Bioactivation of fluorotelomer alcohols in isolated rat hepatocytes

Chemico-Biological Interactions

Volumn 177, Issue 3, 2009, Pages 196-203

  Martin, Jonathan W ^a   Chan, Katie ^b   Mabury, Scott A ^b   O'Brien, Peter J ^b  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

Alkenal toxicity; Bioactivation; Cytotoxicity; Perfluorinated acid; Protein carbonylation; Telomer alcohol

Indexed keywords

ALCOHOL; AMINOBENZOTRIAZOLE; AMINOGUANIDINE; BENZOTRIAZOLE DERIVATIVE; FLUOROTELOMER ALCOHOL; GLUTATHIONE; HYDRALAZINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; CYTOTOXICITY; DEPLETION; LIPID PEROXIDATION; LIVER CELL; MALE; NONHUMAN; PROTEIN CARBONYLATION; RAT;

ANIMALS; BIOTRANSFORMATION; CELLS, CULTURED; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENZYME INHIBITORS; FLUOROCARBONS; GLUTATHIONE; HEPATOCYTES; LIPID PEROXIDATION; MALE; RATS; RATS, SPRAGUE-DAWLEY;

RATTUS; RODENTIA;

EID: 58349110135     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2008.11.001     Document Type: Article

References (51)

