Abstract
The partition coefficient between water and lipid membrane vesicles (K lipw) has been used as an alternative to the 1-octanol-water partition coefficient (Kow) between water and organic solvent, because it more closely represents actual biological membranes. Despite theoretical differences, log Klipw correlates well with log K ow for conventional nonpolar organic pollutants. In the present study, Klipw values of 11 structurally diverse endocrine-disrupting chemicals (EDCs) were measured for three different types of lipid membrane vesicles from dipalmitoylphosphatidylcholine (DPPC), DPPC/cholesterol, and palmitoyloleoylphosphatidylcholine. Correlation analyses were conducted to evaluate the effects of hydrophobicity, molar liquid volume (MLV), and polar surface area (PSA) for 20 EDCs, including nine from a previous study. Correlations that include MLV and PSA reduce the predicted value of log K lipw, suggesting that lipid membranes are less favorable than 1-octanol for a hydrophobic solute because of the higher molar volume and higher hydrogen-bonding potential. These results suggested that Kow alone has limited potential for estimating Klipw and that additional descriptors are required. In addition, Klipw values vary by as much as two orders of magnitude because of the changes in membrane fluidity and the amount of cholesterol in the lipid bilayer. Therefore, lipid components should be chosen carefully to evaluate the bioconcentration of these compounds.
| Original language | English |
|---|---|
| Pages (from-to) | 1984-1992 |
| Number of pages | 9 |
| Journal | Environmental Toxicology and Chemistry |
| Volume | 25 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - 2006 Aug 1 |
| Externally published | Yes |
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Keywords
- Bioconcentration
- Endocrine disrupters
- Lipid bilayer
- Partitioning
ASJC Scopus subject areas
- Environmental Science(all)
- Environmental Chemistry
- Health, Toxicology and Mutagenesis
- Toxicology
Cite this
Partitioning of moderately hydrophobic endocrine disruptors between water and synthetic membrane vesicles. / Kwon, Jung-Hwan; Liljestrand, Howard M.; Katz, Lynn E.
In: Environmental Toxicology and Chemistry, Vol. 25, No. 8, 01.08.2006, p. 1984-1992.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Partitioning of moderately hydrophobic endocrine disruptors between water and synthetic membrane vesicles
AU - Kwon, Jung-Hwan
AU - Liljestrand, Howard M.
AU - Katz, Lynn E.
PY - 2006/8/1
Y1 - 2006/8/1
N2 - The partition coefficient between water and lipid membrane vesicles (K lipw) has been used as an alternative to the 1-octanol-water partition coefficient (Kow) between water and organic solvent, because it more closely represents actual biological membranes. Despite theoretical differences, log Klipw correlates well with log K ow for conventional nonpolar organic pollutants. In the present study, Klipw values of 11 structurally diverse endocrine-disrupting chemicals (EDCs) were measured for three different types of lipid membrane vesicles from dipalmitoylphosphatidylcholine (DPPC), DPPC/cholesterol, and palmitoyloleoylphosphatidylcholine. Correlation analyses were conducted to evaluate the effects of hydrophobicity, molar liquid volume (MLV), and polar surface area (PSA) for 20 EDCs, including nine from a previous study. Correlations that include MLV and PSA reduce the predicted value of log K lipw, suggesting that lipid membranes are less favorable than 1-octanol for a hydrophobic solute because of the higher molar volume and higher hydrogen-bonding potential. These results suggested that Kow alone has limited potential for estimating Klipw and that additional descriptors are required. In addition, Klipw values vary by as much as two orders of magnitude because of the changes in membrane fluidity and the amount of cholesterol in the lipid bilayer. Therefore, lipid components should be chosen carefully to evaluate the bioconcentration of these compounds.
AB - The partition coefficient between water and lipid membrane vesicles (K lipw) has been used as an alternative to the 1-octanol-water partition coefficient (Kow) between water and organic solvent, because it more closely represents actual biological membranes. Despite theoretical differences, log Klipw correlates well with log K ow for conventional nonpolar organic pollutants. In the present study, Klipw values of 11 structurally diverse endocrine-disrupting chemicals (EDCs) were measured for three different types of lipid membrane vesicles from dipalmitoylphosphatidylcholine (DPPC), DPPC/cholesterol, and palmitoyloleoylphosphatidylcholine. Correlation analyses were conducted to evaluate the effects of hydrophobicity, molar liquid volume (MLV), and polar surface area (PSA) for 20 EDCs, including nine from a previous study. Correlations that include MLV and PSA reduce the predicted value of log K lipw, suggesting that lipid membranes are less favorable than 1-octanol for a hydrophobic solute because of the higher molar volume and higher hydrogen-bonding potential. These results suggested that Kow alone has limited potential for estimating Klipw and that additional descriptors are required. In addition, Klipw values vary by as much as two orders of magnitude because of the changes in membrane fluidity and the amount of cholesterol in the lipid bilayer. Therefore, lipid components should be chosen carefully to evaluate the bioconcentration of these compounds.
KW - Bioconcentration
KW - Endocrine disrupters
KW - Lipid bilayer
KW - Partitioning
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UR - http://www.scopus.com/inward/citedby.url?scp=33751068776&partnerID=8YFLogxK
U2 - 10.1897/05-550R.1
DO - 10.1897/05-550R.1
M3 - Article
VL - 25
SP - 1984
EP - 1992
JO - The BMJ
JF - The BMJ
SN - 0730-6512
IS - 8
ER -