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Cyclic dipeptide used for wound healing

A wound repairing and cyclic dipeptide technology, which is applied in the biomedical field, can solve problems such as the application of cyclic dipeptide not seen before, and achieve the effect of good wound repairing effect, obvious treatment effect and shallow scar.

Inactive Publication Date: 2016-06-01
SICHUAN GOODDOCTOR PHARMA GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are no reports on the application of cyclic dipeptides synthesized from alanine, glycine, and leucine in wound repair

Method used

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  • Cyclic dipeptide used for wound healing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1 The preparation method of the cyclic dipeptide (cyclopropyl-glycodipeptide) described in the present invention

[0016] Main pharmaceutical reagents: glycine, alanine protected by Boc amino group

[0017] Process for preparing cyclic ala-gly dipeptide:

[0018] (1) Preparation of glycine methyl ester hydrochloride: Add 10 g of glycine to a mixture of an appropriate amount of methanol and thionyl chloride, and stir at room temperature for 20 h. The completion of the reaction was tracked by TLC, and the solvent was spin-dried under reduced pressure to obtain 13.91 g of glycine methyl ester hydrochloride.

[0019] (2) Neutralization and condensation reaction: Add glycine methyl ester hydrochloride obtained in step (1), 20 g of alanine protected by Boc amino group, 20 ml of pyridine, DMAP (4-dimethylaminopyridine) in 100 ml of anhydrous tetrahydrofuran ), after all mixing, under the protection of argon, add the (Boc) of anhydrous tetrahydrofuran 2 O, stirred...

Embodiment 2

[0022] Embodiment 2 The preparation method of the cyclic dipeptide (cyclopropan-leupeptide) described in the present invention

[0023] Main pharmaceutical reagents: leucine, alanine protected by Boc amino group

[0024] Process for preparing cyclic ala-leu dipeptide:

[0025] (1) Preparation of leucine methyl ester hydrochloride: add 10 g of leucine to a mixture of an appropriate amount of methanol and thionyl chloride, and stir at room temperature for 24 hours. TLC traced the completion of the reaction, and the solvent was spin-dried under reduced pressure to obtain 14.34 g of leucine methyl ester hydrochloride.

[0026] (2) Neutralization and condensation reaction: add leucine methyl ester hydrochloride obtained in step (1), 20 g of alanine protected by Boc amino group, 20 ml of pyridine, DMAP (4-dimethyl aminopyridine), after all mixing, add anhydrous tetrahydrofuran (Boc) under the protection of argon 2 O, stirred at room temperature for 12 hours. The completion of th...

Embodiment 3

[0030] Example 3 Application of the cyclic dipeptide of the present invention in ulcers

[0031] 1. Experimental materials

[0032] 1.1 Samples: Samples prepared according to Example 1-2: Cyclopropane-Glycine dipeptide (ala-gly), Cyclopropane-Leu dipeptide (ala-leu)

[0033] 1.2 Experimental animals: KM mice, 18-22 g, 120, half male and half male. SD rats, 200-220g, 180, half male and half male.

[0034] 1.3 Experimental reagents: ranitidine hydrochloride capsules, Daxi (aluminum magnesium carbonate tablets)

[0035] 2. Method for evaluating the protective function of samples on gastric ulcer mucosa

[0036] 2.1 Absolute ethanol-induced gastric mucosal injury model test in mice

[0037] 40 KM mice were randomly divided into groups according to sex and body weight (see Table 1 for details), and each group was given the corresponding drug. The mice in each group were given the drug for 10 consecutive days. After 3 hours of the last administration of the mice in each group, ...

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Abstract

The invention provides cyclic dipeptide used for wound healing. The cyclic dipeptide is one of ala-gly and ala-leu. The cyclic dipeptide has remarkable therapeutic effect on wound. Inhibition rate of acute and chronic gastric ulcer is high, wound healing speed of burns and scalds is fast, and scars are shallow.

Description

technical field [0001] The invention belongs to the field of biomedicine, in particular to a cyclic dipeptide used for wound repair. Background technique [0002] 2,5-diketopiperazines (DKP), also known as cyclic dipeptides. This type of compound is formed by the condensation and cyclization of two amino acids through peptide bonds. It is the smallest cyclic peptide compound in nature and widely exists in nature. It is found in humans, vertebrates, invertebrates, bacteria and fungi. There are discoveries. 2,5-diketopiperazines have two hydrogen bond donors and two hydrogen bond acceptors, because hydrogen bonds are one of the main ways for receptors to interact with drugs, so the six-membered ring of DKP is important in medicinal chemistry. DKP is an important pharmacophore, and many active natural products have been found to contain the six-membered ring structure of DKP, which has a variety of biological activities such as broad-spectrum antibacterial activity, antitumor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/12C07K1/16C07K1/06A61P17/02A61P1/04
Inventor 耿福能
Owner SICHUAN GOODDOCTOR PHARMA GRP
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