Covalent binding of fluorotelomer unsaturated aldehydes (FTUALs) and carboxylic acids (FTUCAs) to proteins

Environmental Science and Technology

Volumn 47, Issue 3, 2013, Pages 1655-1663

  Rand, Amy A ^a   Mabury, Scott A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BLOOD PLASMA; BOVINE BLOOD PLASMAS; BOVINE SERUM ALBUMINS; COVALENT BINDING; COVALENT INTERACTIONS; COVALENTLY BOUND; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; FLUOROTELOMER UNSATURATED CARBOXYLIC ACIDS; INTERMEDIATE COMPOUND; PROTEIN BINDING; PROTEIN FUNCTIONS; RAT LIVER MICROSOMES; UNSATURATED ALDEHYDES;

ALDEHYDES; BIOCHEMISTRY; BIOCONVERSION; BLOOD; CARBOXYLIC ACIDS; CHEMICAL COMPOUNDS; COVALENT BONDS; MAMMALS; MASS SPECTROMETRY; STOICHIOMETRY; UNSATURATED COMPOUNDS;

PROTEINS;

ALDEHYDE DERIVATIVE; BOVINE SERUM ALBUMIN; CARBOXYLIC ACID DERIVATIVE; FLUOROTELOMER UNSATURATED ALDEHYDE DERIVATIVE; FLUOROTELOMER UNSATURATED CARBOXYLIC ACID DERIVATIVE; PLASMA PROTEIN; UNCLASSIFIED DRUG;

ALDEHYDE; BIOTRANSFORMATION; BLOOD; CARBOXYLIC ACID; MICROCOSM; PLASMA; PROTEIN; RUMINANT; STOCHASTICITY; TOXICITY; UNSATURATED MEDIUM;

ARTICLE; BINDING ASSAY; BIOTRANSFORMATION; CHEMICAL BINDING; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; CONTROLLED STUDY; COVALENT BOND; ELECTROSPRAY MASS SPECTROMETRY; FOOD CONTAMINATION; FOOD PACKAGING; LIVER MICROSOME; NONHUMAN; OXIDATION; PROTEIN BINDING; PROTEIN ISOLATION; RAT; STOICHIOMETRY;

ALDEHYDES; ANIMALS; BIOTRANSFORMATION; CARBOXYLIC ACIDS; CATTLE; ENVIRONMENT; FLUORIDES; HUMANS; HYDROCARBONS, FLUORINATED; MICROSOMES, LIVER; PLASMA; PROTEIN BINDING; RATS; SERUM ALBUMIN, BOVINE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84873467844     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es303760u     Document Type: Article

References (57)

