Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/58512
Type: Artigo de periódico
Title: QSAR model of the phototoxicity of polycyclic aromatic hydrocarbons
Author: Ribeiro, FAD
Ferreira, MMC
Abstract: A Quantitative Structure-Activity Relationship (QSAR) study of 67 polycyclic aromatic hydrocarbons (PAHs) is performed and a prediction rule for the phototoxicity of these compounds is proposed. The geometry of all PAHs was optimized by semi-empirical method and used to calculate the following electronic descriptors: the highest occupied molecular orbital energy (E-HOMO), the lowest unoccupied molecular orbital energy (E-LUMO) and the GAP (E-HOMO - E-LUMO) between them. The relationships between these molecular descriptors and the photo-induced toxicity are non-linear, and Gaussian type functions were used to linearize them. The data set was autoscaled and partial least squares (PLS) with leave-one-out cross-validation was used for building the regression model. After the model was validated, the phototoxicity was predicted for a set of molecules in which experimental measurements are unknown. Pentaphene, benzo[b]chrysene and dibenz[a.j]anthracene are among the compounds potentially phototoxic as predicted by the model. A new GAP range (7.2 +/- 0.7 eV) is proposed for the classification of phototoxic compounds, and a larger cutoff suggested for the normalized lethal time as log(1/ALT)<= - 2.95. (c) 2005 Elsevier B.V. All rights reserved.
Subject: QSAR
PLS
PAH
phototoxicity
PAHs
Country: Holanda
Editor: Elsevier Science Bv
Rights: fechado
Identifier DOI: 10.1016/j.theochem.2005.01.026
Date Issue: 2005
Appears in Collections:Unicamp - Artigos e Outros Documentos

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