1. Taves D.R. Evidence that there are two forms of fluoride in human serum. Nature 217 (1968) 1050-1051
2. Hansen K.J., Clemen L.A., Ellefson M.E., and Johnson H.O. Compound specific quantitative characterization of organic fluorochemicals in biological matrices. Environ. Sci. Technol. 35 (2001) 766-770
3. Kannan K., Corsolini S., Falandysz J., Fillmann G., Kumar Kurunthachalam S., Loganathan Bommanna G., Mohd Mustafa A., Olivero J., Van Wouwe N., Yang Jae H., and Aldoust Kenneth M. Perfluorooctanesulfonate and related fluorochemicals in human blood from several countries. Environ. Sci. Technol. 38 (2004) 4489-4495
4. Calafat A.M., Kuklenyik Z., Caudill S.P., Reidy J.A., and Needham L.L. Perfluorochemicals in pooled serum samples from United States residents in 2001 and 2002. Environ. Sci. Technol. 40 (2006) 2128-2134
5. Kubwabo C., Vais N., and Benoit F.M. A pilot study on the determination of perfluorooctanesulfonate and other perfluorinated compounds in blood of Canadians. J. Environ. Monit. 6 (2004) 540-545
6. Ikeda T., Aiba K., Fukuda K., and Tanaka M. The induction of peroxisome proliferation in rat liver by perfluorinated fatty acids, metabolically inert derivatives of fatty acids. J. Biochem. 98 (1985) 475-482
7. Biegel L.B., Hurtt M.E., Frame S.R., O'Connor J., and Cook J.C. Mechanism of extrahepatic tumor induction by peroxisome proliferators in male rats. Toxicol. Sci. 60 (2001) 44-55
8. Lau C., Butenhoff J.L., and Rogers J.M. The developmental toxicity of perfluoroalkyl acids and their derivatives. Toxicol. Appl. Pharmacol. 198 (2004) 231-241
9. Hagen D.F., Belisle J., Johnson J.D., and 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. 118 (1981) 336-343
10. Martin J.W., Mabury S.A., and O'Brien P.J. Metabolic products and pathways of fluorotelomer alcohols in isolated rat hepatocytes. Chem. Biol. Interact. 155 (2005) 165-180
11. Fasano W.J., Carpenter S.C., Gannon S.A., Snow T.A., Stadler J.C., Kennedy G.L., Buck R.C., Korzeniowski S.H., Hinderliter P.M., and Kemper R.A. Absorption, distribution, metabolism, and elimination of 8-2 fluorotelomer alcohol in the rat. Toxicol. Sci. 91 (2006) 341-355
12. Henderson W.M., and Smith M.A. Perfluorooctanoic acid and perfluorononanoic acid in fetal and neonatal mice following in utero exposure to 8-2 fluorotelomer alcohol. Toxicol. Sci. 95 (2007) 452-461
13. Kudo N., Iwase Y., Okayachi H., Yamakawa Y., and Kawashima Y. Induction of hepatic peroxisome proliferation by 8-2 telomer alcohol feeding in mice: formation of perfluorooctanoic acid in the liver. Toxicol. Sci. 86 (2005) 231-238
14. Barber J.L., Berger U., Chaemfa C., Huber S., Jahnke A., Temme C., and Jones Kevin C. Analysis of per- and polyfluorinated alkyl substances in air samples from Northwest Europe. J. Environ. Monit. 9 (2007) 530-541
15. Martin J.W., Muir D.C.G., Solomon K.R., Moody C.A., Ellis D.A., Kwan W., and Mabury S.A. Collection of airborne fluorinated organics and analysis by gas chromatography-chemical ionization-mass spectrometry. Anal. Chem. 74 (2002) 584-590
16. Stock N.L., Lau F.K., Ellis D.A., Martin J.W., Muir D.C.G., and Mabury S.A. Polyfluorinated telomer alcohols and sulfonamides in the North American troposphere. Environ. Sci. Technol. 38 (2004) 991-996
17. Shoeib M., Harner T., Lee S.C., Lane D., and Zhu J. Sorbent-impregnated polyurethane foam disk for passive air sampling of volatile fluorinated chemicals. Anal. Chem. 80 (2008) 675-682
18. Strynar M.J., and Lindstrom A.B. Perfluorinated compounds in archived house dust samples. Fluoros-International Symposium on Fluorinated Organics in the Environment. Toronto, Canada (2005)
19. Telomer Research Program, TRP Presentation to USEPA OPPT, January 31, 2005, US Public Docket AR226-1914, 2005.
20. Dinglasan-Panlilio M.J.A., and Mabury S.A. Significant residual fluorinated alcohols present in various fluorinated materials. Environ. Sci. Technol. 40 (2006) 1447-1453
21. Begley T.H., White K., Honigfort P., Twaroski M.L., Neches R., and Walker R.A. Perfluorochemicals: potential sources of and migration from food packaging. Food Addit. Contam. 22 (2005) 1023-1031
22. D'Eon J.C., and 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. 41 (2007) 4799-4805
23. Maras M., Vanparys C., Muylle F., Robbens J., Berger U., Barber J.L., Blust R., and De Coen W. Estrogen-like properties of fluorotelomer alcohols as revealed by MCF-7 breast cancer cell proliferation. Environ. Health Perspect. 114 (2006) 100-105
24. Ishibashi H., Ishida H., Matsuoka M., Tominaga N., and Arizono K. Estrogenic effects of fluorotelomer alcohols for human estrogen receptor isoforms a and b in vitro. Biol. Pharm. Bull. 30 (2007) 1358-1359
