Capsaicin, a Powerful <sup>•</sup>OH-Inactivating Ligand

Oxidative conditions are frequently enhanced by the presence of redox metal ions. In this study, the role of capsaicin (8-methyl-N-vanillyl-6-nonenamide, CAP) in copper-induced oxidative stress was investigated using density functional theory simulations. It was found that CAP has the capability to...

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Những tác giả chính: Adriana Pérez-González, Mario Prejanò, Nino Russo, Tiziana Marino, Annia Galano
Định dạng: Bài viết
Ngôn ngữ:English
Được phát hành: MDPI AG 2020-12-01
Loạt:Antioxidants
Những chủ đề:
Truy cập trực tuyến:https://www.mdpi.com/2076-3921/9/12/1247
Miêu tả
Tóm tắt:Oxidative conditions are frequently enhanced by the presence of redox metal ions. In this study, the role of capsaicin (8-methyl-N-vanillyl-6-nonenamide, CAP) in copper-induced oxidative stress was investigated using density functional theory simulations. It was found that CAP has the capability to chelate Cu(II), leading to complexes that are harder to reduce than free Cu(II). CAP fully turns off the Cu(II) reduction by Asc<sup>−</sup>, and slows down the reduction in this cation by O<sub>2</sub><sup>•−</sup>. Therefore, CAP is proposed as an <sup>•</sup>OH-inactivating ligand by impeding the reduction in metal ions (OIL-1), hindering the production of <sup>•</sup>OH via Fenton-like reactions, at physiological pH. CAP is also predicted to be an excellent antioxidant as a scavenger of <sup>•</sup>OH, yielded through Fenton-like reactions (OIL-2). The reactions between CAP-Cu(II) chelates and <sup>•</sup>OH were estimated to be diffusion-limited. Thus, these chelates are capable of deactivating this dangerous radical immediately after being formed by Fenton-like reactions.
số ISSN:2076-3921