Novel Chlorinated Polyfluorinated Ether Sulfonates and Legacy Per-/Polyfluoroalkyl Substances: Placental Transfer and Relationship with Serum Albumin and Glomerular Filtration Rate

Environmental Science and Technology

Volumn 51, Issue 1, 2017, Pages 634-644

  Pan, Yitao ^a   Zhu, Yingshuang ^b   Zheng, Tongzhang ^c   Cui, Qianqian ^a   Buka, Stephen L ^c   Zhang, Bin ^b,d   Guo, Yong ^e   Xia, Wei ^b   Yeung, Leo W Y ^f   Li, Yuanyuan ^b   Zhou, Aifen ^d   Qiu, Lin ^b,d   Liu, Hongxiu ^b   Jiang, Minmin ^b   Wu, Chuansha ^b   Xu, Shunqing ^b   Dai, Jiayin ^a  

^a INSTITUTE OF ZOOLOGY   (China)

^b HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^c BROWN UNIVERSITY   (United States)

^d Women and Children Medical and Healthcare Center of Wuhan   (China)

^e SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^f ÖREBRO UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BODY FLUIDS; CARBOXYLATION; ETHERS;

GLOMERULAR FILTRATION RATE; HIGHER EDUCATION; MATERNAL SERUM; PHYSIOLOGICAL FACTORS; PLACENTAL TRANSFER; POLYFLUOROALKYL SUBSTANCES; STRUCTURE DEPENDENT; TRANSFER EFFICIENCY;

EFFICIENCY;

ALBUMIN; ALKYL GROUP; ETHER DERIVATIVE; POLYFLUOROALKYL SUBSTANCE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG; ETHER; FLUOROCARBON; SERUM ALBUMIN;

ANATOMY; CHEMICAL SUBSTANCE; CONCENTRATION (COMPOSITION); ETHER; PHYSIOLOGY; PROTEIN; REGRESSION ANALYSIS; SERUM; TESTING METHOD;

ADULT; ALBUMIN BLOOD LEVEL; ARTICLE; BLOOD PLACENTA BARRIER; CORD SERUM; FEMALE; GLOMERULUS FILTRATION RATE; HUMAN; MAJOR CLINICAL STUDY; MATERNAL SERUM; NEWBORN; PLACENTAL TRANSFER; CHINA; FETOMATERNAL TRANSFUSION; PREGNANCY;

CHINA; HUBEI; WUHAN;

CHINA; ETHER; ETHERS; FEMALE; FLUOROCARBONS; GLOMERULAR FILTRATION RATE; HUMANS; MATERNAL-FETAL EXCHANGE; PREGNANCY; SERUM ALBUMIN;

EID: 85020869609     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/acs.est.6b04590     Document Type: Article

References (60)

