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Sulfhydrylated hyaluronic acid as well as preparation method and application thereof

A technology of hyaluronic acid and sulfhydrylation, which can be used in biochemical equipment and methods, cosmetic preparations, cosmetics, etc., and can solve the problems of cross-linking agent residue and influence

Pending Publication Date: 2021-05-28
BLOOMAGE BIOTECHNOLOGY CORP LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Aiming at the problem of cross-linking agent residue in the cross-linked hyaluronic acid obtained by adding a cross-linking agent, the present invention provides a mercaptolated hyaluronic acid. It will cause the loss of hydrophilic carboxyl group, and the water solubility and dissolution rate of the product will not be affected

Method used

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  • Sulfhydrylated hyaluronic acid as well as preparation method and application thereof
  • Sulfhydrylated hyaluronic acid as well as preparation method and application thereof
  • Sulfhydrylated hyaluronic acid as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Weigh 21g of sodium hyaluronate with a molecular weight of 250kDa, add 800mL of ethanol with a mass fraction of 75%, stir evenly, swell for 1h, filter, add 800mL of ethanol with a mass fraction of 75% to the filter cake, and adjust the pH of the solution with hydrochloric acid to 3.0, stirred, filtered, repeated use of 75% ethanol with a pH value of 3.0 to stir and replace 5 times, filtered, added 300 mL of water to dissolve, adjusted the pH of the solution to 7.0 with tetrabutylammonium hydroxide (TBA-OH), and freeze-dried 26 g of hyaluronic acid tetrabutylammonium salt (HA-TBA) was obtained.

[0043] Weigh 3.0g of HA-TBA, dissolve it in 300mL DMSO, add 6.67g 3,3'-dithiodipropionic acid (DTDP), 1.93g 4-dimethylaminopyridine (DMAP) and 2.0mL dicarbonate tert-butyl ester (Boc 2 0), stirred and reacted for 30h at 45°C, the reaction solution was packed into a dialysis bag (molecular weight cut-off was 3500Da), dialyzed with 0.2wt% sodium chloride solution, and the dialysa...

Embodiment 2

[0046] Weigh 21g of sodium hyaluronate with a molecular weight of 1200kDa, add 1000mL of acetone with a mass fraction of 70%, stir evenly, swell for 1h, filter, add 1000mL of acetone with a mass fraction of 70% to the filter cake, and adjust the pH of the solution with hydrochloric acid to 2.5, stirred, filtered, repeated use of 70% acetone with a pH value of 2.5 to stir and replace 5 times, filtered, added 300 mL of water to dissolve, adjusted the pH of the solution to 7.5 with tetrabutylammonium hydroxide (TBA-OH), and freeze-dried 28.2 g of HA-TBA was obtained.

[0047] Weigh 3.0g of HA-TBA, dissolve it in 600mL of DMSO, add 6.67g of 3,3'-dithiodipropionic acid (DTDP), 1.93g of 4-dimethylaminopyridine (DMAP) and 2.0mL of dicarbonate tert-butyl ester (Boc 2 0), stirred and reacted for 30h at 45°C, the reaction solution was packed into a dialysis bag (molecular weight cut-off was 3500Da), dialyzed with 0.2wt% sodium chloride solution, and the dialysate was replaced once ever...

Embodiment 3

[0050] Weigh 21g of sodium hyaluronate with a molecular weight of 2000kDa, add 1000mL of ethanol with a mass fraction of 90%, stir evenly, swell for 1h, filter, add 300mL of ethanol with a mass fraction of 90% to the filter cake, and adjust the pH of the solution with hydrochloric acid to 3.5, stirred, filtered, repeated use of 90% ethanol with a pH value of 3.5 to stir and replace 5 times, filtered, added 300 mL of water to dissolve, adjusted the pH of the solution to 6.5 with tetrabutylammonium hydroxide (TBA-OH), and freeze-dried 28.7 g of HA-TBA was obtained.

[0051] Weigh 12.0g of HA-TBA, dissolve it in 600mL DMF, add 25g 3,3'-dithiodipropionic acid (DTDP), 7.72g 4-dimethylaminopyridine (DMAP) and 8.0mL di-tert-dicarbonate Butyl ester (Boc 2 0), stirred and reacted for 30h at 45°C, the reaction solution was packed into a dialysis bag (molecular weight cut-off was 3500Da), dialyzed with 0.2wt% sodium chloride solution, and the dialysate was replaced once every 8h, and th...

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Abstract

The invention discloses sulfhydrylated hyaluronic acid as well as a preparation method and application thereof. The sulfhydrylated hyaluronic acid is obtained by sulfhydrylation modification of hydroxyl sites of hyaluronic acid or salt thereof. According to the invention, the hyaluronic acid or salt thereof reacts with a disulfide compound to generate a hyaluronic acid disulfide compound, and then a reducing agent is added to reduce disulfide bonds into a sulfydryl group, so the sulfhydrylated hyaluronic acid is obtained. The sulfhydrylated hyaluronic acid has the characteristics of controllable sulfydryl substitution degree, fast dissolution, fast gelling and good biocompatibility, and can be applied to the fields of skin care products, joint injection, tissue filling, cell culture and the like.

Description

technical field [0001] The invention relates to a mercaptolated hyaluronic acid and its preparation method and application, and belongs to the technical field of preparation of hyaluronic acid derivatives. Background technique [0002] Hyaluronic acid (HA) is a natural straight-chain polysaccharide that exists in human and animal tissues. In the human body, it is mainly distributed in the umbilical cord, joints, eye vitreous body, skin and other parts, and plays important physiological functions. Hyaluronic acid has good water retention, lubricity, viscoelasticity, biodegradability and excellent biocompatibility, and is widely used in cosmetics, medicine (orthopedics, ophthalmology, plastic surgery, dermatology, gastrointestinal, etc.) It is widely used in China and gradually expanded to new application fields. [0003] In order to resist the degradation effect of hyaluronidase and prolong the physiological effect of hyaluronic acid in the body, hyaluronic acid is usually c...

Claims

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Application Information

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IPC IPC(8): A61K8/73A61Q19/00A61L27/20A61L27/52C12N5/00
CPCA61K8/735A61Q19/00A61L27/20A61L27/52C12N5/00A61L2400/06C12N2501/905C08L5/08
Inventor 魏健李霞郭学平王成山栾贻宏石艳丽耿凤刘爱华
Owner BLOOMAGE BIOTECHNOLOGY CORP LTD
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