1. 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
2. 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, 8067-8074
3. Begley, T. H.; White, K.; Honigfort, P.; Twaroski, M. L.; Neches, R.; Walker, R. A. Perfluorochemicals: Potential sources of and migration from food packaging Food Addit. Contam. 2005, 22, 1023-1031
4. 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. A 2008, 25, 384-390
5. DuPont Performance Chemicals. Zonyl FS-62 fluorosurfactant technical information, DuPont. http://www.jiesen.com/manager/news/Upload/ 200410121111223511.pdf (January 5, 2011).
6. D'eon, J. C.; Mabury, S. A. Production of perfluorinated carboxylic acids (PFCAs) from the biotransformation of polyfluoroalkyl phosphate surfactants (PAPS): Exploring routes of human contamination Environ. Sci. Technol. 2007, 41, 4799-4805
7. D'eon, J. C.; Mabury, S. A. Exploring indirect sources of human exposure to perfluoroalkyl carboxylates (PFCAs): Evaluating uptake, elimination, and biotransformation of polyfluoroalkyl phosphate esters (PAPs) in the rat Environ. Health Perspect. 2010, 119, 344-350
8. Jackson, D. A.; Mabury, S. A. Enzymatic kinetic parameters for polyfluorinated alkyl phosphate hydrolysis by alkaline phosphatase Environ. Toxicol. Chem. 2012, 9, 1966-1971
9. 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, 766-770
10. Yeung, L. W. Y.; So, M. K.; Jiang, G.; Taniyasu, S.; Yamashita, N.; Song, M.; Wu, Y.; Li, J.; Giesy, J. P.; Guruge, K. S.; Lam, P. K. S. Perfluorooctanesulfonate and related fluorochemicals in human blood samples from China Environ. Sci. Technol. 2006, 40, 715-720
11. Calafat, A. M.; Kuklenyik, Z.; Caudill, S. P.; Reidy, J. A.; Needham, L. L. Perfluorochemicals in pooled serum samples from United States residents in 2001 and 2002 Environ. Sci. Technol. 2006, 40, 2128-2134
12. 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, 1596-1602
13. Haug, L. S.; Thomsen, C.; Becher, G. Time trends and the influence of age and gender on serum concentrations of perfluorinated compounds in archived human samples Environ. Sci. Technol. 2009, 43, 2131-2136
14. Olsen, G. W.; Church, T. R.; Miller, J. P.; Burris, J. M.; Hansen, K. J.; Lundberg, J. K.; Armitage, J. B.; Herron, R. M.; Medhdizadehkashi, Z.; Nobiletti, J. B.; O'Neill, E. M.; Mandel, J. H.; Zobel, L. R. Perfluorooctanesulfonate and other fluorochemicals in the serum of American Red Cross adult blood donors Environ. Health Perspect. 2003, 111, 1892-1901
15. Olsen, G. W.; Ellefson, M. E.; Mair, D. C.; Church, T. R.; Goldberg, C. L.; Herron, R. M.; Medhdizadehkashi, Z.; Nobiletti, J. B.; Rios, J. A.; Reagen, W. K.; Zobel, L. R. Analysis of a homologous series of perfluorocarboxylates from American Red Cross adult blood donors, 2000-2001 and 2006 Environ. Sci. Technol. 2011, 45, 8022-8029
16. Olsen, G. W.; Lange, C. C.; Ellefson, M. E.; Mair, D. C.; Church, T. R.; Goldberg, C. L.; Herron, R. M.; Medhdizadehkashi, Z.; Nobiletti, J. B.; Rios, J. A.; Reagen, W. K.; Zobel, L. R. Temporal trends of perfluoroalkyl concentrations in American Red Cross adult blood donors, 2000-2010 Environ. Sci. Technol. 2012, 46, 6330-6338
17. Martin, J. W.; Mabury, S. A.; O'Brien, P. J. Metabolic products and pathways of fluorotelomer alcohols in isolated rat hepatocytes Chem.-Biol. Interact. 2005, 155, 165-180
18. Nabb, D. L.; Szostek, B.; Himmelstein, M. W.; Mawn, M. P.; Gargas, M. L.; Sweeney, L. M.; Stadler, J. C.; Buck, R. C.; Fasano, W. J. In vitro metabolism of 8-2 fluorotelomer alcohol: Interspecies comparisons and metabolic pathway refinement Toxicol. Sci. 2007, 100, 333-344
19. Fasano, W. J. Absorption, distribution, metabolism, and elimination of 8-2 fluorotelomer alcohol in the rat Toxicol. Sci. 2006, 91, 341-355
