Heterocyclic carboxylic acid-modified anti-tumor oligopeptides and their synthesis, anti-tumor effects and application

A heterocyclic carboxylic acid, anti-tumor technology, applied in anti-tumor drugs, peptide/protein components, medical preparations containing active ingredients, etc., can solve the problems of unsatisfactory curative effect and high toxicity

Inactive Publication Date: 2013-12-18
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the unsatisfactory curative effect and high toxicity of anti-tumor drugs in clinical application,

Method used

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  • Heterocyclic carboxylic acid-modified anti-tumor oligopeptides and their synthesis, anti-tumor effects and application
  • Heterocyclic carboxylic acid-modified anti-tumor oligopeptides and their synthesis, anti-tumor effects and application
  • Heterocyclic carboxylic acid-modified anti-tumor oligopeptides and their synthesis, anti-tumor effects and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1 Preparation of Pro-OBzl

[0054] Place 50 mL of benzyl alcohol in a reaction flask cooled in an ice-salt bath and stir vigorously, 20 mL of SOCl 2 Slowly add it dropwise into the reaction flask containing methanol through a constant pressure separatory funnel, remove the ice-salt bath after stirring for 30 minutes, add 5.0g (43.6mmol) L-Pro to the reaction solution, react at room temperature for 48 hours, TLC board monitoring No When the starting point was reached, the reaction was completed. The solution was concentrated to dryness under reduced pressure, and the residue was dissolved in 8 mL of methanol, and then concentrated to dryness under reduced pressure. This operation was repeated at least 2 times. The residue was added with anhydrous diethyl ether, and the diethyl ether was fully contacted with the residue as far as possible, and then concentrated to dryness under reduced pressure. This operation was repeated 2 times. The residue was recrystallize...

Embodiment 2

[0055] Example 2 Preparation of Boc-Pro

[0056] Put 5.75g (50mmol) of L-Pro in a 250mL eggplant-shaped bottle, add 1mL of water to dissolve, and slowly add 25mL of NaOH aqueous solution (2N) dropwise under stirring in an ice bath to obtain solution (I). 13.08g (60mmol) (Boc) 2 O was placed in a 50mL small beaker, and 25mL of dioxane was added to dissolve to obtain solution (II). The solution (II) was added dropwise to the solution (I) under stirring in an ice bath, NaOH aqueous solution (2N) was slowly added dropwise under an ice bath to adjust the pH to 9, and the mixture was stirred under an ice bath. After 30 minutes, the pH of the reaction mixture was checked and adjusted to maintain a pH of 9 with aqueous NaOH (2N). Continue the reaction, adjust the pH value to 9 with NaOH aqueous solution (2N) at any time, and pump out the gas generated by the reaction, and monitor the reaction progress by TLC. The developing system is dichloromethane-methanol (20:1). About 48 hours...

Embodiment 3

[0057] Example 3 Preparation of Boc-Lys(Z)

[0058] Add 6.08g (24.34mmol) of anhydrous copper sulfate to the three-necked flask, add 10mL of distilled water, put it into an oil bath and heat to 100°C, reflux, and dissolve the anhydrous copper sulfate. Then add 5.34g L-Lys into the three-necked flask, and reflux in the oil bath for 2 hours. After the reaction, sodium bicarbonate was added under an ice bath to adjust the pH to 8, and then 10 g (40.2 mmol) of Bzl-OSu was added to react at room temperature for 8 hours. After the reaction, the reaction solution was filtered, and the filter cake was washed once with distilled water, acetone, and ether respectively. Then put the filter cake back into the three-necked flask, add EDTA and stir for 4 hours, filter, repeat the stirring, filter, and dry to obtain 20 g of L-Lys(Z), which is a colorless solid. The obtained 20g (71.4mmol) L-Lys (Z) and 18.69g (85.7mmol) (Boc) 2 O was reacted to afford 16.56 g (61%) of the title compound a...

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Abstract

The invention discloses heterocyclic carboxylic acid-modified anti-tumor oligopeptides. The heterocyclic carboxylic acid-modified anti-tumor oligopeptides have a general formula I. In the general formula I, RCO represents 1,2,3,4-tetrahydro-beta-carboline-3-formyl, beta-carboline-3-formyl, 1,2,3,4-tetrahydroisoquinol-3-formyl, isoquinol-3-formyl, or 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-formyl. The invention also discloses a preparation method of the heterocyclic carboxylic acid-modified anti-tumor oligopeptides, and in-vitro tumor cell proliferation-resistant activity of the heterocyclic carboxylic acid-modified anti-tumor oligopeptides. The invention further discloses heterocyclic carboxylic acid-modified anti-tumor oligopeptide activity of inhibiting weight gain of a tumor in a S180 tumor-loading mice, and application of the heterocyclic carboxylic acid-modified anti-tumor oligopeptides in preparation of anti-tumor drugs. The general formula I is RCO-Leu-Pro-Asn-Ile-Ser-Lys-Pro.

Description

technical field [0001] The present invention relates to a heterocyclic carboxylic acid modified anti-tumor oligopeptide of general formula I, wherein RCO is 1,2,3,4-tetrahydro-β-carboline-3-formyl, β-carboline-3 -formyl, 1,2,3,4-tetrahydroisoquinoline-3-formyl, isoquinoline-3-formyl and 1-methyl-1,2,3,4-tetrahydro-β- Carboline-3-formyl, relating to their preparation method, relating to their anti-tumor cell proliferation activity in vitro, further relating to their activity of inhibiting tumor body weight gain in S180 tumor-bearing mice, and clarifying their role in the preparation of anti-tumor drugs application. The invention belongs to the field of biomedicine. [0002] RCO-Leu-Pro-Asn-Ile-Ser-Lys-Pro I Background technique [0003] Malignant tumor is a common disease that seriously threatens human health. The mortality rate of human beings caused by malignant tumors ranks second in all disease mortality, second only to cardiovascular and cerebrovascular diseases. Tum...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/06C07K1/02A61K38/08A61P35/00
CPCY02P20/55
Inventor 彭师奇赵明王玉记吴建辉甘太平
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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