving moderate amino-terminated ethyl polyphosphate and benzyl L-glutamate amino acid anhydride into CH2Cl2, mixing, stirring and reacting at room temperature for 12-48 hours, after reaction is completed, dropping a product into diethyl ether to precipitate, standing at 2 DEG C for 12-18 hours, filtering, precipitating at 30 DEG C, and drying in vacuum to obtain a target product. Through the invention, the amphiphilic poly-benzyl L-glutamate / ethyl polyphosphate block copolymer is obtained, a micelle with a hydrophobic core and a hydrophilic shell is self-assembled in aqueous solution, a hydrophobic medicine molecule is assembled in the hydrophobic core, the circulating time of the medicine in the blood is improved, and the poly-benzyl L-glutamate / ethyl polyphosphate block copolymer has good application prospect in the biomedical field of controlled release of the medicine, targeted medicine transfer and the like.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a poly-L-glutamic acid-benzyl ester / polyethyl phosphate (PBLG- b -PEEP) block copolymer synthesis method. Background technique [0002] Polyamino acids are a class of biodegradable polymers with the advantages of low toxicity, good biocompatibility, and easy absorption and metabolism by the body. Therefore, they are widely used in medical fields such as controlled drug release and tissue engineering. However, the water solubility of its homopolymer is poor, and its application has certain limitations. [0003] Polyphosphate is a polymer material whose main chain skeleton is similar to nucleic acid and teichoic acid. The phosphate bond on the main chain is easy to be hydrolyzed or enzymatically decomposed under physiological conditions. It has good degradability, biophase Capacitance and low toxicity, and show temperature sensitivity under certain conditions, can be used in the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/42C08G69/08C08G79/04A61K47/34
Inventor 张国林康仁宇姜翠吴秋华宋溪明
Owner LIAONING UNIVERSITY
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