Enantiomer fractions of chiral perfluorooctanesulfonate (PFOS) in human sera

Environmental Science and Technology

Volumn 45, Issue 20, 2011, Pages 8907-8914

  Wang, Yuan ^a   Beesoon, Sanjay ^a   Benskin, Jonathan P ^a   De Silva, Amila O ^b   Genuis, Stephen J ^a   Martin, Jonathan W ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b ENVIRONMENT CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL SAMPLES; ENANTIOMER FRACTIONS; ENANTIOSELECTIVE; EXPOSURE PATHWAYS; GENERAL SOURCE; HPLC-MS/MS; HUMAN EXPOSURES; HUMAN SERUM; MODEL PREDICTION; NORTH AMERICAN; PERFLUOROALKYL CONTAMINANTS; PERFLUOROOCTANE SULFONATES; PREGNANT WOMAN; RELATIVE CONTRIBUTION; SCOTCHGARD; SEMI-QUANTITATIVE; STANDARD DEVIATION;

BODY FLUIDS; CHIRALITY; MAMMALS; TISSUE;

ENANTIOMERS;

PERFLUOROOCTANESULFONIC ACID;

BIOACCUMULATION; BIOMARKER; BIOTRANSFORMATION; BLOOD; EXCRETION; HOMINID; HYPOTHESIS TESTING; ORGANIC POLLUTANT; ORGANOFLUORINE; POLLUTION EXPOSURE; PREGNANCY; RODENT; SERUM; SULFONATE (ESTER);

ADULT; ANIMAL EXPERIMENT; ARTICLE; BIOTRANSFORMATION; BLOOD SAMPLING; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; FAMILY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MALE; MASS SPECTROMETRY; NONHUMAN; RAT;

ADOLESCENT; ADULT; ALKANESULFONIC ACIDS; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ELECTROCHEMISTRY; FEMALE; FLUOROCARBONS; HUMANS; MALE; MIDDLE AGED; PREGNANCY; RATS; RATS, SPRAGUE-DAWLEY; STEREOISOMERISM; TANDEM MASS SPECTROMETRY; YOUNG ADULT;

ALBERTA; CANADA; EDMONTON;

MAMMALIA; RODENTIA;

EID: 80054708548     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es2023434     Document Type: Article

References (63)

