Biodegradation of N-ethyl perfluorooctane sulfonamido ethanol (EtFOSE) and EtFOSE-based phosphate diester (SAmPAP diester) in marine sediments

Environmental Science and Technology

Volumn 47, Issue 3, 2013, Pages 1381-1389

  Benskin, Jonathan P ^a,b   Ikonomou, Michael G ^b   Gobas, Frank A P C ^c   Begley, Timothy H ^d   Woudneh, Million B ^a   Cosgrove, John R ^a  

^a AXYS Analytical Services Ltd   (Canada)

^b INSTITUTE OF OCEAN SCIENCES   (Canada)

^c SIMON FRASER UNIVERSITY   (Canada)

^d CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIODEGRADATION POTENTIALS; BIODEGRADATION STUDIES; COMMERCIAL APPLICATIONS; CONFIDENCE INTERVAL; DIESTERS; ELEVATED CONCENTRATIONS; ENVIRONMENTAL COMPARTMENT; HIGH MOLECULAR WEIGHT; LOW MOLECULAR WEIGHT; LOWER BOUNDS; MARINE SEDIMENTS; MICROBIAL DEGRADATION; PERFLUOROOCTANE SULFONAMIDE; PERFLUOROOCTANE SULFONATES; PRODUCT FORMATION; STANDARD ERROR OF THE MEANS; WASTEWATER TREATMENT PLANTS;

BACTERIA; BIOCHEMISTRY; ETHANOL; MICROBIOLOGY; SUBMARINE GEOLOGY; SULFUR COMPOUNDS;

BIODEGRADATION;

N ETHYL PERFLUOROOCTANE SULFONAMIDE; N ETHYL PERFLUOROOCTANE SULFONAMIDOACETATE; ORGANOPHOSPHATE; PERFLUOROOCTANE SULFONAMIDE; PERFLUOROOCTANE SULFONAMIDOACETATE; PERFLUOROOCTANESULFONIC ACID; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

BACTERIUM; BIODEGRADATION; BIOTRANSFORMATION; DATA SET; ETHANOL; HYDROPHOBICITY; MARINE SEDIMENT; MOLECULAR ANALYSIS; ORGANIC COMPOUND; SEDIMENT POLLUTION; SLUDGE; STABILIZATION; URBAN AREA; WASTEWATER; WATER TREATMENT;

ARTICLE; BIOAVAILABILITY; BIOTRANSFORMATION; CANADA; HYDROPHOBICITY; JAPAN; MICROBIAL DEGRADATION; NONHUMAN; SEDIMENT; SLUDGE TREATMENT; TEMPERATURE; UNITED STATES; WASTE WATER MANAGEMENT;

BACTERIA; BIODEGRADATION, ENVIRONMENTAL; ESTERS; FLUOROCARBONS; GEOLOGIC SEDIMENTS; HALF-LIFE; HYDROCARBONS, FLUORINATED; ORGANOPHOSPHATES; SULFONAMIDES;

CANADA; JAPAN; UNITED STATES;

EID: 84873421639     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es304336r     Document Type: Article

References (46)

