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Trp-Trp-Trp decapeptide modified beta-carboline, and preparation, nanometer structure, activity and application thereof

A carboline and reaction technology, applied in its anti-tumor cell adhesion, invasion and migration effect, the application in the preparation of anti-tumor cell adhesion, invasion and migration drugs, and the preparation of anti-tumor drugs, which can solve the problem of not getting anti-tumor and anti-tumor drugs. Anti-tumor cell migration, adhesion, invasion and metastasis of compounds and other issues

Inactive Publication Date: 2016-01-27
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 inventors have spent a lot of research effort and screened hundreds of compounds, they have not obtained compounds that have both anti-tumor and anti-tumor cell migration, adhesion, invasion and metastasis effects

Method used

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  • Trp-Trp-Trp decapeptide modified beta-carboline, and preparation, nanometer structure, activity and application thereof
  • Trp-Trp-Trp decapeptide modified beta-carboline, and preparation, nanometer structure, activity and application thereof
  • Trp-Trp-Trp decapeptide modified beta-carboline, and preparation, nanometer structure, 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 20.40g (100mmol) of L-tryptophan which has been weighed. Stir at room temperature for 48 hours, monitor the reaction by TLC, stop the reaction when the raw material point disappears, concentrate under reduced pressure to remove the solvent, add 30 mL of methanol, mix well, 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 standing, and a colorless solid was precipitated. After drying, it was recrystallize...

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 ) selenium dioxide was added to a 250mL eggplant bottle, 100mL of dioxane was added to dissolve, placed in an oil bath and heated to 75°C, and reacted for 10h, and the reaction was terminated after the disappearance of the raw material point as monitored by TLC. 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 relates to Trp-Trp-Trp decapeptide modified beta-carboline, discloses a preparation method and the nanometer structure of beta-carboline, relates to the in-vivo and in-vitro antitumor effects of beta-carboline, and relates to effects of beta-carboline to resist tumor cell adhesion invasion and migration. Therefore, the invention discloses application of Trp-Trp-Trp decapeptide modified beta-carboline to prepare antitumor medicines and prepare medicines resisting tumor cell adhesion invasion and migration. The invention belongs to the field of biological medicine.

Description

technical field [0001] The present invention relates to 1-(4-isopropylphenyl)-β-carboline-3-formyl-Trp-Trp-Trp-Leu-Pro-Asn-Ile-Ser-Lys-Pro. It relates to its preparation method, its nanostructure, its in vivo and in vitro anti-tumor effects, and its anti-tumor cell adhesion, invasion, and migration effects. Therefore, the present invention relates to its application in the preparation of anti-tumor drugs, anti-tumor cell adhesion, invasion and migration drugs. The invention belongs to the field of biomedicine. technical background [0002] Malignant tumors seriously threaten human health. In addition to the poor prognosis of cancer patients, the inflammation and metastasis of malignant tumors further worsen the prognosis of patients. For example, more than 90% of malignant tumor patients died of tumor metastasis. [0003] Since the existing anti-tumor drugs do not have anti-tumor cell migration, adhesion and invasion effects, the curative effect is not ideal. It is an u...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/107C07K1/06A61K38/08A61P35/00B82Y30/00
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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