RGDS-modified curcumin and preparation, bioactivity and application thereof

A technology of curcumin and base curcumin, applied in RGDS modified curcumin, its preparation, biological activity and application fields

Active Publication Date: 2017-01-04
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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  • RGDS-modified curcumin and preparation, bioactivity and application thereof
  • RGDS-modified curcumin and preparation, bioactivity and application thereof
  • RGDS-modified curcumin and preparation, bioactivity and application thereof

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 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-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 an...

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Abstract

The invention discloses a conjugate of curcumin and an oligopeptide Arg-Gly-Asp-Ser, a preparation method of the conjugate and the tumor cell proliferation resisting activity, the A549 cell migration and invasion inhibiting effects, the S180 tumor-bearing mouse tumor weight increasing inhibiting activity, the Lewis lung cancer metastasis inhibiting activity, the xylene-induced mouse ear swelling inhibiting activity and the rat thrombus generation inhibiting activity of the conjugate. The conjugate has the following formula (please see the formula in the description).

Description

technical field [0001] The invention relates to a conjugate of curcumin and oligopeptide Arg-Gly-Asp-Ser, to its preparation method, to its anti-tumor cell proliferation activity, to its ability to inhibit the migration and invasion of A549 cells, to its inhibition of The activity of S180 tumor weight gain in tumor-bearing mice relates to its activity of inhibiting the metastasis of Lewis lung cancer, further relates to its activity of inhibiting xylene-induced mouse ear swelling, and further relates to its activity of inhibiting thrombosis in rats. 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K1/06A61K38/08A61P35/00A61P35/04A61P29/00
Inventor 彭师奇赵明宋元博胡西
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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