Synthesis and Electrochemical and Biological Studies of Novel Coumarin–Chalcone Hybrid Compounds

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....

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Bibliographic Details
Published in:Journal of medicinal chemistry 2013-08, Vol.56 (15), p.6136-6145
Main Authors: Pérez-Cruz, Fernanda, Vazquez-Rodriguez, Saleta, Matos, Maria João, Herrera-Morales, Alejandra, Villamena, Frederick A, Das, Amlan, Gopalakrishnan, Bhavani, Olea-Azar, Claudio, Santana, Lourdes, Uriarte, Eugenio
Format: Article
Language:English
Subjects:
Animals
Antioxidants - chemical synthesis
Antioxidants - chemistry
Antioxidants - pharmacology
Cattle
Cell Survival - drug effects
Cells, Cultured
Chalcones - chemical synthesis
Chalcones - chemistry
Chalcones - pharmacology
Coumarins - chemical synthesis
Coumarins - chemistry
Coumarins - pharmacology
Cytoprotection
Cytotoxins - chemical synthesis
Cytotoxins - chemistry
Cytotoxins - pharmacology
Electrochemistry
Electron Spin Resonance Spectroscopy
Endothelial Cells - cytology
Endothelial Cells - drug effects
Free Radical Scavengers - chemical synthesis
Free Radical Scavengers - chemistry
Free Radical Scavengers - pharmacology
Oxidation-Reduction
Reactive Nitrogen Species - metabolism
Reactive Oxygen Species - metabolism
Structure-Activity Relationship
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Summary: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.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm400546y