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We have investigated the precise mechanism of H2O2 production from 5-S-GAD by autoxidation aiming to understand its action toward tumour cells. Using the electron spin resonance (ESR) technique, we detected a strong signal due to radical formation from 5-S-GAD. Surprisingly, the ESR signal of the radicalo derived from 5-S-GAD appeared after incubation for 30 min at 310 K in the buffer at pH 7.4; the signal was persistently detected for 10 h in the absence of catalytic metal ions. The computer simulation of the observed ESR spectrum together with the theoretical calculation of the spin density of the radical species indicates that an o-semiquinone radical anion was formed from 5-S-GAD. We demonstrated that H2O2 is produced via the formation of superoxide anion by the electron-transfer reduction of molecular oxygen by the 5-S-GAD anion, which is in equiliblium with 5-S-GAD in the aqueous solution. 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A Long-Lived o-Semiquinone Radical Anion is Formed from N-beta-alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine (5-S-GAD), an Insect-derived Antibacterial Substance
https://repo.qst.go.jp/records/44939
https://repo.qst.go.jp/records/44939deb658f6-56de-4158-84fc-dd83b129285d
Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2007-08-14 | |||||
タイトル | ||||||
タイトル | A Long-Lived o-Semiquinone Radical Anion is Formed from N-beta-alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine (5-S-GAD), an Insect-derived Antibacterial Substance | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
アクセス権 | ||||||
アクセス権 | metadata only access | |||||
アクセス権URI | http://purl.org/coar/access_right/c_14cb | |||||
著者 |
Akiyama, Nobuko
× Akiyama, Nobuko× Nakanishi, Ikuo× Ohkubo, Kei× Fukuzumi, Shunichi× Ozawa, Toshihiko× et.al× 中西 郁夫× 小澤 俊彦 |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | N-beta-Alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine (5-S-GAD), an insect-induced antibacterial peptide, generates hydrogen peroxyde (H2O2) that exerts antitumour activity. We have investigated the precise mechanism of H2O2 production from 5-S-GAD by autoxidation aiming to understand its action toward tumour cells. Using the electron spin resonance (ESR) technique, we detected a strong signal due to radical formation from 5-S-GAD. Surprisingly, the ESR signal of the radicalo derived from 5-S-GAD appeared after incubation for 30 min at 310 K in the buffer at pH 7.4; the signal was persistently detected for 10 h in the absence of catalytic metal ions. The computer simulation of the observed ESR spectrum together with the theoretical calculation of the spin density of the radical species indicates that an o-semiquinone radical anion was formed from 5-S-GAD. We demonstrated that H2O2 is produced via the formation of superoxide anion by the electron-transfer reduction of molecular oxygen by the 5-S-GAD anion, which is in equiliblium with 5-S-GAD in the aqueous solution. The radical formation and the subsequent H2O2 production were inhibited by superoxide dismutase (SOD), when the antitumour activity of 5-S-GAD was inhibited by SOD. Thus, the formation of the o-semiquinone radical anion would be necessary for the antitumour activity of 5-S-GAD as an intermediate in the production of cytotoxic H2O2. | |||||
書誌情報 |
Journal of Biochemistry 巻 142, 号 1, p. 41-48, 発行日 2007-07 |
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ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 0021-924X |