Abstract
Recently a series of chiral N-(phenoxyalkyl)amides have been reported as potent MT(1) and MT(2) melatonergic ligands. Some of these compounds were selected and tested for their antioxidant properties by measuring their reducing effect against oxidation of 2',7'-dichlorodihydrofluorescein (DCFH) in the DCFH-diacetate (DCFH-DA) assay. Among the tested compounds, N-[2-(3-methoxyphenoxy)propyl]butanamide displayed potent antioxidant activity that was stereoselective, the (R)-enantiomer performing as the eutomer. This compound displayed strong cytoprotective activity against H(2)O(2)-induced cytotoxicity resulting slightly more active than melatonin, and performed as Ca(2+)/calmodulin-dependent kinase II (CaMKII) inhibitor, too.
Copyright © 2012 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amides / chemistry*
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Amides / toxicity
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Antioxidants / chemistry*
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Antioxidants / toxicity
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Calcium-Calmodulin-Dependent Protein Kinase Type 2 / antagonists & inhibitors*
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Calcium-Calmodulin-Dependent Protein Kinase Type 2 / metabolism
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Cell Survival / drug effects
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Hep G2 Cells
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Humans
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Ligands
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Protein Kinase Inhibitors / chemistry*
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Protein Kinase Inhibitors / toxicity
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Receptor, Melatonin, MT1 / chemistry*
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Receptor, Melatonin, MT1 / metabolism
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Receptor, Melatonin, MT2 / chemistry*
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Receptor, Melatonin, MT2 / metabolism
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Amides
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Antioxidants
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Ligands
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Protein Kinase Inhibitors
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Receptor, Melatonin, MT1
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Receptor, Melatonin, MT2
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Calcium-Calmodulin-Dependent Protein Kinase Type 2