Cited by 289

The DOI matches its Crossref record; 67 of the 67 references it cites were found in a registry or an index.

Capacities of Membrane Lipids to Accumulate Neutral Organic Chemicals

Endo, Satoshi, Escher, Beate I., Goss, Kai-Uwe·2011·Environmental Science & Technology

DOI 10.1021/es200855w

Open this paper in CoChat — free account

Abstract

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 (K(lipw)), reported in the literature or measured additionally for this work, were evaluated. Values of log K(lipw) and log K(ow) (octanol-water partition coefficients) differ by 0.4 on average. Polyparameter linear free energy relationships (PP-LFERs) can describe the log K(lipw) data even better (standard deviations = 0.28-0.31) than the log K(ow) 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 K(lipw) 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.

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

Integrity signals

Registry

Crossref · 10.1021/es200855w

Cites

67 of 67 references verified0 citation errors · 0 not checkable

Statistics

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Environmental Organic Chemistry
Schwarzenbach, R. P., Gschwend, P. M., & Imboden, D. M. (2002) · Wiley eBooks · doi:10.1002/0471649643 · Cited by 4,895
Conductor-like Screening Model for Real Solvents: A New Approach to the Quantitative Calculation of Solvation Phenomena
Klamt, A. (1995) · The Journal of Physical Chemistry · doi:10.1021/j100007a062 · Cited by 4,118
Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processes
Abraham, M. H. (1993) · Chemical Society Reviews · doi:10.1039/cs9932200073 · Cited by 1,968
Liposomes: From Physics to Applications
Lasiç, D. D. (1993) · Cited by 1,304
Physiologically based pharmacokinetic modelling 2: Predicting the tissue distribution of acids, very weak bases, neutrals and zwitterions
Rodgers, T., & Rowland, M. (2006) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.20502 · Cited by 946
Atom/Fragment Contribution Method for Estimating Octanol–Water Partition Coefficients
Meylan, W. M., & Howard, P. H. (1995) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.2600840120 · Cited by 860
Octanol-water partition coefficients of polychlorinated biphenyl congeners
Hawker, D. W., & Connell, D. W. (1988) · Environmental Science & Technology · doi:10.1021/es00169a004 · Cited by 846
Hydrogen Bonding. 32. An Analysis of Water-Octanol and Water-Alkane Partitioning and the Δlog P Parameter of Seiler
Abraham, M. H., Chadha, H. S., Whiting, G. S., & Mitchell, R. C. (1994) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.2600830806 · Cited by 766
Phospholipids Handbook
(2018) · CRC Press eBooks · doi:10.1201/9780203743577 · Cited by 587
CRC handbook of lipid bilayers
Marsh, D. (1990) · Medical Entomology and Zoology · Cited by 430
pH-Metric logP 10. Determination of Liposomal Membrane-Water Partition Coefficients of lonizable Drugs
Avdeef, A., Box, K. J., Comer, J. E. A., Hibbert, C., & Tam, K. Y. (1998) · Pharmaceutical Research · doi:10.1023/a:1011954332221 · Cited by 416
Linear Free Energy Relationships Used To Evaluate Equilibrium Partitioning of Organic Compounds
Goss, K.-U., & Schwarzenbach, R. P. (2001) · Environmental Science & Technology · doi:10.1021/es000996d · Cited by 364
Self-citation
General approach for the calculation of tissue to plasma partition coefficients
Schmitt, W. (2008) · Toxicology in Vitro · doi:10.1016/j.tiv.2007.09.010 · Cited by 349
Absorption and Drug Development: Solubility, Permeability, and Charge State
Avdeef, A. (2003) · Wiley eBooks · doi:10.1002/047145026x · Cited by 349
Partition coefficients of organic compounds in lipid-water systems and correlations with fish bioconcentration factors
Chiou, C. T. (1985) · Environmental Science & Technology · doi:10.1021/es00131a005 · Cited by 328
Prediction of Pharmacokinetics Prior to In Vivo Studies. II. Generic Physiologically Based Pharmacokinetic Models of Drug Disposition
Poulin, P., & Theil, F.-P. (2002) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.10128 · Cited by 303
Bioconcentration. Will water-borne organic chemicals accumulate in aquatic animals?
