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Preparation method and applications of ganglioside derivatives containing unsaturated fatty acid chains

An unsaturated fatty acid and ganglioside technology, applied in the biological field, can solve the problem of no systematic research on ganglioside derivatives, affecting the neurite outgrowth activity of gangliosides, and affecting the biological activity of gangliosides. and other problems, to achieve the effect of shortening purification steps and purification time, avoiding cleaning steps, and being easy to remove

Active Publication Date: 2018-09-07
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The fatty acid chains of gangliosides greatly affect the biological activity of gangliosides by interacting with lipid rafts and membrane-associated proteins, but no systematic studies have been conducted on ganglioside derivatives containing unsaturated fatty acid chains
Whether unsaturated fatty acid chains affect the neurite growth-promoting activity of gangliosides, there is no relevant research report

Method used

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  • Preparation method and applications of ganglioside derivatives containing unsaturated fatty acid chains
  • Preparation method and applications of ganglioside derivatives containing unsaturated fatty acid chains
  • Preparation method and applications of ganglioside derivatives containing unsaturated fatty acid chains

Examples

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Effect test

Embodiment 1

[0067] Example 1. Enzymatic synthesis of a library of ganglioside derivatives with unsaturated fatty acid chains

specific Embodiment approach

[0068] Since the ganglioside GM1 has the most clear effect on promoting neurite growth, we first established a derivative library of GM1 with unsaturated fatty acid chains, and the specific implementation method is as follows:

[0069] For enzymatic synthesis of GM1 derivatives containing unsaturated fatty acid chains, see figure 2 .

[0070] First, prepare the sphingolipid ceramide N-deacylase required for the catalytic synthesis reaction and the substrate lysoganglioside GM1 (Lyso-GM1) required for the synthesis of GM1 derivatives. The specific steps follow our previous application Patent (application number: CN201410508221.X) and published articles (J Lipid Res, 2015, 56:1836-1842) for preparation.

[0071] Synthetic reaction system: the reaction system contains about 10% ethylene glycol dimethyl ether (DME), about 20 mg of lyso-GM1, and 1.5 mM unsaturated fatty acid in 20 ml of 50 mM Tris-HCl (pH 7.5). To the reaction system, 1ml of 1mg / ml SCDase was added every 8-12h f...

Embodiment 2

[0076] Example 2: Separation and purification of a library of ganglioside derivatives with unsaturated fatty acid chains

[0077] After the catalytic synthesis reaction is completed, it is necessary to separate and purify the derivatives with unsaturated fatty acid chain gangliosides from the reaction mixture. Sep-Pak tC18 solid-phase extraction column (one 500mg column, one 5g column) of Waters Company was used for separation and purification. Since it does not contain surfactant, the synthesis reaction solution can be purified directly on the solid phase extraction column: first, the reaction mixture flows through a small Sep-Pak tC18 solid phase extraction column (500mg), and then the flow-through solution flows through a A large Sep-Pak tC18 solid-phase extraction cartridge (5g), washed 50ml with water, then 50ml with 50% methanol, and finally washed the derivative with 100% methanol, concentrated by rotary evaporation and lyophilized. In addition, the reaction mixture ca...

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Abstract

The present invention relates to applications of a group of ganglioside derivatives containing unsaturated fatty acid chains in promotion of neurite growth. According to the present invention, the library of ganglioside derivatives containing unsaturated fatty acid chains is synthesized through a sphingolipid ceramide N-deacylase method, and is combined with the classical neurite growth promotioncell model; and the results show that the ganglioside derivatives containing unsaturated fatty acid chains have the significantly-improved biological activity of the neurite growth promotion, and thedifferent number of the carbon chains of the ganglioside sphingosine base can significantly affect the biological activity of the neurite growth promotion.

Description

Technical field [0001] The present invention belongs to the field of biotechnology, and more specifically, the present invention relates to an efficient preparation method of a group of ganglioside derivatives containing unsaturated fatty acids and their application in promoting neurite growth. Background technique [0002] Gangliosides are a type of glycosphingolipid containing sialic acid residues. They are a typical component of the plasma membrane of nerve cells and have important biological functions. Ganglioside GM1 is one of the representative and important gangliosides. It has multiple neurotrophic effects and can promote cell differentiation, induce neurite production, protect neurons from damage, and regulate neural plasticity. Clinically, GM1 has been widely used to treat vascular or traumatic central nervous system injuries, Parkinson's disease and Alzheimer's disease. [0003] Gangliosides exist in large amounts in the mammalian brain, of which GM1, GD1a, GD1b ...

Claims

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Application Information

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IPC IPC(8): A61K31/7028A61P25/00C12P19/44
CPCA61K31/7028C12P19/44A23V2002/00A23V2200/322
Inventor 杨广宇黄锋涛冯雁
Owner SHANGHAI JIAO TONG UNIV
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