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Fine-Tuning of Redox Properties of Substituted 6-Chromanols as Vitamin E Analogues Based on Density Functional Theory Calculations
https://repo.qst.go.jp/records/70683
https://repo.qst.go.jp/records/706830beea1ee-90d8-4832-a82f-aca705edd742
| Item type | 会議発表用資料 / Presentation(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2012-02-20 | |||||
| タイトル | ||||||
| タイトル | Fine-Tuning of Redox Properties of Substituted 6-Chromanols as Vitamin E Analogues Based on Density Functional Theory Calculations | |||||
| 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_c94f | |||||
| 資源タイプ | conference object | |||||
| 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 |
Nakanishi, Ikuo
× Nakanishi, Ikuo× Inami, Keiko× Ohkubo, Kei× Kawashima, Tomonori× Matsumoto, Kenichiro× Fukuhara, Kiyoshi× Mochizuki, Masataka× Fukuzumi, Shunichi× Anzai, Kazunori× Ozawa, Toshihiko× 中西 郁夫× 川島 知憲× 松本 謙一郎 |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | Since phenolic antioxidants, such as vitamin E (alpha-tocopherol) and catechins, are known to show both antioxidative and prooxidative activities under certain conditions, fine-tuning of such activities is of considerable importance to control oxidative stress induced by reactive oxygen species (ROS) in biological redox systems. However, very little is known about the structure-activity relationship of the phenolic antioxidants. In this study, we demonstrate that density functional theory (DFT) calculations of O-H bond dissociation enthalpies and ionization potentials (IP) of phenolic antioxidants are a powerful tool to expect their radical-scavenging activity. In fact, the logarithms of the second-order rate constants (k) for the scavenging reaction of galvinoxyl radical (GO) as an ROS model by various substituted 6-chromanols, which were synthesized as vitamin E analogues, in deaerated acetonitirile are found to correlate linearly with their IP values calculated by DFT. Among the derivatives, 8-amino-2,2-dimethylchroman-6-ol having the smallest IP value showed the highest GO-scavenging activity. Thus, the introduction of substituents, which lower the IP value, to the benzene ring of 6-chromanol results in the enhancement of the antioxidative activity of 6-chromanol derivatives. | |||||
| 会議概要（会議名, 開催地, 会期, 主催者等） | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | 第20回日本学術振興会先端研究拠点事業セミナー：International Redox Core Symposium | |||||
| 発表年月日 | ||||||
| 日付 | 2012-02-06 | |||||
| 日付タイプ | Issued | |||||
