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Trp-Trp-Trp pentapeptide modified beta-carboline, preparation therefor, nanostructure, activity and application thereof

A carboline and reaction technology, which is applied in the field of anti-tumor effect in vitro and in vivo, and the preparation of anti-tumor drugs, can solve the problems of not getting anti-tumor and anti-tumor metastatic compounds and the like

Inactive Publication Date: 2016-01-06
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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  • Trp-Trp-Trp pentapeptide modified beta-carboline, preparation therefor, nanostructure, activity and application thereof
  • Trp-Trp-Trp pentapeptide modified beta-carboline, preparation therefor, nanostructure, activity and application thereof
  • Trp-Trp-Trp pentapeptide modified beta-carboline, preparation therefor, nanostructure, activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1 prepares L-tryptophan methyl ester hydrochloride (1)

[0030] Measure 100mL of methanol into a 250mL eggplant bottle, add 25.5mL of SOCl to the eggplant bottle under ice bath 2 , Plug the drying tube, and after stirring for 30min, add 20.400g (100mmol) of L-tryptophan which has been weighed. Stir at room temperature for 48 h, monitor the reaction by TLC, terminate the reaction when the raw material point disappears, concentrate under reduced pressure to remove the solvent, add 30 mL of methanol, mix, concentrate again under reduced pressure to remove the solvent, and repeat the operation twice. Finally, 50 mL of diethyl ether was added, suspended for 30 min, filtered, and the filter cake was dried and weighed to obtain 22.98 g (90.2%) of the target compound as a gray powder. ESI-MS(m / e): 219[M+H] + .

Embodiment 2

[0031] Example 2 Preparation of (3S)-1-(4-isopropylphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (2)

[0032] Measure 100mL of distilled water into a 250mL eggplant bottle, add 10mL of trifluoroacetic acid under ice bath, stir for 5min, add 20.320g (80mmol) of L-tryptophan methyl ester hydrochloride, stir until dissolved, add 10.672g (88mmol) of iso Propylbenzaldehyde was stirred at room temperature for 24 hours, TLC showed that the raw material point disappeared, and the reaction was terminated. The reactant was filtered under reduced pressure, the filter cake was dissolved with ethyl acetate, and saturated NaHCO 3 The aqueous solution was adjusted to pH 8. The ethyl acetate layer was extracted and washed 3 times with saturated NaCl aqueous solution, and then washed with 5% KHSO 4 The aqueous solution was extracted and washed once, and the ethyl acetate layer was left to stand, and a colorless solid was precipitated. After drying, it was recrystalliz...

Embodiment 3

[0033] Example 3 Preparation of 1-(4-isopropylphenyl)-β-carboline-3-carboxylic acid methyl ester (3)

[0034]Weigh 13.92g (40mmol) (3S)-1-(4-isopropylphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester and 5.772g (52mmol) Add selenium dioxide into a 250mL eggplant bottle, add 100mL dioxane to dissolve, place in an oil bath and heat to 75°C, react for 10h, and stop the reaction after TLC monitors that the raw material point disappears. The reactant was cooled to room temperature, filtered under reduced pressure, and the filtrate was concentrated to dryness under reduced pressure to obtain 12.384 g (95%) of the title compound as a yellow solid. ESI-MS(m / e): 345.2[M+H] + .

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Abstract

The invention discloses 1-(4-isopropyl propyl)-beta-carboline-3-formyl-Trp-Trp-Trp-Lys-Glu structured as follows, a preparation method therefor, a nanostructure thereof, antitumor action thereof, action thereof in resisting adhesion and invasion and migration of tumor cells, and illustrates application thereof in medical science. The formula is shown in the description.

Description

technical field [0001] The present invention relates to 1-(4-isopropylphenyl)-β-carboline-3-formyl-Trp-Trp-Trp-Lys-Glu and its preparation method, its nanostructure, and its in vivo and in vitro The anti-tumor effect involves its anti-tumor cell adhesion, invasion and migration. Therefore, the present invention relates to its application in the preparation of anti-tumor drugs and anti-tumor cell adhesion, invasion and migration drugs. technical background [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) tumor cells that migrate to the dist...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/02B82Y30/00A61K38/08A61P35/00
Inventor 赵明彭师奇王玉记吴建辉王程荣
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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