Exploring MIA-QSPR's for the modeling of biomagnification factors of aromatic organochlorine pollutants
| Autor: | Stephen J. Barigye, Matheus P. Freitas, Estella G. da Mota, Mariene H. Duarte, Teodorico C. Ramalho |
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| Rok vydání: | 2017 |
| Předmět: |
Quantitative structure–activity relationship
Health Toxicology and Mutagenesis Biomagnification 0211 other engineering and technologies Substituent Quantitative Structure-Activity Relationship 02 engineering and technology 010501 environmental sciences 01 natural sciences Electronegativity symbols.namesake chemistry.chemical_compound Computational chemistry Molecular descriptor Hydrocarbons Chlorinated Organic chemistry Van der Waals radius 0105 earth and related environmental sciences Biphenyl 021110 strategic defence & security studies Public Health Environmental and Occupational Health General Medicine Pollution Dibenzofuran chemistry Multivariate Analysis symbols Hydrophobic and Hydrophilic Interactions |
| Zdroj: | Ecotoxicology and Environmental Safety. 135:130-136 |
| ISSN: | 0147-6513 |
| DOI: | 10.1016/j.ecoenv.2016.09.030 |
| Popis: | Biomagnification of organic pollutants in food webs has been usually associated to hydrophobicity and other molecular descriptors. However, direct information on atoms and substituent positions in a molecular scaffold that most affect this biological property is not straightforward using traditional QSPR techniques. This work reports the QSPR modeling of biomagnification factors (logBMF) of a series of aromatic organochlorine compounds using three MIA-QSPR (multivariate image analysis applied to QSPR) approaches. The MIA-QSPR model based on augmented molecular images (described with atoms represented as circles with sizes proportional to the respective van der Waals radii and having colors numerically proportional to the Pauling's electronegativity) encoded better the logBMF data. The average results for the main statistical parameters used to attest the model's predictability were r2=0.85, q2=0.72 and r2test=0.85. In addition, chemical insights on substituents and respective positions at the biphenyl rings A and B, and dibenzo-p-dioxin and dibenzofuran motifs are given to aid the design of more ecofriendly derivatives. |
| Databáze: | OpenAIRE |
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