RGD tetrapeptide-modified β-carbolinoyl-tryptophan, its preparation, nanostructure, activity and application

A technology of carbonoyl and tryptophan, applied to RGD tetrapeptide modified β-carbolyl-tryptophan, which can solve the problem of not getting anti-tumor and anti-tumor metastasis compounds

Inactive Publication Date: 2019-09-13
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the inventor has spent a lot of research effort and screened hundreds of compounds, no compound with both anti-tumor and anti-metastasis effects has been obtained

Method used

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  • RGD tetrapeptide-modified β-carbolinoyl-tryptophan, its preparation, nanostructure, activity and application
  • RGD tetrapeptide-modified β-carbolinoyl-tryptophan, its preparation, nanostructure, activity and application
  • RGD tetrapeptide-modified β-carbolinoyl-tryptophan, its preparation, nanostructure, activity and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 Preparation of 1-acetyl-β-carboline-3-carboxylic acid methyl ester

[0022] Weigh 5g of L-Trp-OMe into a 100ml eggplant bottle, add 10ml of 37°C warm water and stir to dissolve, then add 3.3g of 1,3-dihydroxyacetone. React at room temperature for 36 h, centrifuge, discard the aqueous layer, and dry the precipitate to obtain 1 g (yield 20%) of the title compound as a brown solid, ready to use. ESI-MS(m / e): 257[M+H] + .

Embodiment 2

[0023] Example 2 Preparation of 1-acetyl-β-carboline-3-carboxylic acid

[0024] Weigh 5g of methyl 1-acetyl-β-carboline-3-carboxylate into a 250ml eggplant bottle, add dioxane to dissolve, slowly add 2N NaOH aqueous solution in an ice bath to adjust the pH to 12, and react for 13h. The reaction solution was saturated KHSO 4 The aqueous solution was adjusted to pH 8 and concentrated under reduced pressure. The residue was washed with saturated KHSO 4 The pH was adjusted to 2, the organic layer was extracted 3 times with ethyl acetate and concentrated under reduced pressure to afford 4 g (80%) of the title compound as a tan solid. ESI-MS (m / e): 241 [M-H] - .

Embodiment 3

[0025] Example 3 Preparation of 1-acetyl-β-carbolinyl-tryptophan benzyl ester

[0026] Weigh 2g of 1-acetyl-β-carboline-3-carboxylic acid, dissolve it in 10ml of anhydrous THF, add 2g of DCC and 1.2g of HOBt under ice cooling, and stir for 30min to obtain solution A. 3.2 g of Trp-OBzl was dissolved in 15 ml of anhydrous THF, and N-methylmorpholine was slowly added to adjust the pH of the solution to 9 to obtain solution B. Slowly add solution B into solution A under ice-cooling, adjust the pH to 9 with N-methylmorpholine, react for 12 hours, TLC shows that the raw material disappears (petroleum ether: acetone = 4:1). The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, the residue was extracted 3 times with ethyl acetate, and concentrated under reduced pressure, the obtained 4.38g syrup product was purified by dry column chromatography of petroleum ether / acetone system (petroleum ether / acetone=4 / 1 ) afforded 2 g (46%) of the title compound ...

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Abstract

The invention discloses RGD tetrapeptide modified beta-carboline acyl-tryptophan and discloses a preparation method, a nanostructure, an effect of resisting tumor cell adhesion, an effect of resisting tumor cell invasion, an effect of resisting tumor cell migration, an anti-rumor effect and an effect of inhibiting tumor transfer to lung. The invention discloses application thereof in medicine. The formula is as shown in the specification.

Description

technical field [0001] The present invention relates to RGDV / F / S modified 1-acetyl-beta-carbolinyl-tryptophan of the following structure, RGDV / F / S in the structure represents Arg-Gly-Asp-Val (RGDV), Arg- Gly-Asp-Phe (RGDF) and Arg-Gly-Asp-Ser (RGDS) three tetrapeptides, related to their preparation method, related to their nanostructure, related to their anti-tumor cell adhesion, related to their anti-tumor The role of cell invasion involves their role in anti-tumor cell migration, their anti-tumor effect, and further their role in inhibiting tumor metastasis to the lung. The present invention thus relates to their use in medicine. The invention belongs to the field of biomedicine. [0002] Background technique [0003] Malignant tumors seriously threaten human health. In addition to the poor prognosis of cancer patients, the inflammation, thrombus and metastasis of malignant tumors further worsen the prognosis of patients. For example, more than 90% of malignant tumo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06C07K1/06C07K1/02B82Y30/00A61K38/08A61P35/00A61P35/04
Inventor 彭师奇赵明王玉记吴建辉于翔
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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