title: N-(Phenoxyalkyl)amides as MT(1) and MT(2) ligands: antioxidant properties and inhibition of Ca(2+)/CaM-dependent kinase II.
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.
authors: Dipartimento di Farmacia-Scienze del Farmaco, Università degli Studi di Bari Aldo Moro, Via E. Orabona 4, 70125 Bari, Italy. alessia.carocci@uniba.it
authors: Alessia
authors: A
authors: Carocci
authors: Alessia
authors: A
authors: Catalano
authors: Claudio
authors: C
authors: Bruno
authors: Angelo
authors: A
authors: Lovece
authors: Maria Grazia
authors: MG
authors: Roselli
authors: Maria Maddalena
authors: MM
authors: Cavalluzzi
authors: Francesco
authors: F
authors: De Santis
authors: Annalisa
authors: A
authors: De Palma
authors: Maria Rosaria
authors: MR
authors: Rusciano
authors: Maddalena
authors: M
authors: Illario
authors: Carlo
authors: C
authors: Franchini
authors: Giovanni
authors: G
authors: Lentini
mesh_terms: D000577:Amides / Q000737:chemistry* / Q000633:toxicity; D000975:Antioxidants / Q000737:chemistry* / Q000633:toxicity; D054732:Calcium-Calmodulin-Dependent Protein Kinase Type 2 / Q000037:antagonists & inhibitors* / Q000378:metabolism; D002470:Cell Survival / Q000187:drug effects; D056945:Hep G2 Cells; D006801:Humans; D008024:Ligands; D047428:Protein Kinase Inhibitors / Q000737:chemistry* / Q000633:toxicity; D044122:Receptor, Melatonin, MT1 / Q000737:chemistry* / Q000378:metabolism; D044123:Receptor, Melatonin, MT2 / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D000975:Antioxidants; D008024:Ligands; D047428:Protein Kinase Inhibitors; D044122:Receptor, Melatonin, MT1; D044123:Receptor, Melatonin, MT2; D054732:Calcium-Calmodulin-Dependent Protein Kinase Type 2