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Capsaicin, a Powerful ^•OH-Inactivating Ligand.

ABSTRACT: 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^-, and slows down the reduction in this cation by O₂^•-. Therefore, CAP is proposed as an ^•OH-inactivating ligand by impeding the reduction in metal ions (OIL-1), hindering the production of ^•OH via Fenton-like reactions, at physiological pH. CAP is also predicted to be an excellent antioxidant as a scavenger of ^•OH, yielded through Fenton-like reactions (OIL-2). The reactions between CAP-Cu(II) chelates and ^•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.

SUBMITTER: Perez-Gonzalez A

PROVIDER: S-EPMC7763808 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Capsaicin, a Powerful •OH-Inactivating Ligand.

Pérez-González Adriana A Prejanò Mario M Russo Nino N Marino Tiziana T Galano Annia A

Antioxidants (Basel, Switzerland) 20201208 12

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-, and slows down the reduction in this cation by O2</su ...[more]

PMID: 33302572

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Project description:The number and type of synthetic chemicals that are being produced worldwide continues to increase significantly. While these industrial chemicals provide numerous benefits, there is no doubt that some have potential to damage the environment and health. Toxicity must be evaluated and use must be carefully controlled and monitored in order to minimize potential damage. DNA microarray technology has become an important new technique in toxicology. We are using the yeast Saccharomyces cerevisiae as a model organism for toxicological study because it is a simple, fast-growing eukaryote that has been thoroughly characterized. In order to evaluate toxicity by newly synthesized or mixture chemicals, toxicity-induced gene expression alteration profiles by known chemicals should be collected. In our study, cells need to be exposed with same experimental cellular condition, semi lethal (IC50), respectively. In the case of capsaicin (CAS; 404-86-4), the exposure dose was decided as 250 ppm by growth curve with continuously diluted exposure. Capsaicin, active component of chilli peppers, is an irritant for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. // Studies on the antimicrobial mechanisms of capsaicin using yeast DNA microarray: Capsaicin is a pungent element in a variety of red peppers that are widely used as food additives and considered to be an antimicrobial factor. For our tests, we used yeast DNA micro-array methods to understand the mechanisms of inhibitory effects of capsaicin. The capsaicin treatment significantly induced 39 genes from approximately 6,000 genes. These induced genes were classified as multi-drug resistance transporter genes, membrane biosynthesis genes, genes encoding stress proteins, and uncharacterized genes. The growth abilities of the strains with the deletion of the induced genes suggest that capsaicin is pumped out of the yeast cells by the PDR5 transporter. Keywords: stress response

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Capsaicin, a Powerful ^•OH-Inactivating Ligand.

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

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