ArticleJournal of the American Chemical Society2009
High lipophilicity of perfluoroalkyl carboxylate and sulfonate: implications for their membrane permeability.
Article in Journal of the American Chemical Society, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
25 citing papers in PubMed, 153 citations in OpenAlex.
- Sensitive determination and discrimination of fluorinated ions using ion-transfer voltammetry.Analytical sciences : the international journal of the Japan Society for Analytical Chemistry · 2026Article
- Review
- Toward Comprehensive In Vitro Evaluation of Serum Albumin Binding of Per- and Polyfluoroalkyl Substances.Journal of xenobiotics · 2026Review
- Seasonal Shift in Exposure and Accumulation of PFAS and Heavy Metals in High Arctic Reindeer.Environmental science & technology · 2026Article
- Perfluorooctanoic acid (PFOA) induces lipid accumulation, oxidative stress, and reduced neurogenesis in primary human neuronal progenitor cells.Frontiers in toxicology · 2026Article
- Membrane-Modifying Effects of Perfluoroalkyl Substances in Model Bacterial Membranes.ACS omega · 2025Article
- Biophysical Consequences for Exposure of Model Cell Membranes to Perfluoroalkyl Substances.The journal of physical chemistry. B · 2025Article
- Effect of the alkyl chain length of α,ω-dichloroalkane on the Gibbs energy of transfer for functional groups.Analytical sciences : the international journal of the Japan Society for Analytical Chemistry · 2024Article
- Single-molecule profiling of per- and polyfluoroalkyl substances by cyclodextrin mediated host-guest interactions within a biological nanopore.Science advances · 2024Article
- Perfluoroalkyl functionalized-Au nanoparticle sensor: Employing rate of spectrum shifting for highly selective and sensitive detection of per- and polyfluoroalkyl substances (PFASs) in aqueous environments.Water research X · 2024Article
- From Polyester Plastics to Diverse Monomers via Low-Energy Upcycling.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Determining the Surface pThe journal of physical chemistry. C, Nanomaterials and interfaces · 2024Article
- Associations of perfluoroalkyl substances (PFAS) with lipid and lipoprotein profiles.Journal of exposure science & environmental epidemiology · 2023Article
- Nanoelectrochemistry at liquid/liquid interfaces for analytical, biological, and material applications.Chemical communications (Cambridge, England) · 2023Review
- Article
- Adverse PFAS effects on mouse oocyte in vitro maturation are associated with carbon-chain length and inclusion of a sulfonate group.Cell proliferation · 2023Article
- An Overview of NRF2-Activating Compounds Bearing α,β-Unsaturated Moiety and Their Antioxidant Effects.International journal of molecular sciences · 2022Review
- Calculation of Permeability Coefficients from Solute Equilibration Dynamics: An Assessment of Various Methods.Membranes · 2022Article
- Fluorination Effect on the Gibbs Transfer Energy for Methylene Group from 1,2-Dichloroethane or 1,1,1,2,3,4,4,5,5,5-Decafluoropentane to Water.Analytical sciences : the international journal of the Japan Society for Analytical Chemistry · 2021Article
- Assessing the Ecological Risks of Per- and Polyfluoroalkyl Substances: Current State-of-the Science and a Proposed Path Forward.Environmental toxicology and chemistry · 2021Review
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Here we report on remarkably high lipophilicity of perfluoroalkyl carboxylate and sulfonate. A lipophilic nature of this emerging class of organic pollutants has been hypothesized as an origin of their bioaccumulation and toxicity. Both carboxylate and sulfonate, however, are considered hydrophilic while perfluroalkyl groups are not only hydrophobic but also oleophobic. Partition coefficients of a homologous series of perfluoroalkyl and alkyl carboxylates between water and n-octanol were determined as a measure of their lipophilicity by ion-transfer cyclic voltammetry. Very similar lipophilicity of perfluoroalkyl and alkyl chains with the same length is demonstrated experimentally for the first time by fragment analysis of the partition coefficients. This finding is important for pharmaceutical and biomedical applications of perfluoroalkyl compounds. Interestingly, approximately 2 orders of magnitude higher lipophilicity of a perfluoroalkyl carboxylate or sulfonate in comparison to its alkyl counterpart is ascribed nearly exclusively to their oxoanion groups. The higher lipophilicity originates from a strong electron-withdrawing effect of the perfluoroalkyl group on the adjacent oxoanion group, which is weakly hydrated to decrease its hydrophilicity. In fact, the inductive effect is dramatically reduced for a fluorotelomer with an ethylene spacer between perfluorohexyl and carboxylate groups, which is only as lipophilic as its alkyl counterpart, nonanoate, and is 400 times less lipophilic than perfluorononanoate. The high lipophilicity of perfluoroalkyl carboxylate and sulfonate implies that their permeation across such a thin lipophilic membrane as a bilayer lipid membrane is limited by their transfer at a membrane/water interface. The limiting permeability is lower and less dependent on their lipophilicity than the permeability controlled by their diffusion in the membrane interior as assumed in the classical solubility-diffusion model.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.