Cystamine derivative based on dextran modification as well as preparation and application of cystamine derivative

A technology of dextran and cysteinamide, applied in the field of cysteinamide derivatives, can solve the problems of low drug encapsulation efficiency, high CMC value, and low safety, and achieve high surface activity, reduced adsorption area, solubility and The effect of hardness improvement

Active Publication Date: 2021-11-05
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 prior art, the object of the present invention is to provide a kind of surfactant and application thereof based on dextran-modified cysteine ​​amide derivatives, which connect aromatic acid or Aromatic heterocyclic acid, while the two carboxyl groups of cystine are respectivel...

Method used

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  • Cystamine derivative based on dextran modification as well as preparation and application of cystamine derivative
  • Cystamine derivative based on dextran modification as well as preparation and application of cystamine derivative
  • Cystamine derivative based on dextran modification as well as preparation and application of cystamine derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Dex-NH 2Synthesis: Weigh 4.0g dextran-10 and dissolve it in 50mL dimethyl sulfoxide, add 0.25g sodium cyanoborohydride and 0.20g HDMA to the solution, and stir at room temperature for 24h. Then 0.47 g of hexamethylenediamine was added to the above solution, and the reaction was stirred at room temperature for 24 h. The solution was dialyzed against deionized water for 3 days with a dialysis membrane, concentrated by vacuum rotation and freeze-dried to obtain Dex 10 -NH 2 powder, the synthetic route is as figure 1 shown.

[0042] Synthesis of phenylalanine-cystine-Dex: Weigh 19.38g Fmoc-D-phenylalanine, 20mL chloroform, and 6.0mL thionyl chloride into a 100mL flask, react at 60°C for 2.0h, and depressurize Chloroform and thionyl chloride were distilled off, and then recrystallized from petroleum ether to obtain 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, ad...

Embodiment 2

[0044] Synthesis of Tyrosine-Cystine-Dex

[0045] 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, Dex 10 -NH 2 (Dextran-10K) 100g was dissolved in 600mL of anhydrous DMF, 1.5g of DCC was added, stirred for 48h, precipitated with excess cold ether, suction filtere...

Embodiment 3

[0047] Synthesis of Nicotinic Acid-Cystine-Dex

[0048] 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-cys...

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Abstract

The invention belongs to the field of drug polymer materials and chemical drugs, and relates to a cystamine derivative based on dextran modification, as well as preparation and application of cystamine derivative. The derivative has a structural general formula shown in a formula (I), wherein 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, Dex is dextran, the tail end of the Dex is coupled with a diamine compound, the diamine compound is used as a connecting arm, and the Dex is connected with carboxyl of cystine through an amino group in the connecting arm. As a novel Gemini amino acid surfactant, the dextran-modified cystamine derivative provided by the invention is low in critical micelle concentration, high in surface activity, 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 field of pharmaceutical polymer materials and chemical drugs, and more specifically relates to a dextran-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 compatibility, it has been wi...

Claims

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Application Information

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IPC IPC(8): C08B37/02C07H15/06C07H1/00A61K9/107A61K47/36A61K47/26B01F17/56B82Y5/00C09K23/56
CPCC08B37/0021C07H15/06C07H1/00A61K9/1075A61K47/36A61K47/26B82Y5/00
Inventor 熊瑜甘祥俊徐忠瑞盛剑勇万江陵阮健
Owner 武汉纳乐吉生命科技有限公司
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