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Preparation method of new type hyaluronic acid derivative containing coumarin fluorophore

A technology of sodium hyaluronate and its derivatives, which is applied in the field of biochemistry and can solve the problems that the synthesis of hyaluronic acid derivatives containing coumarin has not been reported in the literature.

Inactive Publication Date: 2010-09-15
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] There is no literature report on the synthesis of our proposed coumarin-containing hyaluronic acid derivatives

Method used

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  • Preparation method of new type hyaluronic acid derivative containing coumarin fluorophore
  • Preparation method of new type hyaluronic acid derivative containing coumarin fluorophore
  • Preparation method of new type hyaluronic acid derivative containing coumarin fluorophore

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 0.1g (0.25mmol) sodium hyaluronate to a 25mL round bottom flask, then add 12mL dimethyl sulfoxide and 3mL water, stir with strong magnetic force to dissolve sodium hyaluronate, add 0.1M NaOH solution drop by drop to make the mixed solution pH=8-12, then add 0.173g (0.75mmol), 4-methyl-7-(2,3-epoxypropoxy)coumarin, and react at 30°C for 20h. The reaction mixture was put into a dialysis bag and dialyzed for 72 hours, and the dialysate was precipitated with ethanol to obtain a white solid, which was lyophilized and vacuum-dried for use in 1 Characterized by H NMR, by comparing 2.0ppm (3H, -NHCOCH 3 ) and 2.45ppm (3H, -CH on the introduced coumarin group 3) signal to calculate the degree of substitution of the product to be 1.8%.

Embodiment 2

[0027] Add 0.1g (0.25mmol) sodium hyaluronate to a 25mL round bottom flask, then add 12mL dimethyl sulfoxide and 3mL water, stir with strong magnetic force to dissolve sodium hyaluronate, add 0.1M NaOH solution drop by drop to make the mixed solution pH = 8-12, then add 0.173g (0.75mmol) coumarin derivative 2, and react at 30°C for 30h. The reaction mixture was put into a dialysis bag and dialyzed for 72 hours, and the dialysate was precipitated with ethanol to obtain a white solid, which was lyophilized and vacuum-dried for use in 1 Characterized by HNMR, by comparing 2.0ppm (3H, -NHCOCH 3 ) and 2.45ppm (3H, -CH on the introduced coumarin group 3 ) signal to calculate the degree of substitution of the product to be 2.4%.

Embodiment 3

[0029] Add 0.1g (0.25mmol) sodium hyaluronate to a 25mL round bottom flask, then add 12mL dimethyl sulfoxide and 3mL water, stir with strong magnetic force to dissolve sodium hyaluronate, add 0.1M NaOH solution drop by drop to make the mixed solution pH = 8-12, then add 0.173g (0.75mmol) coumarin derivative 2, and react at 30°C for 40h. The reaction mixture was put into a dialysis bag and dialyzed for 72 hours, and the dialysate was precipitated with ethanol to obtain a white solid, which was lyophilized and vacuum-dried for use in 1 Characterized by HNMR, by comparing 2.0ppm (3H, -NHCOCH 3 ) and 2.45ppm (3H, -CH on the introduced coumarin group 3 ) signal to calculate the degree of substitution of the product to be 3.6%.

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Abstract

The invention relates to a synthetic method of a new type hyaluronic acid derivative containing coumarin, which uses 4-methyl-7-hydroxyl coumarin as an initial raw material and comprises the steps of:; carrying out an etherification reaction to firstly generate 7-methoxy-4-methyl coumarin-1,2-propylene oxide; then carrying out the etherification reaction on the 7-methoxy-4-methyl coumarin-1,2-propylene oxide and sodium hyaluronate to prepare a hyaluronic acid derivative containing a coumarin structural unit; putting a mixed solution after the reaction into a dialysis bag, with dialysis time of 72 hours; and then precipitating by using absolute ethyl alcohol, freezing and drying to obtain a target product. The invention has the advantages that by introducing coumarin fluorophore into hyaluronic acid which is difficult to detect, the natural structure of the hyaluronic acid is kept, and meanwhile, the hyaluronic acid is endowed with a fluorescence property, which provides an experimental basis for researches of the hyaluronic acid on a plurality of aspects of corresponding drug metabolism, pharmacology and the like in animal or human bodies.

Description

technical field [0001] The invention relates to a method for preparing a novel coumarin-containing hyaluronic acid derivative, belonging to the technical field of biochemistry. Background technique [0002] Hyaluronic acid (hyaluronic acid, hyaluronan, HA), also known as hyaluronic acid or hyaluronic acid, is an acidic mucopolysaccharide, which was first proposed by American Meyer (Meyer K, Palmer J W. The polysaccharide of the vitreous humor[J].J. Biol.Chem.1934, 107:629-634.) etc. isolated from bovine vitreous. HA is a straight-chain linear anionic adhesive composed of β-D-N-acetylglucosamine and β-D-glucuronic acid as structural units, which are alternately connected by β-1,3 and β-1,4-glycoside chains. polysaccharides. The structure determination of HA from different tissue sources shows that the structure is consistent, there is no species difference, only the relative molecular weight is different, the range is 10 5 -10 7 , the number of disaccharide units is 300-1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08C09K11/06
Inventor 席海涛任振缪春宝孙小强
Owner CHANGZHOU UNIV