Bioconcentration potential predictions based on molecular attributes - an early warning approach for chemicals found in humans, birds, fish and wildlife

摘要

The bioaccumulation potential of chemicals is used to indicate when chemicals are likely to contaminate fish, birds and other wildlife, and humans. Together with knowledge of the persistence of chemicals, the bioaccumulation potential is useful in setting priorities for hazard identification as well as environmental monitoring. Because the measurement of the bioaccumulation potential is costly, developing reliable estimates of this important indicator directly from chemical structure has long been a goal of Quantitative Structure Activity Relationship (QSAR) practitioners. Many previous models for predicting bioconcentration factors (BCF) for organic chemicals have been based on linear and bilinear relationships between log(BCF) and octanol-water partition coefficient (log(K_(ow))) , some of which also included other structural parameters such as structural correction factors or molecular connectivity indices, Fujita's characters, etc. Most of these BCF models have been derived for predicting passive diffusion of chemicals with log. octanol-water partition coefficients log(K_(ow)) <7. Most previous models showed large discrepancy for large number of chemicals (predominantly highly lipophilic) found in humans and fish. The effect of steric molecular attributes on predicting BCF was studied using 694 chemicals with available experimental BCF and K_(ow) values. It was found that maximum cross sectional diameters and conformational flexibility of chemicals affect significantly bioconcentration and could be used to explain identification of certain highly hydrophobic chemicals in humans and fish.