Trivalent iron porphrin and its derivative-short peptide compound and its synthesis

A technology of derivatives and ferric iron, applied in the direction of peptides, etc., can solve the problems of many purification process steps, difficult artificial synthesis, complex components, etc., and achieve the effect of broad drug development and application prospects, saving raw materials, and high purity.

Inactive Publication Date: 2005-05-04
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the difficulty in artificial synthesis of microperoxidases, numerous steps in the purification process, time-consuming and laborious, low purity and complex components, and easy degradation in the body, their application is limited.

Method used

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  • Trivalent iron porphrin and its derivative-short peptide compound and its synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1. Determination of the optimum relative position of the active group histidine (His) and sub-heme or heme in the peptide chain

[0019] The sub-heme in the sub-heme-nonapeptide (DhHP-9) of the present invention has a different connection mode with the peptide chain than in MP-9, so the relative positions of His and the sub-heme in the primary structure and spatial structure are also different. Different from MP-9, it is necessary to determine the optimal relative position of His and hypoheme (Dh) in DhHP-9. For this reason, a series of hypoheme-short peptides were synthesized with SP-3 automatic peptide synthesizer: Dh-H, Dh-A-H, Dh-A2-H, Dh-A3-H, Dh-A4-H, Dh-A5 -H, Dh-A6-H.

[0020] The in vitro activity test showed that the specific activity of Dh-A-H enzyme with one Ala between the hypoheme and His was the highest, which was close to the level of natural MP-9 in value, and then the enzyme activity gradually decreased with the increase of the number of Ala. ...

Embodiment 2

[0022] Embodiment 2, the design of optimum short peptide

[0023]The most suitable short peptides were designed according to the experimental results such as assay activity: monomer subhemin-hexapeptide (DhHP-6: Deuterohemin-His-Peptide, Dh-AHTVEK) and heme-hexapeptide. The synthesis is carried out according to the technological process of the present invention by using an automatic polypeptide synthesizer, and the "deprotection coupling cycle" is carried out five times. Vitality assays in vitro showed that the enzyme specific activity (U / μmol) of DhHP-6 had reached the level of natural MP-9. At the same time, heme is replaced by hypoheme in the DhHP-6 molecule, and the peptide chain has three amino acids less than MP-9, so the molecular weight is smaller than natural MP-9, and the specific activity per μg of DhHP-6 is higher than that of natural MP-9, which is An ideal peroxidase mimic.

Embodiment 3

[0024] Embodiment 3, the synthesis of monomer hypoheme-A(D)-HTVEK and monomer heme-β-AHTVEK

[0025] (D)-H and β-A were introduced, and monomeric hypoheme-A(D)-HTVEK and monomeric heme-β-AHTVEK were synthesized with SP-3 automatic peptide synthesizer, both of which were active in vitro.

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Abstract

The trivalent iron porphyrin and its derivative-short peptide compound and its synthesis method belong to the field of biological technology. The composition of the compound includes heme or sub-heme and short peptide; the carboxyl group on the heme or sub-heme is connected with the amino group on the peptide chain by an amide bond; the peptide chain contains histidine residues, and the length of the peptide chain is 1-15 amino acids. The preparation method is: use heme or sub-heme and amino acid derivatives as raw materials, and use dimethylformamide as a solvent. The process includes swelling-deprotection-coupling-deprotection-coupling cycle-heme or sub-heme Conjugation - cleavage. Ferric porphyrin and its derivatives-short peptide compounds have good antioxidant activity in the in vitro system, subcellular level, and tissue organ level, and are a new class of compounds with peroxidase activity. The product has high purity and low toxicity; it has good stability to hydrogen peroxide; it is easier to be absorbed by the body and has high bioavailability.

Description

technical field [0001] The invention belongs to the field of biological technology, in particular to a peroxide mimetic enzyme and a method for synthesizing the peroxide mimetic enzyme. Background technique [0002] Cataract has become one of the main blinding eye diseases in the world today, and its sick population is still on the rise every year. Since the mechanism of oxidative damage has been proved more and more, various exogenous antioxidants and antioxidative traditional Chinese medicine preparations have been used in the treatment of cataract. [0003] Peroxidase (POD) widely exists in animals, plants and aerobic microorganisms, and it can mainly catalyze the following reactions: <chemistry num="001"> <chem file="02144902_cml001.xml" / > < / chemistry> , so it plays an important role in the metabolism of active oxygen in the body. According to the different catalytic groups, peroxidases are divided into two types: one class uses selenocysteine ​​as...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/00C07K7/00
Inventor 李惟刘亚丽郭莉莉
Owner JILIN UNIV
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