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Equilibrium Sorption of Structurally Diverse Organic Ions to Bovine Serum Albumin
journal contribution
posted on 2016-04-20, 00:00 authored by Luise Henneberger, Kai-Uwe Goss, Satoshi EndoReliable
partitioning data are essential for assessing the bioaccumulation
potential and the toxicity of chemicals. In contrast to neutral organic
chemicals, the partitioning behavior of ionogenic organic chemicals
(IOCs) is still a black box for environmental scientists. Partitioning
to serum albumin, the major protein in blood plasma, strongly influences
the freely dissolved concentration of many chemicals (including IOCs),
which affects their transport and distribution in the body. Because
consistent data sets for partitioning of IOCs are rarely available,
bovine serum albumin-water partition coefficients (KBSA/w) were measured in this study for 45 anionic and
4 cationic organic chemicals, including various substituted benzoic
and naphthoic acids, sulfonates and several pesticides and pharmaceuticals.
The results of this study suggest that binding to BSA is substantially
influenced by the three-dimensional structure of the chemicals and
the position of substitutions on the sorbing molecules. For example,
we found a difference of >1.5 log units between isomeric chemicals
such as 3,4-dichlorobenzoic acid and 2,6-dichlorobenzoic acid, and
1-naphthoic acid and 2-naphthoic acid. Conventional modeling approaches
(e.g., based on octanol–water partition coefficients) poorly
predict log KBSA/w of organic ions (R2 ≤ 0.5), partially because they do not
capture the observed steric effects. Hence, alternative modeling strategies
will be required for accurate prediction of serum albumin-water partition
coefficients of organic ions.
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data setsIOCBovine Serum Albumin Reliable partitioning datapartitioning behavioralternative modeling strategiessteric effectsnaphthoic acidscoefficientEquilibrium Sorptionsorbing moleculesBSA4 cationicStructurally Diverse Organic IonsConventional modeling approachesisomeric chemicalsblood plasmaserum albumin
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