A Novel Method for Measuring Membrane-Water Partition Coefficients of Hydrophobic Organic Chemicals: Comparison with 1-Octanol–Water Partitioning

Gobas, Frank A.P.C.; Lahittete, Jean M.; Garofalo, Gil; Shiu, Wan Ying; Mackay, Donald

doi:10.1002/jps.2600770317

Cited by 231 publications

(198 citation statements)

References 30 publications

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“…An exponential decrease of the lipid-water partition coefficients with increasing cross-sectional areas is supported by earlier measurements showing an exponential decrease of binding (Gobas et al, 1988) to −, and permeation through (Lieb & Stein, 1986) lipid membranes with increasing molecular volume.…”

Section: Discussionsupporting

confidence: 70%

“…Quite in contrast to the partitioning into lipid membranes, partitioning into isotropic solvents like hexane or octanol has been shown to increase with the molecular volume of the compound (Gobas et al, 1988). Predictions of passive diffusion through the BBB based on partition coefficient measurements between water and either isotropic solvents or loosely packed anisotropic systems with low lateral packing densities ( < 32 mN/m) will therefore be misleading for molecules with large cross-sectional areas.…”

Section: Discussionmentioning

confidence: 99%

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Blood-Brain Barrier Permeation: Molecular Parameters Governing Passive Diffusion

Fischer

Gottschlich

Seelig

1998

Journal of Membrane Biology

343

302

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Abstract. 53 compounds with clinically established ability to cross or not to cross the blood-brain barrier by passive diffusion were characterized by means of surface activity measurements in terms of three parameters, i.e., the air-water partition coefficient, K aw , the critical micelle concentration, CMC D , and the cross-sectional area, A D . A three-dimensional plot in which the surface area, A D , is plotted as a function of K −1 aw and CMC D shows essentially three groups of compounds: (i) very hydrophobic compounds with large air-water partition coefficients and large cross-sectional areas, A D > 80 Å 2 which do not cross the blood-brain barrier, (ii) compounds with lower air-water partition coefficients and an average cross-sectional area, A D ≅ 50 Å 2 which easily cross the blood-brain barrier, and (iii) hydrophilic compounds with low air-water partition coefficients (A D < 50 Å 2 ) which cross the blood-brain barrier only if applied at high concentrations. It was shown that the lipid membrane-water partition coefficient, K lw , measured previously, can be correlated with the air-water partition coefficient if the additional work against the internal lateral bilayer pressure, bi ‫ס‬ 34 ± 4 mN/m is taken into account. The partitioning into anisotropic lipid membranes decreases exponentially with increasing cross-sectional areas, A D , according to K lw ‫ס‬ const. K aw exp(−A D bi /kT) where kT is the thermal energy. The cross-sectional area of the molecule oriented at a hydrophilic-hydrophobic interface is thus the main determinant for membrane permeation provided the molecule is surface active and has a pK a > 4 for acids and a pK a < 10 for bases.

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Section: Discussionsupporting

confidence: 70%

Section: Discussionmentioning

confidence: 99%

Blood-Brain Barrier Permeation: Molecular Parameters Governing Passive Diffusion

Fischer

Gottschlich

Seelig

1998

Journal of Membrane Biology

343

302

View full text Add to dashboard Cite

show abstract

“…This phenomenon might mainly result from the following two reasons. (1) Very hydrophobic chemicals with log K ow higher than 5 have so large molecular dimensions that they might not be able to permeate fish membranes, as the energy for cavity formation is too high (Gobas et al, 1988). (2) In this study, solvent extractions result in higher C w for PAHs having a log K ow > 5.5.…”

Section: Dongjiangmentioning

confidence: 81%

In-situ partitioning and bioconcentration of polycyclic aromatic hydrocarbons among water, suspended particulate matter, and fish in the Dongjiang and Pearl Rivers and the Pearl River Estuary, China

Huang

et al. 2014

Marine Pollution Bulletin

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“…However, as has been proposed by Anliker and Moser (1987) and Banerjee and Baughman (1991) the lipid solubility of relatively large hydrophobic compounds decreases with increasing Kow. Gobas et al (1988) determined partition coefficients between n-octanol, n-hexane or e-aphosphatidylcholine dimyristoyl (DMPC) membranes and water. They found that for nonpolar chemicals with log Kow values > 5.5, the membrane water partition coefficients (Kmw) did not show a linear increase with larger octanol/water partition coefficients.…”

Section: Relationship Between Log Bcf and Log Kow-valuesmentioning

confidence: 99%

Bioconcentration of polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans in guppies after aqueous exposure to a complex PCDD/PCDF mixture: relationship with molecular structure

et al. 1994

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Bioconcentration of polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans in guppies after aqueous exposure to a complex PCDD/PCDF mixture: relationship with molecular structure. Loonen, H.E.W.M.; Tonkes, M.; Parsons, J.R.; Govers, H.A.J. Disclaimer/Complaints regulationsIf you believe that digital publication of certain material infringes any of your rights or (privacy) interests, please let the Library know, stating your reasons. In case of a legitimate complaint, the Library will make the material inaccessible and/or remove it from the website. Please Ask the Library: http://uba.uva.nl/en/contact, or a letter to: Library of the University of Amsterdam, Secretariat, Singel 425, 1012 WP Amsterdam, The Netherlands. You will be contacted as soon as possible. AbstractGuppies (Poecilia reticulata) were exposed to a complex mixture of polychlorinated dibenzop-dioxins (PCDDs) and polychlorinated dibenzofurans (PCDFs) in water for 21 days. It is the first study in which accumulation data of 15 toxic dioxins and furans were quantified simultaneously in a continuous exposure experiment. First-order uptake rate constants (kl) and firstorder elimination rate constants (k2) were calculated for the toxic, laterally substituted congeners. Bioconcentration factors (BCFs) were calculated from both the ratios of concentrations in fish and water and from the ratios of the rate constants. Dioxins and furans were selectively accumulated in fish tissue. The non-laterally substituted congeners were either not observed in fish tissue or showed lower BCF values than their laterally 2,3,7,8-substituted isomers. The log BCF values of laterally substituted congeners ranged from 3.90 + 0.06 to 5.27 + 0.07. BCF values were smaller than predicted by existing linear relationships with log Kow. Several phenomena were discussed with respect to the observed bioconcentration behaviour, such as limited bioavailability, reduced lipid solubility, reduced membrane permeability and biotransformation. Furthermore, the similarity between structure-activity relationships considering bioaccumulation in fishes and the Ah-affinity in mammals was discussed.

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A Novel Method for Measuring Membrane-Water Partition Coefficients of Hydrophobic Organic Chemicals: Comparison with 1-Octanol–Water Partitioning

Cited by 231 publications

References 30 publications

Blood-Brain Barrier Permeation: Molecular Parameters Governing Passive Diffusion

Blood-Brain Barrier Permeation: Molecular Parameters Governing Passive Diffusion

In-situ partitioning and bioconcentration of polycyclic aromatic hydrocarbons among water, suspended particulate matter, and fish in the Dongjiang and Pearl Rivers and the Pearl River Estuary, China

Bioconcentration of polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans in guppies after aqueous exposure to a complex PCDD/PCDF mixture: relationship with molecular structure

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