Radical scavenger and active oxygen eliminating agent

Inactive Publication Date: 2010-06-03
INBIOTEX
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  • Abstract
  • Description
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AI Technical Summary

Benefits of technology

[0021]In accordance with the invention, there are provided a radical scavenger, an active oxygen-scavenging agent, an antioxidant agent, an agent for preventing and therapeutically treati

Problems solved by technology

Therefore, lipid peroxidation chain reactions, induced by free radicals, not only give damages to membrane structures but also seriously disrupt enzymatic reactions and receptor functions of proteins, which are

Method used

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  • Radical scavenger and active oxygen eliminating agent
  • Radical scavenger and active oxygen eliminating agent
  • Radical scavenger and active oxygen eliminating agent

Examples

Experimental program
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Effect test

example 1

Lipid Peroxide-Suppressing Action

[0062]As an action of capturing free group (free radical-scavenging action), the effect of N-β-alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine (5-S-GAD) on LDL oxidation was examined. As controls, dopamine and Carnosine (under trade name; N-acetylcarnosine as the ingredient name) used as eye drops for cataract were used. LDL was prepared by a fractionation and centrifugation method. A fraction at a specific gravity of 1.019 to 1.063 g / mL in serum was defined as human LDL. 5 μM CuSO4, 5-S-GAD (3 to 100 μM) and N-acetyl-carnosine (100 μM to 10 mM) or L-carnosine (10 μM to 10 mM) were added to 0.2 mg / mL LDL, for incubation at 37° C. for 3 hours. After termination of the incubation, TBARS (a substance reactive with thiobarbituric acid) was assayed. Although the TBA reaction is a non-specific reaction, the reaction is used for a method of assaying various lipid peroxide products including malone dialdehyde. An experiment of peroxidation with copper sul...

example 2

DPPH-Scavenging Action

[0064]DPPH (1,1-diphenyl-2-picrylhydrazyl) is one of nitrogen radicals and is a very stable radical, which is commercially available as a black-purple crystal (Wako Pure Chemical, Co., Ltd., etc.). N-β-Alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine (5-S-GAD) (see Table 2) or Carnosine (under trade name) (see Table 3) was added to an ethanol solution of 50 mM DPPH radical, for reaction at ambient temperature for 5 minutes (see the following reaction scheme). Instead of the test reagent, distilled water was added to the ethanol solution, which was used as a background. The DPPH absorbance at 517 nm was assayed, to calculate the scavenging ratio (%) of the DPPH radical according to the following equation. The scavenging ratio was defined as radical scavenger activity (mean, n=2; see Table 2, Table 3 and FIG. 2).

Radical-scavenging ratio (%)=[assay value of background (mean)−assay value of solution at each concentration] / background assay value (mean)]×100

TABLE 2...

example 3

Superoxide Anion (O2−)-Scavenging Activity

[0066]In a 50 mM carbonate buffer (pH 10) containing 200 μM lucigenin, 100 μM xanthine and 1 mU / mL xanthine oxidase reacted together. The chemiluminescence level depending on the generated superoxide anion (O2−) was assayed with BIOLUMAT (under trade name) (Model type LB 9505, manufactured by EG&G BERTHORD Company) for 10 minutes. The area under the curve indicating the total chemiluminescence over the 10 minutes was calculated. Defining the area under the curve for a group (control) added with PBS(−) instead of the test substance solution at the same amount as that of the solution as 100, the effect of N-β-alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine (5-S-GAD) (Table 4) or Carnosine (under trade name) (Table 5) on the increase of chemiluminescence was examined. The suppressive activity thereof was defined as superoxide anion-scavenging activity (%) (mean, n=2; see Table 4, Table 5 and FIG. 3).

TABLE 41) 5-S-GADConcentration added (μM)R...

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Abstract

It is an object to provide a radical scavenger, an active oxygen-scavenging agent and the like, which are highly efficacious clinically and novel, and so as to attain the object, 3,4-dihydroxyphenylalanine derivatives such as N-β-alanyl-5-S-glutathionyl-1-3,4-dihydroxyphenylalanine (5-S-GAD) or pharmaceutically acceptable salts thereof are contained as an active ingredient.

Description

TECHNICAL FIELD[0001]The present invention relates to novel uses of 3,4-dihydroxyphenylalanine derivatives such as N-β-alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine (5-S-GAD) or salts thereof (radical scavenger, active oxygen-scavenging agent and the like).BACKGROUND ART[0002]As biological target molecules to be damaged with free radicals, for example, lipid, sugar, nucleic acid, enzyme, and protein are important. In particular, highly unsaturated fatty acids locally existing in lipids in all cellular membranes are attacked with free radicals, to generate lipid peroxides through lipid peroxidation chain reactions. Direct or indirect actions with these lipid peroxides are considered as one cause of biological membrane damages by free radicals. Biological membrane is composed of lipid and protein, which not only works as a partition wall separating cells and small organs but also forms places with accumulated diverse functions, including for example a source of physiologically ac...

Claims

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Application Information

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IPC IPC(8): C07C321/28
CPCA01N1/02A01N1/0226C07K5/0215A61K38/063C07K5/0202A61K31/198A61P1/02A61P1/04A61P1/18A61P3/00A61P3/10A61P7/02A61P7/06A61P7/10A61P9/06A61P9/10A61P11/00A61P13/12A61P17/00A61P17/02A61P17/04A61P19/00A61P19/02A61P21/00A61P25/08A61P25/14A61P25/16A61P25/18A61P25/28A61P27/02A61P27/06A61P27/12A61P29/00A61P31/04A61P37/06A61P39/02A61P39/06A61P43/00
Inventor NATORI, SHUNJIOOTSU, KUNIMIKIOKUYAMA, HAJIME
Owner INBIOTEX
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