Toxicity of aromatic pollutants and photooxidative intermediates in water: A QSAR study.

Abstract

Extensive commercial use of aromatic hydrocarbons results with significant amounts of these chemicals and related by-products in waters, causing a severe ecological and health threat, thus requiring an increased attention. This study was aimed at developing models for prediction of the initial toxicity of the aromatic water-pollutants (expressed as EC50 and TU0) as well as the toxicity of their intermediates at half-life of the parent pollutant (TU1/2). For that purpose, toxicity toward Vibrio fischery was determined for 36 single-benzene ring compounds (S-BRCs), diversified by the type, number and position of substituents. Quantitative structure-activity relationship (QSAR) methodology paired with genetic algorithm optimization tool and multiple linear regression was applied to obtain the models predicting the targeted toxicity, which are based on pure structural characteristics of the tested pollutants, avoiding thus additional experimentation. Upon derivation of the models and extensive analysis on training and test sets, 4-, 4- and 5-variable models (for EC50 and TU0, TU1/2, respectively) were selected as the most predictive possessing 0.839<R2< 0.901 and 0.789<Q2< 0.859. The analysis of the selected descriptors indicated three major structural characteristics influencing the toxicity: electronegativity, geometry and electrotopological states of the molecule. Degradation kinetics determining as well the pathways of intermediates formation, reflected over ionization potential, was found to be an important parameter determining the toxicity in half-life.