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Biological cleavage of the C-P bond in perfluoroalkyl phosphinic acids in male Sprague-Dawley rats and the formation of persistent and reactive metabolites
Department of Chemistry, University of Toronto, Toronto ON, Canada.
Örebro University, School of Science and Technology. Department of Chemistry, University of Toronto, Toronto ON, Canada. (Man-Technology-Environment (MTM) Research Centre)ORCID iD: 0000-0001-6800-5658
Department of Chemistry, University of Toronto, Toronto ON, Canada.
2017 (English)In: Journal of Environmental Health Perspectives, ISSN 0091-6765, E-ISSN 1552-9924, Vol. 125, no 11, 117001Article in journal (Refereed) Published
Abstract [en]

BACKGROUND: Perfluoroalkyl phosphinic acids (PFPiAs) have been detected in humans, wildlife, and various environmental matrices. These compounds have been used with perfluoroalkyl phosphonic acids (PFPAs) as surfactants in consumer products and as nonfoaming additives in pesticide formulations. Unlike the structurally related perfluoroalkyl sulfonic and carboxylic acids, little is known about the biological fate of PFPiAs.

OBJECTIVES: We determined the biotransformation products of PFPiAs and some pharmacokinetic parameters in a rat model.

METHODS: Male Sprague-Dawley rats received an oral gavage dose of either C6/C8PFPiA, C8/C8PFPiA, or C8PFPA. Blood was sampled over time, and livers were harvested upon sacrifice. Analytes were quantified using ultra-high-performance liquid chromatography-tandem mass spectrometry or gas chromatography-mass spectrometry.

RESULTS: PFPiAs were metabolized to the corresponding PFPAs and 1H-perfluoroalkanes (1H-PFAs), with 70% and 75% biotransformation 2 wk after a single bolus dose for C6/C8PFPiA and C8/C8PFPiA, respectively. This is the first reported cleavage of a C-P bond in mammals, and the first attempt, with a single-dose exposure, to characterize the degradation of any perfluoroalkyl acid. Elimination half-lives were 1.9±0.5 and 2.8±0.8 days for C6/C8PFPiA and C8/C8PFPiA, respectively, and 0.95±0.17 days for C8PFPA. Although elimination half-lives were not determined for 1H-PFAs, concentrations were higher than the corresponding PFPAs 48 h after rats were dosed with PFPiAs, suggestive of slower elimination.

CONCLUSIONS: PFPiAs were metabolized in Sprague-Dawley rats to form persistent PFPAs as well as 1H-PFAs, which contain a labile hydrogen that may undergo further metabolism. These results in rats produced preliminary findings of the pharmacokinetics and metabolism of PFPiAs, which should be further investigated in humans. If there is a parallel between the disposition of these chemicals in humans and rats, then humans with detectable amounts of PFPiAs in their blood may be undergoing continuous exposure.

Place, publisher, year, edition, pages
National Institute of Environmental Health Sciences (NIEHS) , 2017. Vol. 125, no 11, 117001
National Category
Environmental Sciences
Identifiers
URN: urn:nbn:se:oru:diva-63315DOI: 10.1289/EHP1841ISI: 000416837300004PubMedID: 29135439Scopus ID: 2-s2.0-85033388855OAI: oai:DiVA.org:oru-63315DiVA: diva2:1165031
Note

Funding Agency:

National Science and Engineering Research Council Discovery grant

Available from: 2017-12-12 Created: 2017-12-12 Last updated: 2017-12-19Bibliographically approved

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Yeung, Leo W. Y.

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