Barron, M. G. (1990) · Environmental Science & Technology · doi:10.1021/es00081a001 · Cited by 300
A Novel Method for Measuring Membrane-Water Partition Coefficients of Hydrophobic Organic Chemicals: Comparison with 1-Octanol–Water Partitioning
Gobas, F. A. P. C., Lahittete, J. M., Garofalo, G., Shiu, W. Y., & Mackay, D. (1988) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.2600770317 · Cited by 228
Solute partitioning into lipid bilayer membranes
De Young, L. R., & Dill, K. A. (1988) · Biochemistry · doi:10.1021/bi00414a050 · Cited by 226
Pharmacokinetic Optimization in Drug Research: Biological, Physicochemical, and Computational Strategies
(2001) · Wiley eBooks · doi:10.1002/9783906390437 · Cited by 212
Human Skin Permeation and Partition: General Linear Free‐Energy Relationship Analyses
Abraham, M. H., & Martins, F. (2004) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.20070 · Cited by 209
Partitioning of Substituted Phenols in Liposome−Water, Biomembrane−Water, and Octanol−Water Systems
Escher, B. I., & Schwarzenbach, R. P. (1996) · Environmental Science & Technology · doi:10.1021/es9503084 · Cited by 199
Self-citation
Predicting the equilibrium partitioning of organic compounds using just one linear solvation energy relationship (LSER)
Goss, K.-U. (2005) · Fluid Phase Equilibria · doi:10.1016/j.fluid.2005.04.006 · Cited by 196
Self-citation
Lipid Bilayers Driven to a Wrong Lane in Molecular Dynamics Simulations by Subtle Changes in Long-Range Electrostatic Interactions
Patra, M., Karttunen, M., Hyvönen, M. T., Falck, E., & Vattulainen, I. (2004) · The Journal of Physical Chemistry B · doi:10.1021/jp031281a · Cited by 194
Thermodynamic constants for nonelectrolyte partition between dimyristoyl lecithin and water
Katz, Y., & Diamond, J. M. (1974) · The Journal of Membrane Biology · doi:10.1007/bf01870175 · Cited by 192
Partitioning of Ionizing Molecules between Aqueous Buffers and Phospholipid Vesicles
Austin, R. P., Davis, A. M., & Manners, C. N. (1995) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.2600841008 · Cited by 171
Cationic DMPC/DMTAP Lipid Bilayers: Molecular Dynamics Study
Gurtovenko, A. A., Patra, M., Karttunen, M., & Vattulainen, I. (2004) · Biophysical Journal · doi:10.1529/biophysj.103.038760 · Cited by 168
Prediction of the Vapor Pressure Boiling Point, Heat of Vaporization and Diffusion Coefficient of Organic Compounds
Hilal, S. H., Karickhoff, S. W., & Carreira, L. A. (2003) · QSAR & Combinatorial Science · doi:10.1002/qsar.200330812 · Cited by 155
Mechanistic studies on baseline toxicity and uncoupling of organic compounds as a basis for modeling effective membrane concentrations in aquatic organisms
Escher, B. I., & Schwarzenbach, R. P. (2002) · Aquatic Sciences · doi:10.1007/s00027-002-8052-2 · Cited by 152
Self-citation
Solid Phase Microextraction as a Tool To Determine Membrane/Water Partition Coefficients and Bioavailable Concentrations in in Vitro Systems
Vaes, W. H. J., Ramos, E. U., Hamwijk, C., van Holsteijn, I., Blaauboer, B. J., Seinen, W., Verhaar, H. J. M., & Hermens, J. L. M. (1997) · Chemical Research in Toxicology · doi:10.1021/tx970109t · Cited by 151
A data base for partition of volatile organic compounds and drugs from blood/plasma/serum to brain, and an LFER analysis of the data
Abraham, M. H., Ibrahim, A., Zhao, Y. H., & Acree, W. E. (2006) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.20595 · Cited by 149
Bioconcentration Factor Hydrophobicity Cutoff: An Artificial Phenomenon Reconstructed
Jonker, M. T. O., & van der Heijden, S. A. (2007) · Environmental Science & Technology · doi:10.1021/es0709977 · Cited by 147
Partitioning of nonpolar solutes into bilayers and amorphous n-alkanes
de Young, L. D., & Dill, K. (1990) · The Journal of Physical Chemistry · doi:10.1021/j100365a054 · Cited by 142
ACUTE TOXICITY OF NONPOLAR VERSUS POLAR NARCOSIS: IS THERE A DIFFERENCE?
Vaes, W. H. J., Ramos, E. U., Verhaar, H. J. M., & Hermens, J. L. M. (1998) · Environmental Toxicology and Chemistry · doi:10.1002/etc.5620170723 · Cited by 136
Enthalpy of Solvation Correlations for Gaseous Solutes Dissolved in Water and in 1-Octanol Based on the Abraham Model
