<i>N</i>-Acetylserotonin and 6-Hydroxymelatonin against Oxidative Stress: Implications for the Overall Protection Exerted by Melatonin

Álvarez-Diduk, Ruslán; Galano, Annia; Tan, Dun Xian; Reíter, Russel J.

doi:10.1021/acs.jpcb.5b04920

Cited by 54 publications

(65 citation statements)

References 76 publications

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“…The role of the hydroxyl group in free radical scavenging was also previously underlined for numerous polyphenols (62)(63)(64)(65) and by Fabre et al (66), who studied lipocarbazole derivatives and their location and orientation in lipid bilayers. Similarly, the study conducted by Á lvarez-Diduk et al (67), who examined N-acetylserotonin ROS scavenging capacity, substantiates the importance of the hydroxyl group. They demonstrated using density functional theory that N-acetylserotonin is more efficient to scavenge HOO radical than melatonin itself.…”

Section: Antioxidant Properties and Molecular Structure Of Serotoninmentioning

confidence: 58%

Antioxidant and Membrane Binding Properties of Serotonin Protect Lipids from Oxidation

Azouzi

Santuz

Morandat

et al. 2017

Biophysical Journal

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Serotonin (5-hydroxytryptamine, 5-HT) is a well-known neurotransmitter that is involved in a growing number of functions in peripheral tissues. Recent studies have shown nonpharmacological functions of 5-HT linked to its chemical properties. Indeed, it was reported that 5-HT may, on the one hand, bind lipid membranes and, on the other hand, protect red blood cells through a mechanism independent of its specific receptors. To better understand these underevaluated properties of 5-HT, we combined biochemical, biophysical, and molecular dynamics simulations approaches to characterize, at the molecular level, the antioxidant capacity of 5-HT and its interaction with lipid membranes. To do so, 5-HT was added to red blood cells and lipid membranes bearing different degrees of unsaturation. Our results demonstrate that 5-HT acts as a potent antioxidant and binds with a superior affinity to lipids with unsaturation on both alkyl chains. We show that 5-HT locates at the hydrophobic-hydrophilic interface, below the glycerol group. This interfacial location is stabilized by hydrogen bonds between the 5-HT hydroxyl group and lipid headgroups and allows 5-HT to intercept reactive oxygen species, preventing membrane oxidation. Experimental and molecular dynamics simulations using membrane enriched with oxidized lipids converge to further reveal that 5-HT contributes to the termination of lipid peroxidation by direct interaction with active groups of these lipids and could also contribute to limit the production of new radicals. Taken together, our results identify 5-HT as a potent inhibitor of lipid peroxidation and offer a different perspective on the role of this pleiotropic molecule.

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Section: Antioxidant Properties and Molecular Structure Of Serotoninmentioning

confidence: 58%

Antioxidant and Membrane Binding Properties of Serotonin Protect Lipids from Oxidation

Azouzi

Santuz

Morandat

et al. 2017

Biophysical Journal

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“…In this study, the NAS concentration was neither affected by drought nor nano-ZnO treatment. Although NAS exhibits antioxidant ability in animals, the role of NAS in plant against abiotic stress has not been evidenced [56]. Melatonin is decomposed by enzymatic reaction, pseudo-enzyme reaction, and cascade interaction with free radicals to produce a variety of metabolites, including 2-hydroxymelatonin and AFMK.…”

Section: Discussionmentioning

confidence: 99%

Nano-ZnO-Induced Drought Tolerance Is Associated with Melatonin Synthesis and Metabolism in Maize

Sun

Song

Guo

et al. 2020

IJMS

118

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The applications of ZnO nanoparticles in agriculture have largely contributed to crop growth regulation, quality enhancement, and induction of stress tolerance, while the underlying mechanisms remain elusive. Herein, the involvement of melatonin synthesis and metabolism in the process of nano-ZnO induced drought tolerance was investigated in maize. Drought stress resulted in the changes of subcellular ultrastructure, the accumulation of malondialdehyde and osmolytes in leaf. The nano-ZnO (100 mg L−1) application promoted the melatonin synthesis and activated the antioxidant enzyme system, which alleviated drought-induced damage to mitochondria and chloroplast. These changes were associated with upregulation of the relative transcript abundance of Fe/Mn SOD, Cu/Zn SOD, APX, CAT, TDC, SNAT, COMT, and ASMT induced by nano-ZnO application. It was suggested that modifications in endogenous melatonin synthesis were involved in the nano-ZnO induced drought tolerance in maize.

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“…Two different chelating mechanisms were considered that have been reported before: direct‐chelation mechanism (DCM) and coupled‐deprotonation‐chelation mechanism (CDCM). In addition, the possible roles of DPEN as both monodentate and bidentate ligand have been taken into account.…”

Section: Methodsmentioning

confidence: 99%

How to identify promising metal scavengers? d‐penicillamine with copper as a study case

Martı́nez

Vargas

Galano

2017

Int J of Quantum Chemistry

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Therapeutic chelating agents are used to prevent the effects of the metal accumulation. These are molecules that form complexes with transition metals and they are referred here as metal scavengers. The main idea of this investigation is to recognize the most relevant chemical features to identify potential metal scavengers. D-penicillamine with copper (DPEN-Cu) is used for this purpose. The first requirement that must be fulfilled by a good metal scavenger is the exergonicity of the chelating reaction. In the DPEN-Cu case the most likely complexation pathway was found to have DG equal to 224.3 kcal/mol. It is desirable that the chelating molecule could also be a free radical scavenger. D-penicillamine is a good free radical scavenger following the hydrogen atom transfer reaction. An additional advantage is that the DPEN-Cu may act as ·OH-inactivating ligand.It is proposed that chelating agents fulfilling these requirements may be a promising candidate to be used in metal chelation therapies as metal scavengers. K E Y W O R D S antioxidant, antiradical, chelating therapy, scavenger Int J Quantum Chem. 2018;118:e25457.

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N-Acetylserotonin and 6-Hydroxymelatonin against Oxidative Stress: Implications for the Overall Protection Exerted by Melatonin

Cited by 54 publications

References 76 publications

Antioxidant and Membrane Binding Properties of Serotonin Protect Lipids from Oxidation

Antioxidant and Membrane Binding Properties of Serotonin Protect Lipids from Oxidation

Nano-ZnO-Induced Drought Tolerance Is Associated with Melatonin Synthesis and Metabolism in Maize

How to identify promising metal scavengers? d‐penicillamine with copper as a study case

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