LDV modified 1-acetyl-beta-carboline acyl-tryptophan as well as preparation method, nanostructure, activities and applications thereof

A technology of acetyl and carbolinyl, which is applied in the field of action, can solve the problems of anti-tumor and anti-tumor adhesion, invasion and migration compounds, etc.

Inactive Publication Date: 2016-08-24
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-beta-carboline acyl-tryptophan as well as preparation method, nanostructure, activities and applications thereof
  • LDV modified 1-acetyl-beta-carboline acyl-tryptophan as well as preparation method, nanostructure, activities and applications thereof
  • LDV modified 1-acetyl-beta-carboline acyl-tryptophan as well as preparation method, nanostructure, activities and applications thereof

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°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

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

[0021] 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

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

[0023] 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 to 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 as...

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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-carbolinyl-tryptophan, to its preparation method, to its nanostructure, to its anti-tumor cell adhesion effect, to its anti-tumor cell adhesion The role of tumor cell invasion involves its anti-tumor cell migration, its anti-tumor effect, and its ability to inhibit tumor metastasis to the lung. The present invention thus relates to their use in medicine. The invention belongs to the field of biomedicine. Background technique [0002] People have extracted β-carboline compounds from natural plants, which is a class of indole alkaloids. It has various biological activities and has clear anti-tumor activity. It is used in the treatment of various cancers such as lung cancer, gastric cancer, liver cancer, colon cancer, and breast cancer. However, β-carboline compounds, as traditional cytotoxic compounds, have poor selectivity for tumor cells. With the in-depth study of genetics and molec...

Claims

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Application Information

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Patent Type & Authority Applications(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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