Lys-glu modified curcumin, its preparation, biological activity and application

A technology of the-lys-lys-glu and curcumin, applied in the preparation method of peptides, drug combination, bulk chemical production, etc.

Active Publication Date: 2019-07-12
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these compounds disclosed by the inventors are not compounds with anti-tumor, anti-cancer metastasis, anti-inflammation and anti-thrombotic effects

Method used

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  • Lys-glu modified curcumin, its preparation, biological activity and application
  • Lys-glu modified curcumin, its preparation, biological activity and application
  • Lys-glu modified curcumin, its preparation, biological activity and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Preparation of (E)-6-(4-hydroxyl-3-methoxyphenyl)hex-5-ene-2,4-dione

[0028] Dissolve 30 mL (100.0 mmol) of acetylacetone in 200 mL of ethyl acetate, and heat and stir at 60°C. While stirring, add 12.6g (200mmol) boric anhydride (B 2 o 3 ) and stirred for 1 hour. Then 27mL (100.0mmol) tri-n-butyl borate and 15.6g (100.0mmol) vanillin were added, and heated to 70°C for 30min. Afterwards, 10 mL of n-butylamine was diluted to 100 mL with ethyl acetate and slowly added to the reaction and heated to 100° C. for 2 hours. After the reaction was completed, the temperature was lowered to 60°C and 100 mL of 2N hydrochloric acid was added and stirred for 30 minutes. After the precipitate is fully separated, filter the precipitate and put it in a separatory funnel. Wash three times with saturated potassium bisulfate and saturated sodium chloride respectively. Ethyl acetate layer with anhydrous Na 2 SO 4 Let dry for 12 hours. After filtration, the filtrate was co...

Embodiment 2

[0029] Example 2 Preparation of benzyl-2-(4-formyl-2-methoxyphenoxy) ethyl acetate

[0030] Dissolve 15.6g (100.0mmol) of vanillin in 100mL of anhydrous tetrahydrofuran, add 8.2g (60mmol) of potassium carbonate and stir for 2 hours. Subsequently, 17.4 mL (120 mol) of benzyl bromoacetate was added, and the reaction was heated at 60° C. for 3 days. After the raw material disappeared, the insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure to remove THF. The residue was crystallized from diethyl ether to afford 20.6 g (69%) of the title compound as a colorless solid. ESI +-MS(m / e): 301[M+H] + .

Embodiment 3

[0031] Example 3 Preparation of Benzyl 2-{4-[(1E,6E)-7-(4-Hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-diene-1 -yl]-2-methoxyphenoxy}ethyl acetate

[0032] Dissolve 10 g (42.7 mmol) of (E)-6-(4-hydroxy-3-methoxyphenyl)hex-5-ene-2,4-dione in 100 mL of ethyl acetate, and heat and stir at 60°C. While stirring, add 5.4g (85.4mmol) boric anhydride (B 2 o 3 ), stirred for 1 hour. Then 12mL (42.7mmol) of tri-n-butyl borate and 6.7g (42.7mmol) of ethyl benzyl-2-(4-formyl-2-methoxyphenoxy)acetate were added, and the reaction was heated at 70°C for 30min. After that, a solution of 4.2 mL of n-butylamine and 50 mL of ethyl acetate was added slowly. The temperature was raised to 100° C. for 2 hours. After the reaction was completed, the temperature was lowered to 60°C, 42mL of 2N hydrochloric acid was added, and stirred for 30 minutes. After the precipitate was fully separated, the precipitate was filtered off. The filtrate was washed three times with saturated potassium bisulfate a...

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Abstract

The invention discloses Lys-Glu modified curcumin, and discloses a preparation method of the Lys-Glu modified curcumin, activity of the Lys-Glu modified curcumin in resisting tumor cell proliferation, an effect of the Lys-Glu modified curcumin of inhibiting migration and invasion of A549 cells, activity of the Lys-Glu modified curcumin in inhibiting weight gain of the tumor of a tumor-bearing mice S180, activity of the Lys-Glu modified curcumin in inhibiting transferring of Lewis lung cancer, activity of the Lys-Glu modified curcumin in inhibiting ear swelling, induced by xylene, of the mice, and activity of the Lys-Glu modified curcumin in inhibiting generation of thrombus of a wistar.

Description

technical field [0001] The invention relates to a conjugate of curcumin and oligopeptide Lys-Glu, to its preparation method, to its anti-tumor cell proliferation activity, to its ability to inhibit the migration and invasion of A549 cells, and to its inhibition of S180 tumor-bearing small The activity of mouse tumor weight gain relates to its activity of inhibiting the metastasis of Lewis lung cancer, its activity of inhibiting xylene-induced mouse ear swelling, and its activity of inhibiting rat thrombosis. The invention belongs to the field of biomedicine. Background technique [0002] Malignant tumors are a serious threat to human health. The mortality rate of malignant tumors is second only to cardiovascular and cerebrovascular diseases, ranking second among all diseases. Most patients with malignant tumors are accompanied by metastasis, inflammation and thrombus. Cancer metastasis, inflammation and thrombus make tumor patients face worse prognosis. Inventing drugs wi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/09C07K1/06C07K1/02A61K38/06A61P35/00A61P35/04A61P29/00
CPCY02P20/55
Inventor 彭师奇赵明赵立春胡西
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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