Metal-catalyzed oxidation of 2-alkenals generates genotoxic 4-oxo-2-alkenals during lipid peroxidation

• Material Type: 博士論文
• Title: Metal-catalyzed oxidation of 2-alkenals generates genotoxic 4-oxo-2-alkenals during lipid peroxidation
• Author/Editor: Nuka, Erika; Tomono, Susumu; Ishisaka, Akari; Kato, Yoji; Miyoshi, Noriyuki; Kawai, Yoshichika
• Author Heading: Nuka, Erika; Tomono, Susumu; Ishisaka, Akari; Kato, Yoji; Miyoshi, Noriyuki; Kawai, Yoshichika
• Publication, Distribution, etc.: Taylor & Francis|Japan Society for Bioscience, Biotechnology, and Agrochemistry
• Publication Date: 2016-06-07
• Publication Date (W3CDTF): 2016-06-07
• Alternative Title: 脂質過酸化反応において金属触媒による2-アルケナールの酸化は、遺伝毒性を有する4-オキソ-2-アルケナールを生成する; Metal-catalyzed formation of 4-oxo-2-alkenals
• Periodical title: Bioscience, Biotechnology, and Biochemistry
• No. or year of volume/issue: 80 10
• Volume: 80
• Issue: 10
• Pages: 2007-2013
• ISSN (Periodical Title): ISSN : 0916-8451; ISSN : 1347-6947
• Degree grantor/type: 徳島大学
• Date Granted: 2018-03-23
• Dissertation Number: 甲第3147号
• Degree Type: 博士（栄養学）
• Text Language Code: eng
• Subject Heading: Lipid peroxidation; DNA adducts; LC-MS/MS; 4-oxo-2-alkenals; transition metals
• Target Audience: 一般
• Note (General): Lipid peroxidation products react with cellular molecules, such as DNA bases, to form covalent adducts, which are associated with aging and disease processes. Since lipid peroxidation is a complex process and occurs in multiple stages, there might be yet unknown reaction pathways. Here, we analyzed comprehensively 2’-deoxyguanosine (dG) adducts with oxidized arachidonic acid using liquid chromatography-tandem mass spectrometry and found the formation of 7-(2-oxo-hexyl)-etheno-dG as one of the major unidentified adducts. The formation of this adduct was reproduced in the reaction of dG with 2-octenal and predominantly with 4-oxo-2-octenal (OOE). We also found that other 2-alkenals (with five or more carbons) generate corresponding 4-oxo-2-alkenal-type adducts. Importantly, it was found that transition metals enhanced the oxidation of C4-position of 2-octenal, leading to the formation of OOE-dG adduct. These findings demonstrated a new pathway for the formation of 4-oxo-2-alkenals during lipid peroxidation and might provide a mechanism for metal-catalyzed genotoxicity.
• Format (IMT): application/pdf
• Access Restrictions: インターネット公開
• Rights (production): © 2016 Japan Society for Bioscience, Biotechnology, and Agrochemistry
• Related Material (DOI): 10.1080/09168451.2016.1191334
• Data Provider (Database): 国立情報学研究所 : 学術機関リポジトリデータベース（IRDB）（機関リポジトリ）; https://irdb.nii.ac.jp
• Original Data Provider (Database): 徳島大学 : 徳島大学機関リポジトリ

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