1. Giesy, J. P.; Kannan, K. Global distribution of perfluorooctane sulfonate in wildlife Environ. Sci. Technol. 2001, 35, 1339-1342
2. Yamashita, N.; Kannan, K.; Taniyasu, S.; Horii, Y.; Petrick, G.; Gamo, T. A global survey of perfluorinated acids in oceans Mar. Pollut. Bull. 2005, 51, 658-668
3. Houde, M.; Martin, J. W.; Letcher, R. J.; Solomon, K. R.; Muir, D. C. G. Biological monitoring of polyfluoroalkyl substances: A review Environ. Sci. Technol. 2006, 40, 3463-3473
4. Houde, M.; Czub, G.; Small, J. M.; Backus, S.; Wang, X. W.; Alaee, M.; Muir, D. C. G. Fractionation and bioaccumulation of perfluorooctane sulfonate (PFOS) isomers in a Lake Ontario food web Environ. Sci. Technol. 2008, 42, 9397-9403
5. Houde, M.; Bujas, T. A. D.; Small, J.; Wells, R. S.; Fair, P. A.; Bossart, G. D.; Solomon, K. R.; Muir, D. C. G. Biomagnification of perfluoroalkyl compounds in the bottlenose dolphin (Tursiops truncatus) food web Environ. Sci. Technol. 2006, 40, 4138-4144
6. Kelly, B. C.; Ikonomou, M. G.; Blair, J. D.; Surridge, B.; Hoover, D.; Grace, R.; Gobas, F. A. P. C. Perfluoroalkyl contaminants in an Arctic marine food web: Trophic magnification and wildlife exposure Environ. Sci. Technol. 2009, 43, 4037-4043
7. Wang, M.; Chen, J.; Lin, K.; Chen, Y.; Hu, W.; Tanguay, R. L.; Huang, C.; Dong, Q. Chronic zebrafish PFOS exposure alters sex ratio and maternal related effects in F1 offspring Environ. Toxicol. Chem. 2011, 30, 2073-2080
8. Arukwe, A.; Mortensen, A. S. Lipid peroxidation and oxidative stress responses of salmon fed a diet containing perfluorooctane sulfonic- or perfluorooctane carboxylic acids Comp. Biochem. Physiol., C: Toxicol. Pharmacol. 2011, 154, 288-295
9. U.S. Environmental Protection Agency. Perfluoroalkyl Sulfonates; Significant New Use Rule (SNUR); EPA-HQ-OPPT-2002-0043; Washington, DC.
10. Ministry of Environmental Protection of China. Additional information on production and use of PFOS; Stockholm Convention on Persistent Organic Pollutants: Stockholm, Sweden, 2008.
11. Moody, C. A.; Martin, J. W.; Kwan, W. C.; Muir, D. C. G.; Mabury, S. A. Monitoring perfluorinated surfactants in biota and surface water samples following an accidental release of fire-fighting foam into Etobicoke Creek Environ. Sci. Technol. 2002, 36, 545-551
12. 2OH: Kinetics and mechanism of reaction with OH Environ. Sci. Technol. 2006, 40, 1862-1868
13. Tomy, G. T.; Tittlemier, S. A.; Palace, V. P.; Budakowski, W. R.; Braekevelt, E.; Brinkworth, L.; Friesen, K. Biotransformation of N-ethyl perfluorooctanesulfonamide by rainbow trout (Onchorhynchus mykiss) liver microsomes Environ. Sci. Technol. 2004, 38, 758-762
14. Rhoads, K. R.; Janssen, E. M.-L.; Luthy, R. G.; Criddle, C. S. Aerobic biotransformation and fate of N-ethyl perfluorooctane sulfonamidoethanol (N-EtFOSE) in activated sludge Environ. Sci. Technol. 2008, 42, 2873-2878
15. Carloni, D. Perfluorooctane sulfonate (PFOS) production and use: Past and current evidence. Prepared for UNIDO. Accessed from http://www.unido.org/ fileadmin/user-media/Services/Environmental-Management/Stockholm-Convention/ POPs/DC-Perfluorooctane%20Sulfonate%20Report.PDF; 2009.
16. 3M Co. Fluorochemical use, distribution and release overview; U.S. Environmental Protection Agency Docket AR226-0550; 1999.
17. Armitage, J. M.; Schenker, U.; Scheringer, M.; Martin, J. W.; MacLeod, M.; Cousins, I. T. Modeling the global fate and transport of perfluorooctane sulfonate (PFOS) and precursor compounds in relation to temporal trends in wildlife exposure Environ. Sci. Technol. 2009, 43, 9274-9280
18. Martin, J. W.; Asher, B. J.; Beesoon, S.; Benskin, J. P.; Ross, M. S. PFOS or PreFOS? Are perfluorooctane sulfonate precursors (PreFOS) important determinants of human and environmental perfluorooctane sulfonate (PFOS) exposure? J. Environ. Monit. 2010, 12, 1979-2004
19. Boulanger, B.; Vargo, J. D.; Schnoor, J. L.; Hornbuckle, K. C. Evaluation of perfluorooctane surfactants in a wastewater treatment system and in a commercial surface protection product Environ. Sci. Technol. 2005, 39, 5524-5530
20. Lange, C. C. The aerobic biodegradation of N-EtFOSE alcohol by the microbial activity present in municipal wastewater treatment sludge; U.S. Environmental Protection Agency Docket AR-226-058; 2000.
21. Olsen, G. W.; Huang, H.-Y.; Helzlsouer, K. J.; Hansen, K. J.; Butenhoff, J. L.; Mandel, J. H. Historical comparison of perfluorooctanesulfonate, perfluorooctanoate, and other fluorochemicals in human blood Environ. Health Perspect. 2005, 113, 539-545
22. Begley, T. H.; Hsu, W.; Noonan, G.; Diachenko, G. Migration of fluorochemical paper additives from food-contact paper into foods and food simulants Food Addit. Contam., Part A 2008, 25, 384-390
23. 3M Co. Sulfonated perfluorochemicals: U. S. release estimation -1997 Part 1: Life-cycle waste stream estimates-Final report for 3M specialty materials; prepared by Battelle Memorial Institute; U.S. Environmental Protection Agency Docket AR 226-0681; 2000.
