Isomer-Specific Binding Affinity of Perfluorooctanesulfonate (PFOS) and Perfluorooctanoate (PFOA) to Serum Proteins. 2015

Sanjay Beesoon, and Jonathan W Martin

Perfluorooctanesulfonate (PFOS) and perfluorooctanoate (PFOA) are among the most prominent contaminants in human serum, and these were historically manufactured as technical mixtures of linear and branched isomers. The isomers display unique pharmacokinetics in humans and in animal models, but molecular mechanisms underlying isomer-specific PFOS and PFOA disposition have not previously been studied. Here, ultrafiltration devices were used to examine (i) the dissociation constants (Kd) of individual PFOS and PFOA isomers with human serum albumin (HSA) and (ii) relative binding affinity of isomers in technical mixtures spiked to whole calf serum and human serum. Measurement of HSA Kd's demonstrated that linear PFOS (Kd=8(±4)×10(-8) M) was much more tightly bound than branched PFOS isomers (Kd range from 8(±1)×10(-5) M to 4(±2)×10(-4) M). Similarly, linear PFOA (Kd=1(±0.9)×10(-4) M) was more strongly bound to HSA compared to branched PFOA isomers (Kd range from 4(±2)×10(-4) M to 3(±2)×10(-4) M). The higher binding affinities of linear PFOS and PFOA to total serum protein were confirmed when both calf serum and human serum were spiked with technical mixtures. Overall, these data provide a mechanistic explanation for the longer biological half-life of PFOS in humans, compared to PFOA, and for the higher transplacental transfer efficiencies and renal clearance of branched PFOS and PFOA isomers, compared to the respective linear isomer.

UI MeSH Term Description Entries
D007536 Isomerism The phenomenon whereby certain chemical compounds have structures that are different although the compounds possess the same elemental composition. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Isomerisms
D007700 Kinetics The rate dynamics in chemical or physical systems.
D002210 Caprylates Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure. Caprylate,Octanoates,Caprylic Acids,Octanoic Acids,Acids, Caprylic,Acids, Octanoic
D002417 Cattle Domesticated bovine animals of the genus Bos, usually kept on a farm or ranch and used for the production of meat or dairy products or for heavy labor. Beef Cow,Bos grunniens,Bos indicus,Bos indicus Cattle,Bos taurus,Cow,Cow, Domestic,Dairy Cow,Holstein Cow,Indicine Cattle,Taurine Cattle,Taurus Cattle,Yak,Zebu,Beef Cows,Bos indicus Cattles,Cattle, Bos indicus,Cattle, Indicine,Cattle, Taurine,Cattle, Taurus,Cattles, Bos indicus,Cattles, Indicine,Cattles, Taurine,Cattles, Taurus,Cow, Beef,Cow, Dairy,Cow, Holstein,Cows,Dairy Cows,Domestic Cow,Domestic Cows,Indicine Cattles,Taurine Cattles,Taurus Cattles,Yaks,Zebus
D005466 Fluorocarbons Liquid perfluorinated carbon compounds which may or may not contain a hetero atom such as nitrogen, oxygen or sulfur, but do not contain another halogen or hydrogen atom. This concept includes fluorocarbon emulsions, and fluorocarbon blood substitutes. Perfluorinated and related polyfluorinated chemicals are referred to as PFAS and are defined as chemicals with at least two adjacent carbon atoms, where one carbon is fully fluorinated and the other is at least partially fluorinated. Fluorocarbon,Fluorocarbon Emulsion,Fluorocarbon Emulsions,Fluorotelomer Phosphate Esters,N-Alkyl Perfluoroalkyl Sulfonamido Carboxylates,PFAS Per- and Polyfluoroalkyl Substances,PFC Perfluorinated Chemicals,PFECAs Perfluoropolyether Carboxylic Acids,Per- and Polyfluoroalkyl Substances,Perfluoroalkane Sulfonamides,Perfluoroalkyl Carboxylates,Perfluoroalkyl Ether Carboxylates,Perfluoroalkyl Polyether Carboxylates,Perfluorocarbon,Perfluorocarbons,Perfluoropolyether Carboxylic Acids,Polyfluorocarbons,Fluorinated Telomer Alcohols,Fluoro-Telomer Alcohols,Polyfluorinated Telomer Alcohols,Telomer Fluorocarbons,Acids, Perfluoropolyether Carboxylic,Alcohols, Fluorinated Telomer,Alcohols, Fluoro-Telomer,Alcohols, Polyfluorinated Telomer,Carboxylates, Perfluoroalkyl,Carboxylates, Perfluoroalkyl Ether,Carboxylates, Perfluoroalkyl Polyether,Carboxylic Acids, Perfluoropolyether,Chemicals, PFC Perfluorinated,Emulsion, Fluorocarbon,Emulsions, Fluorocarbon,Esters, Fluorotelomer Phosphate,Ether Carboxylates, Perfluoroalkyl,Fluoro Telomer Alcohols,Fluorocarbons, Telomer,N Alkyl Perfluoroalkyl Sulfonamido Carboxylates,PFAS Per and Polyfluoroalkyl Substances,Per and Polyfluoroalkyl Substances,Perfluorinated Chemicals, PFC,Phosphate Esters, Fluorotelomer,Polyether Carboxylates, Perfluoroalkyl,Sulfonamides, Perfluoroalkane,Telomer Alcohols, Fluorinated,Telomer Alcohols, Polyfluorinated
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D001665 Binding Sites The parts of a macromolecule that directly participate in its specific combination with another molecule. Combining Site,Binding Site,Combining Sites,Site, Binding,Site, Combining,Sites, Binding,Sites, Combining
D012709 Serum Albumin A major protein in the BLOOD. It is important in maintaining the colloidal osmotic pressure and transporting large organic molecules. Plasma Albumin,Albumin, Serum
D017738 Alkanesulfonic Acids Sulfonic acid derivatives that are substituted with an aliphatic hydrocarbon group. Acids, Alkanesulfonic

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