1. 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. Perfluoroalkyl and polyfluoroalkyl substances in the environment: Terminology, classification, and origins Integr. Environ. Assess. Manage. 2011, 7 (4) 513-541 10.1002/ieam.258
2. Kissa, E. Fluorinated Surfactants and Repellents, 2 nd ed.; Marcel Dekker Inc.: New York, 2001.
3. Lau, C.; Anitole, K.; Hodes, C.; Lai, D.; Pfahles-Hutchens, A.; Seed, J. Perfluoroalkyl acids: A review of monitoring and toxicological findings Toxicol. Sci. 2007, 99 (2) 366-394 10.1093/toxsci/kfm128
4. Olsen, G. W.; Burris, J. M.; Ehresman, D. J.; Froehlich, 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 10.1289/ehp.10009
5. U.S. EPA (U.S. Environmental Protection Agency) 2000. Perfluorooctyl Sulfonates; Proposed Significant New Use Rule. https://www.gpo.gov/fdsys/pkg/FR-2000-10-18/pdf/00-26751.pdf [accessed 16 Dec 2016, ].
6. Stockholm Convention 2009. Governments unite to step-up reduction on global DDT reliance and add nine new chemicals under international treaty. http://chm.pops.int/Convention/Pressrelease/COP4Geneva9May2009/tabid/542/languages/en-US/Default.aspx [accessed 20 July 2016, ].
7. U.S. EPA (U.S. Environmental Protection Agency). 2010/2015PFOA Stewardship Program. http://www.epa.gov/oppt/pfoa/pubs/stewardship/pfoastewardshipbasics.html [accessed 20 July 2016, ].
8. Lindstrom, A. B.; Strynar, M. J.; Libelo, E. L. Polyfluorinated compounds: Past, present, and future Environ. Sci. Technol. 2011, 45 (19) 7954-7961 10.1021/es2011622
9. Calafat, A. M.; Wong, L. Y.; Kuklenyik, Z.; Reidy, J. A.; Needham, L. L. Polyfluoroalkyl chemicals in the U.S. population: Data from the National Health and Nutrition Examination Survey (NHANES) 2003-2004 and comparisons with NHANES 1999-2000 Environ. Health Perspect. 2007, 115 (11) 1596-602 10.1289/ehp.10598
10. 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 10.1016/j.chemosphere.2006.12.031
11. Glynn, A.; Berger, U.; Bignert, A.; Ullah, S.; Aune, M.; Lignell, S.; Darnerud, P. O. Perfluorinated alkyl acids in blood serum from primiparous women in Sweden: Serial sampling during pregnancy and nursing, and temporal trends 1996-2010 Environ. Sci. Technol. 2012, 46 (16) 9071-9079 10.1021/es301168c
12. Yeung, L. W. Y.; Robinson, S. J.; Koschorreck, J.; Mabury, S. A. Part ii. A temporal study of PFOS and its precursors in human plasma from two German cities in 1982-2009 Environ. Sci. Technol. 2013, 47 (8) 3875-3882 10.1021/es4004153
13. Gebbink, W. A.; Glynn, A.; Berger, U. Temporal changes (1997-2012) of perfluoroalkyl acids and selected precursors (including isomers) in Swedish human serum Environ. Pollut. 2015, 199, 166-173 10.1016/j.envpol.2015.01.024
14. Lee, H.; Mabury, S. A. A pilot survey of legacy and current commercial fluorinated chemicals in human sera from United States donors in 2009 Environ. Sci. Technol. 2011, 45 (19) 8067-8074 10.1021/es200167q
15. Shi, Y. L.; Vestergren, R.; Xu, L.; Zhou, Z.; Li, C. X.; Liang, Y.; Cai, Y. Q. Human exposure and elimination kinetics of chlorinated polyfluoroalkyl ether sulfonic acids (Cl-PFESAS) Environ. Sci. Technol. 2016, 50 (5) 2396-2404 10.1021/acs.est.5b05849
16. Wang, S. W.; Huang, J.; Yang, Y.; Hui, Y. M.; Ge, Y. X.; Larssen, T.; Yu, G.; Deng, S. B.; Wang, B.; Harman, C. First report of a Chinese PFOS alternative overlooked for 30 years: Its toxicity, persistence, and presence in the environment Environ. Sci. Technol. 2013, 47 (18) 10163-10170 10.1021/es401525n
17. Ruan, T.; Lin, Y. F.; Wang, T.; Liu, R. Z.; Jiang, G. B. Identification of novel polyfluorinated ether sulfonates as PFOS alternatives in municipal sewage sludge in China Environ. Sci. Technol. 2015, 49 (11) 6519-6527 10.1021/acs.est.5b01010
