Density functional theory-based first principles calculations of rhododendrol-quinone reactions: Preference to thiol binding over cyclization

Ryo Kishida, Hideaki Kasai, Susan Meñez Aspera, Ryan Lacdao Arevalo, Hiroshi Nakanishi

研究成果: Contribution to journalArticle査読

7 被引用数 (Scopus)

抄録

Using density functional theory-based first principles calculations, we investigated the changes in the energetics and electronic structures of rhododendrol (RD)-quinone for the initial step of two important reactions, viz., cyclization and thiol binding, to give significant insights into the mechanism of the cause of cytotoxic effects. We found that RD-quinone in the electroneutral structure cannot undergo cyclization, indicating a slow cyclization of RD-quinone at neutral pH. Furthermore, using methane thiolate ion as a model thiol, we found that the oxidized form of the cyclized RD-quinone, namely RD-cyclic quinone, exhibited a reduced binding energy for thiols. However, this reduction of binding energy is clearly smaller than the case of dopaquinone, which is a molecule originally involved in the melanin synthesis. This study clearly shows that RD-quinone has a preference toward thiol bindings than cyclization compared to the case of dopaquinone. Considering that thiol bindings have been reported to induce cytotoxic effects in various ways, the preference toward thiol bindings is an important chemical property for the cytotoxicity caused by RD.

本文言語英語
論文番号024804
ジャーナルjournal of the physical society of japan
86
2
DOI
出版ステータス出版済み - 2017
外部発表はい

All Science Journal Classification (ASJC) codes

  • 物理学および天文学(全般)

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