American Chemical Society
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Capacities of Membrane Lipids to Accumulate Neutral Organic Chemicals

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journal contribution
posted on 2011-07-15, 00:00 authored by Satoshi Endo, Beate I. Escher, Kai-Uwe Goss
Lipids have been considered as the predominant components for bioaccumulation of organic chemicals. However, differences in accumulation properties between different types of lipid (e.g., storage and membrane lipids) have rarely been considered. Moreover, in view of toxic effects on organisms, chemical accumulation specifically in biological membranes is of particular importance. In this review article, partition coefficients of 240 neutral organic compounds between liposomes (phospholipid membrane vesicles) and water (Klipw), reported in the literature or measured additionally for this work, were evaluated. Values of log Klipw and log Kow (octanol–water partition coefficients) differ by 0.4 on average. Polyparameter linear free energy relationships (PP-LFERs) can describe the log Klipw data even better (standard deviations = 0.28–0.31) than the log Kow model. Recent experimental data for highly hydrophobic compounds fit well to the PP-LFERs and do not indicate the existence of a previously postulated “hydrophobicity cutoff”. Predictive approaches based only on the molecular structure (KOWWIN, SPARC, COSMOthermX, COSMOmic) were also evaluated for Klipw prediction. The PP-LFERs revealed that partition coefficients into membrane lipids can be two log units higher than those into storage lipids for H-bond donor compounds, suggesting that distinguishing between the two lipids is necessary to account for the bioaccumulation of these compounds, and that tissues rich in membrane lipids (e.g., kidneys, liver) instead of fat tissue can be the primary phase for accumulation.