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Tetrahydrocurcumin compound-GelMA hydrogel as well as preparation method and application thereof

A technology of tetrahydrocurcumin and compound is applied in the field of tetrahydrocurcumin compound-GelMA hydrogel and preparation thereof, and can solve the problems of low bioavailability, insoluble in water, poor water solubility of tetrahydrocurcumin and the like

Pending Publication Date: 2022-02-15
BAYECAO HEALTH IND RES INST (XIAMEN) CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although tetrahydrocurcumin has better biological activity than curcumin in all aspects, it is equally difficult to dissolve in water.
At present, tetrahydrocurcumin is mostly administered in the form of solid dispersion, which can well solve the problems of poor water solubility and low bioavailability of tetrahydrocurcumin
However, the sustained-release effect of solid dispersion administration is poor

Method used

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  • Tetrahydrocurcumin compound-GelMA hydrogel as well as preparation method and application thereof
  • Tetrahydrocurcumin compound-GelMA hydrogel as well as preparation method and application thereof
  • Tetrahydrocurcumin compound-GelMA hydrogel as well as preparation method and application thereof

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preparation example Construction

[0030] In the present invention, the preparation method of described tetrahydrocurcumin cinnamic acid diester preferably comprises the following steps:

[0031] In the presence of a pyridine catalyst and a dehydrating agent, tetrahydrocurcumin is esterified with cinnamic acid to obtain tetrahydrocurcumin cinnamic acid diester.

[0032] In the present invention, the pyridine catalyst is preferably one or more of 4-dimethylaminopyridine, pyridine, 4-dimethylaminopyridine N-oxide and polypyrrole.

[0033] In the present invention, the dehydrating agent is preferably 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and / or N,N'-dicyclohexylcarbodiimide. The invention uses a dehydrating agent, which can remove the water produced in the esterification process and improve the product yield.

[0034] In the present invention, the molar ratio of tetrahydrocurcumin to cinnamic acid is preferably 1:(1-4), more preferably 1:(2-3).

[0035] In the present invention, the molar r...

Embodiment 1

[0061] 1) Synthesis of GelMA hydrogel: 10 g of gelatin was dissolved in 100 mL of carbonate buffer, heated in a water bath to 50° C., and magnetically stirred until completely dissolved. Adjust the pH of the solution to 9. 0.1 mL of methacrylic acid (MAA) was added dropwise, and the reaction was stirred for 1 h. Adjust the pH value of the solution to 7.4 again to stop the reaction. The product was dialyzed against deionized water for 7 days with a dialysis bag with a molecular weight cut-off of 12-14 kDa. After filtering with a 0.22 μm filter membrane, freeze-dry and save for future use. The scanning electron microscope picture of gained GelMA hydrogel is as follows figure 1 shown by figure 1 It can be seen that after freeze-drying, the GelMA hydrogel has a regular structure of fold-like lamination connections, so its fold-like lamination structure can be used to coat drugs for drug loading research.

[0062] 2) Preparation of tetrahydrocurcumin-GelMA hydrogel: first put ...

Embodiment 2

[0066] 1) Synthesis of GelMA hydrogel: 10 g of gelatin was dissolved in 100 mL of carbonate buffer, heated in a water bath to 40° C., and magnetically stirred until completely dissolved. Adjust the pH of the solution to 9. 0.125 mL of methacrylic acid (MAA) was added dropwise, and the reaction was stirred for 3.4 h. Adjust the pH value of the solution to 7.4 again to stop the reaction. The product was dialyzed against deionized water for 7 days with a dialysis bag with a molecular weight cut-off of 12-14 kDa. After filtering with a 0.22 μm filter membrane, freeze-dry and save for future use.

[0067] 2) Preparation of tetrahydrocurcumin-GelMA hydrogel: first put 0.3 g of GelMA hydrogel that has been freeze-dried into ethanol for swelling. Put the swollen hydrogel into 10mL THC (4×10 -2 mol / L) drug solution, the drug was loaded at room temperature for 24 hours, and it was oscillated intermittently during drug loading to obtain tetrahydrocurcumin-GelMA hydrogel.

[0068] Af...

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Abstract

The invention provides tetrahydrocurcumin compound-GelMA hydrogel, and belongs to the technical field of medicine polymer synthesis. GelMA is methacrylic anhydride modified gelatin and has a cross-linked three-dimensional network structure, and GelMA hydrogel has the characteristics of high water content, high water absorption, high water retention and the like, has the characteristics of relatively high viscosity and good biocompatibility, and has a wrinkle-like laminated and connected regular structure microcosmically. According to the invention, tetrahydrocurcumin is loaded on GelMA hydrogel to obtain the tetrahydrocurcumin-GelMA hydrogel with a drug sustained release effect, and the GelMA hydrogel is safe and non-toxic. The result of the embodiment shows that the tetrahydrocurcumin-GelMA hydrogel provided by the invention can be continuously released for more than 70 hours in a normal physiological environment and a simulated focus site environment.

Description

technical field [0001] The invention relates to the technical field of medical polymer synthesis, in particular to a tetrahydrocurcumin compound-GelMA hydrogel and its preparation method and application. Background technique [0002] Tetrahydrocurcumin (THC) is the main in vivo metabolite of curcumin, which has anti-fatty liver, anti-cancer, anti-inflammatory and other activities. The article "The prevention and treatment effect of tetrahydrocurcumin on H22 ascites tumor model mice" (Yu Fei et al. Zhejiang Clinical Medicine, 2019 (21) 2: 179-180 pages) discussed the effect of tetrahydrocurcumin on H22 ascites tumor model mice. As a result, it was found that tetrahydrocurcumin can improve the quality of life and survival cycle of mice with ascites tumors, and reduce the weight and amount of ascites in mice. Further mechanism studies showed that tetrahydrocurcumin could up-regulate the level of Bax protein and down-regulate the level of Be-2 protein, suggesting that THC could...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/06A61K31/216A61K47/42A61P29/00A61P35/00C08F289/00C08F220/06
CPCA61K31/216A61K9/06A61K47/42C08F289/00A61P29/00A61P35/00C08F220/06
Inventor 汤须崇黄韵霏邓爱华谢嘉斌
Owner BAYECAO HEALTH IND RES INST (XIAMEN) CO LTD