18. Shi, Y. L.; Vestergren, R.; Zhou, Z.; Song, X. W.; Xu, L.; Liang, Y.; Cai, Y. Q. Tissue distribution and whole body burden of the chlorinated polyfluoroalkyl ether sulfonic acid F-53B in crucian carp (carassius carassius): Evidence for a highly bioaccumulative contaminant of emerging concern Environ. Sci. Technol. 2015, 49 (24) 14156-14165 10.1021/acs.est.5b04299
19. Gebbink, W. A.; Bossi, R.; Riget, F. F.; Rosing-Asvid, A.; Sonne, C.; Dietz, R. Observation of emerging per- and polyfluoroalkyl substances (PFASs) in Greenland marine mammals Chemosphere 2016, 144, 2384-2391 10.1016/j.chemosphere.2015.10.116
20. Bach, C. C.; Bech, B. H.; Brix, N.; Nohr, E. A.; Bonde, J. P. E.; Henriksen, T. B. Perfluoroalkyl and polyfluoroalkyl substances and human fetal growth: a systematic review Crit. Rev. Toxicol. 2015, 45 (1) 53-67 10.3109/10408444.2014.952400
21. Bach, C. C.; Bech, B. H.; Nohr, E. A.; Olsen, J.; Matthiesen, N. B.; Bonefeld-Jorgensen, E. C.; Bossi, R.; Henriksen, T. B. Perfluoroalkyl acids in maternal serum and indices of fetal growth: the Aarhus birth cohort Environ. Health Perspect. 2016, 124 (6) 848-854 10.1289/ehp.1510046
22. Fei, C. Y.; McLaughlin, J. K.; Tarone, R. E.; Olsen, J. Perfluorinated chemicals and fetal growth: a study within the Danish national birth cohort Environ. Health Perspect. 2007, 115 (11) 1677-1682 10.1289/ehp.10506
23. Whitworth, K. W.; Haug, L. S.; Baird, D. D.; Becher, G.; Hoppin, J. A.; Skjaerven, R.; Thomsen, C.; Eggesbo, M.; Travlos, G.; Wilson, R.; Cupul-Uicab, L. A.; Brantsaeter, A. L.; Longnecker, M. P. Perfluorinated compounds in relation to birth weight in the Norwegian mother and child cohort study Am. J. Epidemiol. 2012, 175 (12) 1209-1216 10.1093/aje/kwr459
24. Kim, S.; Choi, K.; Ji, K.; Seo, J.; Kho, Y.; Park, J.; Kim, S.; Park, S.; Hwang, I.; Jeon, J.; Yang, H.; Giesy, J. P. Trans-placental transfer of thirteen perfluorinated compounds and relations with fetal thyroid hormones Environ. Sci. Technol. 2011, 45 (17) 7465-72 10.1021/es202408a
25. Vested, A.; Ramlau-Hansen, C. H.; Olsen, S. F.; Bonde, J. P.; Kristensen, S. L.; Halldorsson, T. I.; Becher, G.; Haug, L. S.; Ernst, E. H.; Toft, G. Associations of in utero exposure to perfluorinated alkyl acids with human semen quality and reproductive hormones in adult men Environ. Health Perspect. 2013, 121 (4) 453-458 10.1289/ehp.1205118
26. 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 10.1016/j.taap.2003.11.031
27. Cariou, R.; Veyrand, B.; Yamada, A.; Berrebi, A.; Zalko, D.; Durand, S.; Pollono, C.; Marchand, P.; Leblanc, J. C.; Antignac, J. P.; Le Bizec, B. Perfluoroalkyl acid (PFAA) levels and profiles in breast milk, maternal and cord serum of French women and their newborns Environ. Int. 2015, 84, 71-81 10.1016/j.envint.2015.07.014
28. Fromme, H.; Mosch, C.; Morovitz, M.; Alba-Alejandre, I.; Boehmer, S.; Kiranoglu, M.; Faber, F.; Hannibal, I.; Genzel-Boroviczeny, O.; Koletzko, B.; Volkel, W. Pre- and postnatal exposure to perfluorinated compounds (PFCs) Environ. Sci. Technol. 2010, 44 (18) 7123-7129 10.1021/es101184f
29. Gutzkow, K. B.; Haug, L. S.; Thomsen, C.; Sabaredzovic, A.; Becher, G.; Brunborg, G. Placental transfer of perfluorinated compounds is selective-a Norwegian mother and child sub-cohort study Int. J. Hyg. Environ. Health 2012, 215 (2) 216-219 10.1016/j.ijheh.2011.08.011
30. Hanssen, L.; Rollin, H.; Odland, J. O.; Moe, M. K.; Sandanger, T. M. Perfluorinated compounds in maternal serum and cord blood from selected areas of South Africa: results of a pilot study J. Environ. Monit. 2010, 12 (6) 1355-1361 10.1039/b924420d