25. Mylchreest E., Munley S.M., and Kennedy G.L. Evaluation of the developmental toxicity of 8:2 telomer B alcohol. Drug Chem. Toxicol. 28 (2005) 315-328
26. Mylchreest E., Ladics G.S., Munley S.M., Buck R.C., and Stadler J.C. Evaluation of the reproductive and developmental toxicity of a fluoroalkylethanol mixture. Drug Chem. Toxicol. 28 (2005) 159-175
27. Telomer Research Program Consortium, Purified 8-2 alcohol: Salmonella-Escherichia coli/mammalian-microsome reverse mutation assay with a confirmation assay, Covance Study 22900-0-409OECD, Submitted to US EPA AR226-1197, Covance Laboratories Inc, Vienna, VA, 2002.
28. Telomer Research Program Consortium, In vivo rat micronucleus assay. Covance Study 22900-0-454OECD, Submitted to US EPA AR226-1198, Covance Laboratories Inc., Vienna, VA, 2002.
29. O'Brien P., and Siraki A. Accelerated cytotoxicity mechanism screening using drug metabolizing enzyme modulators. Curr. Drug Metab. 6 (2005) 101-109
30. Dinglasan M.J., Ye Y., Edwards E., and Mabury S.A. Fluorotelomer alcohol biodegradation yields poly- and perfluorinated acids. Environ. Sci. Technol. 38 (2004) 2857-2864
31. Moldéus P., Högberg J., and Orrenius S. Isolation and use of liver cells. Methods Enzymol. 52 (1978) 302-310
32. Reed D.J., Babson J.R., Beatty J.W., Brodie A.E., Ellis W.W., and Potter D.W. High-performance liquid chromatography analysis of nanomole levels of glutathione, glutathione disulfide and related thiols and disulfides. Anal. Biochem. 106 (1980) 55-62
33. Smith M.T., Thor H., Hartzell P., and Orrenius S. The measurement of lipid peroxidation in isolated hepatocytes. Biochem. Pharmacol. 31 (1982) 19-26
34. Sedlak J., and Lindsay R. Estimation of total, protein-bound, and nonprotein sulfhydryl groups in tissue with Ellman's reagent. Anal. Biochem. 25 (1968) 192-205
35. Ellman G. Colorimetric method for determining low concentrations of mercaptans. Arch. Biochem. Biophys. 74 (1958)
36. Bradford M.M. A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
37. Mugford C.A., Mortillo M., Mico B.A., and Tarloff J.B. 1-Aminobenzotriazole-induced destruction of hepatic and renal cytochromes P450 in male Sprague-Dawley rats. Fundam. Appl. Toxicol. 19 (1992) 43-49
38. Peter R., Boecker R., Beaune P.H., Iwasaki M., Guengerich F.P., and Yang C.S. Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450IIE1. Chem. Res. Toxicol. 3 (1990) 566-573
39. Moridani M., Cheon S., Khan S., and O'Brien P. Metabolic activation of 4-hydroxyanisole by isolated rat hepatocytes. Drug Metab. Dispos. 30 (2002) 1063-1069
40. Theorell H., and Yonetani T. Liver alcohol dehydrogenase-dpn-pyrazole complex: a model of a ternary intermediate in the enzyme reaction. Biochem. Z. 338 (1963) 537-553
41. Bolton J., Trush M., Penning T., Dryhurst G., and Monks T. Role of quinones in toxicology. Chem. Res. Toxicol. 13 (2000) 135-160
42. O'Brien P.J. Molecular mechanisms of quinone cytotoxicity. Chem. Biol. Interact. 80 (1991) 1-41
43. Kaminskas L., Pyke S., and Burcham P. Strong protein adduct-trapping accompanies abolition of acrolein-mediated hepatotoxicity by hydralazine in mice. J. Pharmacol. Exp. Ther. 310 (2004) 1003-1010
44. Thornally P., Yurek-George A., and Argirov O. Kinetics and mechanism of the reaction of aminoguanidine with the alpha-oxoaldehydes glyoxal, methylglyoxal, and 3-deoxyglucosone under physiological conditions. Biochem. Pharmacol. 60 (2000) 55-65
45. Anders M. Chemical toxicology of reactive intermediates formed by the glutathione-dependent bioactivation of halogen-containing compounds. Chem. Res. Toxicol. 21 (2007) 145-159
46. O'Brien P., Siraki A., and Shangari N. Aldehyde sources, metabolism, molecular toxicity mechanisms, and possible effects on human health. Crit. Rev. Toxicol. 35 (2005) 609-662
47. Petersen D., and Doorn J. Reactions of 4-hydroxynonenal with proteins and cellular targets. Free Radic. Biol. Med. 37 (2004) 937-945
48. Shacter E. Quantification and significance of protein oxidation in biological samples. Drug Metab. Rev. 32 (2000) 307-326
49. Lashin O., Szweda P., Szweda L., and Romani A. Decreased complex II respiration and HNE-modified SDH subunit in diabetic heart. Free Radic. Biol. Med. 40 (2006) 886-896
50. Niknahad H., Siraki A., Shuhendler A., Khan S., Teng S., Galati G., Easson E., Poon R., and O'Brien P.J. Modulating carbonyl cytotoxicity in intact rat hepatocytes by inhibiting carbonyl-metabolizing enzymes. I. Aliphatic alkenals. Chem. Biol. Interact. 143-144 (2003) 107-117
51. Olsen G.W., Burris J.M., Ehresman D.J., Froehlich J.W., Seacat Andrew M., Butenhoff J.L., and Zobel L.R. Half-life of serum elimination of perfluorooctanesulfonate,perfluorohexanesulfonate, and perfluorooctanoate in retired fluorochemical production workers. Environ. Health Perspect. 115 (2007) 1298-1305