LDV-modified 1-acetyl-β-carbolinoyl-tryptophan, its preparation, nanostructure, activity and application

A technology of acetyl and carbolyl, applied to LDV modified 1-acetyl-β-carbolyl-tryptophan, which can solve the problems of anti-tumor and anti-tumor adhesion, invasion and migration 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 anti-tumor and anti-tumor adhesion, invasion and migration effects has been obtained

Method used

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  • LDV-modified 1-acetyl-β-carbolinoyl-tryptophan, its preparation, nanostructure, activity and application
  • LDV-modified 1-acetyl-β-carbolinoyl-tryptophan, its preparation, nanostructure, activity and application
  • LDV-modified 1-acetyl-β-carbolinoyl-tryptophan, its preparation, nanostructure, activity and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1 Preparation of 1-acetyl-β-carboline-3-carboxylic acid methyl ester

[0019] Weigh 5g of L-Trp-OMe into a 100ml eggplant bottle, add 10ml of 37℃ warm water and stir to dissolve, add 3.3g of 1,3-dihydroxyacetone. React at room temperature for 36 hours, centrifuge, discard the water layer, and dry the precipitate to obtain 1 g (yield 20%) of the title compound as a brown solid, ready for use. ESI-MS(m / e): 257[M+H] + .

Embodiment 2

[0020] Example 2 Preparation of 1-acetyl-β-carboline-3-carboxylic acid

[0021] Weigh 5g of 1-acetyl-β-carboline-3-carboxylic acid methyl ester into a 250ml eggplant bottle, add dioxane to dissolve it, slowly add 2N NaOH aqueous solution in an ice bath to adjust pH 12, and react for 13h. Saturated KHSO for reaction liquid 4 The aqueous solution was adjusted to pH 8, and concentrated under reduced pressure. Saturated KHSO for residue 4 The pH was adjusted to 2, the organic layer was extracted 3 times with ethyl acetate, and concentrated under reduced pressure to obtain 4 g (80%) of the title compound as a tan solid. ESI-MS(m / e): 241[M-H] - .

Embodiment 3

[0022] Example 3 Preparation of 1-acetyl-β-carboline-tryptophan benzyl ester

[0023] Weigh 2g of 1-acetyl-β-carboline-3-carboxylic acid, dissolve it with 10ml of anhydrous THF, add 2g of DCC, 1.2g of HOBt under ice bath, and stir for 30min to obtain solution A. 3.2g Trp-OBzl was dissolved in 15ml anhydrous THF, and N-methylmorpholine was slowly added to adjust the pH of the solution to 9 to obtain solution B. Slowly add liquid B into liquid A under ice bath, adjust pH 9 with N-methylmorpholine, react for 12 hours, TLC shows that the raw material disappeared (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 4.38 g syrupy product was purified by dry column chromatography with petroleum ether / acetone system (petroleum ether / acetone=4 / 1 ) 2g (46%) of the title compound was obtained as a yellow solid in yie...

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Abstract

The invention discloses Leu-Asp-Val (LDV) modified 1-acetyl-beta-carboline acyl-tryptophan with a structure shown in the specification as well as a preparation method and nanostructure thereof. The invention discloses tumor cell adhesion, tumor cell invasion, tumor cell migration and tumor resistant effects of LDV modified 1-acetyl-beta-carboline acyl-tryptophan and further discloses an inhibiting effect of LDV modified 1-acetyl-beta-carboline acyl-tryptophan on tumor metastasis to the lung. Therefore, the invention discloses applications of LDV modified 1-acetyl-beta-carboline acyl-tryptophan, the preparation method and the nanostructure to medicines. The formula is as shown in the specification.

Description

Technical field [0001] The present invention relates to Leu-Asp-Val modified 1-acetyl-β-carboline-tryptophan, its preparation method, its nanostructure, its anti-tumor cell adhesion effect, and its anti-tumor cell adhesion effect. The role of tumor cell invasion involves its anti-tumor cell migration, its anti-tumor effect, and its anti-tumor effect, which further relates to its inhibiting tumor metastasis to the lung. Therefore, the present invention relates to their application in medicine. The invention belongs to the field of biomedicine. Background technique [0002] People have extracted β-carboline compounds from natural plants, which are a class of indole alkaloids. It has a variety of biological activities and has clear anti-tumor activity. It is used for the treatment of lung cancer, stomach cancer, liver cancer, colon cancer, breast cancer and other cancers. However, β-carboline compounds, as traditional cytotoxic compounds, have poor selectivity for tumor cells. ...

Claims

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Application Information

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