24. Robinson, S. J. Commercial Fluorosurfactants and Their Metabolites in Human Blood. MSc Thesis, University of Toronto, Toronto, ON, Canada, 2011.
25. Benskin, J. P.; Ikonomou, M. G.; Gobas, F. A.; Woudneh, M. B.; Cosgrove, J. R. Observation of a novel PFOS-precursor, the perfluorooctane sulfonamido ethanol-based phosphate (SAmPAP) diester, in marine sediments Environ. Sci. Technol. 2012, 46, 6505-6514
26. D'Eon, J. C.; Crozier, P. W.; Furdui, V. I.; Reiner, E. J.; Libelo, E. L.; Mabury, S. A. Observation of a commercial fluorinated material, the polyfluoroalkyl phosphoric acid diesters, in human sera, wastewater treatment plant sludge, and paper fibers Environ. Sci. Technol. 2009, 43, 4589-4594
27. Lee, H.; D'eon, J.; Mabury, S. A. Biodegradation of Polyfluoroalkyl phosphates as a source of perfluorinated acids to the environment Environ. Sci. Technol. 2010, 44, 3305-3310
28. Higgins, C. P.; Field, J. A.; Criddle, C. S.; Luthy, R. G. Quantitative determination of perfluorochemicals in sediments and domestic sludge Environ. Sci. Technol. 2005, 39, 3946-3956
29. Ahrens, L.; Yamashita, N.; Yeung, L. W. Y.; Taniyasu, S.; Horii, Y.; Lam, P. K. S.; Ebinghaus, R. Partitioning behavior of per- and polyfluoroalkyl compounds between pore water and sediment in two sediment cores from Tokyo Bay, Japan Environ. Sci. Technol. 2009, 43, 6969-6975
30. Otton, S. V.; Sura, S.; Blair, J.; Ikonomou, M. G.; Gobas, F. A. Biodegradation of mono-alkyl phthalate esters in natural sediments Chemosphere 2008, 71, 2011-2016
31. Powley, C. R.; George, S. W.; Ryan, T. W.; Buck, R. C. Matrix effect-free analytical methods for determination of perfluorinated carboxylic acids in environmental matrixes Anal. Chem. 2005, 77, 6353-6358
32. Parsons, J. R.; Saez, M.; Dolfing, J.; de Voogt, P. Biodegradation of perfluorinated compounds Rev. Environ. Contam. Toxicol. 2008, 196, 53-71
33. Kickham, P.; Otton, S. V.; Moore, M. M.; Ikonomou, M. G.; Gobas, F. A. P. C. Relationship between sorption and biodegradation of phthalate esters and their metabolites in natural sediments Environ. Toxicol. Chem. 2012, 31, 1730-1737
34. Jackson, D. A.; Mabury, S. A. Polyfluorinated amides as a historical PFCA source by electrochemical fluorination of alkyl sulfonyl fluorides Environ. Sci. Technol. 2013, 47, 382-389
35. Howard, P. H.; Muir, D. C. Identifying new persistent and bioaccumulative organics among chemicals in commerce Environ. Sci. Technol. 2010, 44, 2277-2285
36. Washington, J. W.; Ellington, J.; Jenkins, T. M.; Evans, J. J.; Yoo, H.; Hafner, S. C. Degradability of an acrylate-linked, fluorotelomer polymer in soil Environ. Sci. Technol. 2009, 43, 6617-6623
37. Russell, M. H.; Berti, W. R.; Szostek, B.; Buck, R. C. Investigation of the biodegradation potential of a fluoroacrylate polymer product in aerobic soils Environ. Sci. Technol. 2008, 42, 800-807
38. Wang, Z. M., M.; Cousins, I. T.; Scheringer, M.; Hungerbuhler, K. Using COSMOtherm to predict physicochemical properties of poly- and perfluorinated alkyl substances (PFASs) Enviro. Chem. 2011, 8, 389-398
39. United Nations Environment Program. Final act of the conference of plenipotentiaries on the Stockholm convention on persistent organic pollutants; Geneva, Switzerland, 2001.
40. Houtz, E. F.; Sedlak, D. L. Oxidative conversion as a means of detecting precursors to perfluoroalkyl acids in urban runoff Environ. Sci. Technol. 2012, 46, 9342-9349
41. Seacat, A. M.; Luebker, D. L. Diester-Pharmacokinetic Study in Rats (Study T-7043.1, DT-26); U.S. Environmental Protection Agency Docket MK 279511; 2000.
42. Xu, L.; Krenitsky, D. M.; Seacat, A. M.; Butenhoff, J. L.; Anders, M. W. Biotransformation of N-Ethyl-N-(2-hydroxyethyl)perfluorooctanesulfonamide by Rat Liver Microsomes, Cytosol, and Slices and by Expressed Rat and Human Cytochromes P450 Chem. Res. Toxicol. 2004, 17, 767-775
43. Higgins, C. P.; McLeod, P. B.; MacManus-Spencer, L. A.; Luthy, R. G. Bioaccumulation of perfluorochemicals in sediments by the aquatic oligochaete Lumbriculus variegatus Environ. Sci. Technol. 2007, 41, 4600-4606
44. Martin, J. W.; Whittle, D. M.; Muir, D. C. G.; Mabury, S. A. Perfluoroalkyl contaminants in a food web from Lake Ontario Environ. Sci. Technol. 2004, 38, 5379-5385
45. Asher, B. J.; Wang, Y.; De Silva, A. O.; Backus, S.; Muir, D. C. G.; Wong, C. S.; Martin, J. W. Enantiospecific perfluorooctane sulfonate (PFOS) analysis reveals evidence for the source contribution of PFOS-precursors to the Lake Ontario foodweb Environ. Sci. Technol. 2012, 46, 7653-7660
46. Loi, E. I. H.; Yeung, L. W. Y.; Taniyasu, S.; Lam, P. K. S.; Kannan, K.; Yamashita, N. Trophic magnification of poly- and perfluorinated compounds in a subtropical food web Environ. Sci. Technol. 2011, 45, 5506-5513