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RGD tetrapeptide-modified beta-carboline, preparation, activity and application thereof

A carboline, reaction technology, applied in the field of nanostructures and applications, can solve the problem of not getting anti-tumor, anti-inflammatory, anti-thrombotic and anti-tumor cell adhesion, migration and infiltration compounds and other problems

Inactive Publication Date: 2016-01-27
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the inventors have paid a lot of research effort and screened hundreds of compounds, they have not obtained compounds with anti-tumor, anti-inflammation, anti-thrombotic and anti-tumor cell adhesion migration and infiltration effects

Method used

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  • RGD tetrapeptide-modified beta-carboline, preparation, activity and application thereof
  • RGD tetrapeptide-modified beta-carboline, preparation, activity and application thereof
  • RGD tetrapeptide-modified beta-carboline, preparation, activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Preparation of methyl 5-formylsalicylate

[0032] Weigh 1.660g (10.0mmol) of 5-formylsalicylic acid in a microwave reactor, add 25mL methanol and 1mL concentrated H 2 SO 4 , React in a microwave reactor at 90°C for 2 hours, monitor by TLC until the spots of the raw materials disappear, stop the reaction and cool to room temperature, transfer the reaction solution to a 100 mL eggplant-shaped flask, adjust the pH to 7-8 with concentrated ammonia, and start the reaction After the solution was concentrated to dryness under reduced pressure, a large amount of ethyl acetate was added to dissolve it, and the ethyl acetate layer was successively washed 3 , Washed with saturated NaCl three times, and then use anhydrous Na 2 SO 4 After drying for 2 hours, filtering, and concentrating under reduced pressure to dryness, crystals precipitate out after standing overnight at room temperature to obtain 1.635 g (90.8%) of the target compound as light yellow needle-like crystals. E...

Embodiment 2

[0033] Example 2 Preparation of L-tryptophan benzyl ester

[0034] Weigh 15.0g (44.4mmol) of polyphosphoric acid in a 500mL eggplant-shaped flask, add 80mL of benzyl alcohol, and dissolve it in an oil bath at 50℃. After the solution temperature rises to 75℃, weigh 10g (49.0mmol)L -Tryptophan was added and reacted at 75°C for 48 hours, monitored by TLC until the raw material spots disappeared. After stopping the reaction and cooling down, pour 400 mL of anhydrous ether into the reaction flask under ice bath stirring. At this time, a white solid precipitated out. Stir After overnight filtration, the white solid was suspended in 200 mL of ethyl acetate and 10 mL of water. The pH of the solution was adjusted to about 8 with triethylamine. The solution became clear. Let it stand for liquid separation. The separated ester layer was successively used with saturated NaHCO 3 , Saturated NaCl each wash three times, ethyl acetate layer with anhydrous Na 2 SO 4 Dry for 2h, filter, and concent...

Embodiment 3

[0035] Example 3 Preparation of 1-(4-hydroxy-3-methoxycarbonylphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (1)

[0036] Add 100mLCH to a 250mL eggplant-shaped bottle 2 Cl 2 And 10mLTFA, stir evenly, weigh 11.76g (40.0mmol) L-tryptophan benzyl ester and 7.92g (44.0mmol) 5-formylsalicylic acid methyl ester, add it, the reaction solution turns reddish after a few minutes, After 2 days, the reaction solution turned black. Under ice bath stirring, concentrated ammonia water was slowly added dropwise to adjust the pH value of the reaction solution to 8. The reaction solution was allowed to stand for liquid separation to separate CH 2 Cl 2 Saturated NaHCO 3 , Wash three times each with saturated NaCl, CH 2 Cl 2 Anhydrous Na for layer 2 SO 4 Dry for 2h, filter, and concentrate to dryness under reduced pressure to obtain 14.59g (80%) of the target compound as a yellow solid. ESI-MS(m / e): 457[M+H] + .

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Abstract

The invention discloses 1-(4-hydroxy-3-methoxycarbonylphenyl)-beta-carboline-3-formyl-RGD tetrapeptide with a structure as shown in the formula. The invention also discloses a preparation method of the compound, a nano-structure of the compound, an anti-tumor effect of the compound, an effect of the compound in inhibiting adhesion, invasion and migration of tumor cells, further discloses anti-inflammatory and antithrombotic effects of the compound and expounds an application of the compound in medical science.

Description

Technical field [0001] The present invention relates to 1-(4-hydroxy-3-methoxycarbonylphenyl)-β-carboline-3-formyl-Arg-Gly-Asp-Ser, 1-(4-hydroxy-3-methoxycarbonylbenzene Group)-β-carboline-3-formyl-Arg-Gly-Asp-Phe and 1-(4-hydroxy-3-methoxycarbonylphenyl)-β-carboline-3-formyl-Arg-Gly -Asp-Val, related to their preparation method, related to their nanostructure and application. The invention belongs to the field of biomedicine. technical background [0002] Malignant tumors seriously threaten human health. In addition to the poor prognosis of tumor patients, the inflammation, thrombosis and metastasis of malignant tumors further worsen the prognosis of patients. For example, more than 90% of patients with malignant tumors die from tumor metastasis. Tumor metastasis depends on four factors: 1) microthrombi formed on the surface of tumor cells to escape macrophages and migrate to the distal end through the blood circulation; 2) tumor cells that migrate to the distal end adhere t...

Claims

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Application Information

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IPC IPC(8): C07K7/06A61K38/08A61P35/00A61P35/04A61P29/00A61P7/02B82Y30/00
Inventor 赵明彭师奇王玉记吴建辉李珊
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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