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Curcumin modified by yigsr, its preparation, biological activity and application

A technology of curcumin and base curcumin, applied to YIGSR modified curcumin, its preparation, biological activity and application fields

Active Publication Date: 2019-07-26
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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  • Curcumin modified by yigsr, its preparation, biological activity and application
  • Curcumin modified by yigsr, its preparation, biological activity and application
  • Curcumin modified by yigsr, 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 30mL (100.0mmol) of acetylacetone in 200mL 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, 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 concentra...

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) 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 give 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-hydroxyl-3-methoxyphenyl)-3,5-dioxohepta-1,6-diene-1 -yl]-2-methoxyphenoxy}ethyl acetate

[0032] Dissolve 10g (42.7mmol) (E)-6-(4-hydroxy-3-methoxyphenyl)hex-5-ene-2,4-dione in 100mL 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 analyzed, the precipitate was filtered off. The filtrate was washed three times with saturated potassium bisulfate and satura...

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Abstract

The invention discloses a curcumin and oligopeptide Tyr-Ile-Gly-Ser-Arg conjugate of the following formula, a preparation method thereof, its activity of inhibiting tumor cell proliferation, its effect of inhibiting migration and invasion of A549 cells, its activity of inhibiting S180 tumor-bearing mice tumor weight increase, its activity of inhibiting Lewis lung cancer metastasis, its activity of inhibiting xylene induced mice ear swelling, and further discloses its activity of inhibiting rat thrombosis.

Description

technical field [0001] The present invention relates to a conjugate of curcumin and oligopeptide Lys(The)Tyr-Ile-Gly-Ser-Arg, to its preparation method, to its anti-tumor cell proliferation activity, and to its inhibition of A549 cell migration and invasion It involves its activity of inhibiting the tumor body weight gain of S180 tumor-bearing mice, its activity of inhibiting the metastasis of Lewis lung cancer, its activity of inhibiting xylene-induced ear swelling in mice, and its activity of inhibiting thrombosis in rats. active. 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 prog...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06C07K1/06A61K38/08A61P35/00A61P35/04A61P29/00
CPCY02P20/55
Inventor 彭师奇赵明王渊璟胡西
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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