Mintz, C., Clark, M., Acree, W. E., & Abraham, M. H. (2006) · Journal of Chemical Information and Modeling · doi:10.1021/ci600402n · Cited by 130
Evaluation of Liposome−Water Partitioning of Organic Acids and Bases. 1. Development of a Sorption Model
Escher, B. I., Schwarzenbach, R. P., & Westall, J. C. (2000) · Environmental Science & Technology · doi:10.1021/es0010709 · Cited by 114
Self-citation
Solid Phase Dosing and Sampling Technique To Determine Partition Coefficients of Hydrophobic Chemicals in Complex Matrixes
ter Laak, T. L., Durjava, M. F., Struijś, J., & Hermens, J. L. M. (2005) · Environmental Science & Technology · doi:10.1021/es048406p · Cited by 110
Combination of the CHARMM27 force field with united‐atom lipid force fields
Sapay, N., & Tieleman, D. P. (2010) · Journal of Computational Chemistry · doi:10.1002/jcc.21726 · Cited by 108
Polyparameter Linear Free Energy Models for Polyacrylate Fiber−Water Partition Coefficients to Evaluate the Efficiency of Solid-Phase Microextraction
Endo, S., Droge, S. T. J., & Goss, K. (2011) · Analytical Chemistry · doi:10.1021/ac102868e · Cited by 104
Self-citation
The pH-dependent toxicity of basic pharmaceuticals in the green algae Scenedesmus vacuolatus can be explained with a toxicokinetic ion-trapping model
Neuwoehner, J., & Escher, B. I. (2010) · Aquatic Toxicology · doi:10.1016/j.aquatox.2010.10.008 · Cited by 103
Self-citation
A method for measuring nonelectrolyte partition coefficients between liposomes and water
Katz, Y., & Diamond, J. M. (1974) · The Journal of Membrane Biology · doi:10.1007/bf01870173 · Cited by 96
Partition coefficients in vitro: artificial membranes as a standardized distribution model
Pauletti, G. M., & Wunderli‐Allenspach, H. (1994) · European Journal of Pharmaceutical Sciences · doi:10.1016/0928-0987(94)90022-1 · Cited by 90
Experimental Determination of LSER Parameters for a Set of 76 Diverse Pesticides and Pharmaceuticals
Tülp, H. C., Goss, K., Schwarzenbach, R. P., & Fenner, K. (2008) · Environmental Science & Technology · doi:10.1021/es702473f · Cited by 88
Self-citation
Partition behaviour of acids and bases in a phosphatidylcholine liposome–buffer equilibrium dialysis system
Ottiger, C., & Wunderli‐Allenspach, H. (1997) · European Journal of Pharmaceutical Sciences · doi:10.1016/s0928-0987(97)00278-9 · Cited by 86
Towards the Predictability of Drug-Lipid Membrane Interactions: The pH-Dependent Affinity of Propranolol to Phosphatidylinositol Containing Liposomes
Krämer, S. D., Braun, A., Jakits‐Deiser, C., & Wunderli‐Allenspach, H. (1998) · Pharmaceutical Research · doi:10.1023/a:1011923103938 · Cited by 85
How do protons cross the membrane-solution interface? Kinetic studies on bilayer membranes exposed to the protonophore S-13 (5-chloro-3-tert-butyl-2′-chloro-4′ nitrosalicylanilide)
Kasianowicz, J. J., Benz, R., & McLaughlin, S. (1987) · The Journal of Membrane Biology · doi:10.1007/bf01869632 · Cited by 81
Partition of Volatile Organic Compounds from Air and from Water into Plant Cuticular Matrix: An LFER Analysis
Platts, J. A., & Abraham, M. H. (1999) · Environmental Science & Technology · doi:10.1021/es9906195 · Cited by 79
Acute toxicity of (chloro-)catechols and (chloro-)catechol-copper combinations inEscherichia colicorresponds to their membrane toxicity in vitro
Schweigert, N., Hunziker, R., Escher, B. I., & Eggen, R. I. L. (2001) · Environmental Toxicology and Chemistry · doi:10.1002/etc.5620200203 · Cited by 77
Self-citation
LFERs for Soil Organic Carbon−Water Distribution Coefficients (KOC) at Environmentally Relevant Sorbate Concentrations
Endo, S., Grathwohl, P., Haderlein, S. B., & Schmidt, T. C. (2009) · Environmental Science & Technology · doi:10.1021/es803157e · Cited by 73
Self-citation
Toward a Class-Independent Quantitative Structure−Activity Relationship Model for Uncouplers of Oxidative Phosphorylation
Spycher, S., Smejtek, P., Netzeva, T. I., & Escher, B. I. (2008) · Chemical Research in Toxicology · doi:10.1021/tx700391f · Cited by 72
Self-citation
Partitioning of moderately hydrophobic endocrine disruptors between water and synthetic membrane vesicles
Kwon, J., Liljestrand, H. M., & Katz, L. E. (2006) · Environmental Toxicology and Chemistry · doi:10.1897/05-550r.1 · Cited by 70