1. Giesy, J. P.; Kannan, K. Global distribution of perfluorooctane sulfonate in wildlife Environ. Sci. Technol. 2001, 35, 1339-1342
2. Hansen, K. J.; Clemen, L. A.; Ellefson, M. E.; Johnson, H. O. Compound-specific, quantitative characterization of organic fluorochemicals in biological matrices Environ. Sci. Technol. 2001, 35 (4) 766-770
3. Martin, J. W.; Smithwick, M. M.; Braune, B. M.; Hoekstra, P. F.; Muir, D. C. G.; Mabury, S. A. Identification of long-chain perfluorinated acids in biota from the Canadian Arctic Environ. Sci. Technol. 2004, 38 (2) 373-380
4. Smithwick, M.; Muir, D. C. G.; Mabury, S. A.; Solomon, K. R.; Martin, J. W.; Sonne, C.; Born, E. W.; Letcher, R. J.; Dietz, R. Perfluoroalkyl contaminants in liver tissue from east greenland polar bears (Ursus maritimus) Environ. Toxicol. Chem. 2005, 24 (4) 981-986
5. Gabos, S.; Zemanek, M.; Cheperdak, L.; Kinniburgh, D.; Lee, B.; Hrudey, S.; Le, C.; Li, X. F.; Mandal, R.; Martin, J. W.; Schopflocher, D. Chemical biomonitoring in serum of pregnant women in Alberta (2005) The Alberta Biomonitoring Program 2008, 71-77
6. Olsen, G. W.; Burris, J. M.; Ehresman, D. J.; Froelich, J. W.; Seacat, A. M.; Butenhoff, J. L.; Zobel, L. R. Half-life of serum elimination of perfluorooctanesulfonate, perfluorohexanesulfonate, and perfluorooctanoate in retired fluorochemical production workers Environ. Health Perspect. 2007, 115 (9) 1298-1305
7. 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 (20) 5379-5385
8. Houde, M.; Czub, G.; Small, J. M.; Backus, S.; Wang, X.; 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
9. Powley, C. R.; George, S. W.; Russell, M. H.; Hoke, R. A.; Buck, R. C. Polyfluorinated chemicals in a spatially and temporally integrated food web in the western Arctic Chemosphere 2008, 70 (4) 664-672
10. Lau, C.; Butenhoff, J. L.; Rogers, J. M. The developmental toxicity of perfluoroalkyl acids and their derivatives Toxicol. Appl. Pharmacol. 2004, 198 (2) 231-241
11. Shi, X. J.; Du, Y. B.; Lam, P. K. S.; Wu, R. S. S.; Zhou, B. S. Developmental toxicity and alteration of gene expression in zebrafish embryos exposed to PFOS Toxicol. Appl. Pharmacol. 2008, 230 (1) 23-32
12. Jensen, A. A.; Leffers, H. Emerging endocrine disrupters: Perfluoroalkylated substances Int. J. Androl. 2008, 31 (2) 161-169
13. Wang, T.; Wang, Y. W.; Liao, C. Y.; Cai, Y. Q.; Jiang, G. B. Perspectives on the inclusion of perfluorooctane sulfonate into the Stockholm Convention on persistent organic pollutants Environ. Sci. Technol. 2009, 43 (14) 5171-5175
14. 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 (11) 1979-2004
15. Paul, A. G.; Jones, K. C.; Sweetman, A. J. A first global production, emission, and environmental inventory for perfluorooctane sulfonate Environ. Sci. Technol. 2009, 43 (2) 386-92
16. 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 (24) 9274-9280
17. Yeung, L. W. Y.; Miyake, Y.; Taniyasu, S.; Wang, Y.; Yu, H. X.; So, M. K.; Jiang, G. B.; Wu, Y. N.; Li, J. G.; Giesy, J. P.; Yamashita, N.; Lam, P. K. S. Perfluorinated compounds and total and extractable organic fluorine in human blood samples from china Environ. Sci. Technol. 2008, 42 (21) 8140-8145
18. Martin, J. W.; Muir, D. C. G.; Moody, C. A.; Ellis, D. A.; Kwan, W. C.; Solomon, K. R.; Mabury, S. A. Collection of airborne fluorinated organics and analysis by gas chromatography/chemical ionization mass spectrometry Anal. Chem. 2002, 74 (3) 584-590
19. Shoeib, M.; Harner, T.; Ikonomou, M.; Kannan, K. Indoor and outdoor air concentrations and phase partitioning of perfluoroalkyl sulfonamides and polybrominated diphenyl ethers Environ. Sci. Technol. 2004, 38 (5) 1313-1320
20. Olsen, G. W.; Church, T. R.; Larson, E. B.; van Belle, G.; Lundberg, J. K.; Hansen, K. J.; Burris, J. M.; Mandel, J. H.; Zobel, L. R. Serum concentrations of perfluorooctanesulfonate and other fluorochemicals in an elderly population from Seattle, Washington Chemosphere 2004, 54 (11) 1599-1611
21. Shoeib, M.; Harner, T.; Vlahos, P. Perfluorinated chemicals in the Arctic atmosphere Environ. Sci. Technol. 2006, 40 (24) 7577-7583
22. Ahrens, L.; Barber, J. L.; Xie, Z.; Ebinghaus, R. Longitudinal and latitudinal distribution of perfluoroalkyl compounds in the surface water of the Atlantic Ocean Environ. Sci. Technol. 2009, 43, 3122-3127
