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Polyethylene glycol modified cystamine derivative as well as preparation and application thereof

A technology of polyethylene glycol and cystinamide, which is applied in the field of cystinamide derivatives, can solve the problems of low drug encapsulation efficiency, high CMC value, and poor stability, and achieve high surface activity, reduced adsorption area, and enhanced The effect of fat solubility

Active Publication Date: 2021-10-22
武汉纳乐吉生命科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the defects of the prior art, the object of the present invention is to provide a polyethylene glycol-modified cystinamide derivative, its preparation and application, which are respectively linked to an aromatic acid or Aromatic heterocyclic acid, while the two carboxyl groups of cystine are respectively modified by polyethylene glycol, a Gemini surfactant is synthesized and used as a drug delivery system carrier, aiming to solve the prior art cystine-based Gemini Surfactants are used in the technical problems of drug delivery system carriers such as low safety, high CMC value, low drug encapsulation efficiency, poor stability, etc.

Method used

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  • Polyethylene glycol modified cystamine derivative as well as preparation and application thereof
  • Polyethylene glycol modified cystamine derivative as well as preparation and application thereof
  • Polyethylene glycol modified cystamine derivative as well as preparation and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Synthesis of Phenylalanine-Cystine-mPEG

[0042]Weigh 19.38g of Fmoc-D-phenylalanine, 20mL of chloroform, and 6.0mL of thionyl chloride into a 100mL flask, react at 60°C for 2.0h, distill off chloroform and thionyl chloride under reduced pressure, and then weigh them in petroleum ether. Crystallization gave white crystals of Fmoc-D-phenylalanine acid chloride. Weigh 20.23g of Fmoc-D-phenylalanine acid chloride and dissolve it in 25mL of acetone for later use, add 12.01g of L-cystine and 10mL of acetone into a 100mL flask, and slowly add Fmoc-D dropwise under ice bath and magnetic stirring conditions -Phenylalanine acid chloride acetone solution, after the dropwise addition, warm up to room temperature, stir for 4 hours, distill off acetone under reduced pressure, and a solid precipitates, filter with suction, wash, and dry to obtain Fmoc-D-phenylalanine-L - Cystine.

[0043] Weigh Fmoc-D-phenylalanine-L-cystine 2.1g, mPEG 2000 -NH 2 24g was dissolved in 300mL of an...

Embodiment 2

[0045] Synthesis of Tyrosine-Cystine-mPEG

[0046] Weigh 12.01g of Fmoc-L-tyrosine, 20mL of chloroform, and 6.0mL of thionyl chloride into a 100mL flask, react at 60°C for 2.0h, evaporate chloroform and thionyl chloride under reduced pressure, and then recrystallize from petroleum ether , to obtain white crystals of Fmoc-L-tyrosine acid chloride. Weigh 21.14g of Fmoc-L-tyrosine acid chloride and dissolve it with 25mL DMF for later use, add 12.01gL-cystine, 20mL concentrated ammonia water and 15mL DMF into a 100mL flask, slowly add Fmoc -L-tyrosine acid chloride DMF solution, warm up to room temperature after the dropwise addition, stir for 4 hours, evaporate DMF under reduced pressure, and recrystallize with ethanol / water / ethyl acetate to obtain Fmoc-L-tyrosine-L-cyst acid. Weigh Fmoc-L-tyrosine-L-cystine 2.4g, mPEG 4000 -NH 2 40g was dissolved in 400mL of anhydrous dichloromethane, 1.5g of DCC was added, stirred and reacted for 48h, precipitated with excess cold diethyl ...

Embodiment 3

[0048] Synthesis of Nicotinic Acid-Cystine-mPEG

[0049] Weigh 5.56g of nicotinic acid, 20mL of chloroform, and 6.0mL of thionyl chloride into a 100mL flask, react at 60°C for 2.0 hours, evaporate chloroform and thionyl chloride under reduced pressure, and then recrystallize petroleum ether to obtain white crystal smoke Acid chloride. Weigh 7.12g of nicotinic acid chloride and dissolve it in 25mL of acetone for later use, add 12.01g of L-cystine, 25.0mL of sodium hydroxide solution (2.5mol / L) and 10mL of acetone in a 100mL flask, and place under ice bath and magnetic stirring conditions , slowly add nicotinic acid chloride acetone solution and 5.0mL sodium hydroxide solution (0.5mol / L) dropwise, warm up to room temperature after the dropwise addition, stir for 4 hours, evaporate acetone under reduced pressure, add dilute sulfuric acid solution dropwise to adjust the solution to Weakly acidic, with solid precipitation, suction filtration, washing, drying, to obtain niacin-L-cy...

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Abstract

The invention belongs to the technical field of drug polymer materials and chemical drugs, and more specifically relates to a polyethylene glycol modified cystamine derivative as well as preparation and application thereof. The derivative has a general formula represented by a formula (I), wherein in the formula (I), R1 and R2 are respectively and independently C6-C30 monocyclic or polycyclic aromatic acid or aromatic heterocyclic acid connected with amino of cystine through an amido bond; mPEG represents polyethylene glycol, the single tail end of the polyethylene glycol is terminated by an inert group, and the other end of the polyethylene glycol is respectively connected with two carboxyl groups of cystine through connected X1 and X2 groups; and X1 and X2 are respectively and independently amino or hydrazide. As a novel Gemini amino acid surfactant, the polyethylene glycol modified cystamine derivative provided by the invention is low in critical micelle concentration, safe, non-toxic, non-irritant and good in biodegradability, and can be used as a water-insoluble and fat-soluble drug delivery system carrier.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical polymer materials and chemical medicines, and more specifically relates to a polyethylene glycol-modified cystinamide derivative, its preparation and application. Background technique [0002] The molecular structure of Gemini surfactant contains two molecules of monomeric surfactants, which are connected at the ionic head group through chemical bonds. Its structure is novel and its performance is superior to traditional monomeric surfactants, but it is relatively expensive. It can be produced industrially on a large scale. [0003] Amino acid surfactants are a class of surfactants that use amino acids or short peptides as hydrophilic groups. They not only have the basic properties of surfactants such as wetting, washing, foaming, solubilizing, and emulsifying, but also have low Due to the advantages of irritation, low toxicity, good surface activity, biodegradability and environmental com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/334A61K9/107A61K47/18
CPCC08G65/3348A61K9/1075A61K47/18
Inventor 熊瑜徐忠瑞阮健盛剑勇甘祥俊万江陵
Owner 武汉纳乐吉生命科技有限公司
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