31. Hanssen, L.; Dudarev, A. A.; Huber, S.; Odland, J. O.; Nieboer, E.; Sandanger, T. M. Partition of perfluoroalkyl substances (PFASs) in whole blood and plasma, assessed in maternal and umbilical cord samples from inhabitants of Arctic Russia and Uzbekistan Sci. Total Environ. 2013, 447, 430-7 10.1016/j.scitotenv.2013.01.029
32. Kim, S. K.; Lee, K. T.; Kang, C. S.; Tao, L.; Kannan, K.; Kim, K. R.; Kim, C. K.; Lee, J. S.; Park, P. S.; Yoo, Y. W.; Ha, J. Y.; Shin, Y. S.; Lee, J. H. Distribution of perfluorochemicals between sera and milk from the same mothers and implications for prenatal and postnatal exposures Environ. Pollut. 2011, 159 (1) 169-174 10.1016/j.envpol.2010.09.008
33. Liu, J. Y.; Li, J. G.; Liu, Y.; Chan, H. M.; Zhao, Y. F.; Cai, Z. W.; Wu, Y. N. Comparison on gestation and lactation exposure of perfluorinated compounds for newborns Environ. Int. 2011, 37 (7) 1206-1212 10.1016/j.envint.2011.05.001
34. Manzano-Salgado, C. B.; Casas, M.; Lopez-Espinosa, M. J.; Ballester, F.; Basterrechea, M.; Grimalt, J. O.; Jimenez, A. M.; Kraus, T.; Schettgen, T.; Sunyer, J.; Vrijheid, M. Transfer of perfluoroalkyl substances from mother to fetus in a Spanish birth cohort Environ. Res. 2015, 142, 471-478 10.1016/j.envres.2015.07.020
35. Monroy, R.; Morrison, K.; Teo, K.; Atkinson, S.; Kubwabo, C.; Stewart, B.; Foster, W. G. Serum levels of perfluoroalkyl compounds in human maternal and umbilical cord blood samples Environ. Res. 2008, 108 (1) 56-62 10.1016/j.envres.2008.06.001
36. Needham, L. L.; Grandjean, P.; Heinzow, B.; Jorgensen, P. J.; Nielsen, F.; Patterson, D. G.; Sjodin, A.; Turner, W. E.; Weihe, P. Partition of environmental chemicals between maternal and fetal blood and tissues Environ. Sci. Technol. 2011, 45 (3) 1121-1126 10.1021/es1019614
37. Porpora, M. G.; Lucchini, R.; Abballe, A.; Ingelido, A. M.; Valentini, S.; Fuggetta, E.; Cardi, V.; Ticino, A.; Marra, V.; Fulgenzi, A. R.; De Felip, E. Placental transfer of persistent organic pollutants: a preliminary study on mother-newborn pairs Int. J. Environ. Res. Public Health 2013, 10 (2) 699-711 10.3390/ijerph10020699
38. Zhang, T.; Sun, H. W.; Lin, Y.; Qin, X. L.; Zhang, Y. F.; Geng, X.; Kannan, K. Distribution of poly- and perfluoroalkyl substances in matched samples from pregnant women and carbon chain length related maternal transfer Environ. Sci. Technol. 2013, 47 (14) 7974-7981 10.1021/es400937y
39. Kato, K.; Wong, L. Y.; Chen, A.; Dunbar, C.; Webster, G. M.; Lanphear, B. P.; Calafat, A. M. Changes in serum concentrations of maternal poly- and perfluoroalkyl substances over the course of pregnancy and predictors of exposure in a multiethnic cohort of Cincinnati, Ohio pregnant women during 2003-2006 Environ. Sci. Technol. 2014, 48 (16) 9600-9608 10.1021/es501811k
40. Ouzounian, J. G.; Elkayam, U. Physiologic changes during normal pregnancy and delivery Cardiol. Clin. 2012, 30 (3) 317-329 10.1016/j.ccl.2012.05.004
41. 35S-labelled perfluorooctane sulfonate (PFOS) in C57BL/6 mice following late gestational exposure Reprod. Toxicol. 2010, 30 (4) 558-565 10.1016/j.reprotox.2010.07.004
42. Beesoon, S.; Webster, G. M.; Shoeib, M.; Harner, T.; Benskin, J. P.; Martin, J. W. Isomer profiles of perfluorochemicals in matched maternal, cord, and house dust samples: manufacturing sources and transplacental transfer Environ. Health Perspect. 2011, 119 (11) 1659-1664 10.1289/ehp.1003265
43. Sagiv, S. K.; Rifas-Shiman, S. L.; Webster, T. F.; Mora, A. M.; Harris, M. H.; Calafat, A. M.; Ye, X. Y.; Gillman, M. W.; Oken, E. Sociodemographic and perinatal predictors of early pregnancy per- and polyfluoroalkyl substance (PFAS) concentrations Environ. Sci. Technol. 2015, 49 (19) 11849-11858 10.1021/acs.est.5b02489