23. Mendel, A. 3M technical report: "Analytical methodology on fm 3422"; 1977; AR226-0364.
24. Martin, J. W.; Ellis, D. A.; Mabury, S. A.; Hurley, M. D.; Wallington, T. J. Atmospheric chemistry of perfluoroalkanesulfonamides: Kinetic and product studies of the OH radical and Cl atom initiated oxidation of n-ethyl perfluorobutanesulfonamide Environ. Sci. Technol. 2006, 40 (3) 864-872
25. 2OH: Kinetics and mechanism of reaction with OH Environ. Sci. Technol. 2006, 40 (6) 1862-1868
26. 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
27. 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
28. Xie, W.; Wu, Q.; Kania-Korwel, I.; Tharappel, J. C.; Telu, S.; Coleman, M. C.; Glauert, H. P.; Kannan, K.; Mariappan, S. V. S.; Spitz, D. R.; Weydert, J.; Lehmler, H. J. Subacute exposure to n-ethyl perfluorooctanesulfonamidoethanol results in the formation of perfluorooctanesulfonate and alters superoxide dismutase activity in female rats Arch. Toxicol. 2009, 83 (10) 909-924
29. 3M Company. Health and Environmental Assessment of Perfluorooctane Sulfonic Acid and Its Salts; U.S. EPA docket AR-226-1486; U.S. Environmental Protection Agency: Washington, DC, 2003.
30. Butt, C. M.; Muir, D. C. G.; Stirling, I.; Kwan, M.; Mabury, S. A. Rapid response of arctic ringed seals to changes in perfluoroalkyl production Environ. Sci. Technol. 2007, 41 (1) 42-49
31. Hart, K.; Gill, V. A.; Kannan, K. Temporal trends (1992-2007) of perfluorinated chemicals in northern sea otters (Enhydra lutris kenyoni) from south-central Alaska Arch. Environ. Contam. Toxicol. 2009, 56 (3) 607-614
32. Bossi, R.; Riget, F. F.; Dietz, R. Temporal and spatial trends of perfluorinated compounds in ringed seal (Phoca hispida) from Greenland Environ. Sci. Technol. 2005, 39 (19) 7416-7422
33. Dietz, R.; Bossi, R.; Riget, F. F.; Sonne, C.; Born, E. W. Increasing perfluoroalkyl contaminants in East Greenland polar bears (Ursus maritimus): A new toxic threat to the arctic bears Environ. Sci. Technol. 2008, 42 (7) 2701-2707
34. Olsen, G. W.; Mair, D. C.; Reagen, W. K.; Ellefson, M. E.; Ehresman, D. J.; Butenhoff, J. L.; Zobel, L. R. Preliminary evidence of a decline in perfluorooctanesulfonate (PFOS) and perfluorooctanoate (PFOA) concentrations in American Red Cross blood donors Chemosphere 2007, 68 (1) 105-111
35. Chen, C. L.; Lu, Y. L.; Zhang, X.; Geng, J.; Wang, T. Y.; Shi, Y. J.; Hu, W. Y.; Li, J. A review of spatial and temporal assessment of PFOS and PFOA contamination in China Chem. Ecol. 2009, 25 (3) 163-177
36. Wang, Y.; Jiang, G. The research of human exposure to polybrominated diphenyl ethers and perfluoroocatane sulfonate Chin. Sci. Bull. 2008, 53 (4) 481-492
37. Fromme, H.; Tittlemier, S. A.; Volkel, W.; Wilhelm, M.; Twardella, D. Perfluorinated compounds-exposure assessment for the general population in western countries Int. J. Hyg. Environ. Health 2009, 212 (3) 239-270
38. Vestergren, R.; Cousins, I. T.; Trudel, D.; Wormuth, M.; Scheringer, M. Estimating the contribution of precursor compounds in consumer exposure to PFOS and PFOA Chemosphere 2008, 73 (10) 1617-1624
39. Benskin, J. P.; Holt, A.; Martin, J. W. Isomer-specific biotransformation rates of a perfluorooctane sulfonate (PFOS)-precursor by cytochrome p450 isozymes and human liver microsomes Environ. Sci. Technol. 2009, 43 (22) 8566-8572
40. Kärrman, A.; Langlois, I.; van Bavel, B.; Lindström, G.; Oehme, M. Identification and pattern of perfluorooctane sulfonate (PFOS) isomers in human serum and plasma Environ. Int. 2007, 33, 782-788
41. Riddell, N.; Arsenault, G.; Benskin, J. P.; Chittim, B.; Martin, J. W.; McAlees, A.; McCrindle, R. Branched perfluorooctane sulfonate isomer quantification and characterization in blood serum samples by HPLC/ESI-MS(/MS) Environ. Sci. Technol. 2009, 43 (20) 7902-7908
42. Sharpe, R. L.; Benskin, J. P.; Laarman, A. H.; Macleod, S. L.; Martin, J. W.; Wong, C. S.; Goss, G. G. Perfluorooctane sulfonate toxicity, isomer-specific accumulation, and maternal transfer in zebrafish (Danio rerio) and rainbow trout (Oncorhynchus mykiss) Environ. Toxicol. Chem. 2010, 29 (9) 1957-66
43. Arsenault, G.; Chittim, B.; Gu, J.; McAlees, A.; McCrindle, R.; Robertson, V. Separation and fluorine nuclear magnetic resonance spectroscopic (F-19 NMR) analysis of individual branched isomers present in technical perfluorooctanesulfonic acid (PFOS) Chemosphere 2008, 73 (1) S53-S59
