title: Synthesis and electrochemical and biological studies of novel coumarin-chalcone hybrid compounds.
abstract: A series of novel hydroxy-coumarin-chalcone hybrid compounds 2a-i has been synthesized by employing a simple and efficient methodology. An electrochemical characterization using cyclic voltammetry and ESR spectroscopy were carried out to characterize the oxidation mechanism for the target compounds. The antioxidant capacity and reactivity were determined by ORAC and ESR assays, respectively. Biological assays were assessed to evaluate the cytotoxicity and cytoprotection capacity against ROS/RNS on BAEC. The results revealed that all tested compounds present ORAC values that are much higher than other well-known antioxidant compounds such as quercetin and catechin. Compound 2e showed the highest ORAC value (14.1) and also presented a low oxidation potential, good scavenging capacity against hydroxyl radicals, low cytotoxicity, and high cytoprotective activity.
authors.affiliation: Free Radical and Antioxidants Laboratory, Inorganic and Analytical Department, Faculty of Chemical and Pharmaceutical Sciences, University of Chile, Sergio Livingstone Polhammer 1007, Independencia, Santiago, Chile.
authors.forename: Fernanda
authors.initials: F
authors.lastname: Pérez-Cruz
authors.forename: Saleta
authors.initials: S
authors.lastname: Vazquez-Rodriguez
authors.forename: Maria João
authors.initials: MJ
authors.lastname: Matos
authors.forename: Alejandra
authors.initials: A
authors.lastname: Herrera-Morales
authors.forename: Frederick A
authors.initials: FA
authors.lastname: Villamena
authors.forename: Amlan
authors.initials: A
authors.lastname: Das
authors.forename: Bhavani
authors.initials: B
authors.lastname: Gopalakrishnan
authors.forename: Claudio
authors.initials: C
authors.lastname: Olea-Azar
authors.forename: Lourdes
authors.initials: L
authors.lastname: Santana
authors.forename: Eugenio
authors.initials: E
authors.lastname: Uriarte
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002417:Cattle; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D047188:Chalcones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019610:Cytoprotection; D003603:Cytotoxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004563:Electrochemistry; D004578:Electron Spin Resonance Spectroscopy; D042783:Endothelial Cells / Q000166:cytology / Q000187:drug effects; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D010084:Oxidation-Reduction; D026361:Reactive Nitrogen Species / Q000378:metabolism; D017382:Reactive Oxygen Species / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: C584251:6-hydroxy-3-(4'-hydroxybenzoyl)coumarin; D000975:Antioxidants; D047188:Chalcones; D003374:Coumarins; D003603:Cytotoxins; D016166:Free Radical Scavengers; D026361:Reactive Nitrogen Species; D017382:Reactive Oxygen Species