title: Development of an in Silico Model of DPPH• Free Radical Scavenging Capacity: Prediction of Antioxidant Activity of Coumarin Type Compounds.
abstract: A quantitative structure-activity relationship (QSAR) study of the 2,2-diphenyl-l-picrylhydrazyl (DPPH•) radical scavenging ability of 1373 chemical compounds, using DRAGON molecular descriptors (MD) and the neural network technique, a technique based on the multilayer multilayer perceptron (MLP), was developed. The built model demonstrated a satisfactory performance for the training ( R 2 = 0.713 ) and test set ( Q ext 2 = 0.654 ) , respectively. To gain greater insight on the relevance of the MD contained in the MLP model, sensitivity and principal component analyses were performed. Moreover, structural and mechanistic interpretation was carried out to comprehend the relationship of the variables in the model with the modeled property. The constructed MLP model was employed to predict the radical scavenging ability for a group of coumarin-type compounds. Finally, in order to validate the model's predictions, an in vitro assay for one of the compounds (4-hydroxycoumarin) was performed, showing a satisfactory proximity between the experimental and predicted pIC50 values.
authors.affiliation: Pharmacy Department, Faculty of Chemistry and Pharmacy, Central University "Marta Abreu" of Las Villas, C-54830 Santa Clara, Cuba. egoyaj@gmail.com.
authors.forename: Elizabeth
authors.initials: E
authors.lastname: Goya Jorge
authors.affiliation: Equipe de Chimie Mol&#233;culaire du Laboratoire CMGPCE, EA 7341, Conservatoire National des Arts et M&#233;tiers, 2 rue Cont&#233;, 75003 Paris, France. anitarayar@hotmail.fr.
authors.forename: Anita Maria
authors.initials: AM
authors.lastname: Rayar
authors.affiliation: Department of Chemistry, Federal University of Lavras, P.O. Box 3037, 37200-000 Lavras, Brazil. sjbarigye@gmail.com.
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Barigye
authors.affiliation: Pharmacy Department, Faculty of Chemistry and Pharmacy, Central University "Marta Abreu" of Las Villas, C-54830 Santa Clara, Cuba. elisajorge@yahoo.es.
authors.forename: María Elisa
authors.initials: ME
authors.lastname: Jorge Rodríguez
authors.affiliation: Equipe de Chimie Mol&#233;culaire du Laboratoire CMGPCE, EA 7341, Conservatoire National des Arts et M&#233;tiers, 2 rue Cont&#233;, 75003 Paris, France. maite.sylla@lecnam.net.
authors.forename: Maité
authors.initials: M
authors.lastname: Sylla-Iyarreta Veitía
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000037:antagonists & inhibitors / Q000737:chemistry*; D003198:Computer Simulation; D003374:Coumarins / Q000737:chemistry / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000737:chemistry* / Q000494:pharmacology; D008962:Models, Theoretical; D010851:Picrates / Q000037:antagonists & inhibitors / Q000737:chemistry*; D021281:Quantitative Structure-Activity Relationship
chemical_list: D000975:Antioxidants; D001713:Biphenyl Compounds; D003374:Coumarins; D016166:Free Radical Scavengers; D010851:Picrates; C004931:1,1-diphenyl-2-picrylhydrazyl
keywords: DPPH•; MLP; QSAR; antioxidant; artificial neural networks; coumarin; free radical scavenger