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Conjugates of beta-carboline-3-carboxylic acid and oligopeptides, preparation, nano structure, and application thereof as antitumor agent

A conjugate, arg-gly-asp-val technology, is applied in the field of conjugation of β-carboline-3-carboxylic acid and 6 kinds of oligopeptides, which can solve the problems of toxic reaction and inhibition of tumor cell proliferation

Inactive Publication Date: 2014-12-17
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This form of cuttings, in addition to causing inhibition of tumor cell proliferation, can also cause severe toxic reactions

Method used

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  • Conjugates of beta-carboline-3-carboxylic acid and oligopeptides, preparation, nano structure, and application thereof as antitumor agent
  • Conjugates of beta-carboline-3-carboxylic acid and oligopeptides, preparation, nano structure, and application thereof as antitumor agent
  • Conjugates of beta-carboline-3-carboxylic acid and oligopeptides, preparation, nano structure, and application thereof as antitumor agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1 prepares 3S-1,2,3,4-tetrahydro-β-carboline 3-carboxylic acid (1)

[0027] Slowly drop 0.1 mL of concentrated sulfuric acid into 200 mL of distilled water with stirring at room temperature. Add 2.520 g (12.4 mmol) of L-tryptophan to the obtained dilute sulfuric acid solution and ultrasonically shake until the L-tryptophan is completely dissolved. To the resulting solution was added 5 mL of 37% formaldehyde solution. The resulting colorless solution was stirred at room temperature for 6 hours, monitored by thin layer chromatography (dichloromethane:methanol, 3:1) until L-tryptophan disappeared, and the reaction was terminated. Concentrated ammonia water was slowly added dropwise to the reaction solution, adjusted to pH 6, and left to stand for half an hour. Buchner funnel decompressed to filter out the generated precipitate, washed the precipitate with water and acetone repeatedly 3 times, spread the filtered colorless solid on a petri dish, placed it in a ...

Embodiment 2

[0028] Example 2 Preparation of 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (2)

[0029] Slowly add 2.6 mL of thionyl chloride dropwise into 25 mL of methanol under ice-cooling and stirring. After activation for 30 minutes, add 2.16 g (10 mmol) of 3S-1,2,3,4-tetrahydro-β-carboline-3 -Carboxylic acid (1), the resulting colorless solution was stirred at room temperature for 18 hours, monitored by thin layer chromatography (dichloromethane:methanol, 2:1) until the starting point disappeared, and the reaction was terminated. The reaction mixture was concentrated to dryness under reduced pressure, the residue was dissolved in 30 mL of methanol, and the resulting solution was concentrated to dryness under reduced pressure. This operation was repeated once more. The residue was dissolved in 30 mL of ether, and the resulting solution was concentrated to dryness under reduced pressure. This operation was repeated once more. The residue was purified by column chr...

Embodiment 3

[0030] Embodiment 3 prepares β-carboline-3-carboxylic acid methyl ester (3)

[0031] Add 2.0g (9.26mmol) 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester to 100mL acetone under ice bath and stirring, slowly add 3.1g (13.89mmol) Potassium manganate powder. The reaction mixture was stirred at room temperature for 12 h, monitored by thin layer chromatography (dichloromethane:methanol, 10:1) until the disappearance of 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylate methyl ester, terminated reaction. Add 100 mL of ethanol and stir for 30 minutes to quench the unreacted potassium permanganate, remove manganese dioxide by filtration under reduced pressure, and concentrate the filtrate to dryness under reduced pressure to obtain a light yellow oil. The resulting mixture was separated by column chromatography (dichloromethane:methanol, 25:1) to afford 1.05 g (54%) of the title compound as a colorless powder. ESI-MS(m / e): 228[M+H] + .

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Abstract

The invention discloses conjugates of beta-carboline-3-carboxylic acid and oligopeptides, preparation, a nano structure, and an application thereof as an antitumor agent. The invention discloses conjugates (8a-f) of beta-carboline-3-carboxylic acid and six oligopeptides, wherein the six oligopeptides are Leu-Pro-Asn-Ile-Ser-Lys-Pro (LPNISKP), Arg-Gly-Asp-Ser (RGDS), Arg-Gly-Asp-Phe (RGDF), Arg-Gly-Asp-Val (RGDV), Leu-Asp-Ser (LDV), and Lys-Glu (KE). The invention discloses a preparation method and nano structure of the conjugates, discloses an inhibition effect of the conjugates on five tumor cell strains namely HL60, HCT-8, HeLa, BEL-7402, and HepG2, and further discloses an inhibition effect on tumor growth of S180 tumor-bearing mice. The experiment results show that the provided conjugates of beta-carboline-3-carboxylic acid and six oligopeptides have an excellent antitumor effect, so that the conjugates is advantageous for being used as an antitumor drug in clinic.

Description

field of invention [0001] The present invention relates to figure 1 Structured β-carboline-3-carboxylic acid conjugates (8a-f) with 6 oligopeptides selected from Leu-Pro-Asn-Ile-Ser-Lys-Pro(LPNISKP), Arg - Gly-Asp-Ser (RGDS), Arg-Gly-Asp-Phe (RGDF), Arg-Gly-Asp-Val (RGDV), Leu-Asp-Val (LDV) and Lys-Glu (KE). methods of their preparation. Involving their nanostructures. It involves their inhibitory effect on the proliferation of five tumor cell lines of HL60, HCT-8, HeLa, BEL-7402, and HepG2, and further involves their inhibitory effect on tumor growth in S180-bearing mice. The results show that the conjugates of β-carboline-3-carboxylic acid and six oligopeptides of the present invention have excellent antitumor effects. Therefore, the conjugates of β-carboline-3-carboxylic acid and six oligopeptides of the present invention have clinical application prospects as antitumor drugs. The invention belongs to the field of biomedicine. Background technique [0002] Malignant...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P35/00A61K31/437A61K47/48C07K5/11C07K7/06C07K5/09
Inventor 赵明彭师奇王玉记吴建辉杨帅
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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