44. Rayne, S.; Forest, K.; Friesen, K. J. Congener-specific numbering systems for the environmentally relevant C4 through C8 perfluorinated homologue groups of alkyl sulfonates, carboxylates, telomer alcohols, olefins, and acids, and their derivatives J. Environ. Sci. Health, Part A 2008, 43 (12) 1391-1401
45. Wang, Y.; Arsenault, G.; Riddell, N.; McCrindle, R.; McAlees, A.; Martin, J. W. Perfluorooctane sulfonate (PFOS) precursors can be metabolized enantioselectively: Principle for a new PFOS source tracking tool Environ. Sci. Technol. 2009, 43 (21) 8283-8289
46. Benskin, J. P.; De Silva, A. O.; Martin, L. J.; Arsenault, G.; McCrindle, R.; Riddell, N.; Mabury, S. A.; Martin, J. W. Disposition of perfluorinated acid isomers in Sprague Dawley rats; Part 1: Single dose Environ. Toxicol. Chem. 2009, 28 (3) 542-554
47. De Silva, A. O.; Benskin, J. P.; Martin, L. J.; Arsenault, G.; McCrindle, R.; Riddell, N.; Martin, J. W.; Mabury, S. A. Disposition of perfluorinated acid isomers in Sprague-Dawley rats; Part 2: Subchronic dose Environ. Toxicol. Chem. 2009, 28 (3) 555-567
48. Kestner, T. Fluorochemical Isomer Distribution by 19F-NMR Spectroscopy; U.S. Environmental Protection Agency Public Docket AR226-0564; Washington, DC, 1997.
49. Chan, E.; Sandhu, M.; Benskin, J. P.; Ralitsch, M.; Thibault, N.; Birkholz, D.; Martin, J. W. Endogenous high-performance liquid chromatography/tandem mass spectrometry interferences and the case of perfluorohexane sulfonate (PFHXS) in human serum; Are we overestimating exposure? Rapid Commun. Mass Spectrom. 2009, 23, 1405-1410
50. Kuklenyik, Z.; Reich, J. A.; Tully, J. S.; Needham, L. L.; Calafat, A. M. Automated solid-phase extraction and measurement of perfluorinated organic acids and amides in human serum and milk Environ. Sci. Technol. 2004, 38, 3698-3704
51. Benskin, J. P.; Bataineh, M.; Martin, J. W. Simultaneous characterization of perfluoroalkyl carboxylate, sulfonate, and sulfonamide isomers by liquid chromatography-tandem mass spectrometry Anal. Chem. 2007, 79 (17) 6455-6464
52. Asher, B. J.; D'Agostino, L. A.; Way, J. D.; Wong, C. S.; Harynuk, J. J. Comparison of peak integration methods for the determination of enantiomeric fraction in environmental samples Chemosphere 2009, 75 (8) 1042-1048
53. Benskin, J. P.; De Silva, A. O.; Martin, J. W. Isomer profiling of perfluorinated substances as a tool for source tracking: A review of early findings and future applications Rev. Environ. Contam. Toxicol. 2010, 208, 111-160
54. Pirkle, W. H.; Pochapsky, T. C. Considerations of chiral recognition relevant to the liquid chromatographic separation of enantiomers Chem. Rev. 1989, 89 (2) 347-362
55. Okamoto, Y.; Yashima, E. Polysaccharide derivatives for chromatographic separation of enantiomers Angew. Chem., Int. Ed. 1998, 37, 1020-1043
56. Lindner, W.; Laemmerhofer, M.; Maier, N. Cinchonan based chiral selectors for separation of stereoisomers. U.S. Patent 6313247, 2001.
57. Hoffmann, C. V.; Pell, R.; Lämmerhofer, M.; Lindner, W. Synergistic effects on enantioselectivity of zwitterionic chiral stationary phases for separation of chiral acids, bases, and amino acids by HPLC Anal. Chem. 2008, 80 (22) 8780-8789
58. Krawinkler, K. H.; Maier, N. M.; Sajovic, E.; Lindner, W. Novel urea-linked cinchona-calixarene hybrid-type receptors for efficient chromatographic enantiomer separation of carbamate-protected cyclic amino acids J Chromatogr., A 2004, 1053 (1-2) 119-131
59. Gyimesi-Forras, K.; Maier, N. M.; Kokosi, J.; Gergely, A.; Lindner, W. Enantiomer separation of imidazo-quinazoline-dione derivatives on quinine carbamate-based chiral stationary phase in normal phase mode Chirality 2009, 21 (1) 199-207
60. Brocks, D. R. Drug disposition in three dimensions: An update on stereoselectivity in pharmacokinetics Biopharm Drug Dispos. 2006, 27 (8) 387-406
61. 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 (11) 1979-2004
62. Vestergren, R.; Cousins, I. T. Tracking the pathways of human exposure to perfluorocarboxylates Environ. Sci. Technol. 2009, 43 (15) 5565-5575
63. Lehmler, H.-J.; Harrad, S. J.; Hühnerfuss, H.; Kania-Korwel, I.; Lee, C. M.; Lu, Z.; Wong, C. S. Chiral polychlorinated biphenyl transport, metabolism, and distribution: A review Environ. Sci. Technol. 2010, 44, 2757-2766