KE modified 1-acetyl-beta-carboline acyl-tryptophan and preparation, nanostructure, activity and application thereof

An acetyl and carboline acyl technology is applied in the field of inhibiting tumor metastasis to the lung. In the field of 1-acetyl-β-carboline acyl-tryptophan, it can solve the problem of not obtaining anti-tumor and anti-tumor metastatic compounds, etc. question

Inactive Publication Date: 2016-08-24
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • KE modified 1-acetyl-beta-carboline acyl-tryptophan and preparation, nanostructure, activity and application thereof
  • KE modified 1-acetyl-beta-carboline acyl-tryptophan and preparation, nanostructure, activity and application thereof
  • KE modified 1-acetyl-beta-carboline acyl-tryptophan and preparation, nanostructure, activity and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

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

[0021] 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

[0022] Example 2 Preparation of 1-acetyl-β-carboline-3-carboxylic acid

[0023] 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

[0024] Example 3 Preparation of 1-ethyl-acyl-β-carbolinyl-tryptophan benzyl ester

[0025] 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 compo...

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Abstract

The invention discloses Lys-Glu(KE) modified 1-acetyl-beta-carboline acyl-tryptophan with a structure shown in the specification 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 of Lys-Glu(KE) modified 1-acetyl-beta-carboline acyl-tryptophan in medicines.

Description

technical field [0001] The present invention relates to Lys-Glu modified 1-acetyl-β-carbolinyl-tryptophan, its preparation method, its nanostructure, its anti-tumor cell adhesion effect, and its anti-tumor cell The role of invasion involves its role in anti-tumor cell migration, its anti-tumor effect, and its role in inhibiting tumor metastasis to the lung. The present invention thus relates to its use in medicine. The invention belongs to the field of biomedicine. Background technique [0002] 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 tumor patients died of tumor metastasis. Tumor metastasis depends on four factors: 1) microthrombosis forms on the surface of tumor cells, escapes macrophage phagocytosis, and migrates to the distal end through blood circulation; 2) tumo...

Claims

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Application Information

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IPC IPC(8): C07K5/113C07K1/06C07K1/02B82Y30/00A61K38/07A61P35/00A61P35/04
Inventor 彭师奇赵明王玉记吴建辉于翔
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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