The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Biotransformation of N-Ethyl Perfluorooctanesulfonamide by Rainbow Trout (Onchorhynchus mykiss) Liver Microsomes
Abstract
Rainbow trout (Onchorhynchus mykiss) liver microsomes were incubated with N-ethyl perfluorooctanesulfonamide [N-EtPFOSA, C8F17SO2NH(C2H5)], to examine the possibility of in vitro biotransformation to perfluorooctane sulfonate (PFOS, C8F17SO3-) and perfluorooctanoate (PFOA, C7F15COO-). Incubations were performed by exposing trout liver microsomes to N-EtPFOSA at 8 degrees C in the dark. Reaction mixtures were analyzed after incubation periods of 0, 2, 4, 8, 16, and 30 h for N-EtPFOSA, PFOS, PFOA, and perfluorooctanesulfonamide (PFOSA, C8F17SO2NH2), a suspected intermediate. Amounts of PFOS and PFOSA were found to increase with incubation time, but only background levels of PFOA were detected. Three possible reaction pathways are proposed for the conversion of N-EtPFOSA to PFOS: (i) direct conversion of N-EtPFOSA to PFOS by deethylamination accompanied by conversion of the sulfone group to sulfonate, (ii) deethylation of N-EtPFOSA to PFOSA, followed by deamination to form PFOS, and (iii) direct hydrolysis of N-EtPFOSA. These findings represent the first report indicating a possible biotransformation of a perfluorosulfonamide to PFOS in fish and may help to explain the detection of PFOS, which is relatively involatile, and thus not likely to undergo atmospheric transport, in biota from remote regions.
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Cites
Global Distribution of Perfluorooctane Sulfonate in Wildlife
Giesy, J. P., & Kannan, K. (2001) · Environmental Science & Technology · doi:10.1021/es001834k · Cited by 2,750
Compound-specific, quantitative characterization of organic fluorochemicals in biological matrices
Hansen, K. J., Clemen, L. A., Ellefson, M. E., & Johnson, H. O. (2001) · Environmental Science & Technology · doi:10.1021/es001489z · Cited by 923
Martin, J. W., Muir, D. C. G., Moody, C. A., Ellis, D. A., Kwan, W. C., Solomon, K. R., & Mabury, S. A. (2002) · Analytical Chemistry · doi:10.1021/ac015630d · Cited by 299
Cited by
Buck, R. C., Franklin, J., Berger, U., Conder, J. M., Cousins, I. T., de Voogt, P., Jensen, A. A., Kannan, K., Mabury, S. A., & van Leeuwen, S. P. (2011) · Integrated Environmental Assessment and Management · doi:10.1002/ieam.258 · Cited by 4,641
Monitoring of Perfluorinated Compounds in Aquatic Biota: An Updated Review: PFCs in Aquatic Biota
Houde, M., De Silva, A. O., Muir, D. C. G., & Letcher, R. J. (2011) · Environmental Science & Technology · doi:10.1021/es104326w · Cited by 847
Xiao, F. (2017) · Water Research · doi:10.1016/j.watres.2017.07.024 · Cited by 634
Taniyasu, S., Kannan, K., So, M. K., Gulkowska, A., Sinclair, E., Okazawa, T., & Yamashita, N. (2005) · Journal of Chromatography A · doi:10.1016/j.chroma.2005.07.053 · Cited by 602
Perfluorinated compounds in aquatic organisms at various trophic levels in a Great Lakes food chain
Kannan, K., Tao, L., Sinclair, E., Pastva, S. D., Jude, D. J., & Giesy, J. P. (2005) · Archives of Environmental Contamination and Toxicology · doi:10.1007/s00244-004-0133-x · Cited by 530
Metadata
- Authors
- Tomy, G. T., Tittlemier, S. A., Palace, V. P., Budakowski, W. R., Braekevelt, E., Brinkworth, L., & Friesen, K.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-12-03
- Volume
- 38
- Issue
- 3
- Pages
- 758-762
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W2003525539
- Cited by
- 232
- References
- 3
- FWCI
- 7.33
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Biotransformation of N-Ethyl Perfluorooctanesulfonamide by Rainbow Trout (Onchorhynchus mykiss) Liver Microsomes. https://app.cochat.ai/papers/10.1021/es034550j
- The paper
- Tomy, G. T., Tittlemier, S. A., Palace, V. P., Budakowski, W. R., Braekevelt, E., Brinkworth, L., & Friesen, K. (2004). Biotransformation of N-Ethyl Perfluorooctanesulfonamide by Rainbow Trout (Onchorhynchus mykiss) Liver Microsomes. Environmental Science & Technology. https://doi.org/10.1021/es034550j
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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).
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