Updated Abraham Solvation Parameters for Polychlorinated Biphenyls
van Noort, P. C. M., Haftka, J. J. H., & Parsons, J. R. (2010) · Environmental Science & Technology · doi:10.1021/es102210g · Cited by 69
Retention characteristics of an immobilized artificial membrane column in reversed-phase liquid chromatography
Lepont, C., & Poole, C. F. (2002) · Journal of Chromatography A · doi:10.1016/s0021-9673(01)01579-5 · Cited by 68
Understanding and Estimating Membrane/Water Partition Coefficients: Approaches To Derive Quantitative Structure Property Relationships
Vaes, W. H. J., Ramos, E. U., Verhaar, H. J. M., Cramer, C. J., & Hermens, J. L. M. (1998) · Chemical Research in Toxicology · doi:10.1021/tx970210y · Cited by 68
Partitioning of Selected Estrogenic Compounds between Synthetic Membrane Vesicles and Water: Effects of Lipid Components
Yamamoto, H., & Liljestrand, H. M. (2004) · Environmental Science & Technology · doi:10.1021/es034311w · Cited by 64
Evaluation of Liposome−Water Partitioning for Predicting Bioaccumulation Potential of Hydrophobic Organic Chemicals
van der Heijden, S. A., & Jonker, M. T. O. (2009) · Environmental Science & Technology · doi:10.1021/es902278x · Cited by 64
Development of a dynamic delivery method for in vitro bioassays
Kwon, J., Wuethrich, T., Mayer, P., & Escher, B. I. (2009) · Chemosphere · doi:10.1016/j.chemosphere.2009.02.023 · Cited by 62
Self-citation
Functional group contributions to the partitioning of phenols between liposomes and water
Rogers, J. A., & Davis, S. S. (1980) · Biochimica et Biophysica Acta (BBA) - Biomembranes · doi:10.1016/0005-2736(80)90017-6 · Cited by 61
Pyrene metabolites in the hepatopancreas and gut of the isopod porcellio scaber, a new biomarker for polycyclic aromatic hydrocarbon exposure in terrestrial ecosystems
Stroomberg, G. J., de Knecht, J. A., Ariese, F., van Gestel, C. A. M., & Velthorst, N. H. (1999) · Environmental Toxicology and Chemistry · doi:10.1002/etc.5620181014 · Cited by 58
MEMBRANE BURDENS OF CHLORINATED BENZENES LOWER THE MAIN PHASE TRANSITION TEMPERATURE IN DIPALMITOYL-PHOSPHATIDYLCHOLINE VESICLES: IMPLICATIONS FOR TOXICITY BY NARCOTIC CHEMICALS
van Wezel, A. P., Cornelissen, G., van Miltenburg, J. C., & Opperhuizen, A. (1996) · Environmental Toxicology and Chemistry · doi:10.1002/etc.5620150219 · Cited by 56
Membrane-Water Partitioning of Polychlorinated Biphenyls in Small Unilamellar Vesicles of Four Saturated Phosphatidylcholines
Dulfer, W. J., & Govers, H. A. J. (1995) · Environmental Science & Technology · doi:10.1021/es00010a014 · Cited by 56
Nature of alcohol and anesthetic action on cooperative membrane equilibria.
Janes, N., Hsu, J. W., Rubin, E., et al. (1992) · Biochemistry · doi:10.1021/bi00154a020 · Cited by 52
Solubility of organic chemicals in octanol, triolein and cod liver oil and relationships between solubility and partition coefficients
Niimi, A. J. (1991) · Water Research · doi:10.1016/0043-1354(91)90182-p · Cited by 47
Characterization of the retention behavior of organic and pharmaceutical drug molecules on an immobilized artificial membrane column with the Abraham model
Sprunger, L. M., Blake-Taylor, B. H., Wairegi, A., Acree, W. E., & Abraham, M. H. (2007) · Journal of Chromatography A · doi:10.1016/j.chroma.2007.05.051 · Cited by 38
Comments regarding “predicting the equilibrium partitioning of organic compounds using just one linear solvation energy relationship (LSER)”
Flanagan, K. B., Acree, W. E., & Abraham, M. H. (2005) · Fluid Phase Equilibria · doi:10.1016/j.fluid.2005.08.003 · Cited by 27
Bioaccumulation potential of air contaminants: Combining biological allometry, chemical equilibrium and mass-balances to predict accumulation of air pollutants in various mammals
Veltman, K., McKone, T. E., Huijbregts, M. A. J., & Hendriks, A. J. (2009) · Toxicology and Applied Pharmacology · doi:10.1016/j.taap.2009.04.012 · Cited by 21
Mathematical Correlations for Gas‐to‐Olive Oil, Gas‐to‐Saline Solution, and Saline Solution‐to‐Olive Oil Partition Coefficients Based on the Goss Modified Abraham Model
Sprunger, L. M., Acree, W. E., & Abraham, M. H. (2008) · QSAR & Combinatorial Science · doi:10.1002/qsar.200860003 · Cited by 18