20. Fasano, W. J.; Sweeney, L. M.; Mawn, M. P.; Nabb, D. L.; Szostek, B.; Buck, R. C.; Gargas, M. L. Kinetics of 8-2 fluorotelomer alcohol and its metabolites, and liver glutathione status following daily oral dosing for 45 days in male and female rats Chem.-Biol. Interact. 2009, 180, 281-295
21. Andersen, M. E.; Butenhoff, J. L.; Chang, S.-C.; Farrar, D. G.; Kennedy, G. L.; Lau, C.; Olsen, G. W.; Seed, J.; Wallace, K. B. Perfluoroalkyl acids and related chemistries - toxicokinetics and modes of action Toxicol. Sci. 2007, 102, 3-14
22. 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, 366-394
23. Martin, J.; Chan, K.; Mabury, S.; Obrien, P. Bioactivation of fluorotelomer alcohols in isolated rat hepatocytes Chem.-Biol. Interact. 2009, 177, 196-203
24. Rand, A. A.; Mabury, S. A. Assessing the structure-activity relationships of fluorotelomer acids and aldehydes with glutathione Cell Biol. Toxicol. 2012, 28, 115-124
25. Rand, A. A.; Mabury, S. A. In vitro interactions of biological nucleophiles with fluorotelomer unsaturated acids and aldehydes: Fate and consequences Environ. Sci. Technol. 2012, 46, 7398-7406
26. Liebler, D. C. Protein damage by reactive electrophiles: Targets and consequences Chem. Res. Toxicol. 2008, 21, 117-128
27. Han, X.; Snow, T. A.; Kemper, R. A.; Jepson, G. W. Binding of perfluorooctanoic acid to rat and human plasma proteins Chem. Res. Toxicol. 2003, 16, 775-781
28. Han, X.; Kemper, R. A.; Jepson, G. W. Subcellular distribution and protein binding of perfluorooctanoic acid in rat liver and kidney Drug Chem. Toxicol. 2005, 28, 197-209
29. Bischel, H. N.; MacManus-Spencer, L. A.; Luthy, R. G. Noncovalent interactions of long-chain perfluoroalkyl acids with serum albumin Environ. Sci. Technol. 2010, 44, 5263-5269
30. D'eon, J. C.; Simpson, A. J.; Kumar, R.; Baer, A. J.; Mabury, S. A. Determining the molecular interactions of perfluorinated carboxylic acids with human sera and isolated human serum albumin using nuclear magnetic resonance spectroscopy Environ. Toxicol. Chem. 2010, 29, 1678-88
31. MacManus-Spencer, L. A.; Tse, M. L.; Hebert, P. C.; Bischel, H. N.; Luthy, R. G. Binding of perfluorocarboxylates to serum albumin: A comparison of analytical methods Anal. Chem. 2010, 82, 974-981
32. Easterbrook, J.; Lu, C.; Sakai, Y.; Li, A. P. Effects of organic solvents on the activities of cytochrome P450 isoforms, UDP-dependent glucuronyl transferase, and phenol sulfotransferase in human hepatocytes Drug Metab. Dispos. 2001, 29, 141-144
33. Evans, D. C.; Watt, A. P.; Nicoll-Griffith, D. A.; Baillie, T. A. Drug-protein adducts: An industry perspective on minimizing the potential for drug bioactivation in drug discovery and development Chem. Res. Toxicol. 2004, 17, 3-16
34. Masubuchi, N.; Makino, C.; Murayama, N. Prediction of in vivo potential for metabolic activation of drugs into chemically reactive intermediate: Correlation of in vitro and in vivo generation of reactive Intermediates and in vitro glutathione conjugate formation in rats and humans Chem. Res. Toxicol. 2007, 20, 455-464
35. Takakusa, H.; Masumoto, H.; Yukinaga, H.; Makino, C.; Nakayama, S.; Okazaki, O.; Sudo, K. Covalent binding and tissue distribution/retention assessment of drugs associated with idiosyncratic drug toxicity Drug Metab. Dispos. 2008, 36, 1770-1779
36. Miyake, Y.; Yamashita, N.; So, M.; Rostkowski, P.; Taniyasu, S.; Lam, P.; Kannan, K. Trace analysis of total fluorine in human blood using combustion ion chromatography for fluorine: A mass balance approach for the determination of known and unknown organofluorine compounds J. Chrom. A 2007, 1154, 214-221
37. Franks, F. Characterization of Proteins; Humana Press: New York, 1988.
38. Colantonio, D. A.; Dunkinson, C.; Bovenkamp, D. E.; Van Eyk, J. E. Effective removal of albumin from serum Proteomics 2005, 5, 3831-3835
