Abstract
The thermodynamics of partitioning of selected endocrine disruptors between water and synthetic membrane vesicles were investigated. For most of the chemicals investigated, partitioning is dominated by the enthalpy change for unsaturated lipid membrane vesicles and by the entropy contribution for saturated lipid membrane vesicles. The contribution of the entropy terms in determining the free-energy change becomes more important compared with the enthalpy terms with increased branching of p-substituted phenols. These results suggest that the thermal energy required for and the entropy gain associated with the creation of the cavity in the lipid bilayer is of critical importance in differentiating the process from 1-octanol/water partitioning. In addition, partitioning thermodynamics are significantly influenced by cholesterol content in the lipid membranes. Results of the present study and those in the literature suggest that partitioning processes significantly depend on the physical state of the lipid membranes and log Kow-based quantitative structure-activity relationships should be carefully applied for predicting bioconcentration by considering lipid compositions.
| Original language | English |
|---|---|
| Pages (from-to) | 4011-4018 |
| Number of pages | 8 |
| Journal | Environmental Science and Technology |
| Volume | 41 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - 2007 Jun 1 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Environmental Science(all)
- Environmental Chemistry
- Environmental Engineering
Cite this
Partitioning thermodynamics of selected endocrine disruptors between water and synthetic membrane vesicles : Effects of membrane compositions. / Kwon, Jung-Hwan; Liljestrand, Howard M.; Katz, Lynn E.; Yamamoto, Hiroshi.
In: Environmental Science and Technology, Vol. 41, No. 11, 01.06.2007, p. 4011-4018.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Partitioning thermodynamics of selected endocrine disruptors between water and synthetic membrane vesicles
T2 - Effects of membrane compositions
AU - Kwon, Jung-Hwan
AU - Liljestrand, Howard M.
AU - Katz, Lynn E.
AU - Yamamoto, Hiroshi
PY - 2007/6/1
Y1 - 2007/6/1
N2 - The thermodynamics of partitioning of selected endocrine disruptors between water and synthetic membrane vesicles were investigated. For most of the chemicals investigated, partitioning is dominated by the enthalpy change for unsaturated lipid membrane vesicles and by the entropy contribution for saturated lipid membrane vesicles. The contribution of the entropy terms in determining the free-energy change becomes more important compared with the enthalpy terms with increased branching of p-substituted phenols. These results suggest that the thermal energy required for and the entropy gain associated with the creation of the cavity in the lipid bilayer is of critical importance in differentiating the process from 1-octanol/water partitioning. In addition, partitioning thermodynamics are significantly influenced by cholesterol content in the lipid membranes. Results of the present study and those in the literature suggest that partitioning processes significantly depend on the physical state of the lipid membranes and log Kow-based quantitative structure-activity relationships should be carefully applied for predicting bioconcentration by considering lipid compositions.
AB - The thermodynamics of partitioning of selected endocrine disruptors between water and synthetic membrane vesicles were investigated. For most of the chemicals investigated, partitioning is dominated by the enthalpy change for unsaturated lipid membrane vesicles and by the entropy contribution for saturated lipid membrane vesicles. The contribution of the entropy terms in determining the free-energy change becomes more important compared with the enthalpy terms with increased branching of p-substituted phenols. These results suggest that the thermal energy required for and the entropy gain associated with the creation of the cavity in the lipid bilayer is of critical importance in differentiating the process from 1-octanol/water partitioning. In addition, partitioning thermodynamics are significantly influenced by cholesterol content in the lipid membranes. Results of the present study and those in the literature suggest that partitioning processes significantly depend on the physical state of the lipid membranes and log Kow-based quantitative structure-activity relationships should be carefully applied for predicting bioconcentration by considering lipid compositions.
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UR - http://www.scopus.com/inward/citedby.url?scp=34250195738&partnerID=8YFLogxK
U2 - 10.1021/es0618200
DO - 10.1021/es0618200
M3 - Article
C2 - 17612183
AN - SCOPUS:34250195738
VL - 41
SP - 4011
EP - 4018
JO - Environmental Science and Technology
JF - Environmental Science and Technology
SN - 0013-936X
IS - 11
ER -