Applications of Polyparameter Linear Free Energy Relationships in Environmental Chemistry
Endo, S., & Goss, K.-U. (2014) · Environmental Science & Technology · doi:10.1021/es503369t · Cited by 302
Self-citation
A modeling assessment of the physicochemical properties and environmental fate of emerging and novel per- and polyfluoroalkyl substances
Gomis, M. I., Wang, Z., Scheringer, M., & Cousins, I. T. (2015) · Science of The Total Environment · doi:10.1016/j.scitotenv.2014.10.062 · Cited by 211
Cytotoxicity Burst? Differentiating Specific from Nonspecific Effects in Tox21 in Vitro Reporter Gene Assays
Escher, B. I., Henneberger, L., König, M., Schlichting, R., & Fischer, F. C. (2020) · Environmental Health Perspectives · doi:10.1289/ehp6664 · Cited by 123
Self-citation
Membrane-water partition coefficients to aid risk assessment of perfluoroalkyl anions and alkyl sulfates
Droge, S. T. J. (2019) · Environmental Science & Technology · doi:10.1021/acs.est.8b05052 · Cited by 112
Predicting Partition Coefficients of Polyfluorinated and Organosilicon Compounds using Polyparameter Linear Free Energy Relationships (PP-LFERs)
Endo, S., & Goss, K.-U. (2014) · Environmental Science & Technology · doi:10.1021/es405091h · Cited by 61
Self-citation

See all 289

Authors: Endo, S., Escher, B. I., & Goss, K.-U.
Venue: Environmental Science & Technology
Publisher: American Chemical Society (ACS)
Published: 2011-06-28
Volume: 45
Issue: 14
Pages: 5912-5921
ISSN: 0013-936X (ISSN-L)
1520-5851
DOI: 10.1021/es200855w
OpenAlex: W1990458835
Cited by: 289
References: 67
FWCI: 13.08
Type: journal article
Language: en
Open access: closed

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

Data sources

Bibliographic data: Semantic Scholar, OpenAlex, Crossref.

Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).

Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.

Capacities of Membrane Lipids to Accumulate Neutral Organic Chemicals

Abstract

Overview

Integrity signals

Verification

Claims the paper makes

Self-check

Citations

Cites

Cited by

Metadata

Record

About these checks

Data sources