39. Phillips, M. M.; Dinglasan-Panlilio, M. J. A.; Mabury, S. A.; Solomon, K. R.; Sibley, P. K. Chronic toxicity of fluorotelomer acids to Daphnia magna and Chironomus dilutus Environ. Toxicol. Chem. 2010, 29, 1123-1131
40. Hu, W.; Jones, P. D.; DeCoen, W.; Newsted, J. L.; Giesy, J. P. Comparison of gene expression methods to identify genes responsive to perfluorooctane sulfonic acid Environ. Toxicol. Pharmacol. 2005, 19, 153-160
41. Liu, W.; Chen, S.; Quan, X.; Jin, Y.-H. Toxic effect of serial perfluorosulfonic and perfluorocarboxylic acids on the membrane system of a freshwater alga measured by flow cytometry Environ. Toxicol. Chem. 2008, 27, 1597
42. Hagenaars, A.; Knapen, D.; Meyer, I. J.; Van der Ven, K.; Hoff, P.; De Coen, W. Toxicity evaluation of perfluorooctane sulfonate (PFOS) in the liver of common carp (Cyprinus carpio) Aquat. Toxicol. 2008, 88, 155-163
43. Peters, T., Jr. Serum albumin Adv. Protein Chem. 1985, 37, 161-245
44. Loo, J. A.; Edmonds, C. G.; Smith, R. D. Tandem mass spectrometry of very large molecules. 2. Dissociation of multiply charged proline-containing proteins from electrospray ionization Anal. Chem. 1993, 65, 425-438
45. Aldini, G.; Gamberoni, L.; Orioli, M.; Beretta, G.; Regazzoni, L.; Maffei Facino, R.; Carini, M. Mass spectrometric characterization of covalent modification of human serum albumin by 4-hydroxy-trans-2-nonenal J. Mass Spectrom. 2006, 41, 1149-1161
46. Bruenner, B. A.; Jones, A. D.; German, J. B. Direct Characterization of Protein Adducts of the Lipid Peroxidation Product 4-Hydroxy-2-nonenal Using Electrospray Mass Spectrometry Chem. Res. Toxicol. 1995, 8, 552-559
47. Hagen, D. F.; Belisle, J.; Johnson, J. D.; Venkateswarlu, P. Characterization of fluorinated metabolites by a gas chromatographic-helium microwave plasma detector-the biotransformation of 1H, 1H, 2H, 2H perfluorodecanol to perfluorooctanoate Anal. Biochem. 1981, 118, 336-343
48. Henderson, W. M.; Smith, M. A. Perfluorooctanoic acid and perfluorononanoic acid in fetal and neonatal mice following in utero exposure to 8-2 fluorotelomer alcohol Toxicol. Sci. 2006, 95, 452-461
49. Kudo, N. Induction of hepatic peroxisome proliferation by 8-2 telomer alcohol feeding in mice: Formation of perfluorooctanoic acid in the liver Toxicol. Sci. 2005, 86, 231-238
50. Dinglasan, M. J. A.; Ye, Y.; Edwards, E. A.; Mabury, S. A. Fluorotelomer alcohol biodegradation yields poly- and perfluorinated acids Environ. Sci. Technol. 2004, 38, 2857-2864
51. Wang, N.; Szostek, B.; Buck, R. C.; Folsom, P. W.; Sulecki, L. M.; Gannon, J. T. 8-2 Fluorotelomer alcohol aerobic soil biodegradation: Pathways, metabolites, and metabolite yields Chemosphere 2009, 75, 1089-1096
52. Indirect food additives: Paper and paperboard components; Code of Federal Regulations, 21 CFR 176.170, U.S. Food and Drug Administration; U.S. Government Printing Office: Washington, DC, 2003.
53. Perfluoroalcohol phosphate treatment, Ref. Pft-001. Kobo Products. http://www.koboproductsinc.com/Downloads/PerfluoroTreatment.pdf. (December 9, 2010).
54. D'eon, J. C.; Mabury, S. A. Is indirect exposure a significant contributor to the burden of perfluorinated acids observed in humans? Environ. Sci. Technol. 2011, 45, 7974-7984
55. Rappaport, S. M.; Li, H.; Grigoryan, H.; Funk, W. E.; Williams, E. R. Adductomics: characterizing exposures to reactive electrophiles Toxicol. Lett. 2011, 213, 83-90
56. Baillie, T. A. Future of toxicology metabolic activation and drug design: Challenges and opportunities in chemical toxicology Chem. Res. Toxicol. 2006, 19, 889-893
57. Park, B. K.; Laverty, H.; Srivastava, A.; Antoine, D. J.; Naisbitt, D.; Williams, D. P. Drug bioactivation and protein adduct formation in the pathogenesis of drug-induced toxicity Chem.-Biol. Interact. 2011, 192, 30-36