Effects of Phenyl Derivatives of Dihydropyrazines with Ability to Generate Radical Species on Escherichia coli

Osamu Takeda; Shinji Takechi; Shigeru Ito; Hisamitsu Omori; Takahiko Katoh; Tadatoshi Yamaguchi

doi:10.1248/bpb.30.1663

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Effects of Phenyl Derivatives of Dihydropyrazines with Ability to Generate Radical Species on Escherichia coli

Osamu Takeda, Shinji Takechi, Shigeru Ito, Hisamitsu Omori, Takahiko Katoh, Tadatoshi Yamaguchi

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Keywords: dihydropyrazine, superoxide anion, lethal effect, Escherichia coli

JOURNAL FREE ACCESS

2007 Volume 30 Issue 9 Pages 1663-1667

DOI https://doi.org/10.1248/bpb.30.1663

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Abstract

Phenyl-substituted dihydropyrazines (Ph-DHPs) are derivatives of 2,3-dihydro-5,6-dimethylpyrazine (Me-DHP). Upon the addition of Cu²⁺, Me-DHP inhibits the growth of Escherichia coli by generating hydroxyl and carbon-centered radicals that cause DNA strand breakage. Here, we investigated the toxic effect of Ph-DHPs in several DNA repair-deficient or detoxifying enzyme-deficient mutant strains. Ph-DHPs caused cytotoxic and genotoxic damage, but, in a sodA sodB strain, the effects in the presence or absence of Cu²⁺ were different than those of Me-DHP. Our results suggest that the action of the generated superoxide anion in the interior side of the cell is remarkable.

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