44. Watkins, D. J.; Josson, J.; Elston, B.; Bartell, S. M.; Shin, H. M.; Vieira, V. M.; Savitz, D. A.; Fletcher, T.; Wellenius, G. A. Exposure to perfluoroalkyl acids and markers of kidney function among children and adolescents living near a chemical plant Environ. Health Perspect. 2013, 121 (5) 625-630 10.1289/ehp.1205838
45. Beesoon, S.; Martin, J. W. Isomer-specific binding affinity of perfluorooctanesulfonate (PFOS) and perfluorooctanoate (PFOA) to serum proteins Environ. Sci. Technol. 2015, 49 (9) 5722-5731 10.1021/es505399w
46. 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 10.1021/es001489z
47. 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 10.1021/es800631n
48. Velez, M. P.; Arbuckle, T. E.; Fraser, W. D. Maternal exposure to perfluorinated chemicals and reduced fecundity: The mirec study Hum. Reprod. 2015, 30 (3) 701-709 10.1093/humrep/deu350
49. Jiang, W.; Zhang, Y.; Zhu, L.; Deng, J. Serum levels of perfluoroalkyl acids (PFAAs) with isomer analysis and their associations with medical parameters in Chinese pregnant women Environ. Int. 2014, 64, 40-7 10.1016/j.envint.2013.12.001
50. Yang, L.; Li, J. G.; Lai, J. Q.; Luan, H. M.; Cai, Z. W.; Wang, Y. B. N.; Zhao, Y. F.; Wu, Y. N. Placental transfer of perfluoroalkyl substances and associations with thyroid hormones: Beijing prenatal exposure study Sci. Rep. 2016, 6, 21699 10.1038/srep21699
51. 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 10.1021/es800631n
52. Syme, M. R.; Paxton, J. W.; Keelan, J. A. Drug transfer and metabolism by the human placenta Clin. Pharmacokinet. 2004, 43 (8) 487-514 10.2165/00003088-200443080-00001
53. Zhang, L. Y.; Ren, X. M.; Guo, L. H. Structure-based investigation on the interaction of perfluorinated compounds with human liver fatty acid binding protein Environ. Sci. Technol. 2013, 47 (19) 11293-11301 10.1021/es4026722
54. Bischel, H. N.; MacManus-Spencer, L. A.; Zhang, C. J.; Luthy, R. G. Strong associations of short-chain perfluoroalkyl acids with serum albumin and investigation of binding mechanisms Environ. Toxicol. Chem. 2011, 30 (11) 2423-2430 10.1002/etc.647
55. Chen, Y. M.; Guo, L. H. Fluorescence study on site-specific binding of perfluoroalkyl acids to human serum albumin Arch. Toxicol. 2009, 83 (3) 255-261 10.1007/s00204-008-0359-x
56. Qin, P. F.; Liu, R. T.; Pan, X. R.; Fang, X. Y.; Mou, Y. Impact of carbon chain length on binding of perfluoroalkyl acids to bovine serum albumin determined by spectroscopic methods J. Agric. Food Chem. 2010, 58 (9) 5561-5567 10.1021/jf100412q
57. Lambot, N.; Lybaert, P.; Boom, A.; Delogne-Desnoeck, J.; Vanbellinghen, A. M.; Graff, G.; Lebrun, P.; Meuris, S. Evidence for a clathrin-mediated recycling of albumin in human term placental Biol. Reprod. 2006, 75 (1) 90-97 10.1095/biolreprod.105.050021
58. Reynolds, L. P.; Borowicz, P. P.; Caton, J. S.; Vonnahme, K. A.; Luther, J. S.; Buchanan, D. S.; Hafez, S. A.; Grazul-Bilska, A. T.; Redmer, D. A. Uteroplacental vascular development and placental function: an update Int. J. Dev. Biol. 2010, 54 (2-3) 355-365 10.1387/ijdb.082799lr
59. Morken, N. H.; Travlos, G. S.; Wilson, R. E.; Eggesbo, M.; Longnecker, M. P. Maternal glomerular filtration rate in pregnancy and fetal size PLoS One 2014, 9 (7) e101897 10.1371/journal.pone.0101897
60. Vesterinen, H. M.; Johnson, P. I.; Atchley, D. S.; Sutton, P.; Lam, J.; Zlatnik, M. G.; Sen, S.; Woodruff, T. J. Fetal growth and maternal glomerular filtration rate: a systematic review J. Matern.-Fetal Neonat. Med. 2015, 28 (18) 2176-2181 10.3109/14767058.2014.980809