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A preparation method of amino acid-based polyzwitterionic nanoparticles

A polyzwitterion and nanoparticle technology, which is applied in the field of lysine-based polyzwitterion nanoparticles and their preparation, can solve the problems of unsatisfactory use, difficulty in excretion, non-degradability of raw materials, etc., and achieves stability and sensitivity. Effects of pH Sensitivity

Active Publication Date: 2018-02-09
深圳百奥捷生物科技有限公司 +2
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  • Claims
  • Application Information

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Problems solved by technology

[0004] However, there are few literatures on polyzwitterions with both pH and reduction sensitivity reported in the literature, and the raw materials usually selected are non-degradable, difficult to excrete in the body, and do not meet the requirements for use in the human body, so they become such materials. Bottleneck Problems in Practical Applications

Method used

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  • A preparation method of amino acid-based polyzwitterionic nanoparticles
  • A preparation method of amino acid-based polyzwitterionic nanoparticles
  • A preparation method of amino acid-based polyzwitterionic nanoparticles

Examples

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Embodiment 1

[0025] Embodiment 1: the synthesis of N,N-bisacryloyl cystamine:

[0026] Add 11.6 g of cystamine dihydrochloride into a 250 mL one-necked flask, then add 50 mL of distilled water to stir and dissolve cystamine dihydrochloride. Place the flask in a mixture of ice and water at 0°C; in addition, weigh 8g of solid sodium hydroxide and dissolve it in 20mL of distilled water, add the dissolved sodium hydroxide solution to the single-necked flask at one time, and add 19mL of pre-refined Acryloyl chloride was mixed with 3mL of dichloromethane to form a solution, which was added dropwise into a single-necked flask through a constant pressure dropping funnel. After the dropwise addition was completed within 40 minutes, the reaction was controlled at 25°C for 16h. The product was filtered, washed three times with deionized water, finally recrystallized with ethyl acetate, and dried in a vacuum oven for 24 hours to obtain the product.

Embodiment 2

[0027] Embodiment 2: Preparation of polyzwitterionic nanoparticles based on amino acids:

[0028] In a 25mL three-neck flask, mix 1.7mL of distilled water and 3.3mL of absolute ethanol, dissolve 0.26g of N,N-bisacryloylcystamine and 0.103g of octylamine in the above solution, and adjust the pH range to 9.5-10 , under the protection of nitrogen, heat the reaction solution to 40°C through an oil bath, and stir and react at a constant temperature for 48 hours;

[0029] Dissolve 0.26g of N,N-bisacryloylcystamine and 0.175g of lysine in a mixed solvent of 1.7mL of distilled water and 3.3mL of absolute ethanol, and then add it to the above copolymer solution to adjust the pH value to 10-11. Stir at a constant temperature of 55°C, and continue to react for 72 hours to obtain a triblock copolymer containing N,N-bisacryloylcystamine, octylamine and lysine.

[0030] Add ultrapure water to the above copolymer solution, stir for 5 hours, and then use anhydrous ether 5 times the volume of...

Embodiment 3

[0032] Same as Example 2, but replace 0.103 g of octylamine with 0.148 g of dodecylamine, and keep the other conditions and operations unchanged, and synthesize a three-block copolymer containing N,N-bisacryloylcystamine, dodecylamine and lysine to further synthesize nanoparticles.

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Abstract

The invention relates to a preparing method for poly-zwitter-ion nanoparticles based on amino acid .A triblock copolymer with the middle section hydrophobic and the two end chain segments containing poly-zwitter-ions is synthesized with a two-step method .The method comprises the steps that firstly, N,N-bisacrylylcystamine and aliphatic primary amine are dissolved in a mixed solvent of deionized water and ethyl alcohol, and an alternating copolymer is obtained through nucleophilic addition; then, a mixture solution of N,N-bisacrylylcystamine and lysine is added into the copolymer, a reaction continues, and the triblock copolymer containing N,N-bisacrylylcystamine, aliphatic primary amine and lysine is obtained; the triblock copolymer forms nanoparticles in an aqueous solution in a self-assembling mode .The poly-zwitter-ion nanoparticles have pH and reduction sensitivity and excellent protein nonspecific adsorption resisting performance, are free of cytotoxicity and have application prospects on serving as anti-cancer medicine carriers .

Description

technical field [0001] The invention relates to the technical field of biomedical materials, in particular to a lysine-based polyzwitterion nanoparticle and a preparation method thereof. Background technique [0002] In recent years, the application of nanotechnology in medicine, especially the development of nanomedicine, has promoted the development of various nanomedicine delivery systems, especially nanoparticles based on liposomes and polymers. However, the application of nanoparticles in drug delivery systems is facing two bottlenecks. First, the accumulation of nanoparticles in tumor tissues is poor because nanoparticles are easily cleared by the endothelial reticulum system (RES) and lack tumor targeting. ability, which inevitably leads to undesirable side effects. Another important issue is the bioavailability of nanoparticle-based drug delivery systems. High availability means that once the nanoparticles are attached to the solid tumor, the drug-encapsulated nano...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/00A61K31/704A61P35/00B82Y5/00A61K47/59A61K9/14
CPCA61K9/146A61K31/704B82Y5/00C08G73/00
Inventor 郑超秦伟李慧张宏
Owner 深圳百奥捷生物科技有限公司
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