Enantioselective biotransformation of hexabromocyclododecane by in vitro rat and trout hepatic sub-cellular fractions

Environmental Science and Technology

Volumn 48, Issue 5, 2014, Pages 2732-2740

  Abdallah, Mohamed Abou Elwafa ^a,b   Uchea, Chibuzor ^a   Chipman, J Kevin ^a   Harrad, Stuart ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b Assiut University   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCONVERSION; ENANTIOSELECTIVITY; ISOMERS; METABOLISM; METABOLITES;

CONCENTRATION LEVELS; DEGRADATION PROFILES; ENANTIOSELECTIVE ANALYSIS; FIRST ORDER KINETICS; HEXABROMOCYCLODODECANES; METABOLIC DEGRADATION; METABOLIC PATHWAYS; REDUCTIVE DEBROMINATION;

RATS;

2 TETRABROMOCYCLODODECADIENE; DODECANE; HEXABROMOCYCLODODECANE; PENTABROMOCYCLODODECENE; UNCLASSIFIED DRUG; BROMINATED HYDROCARBON;

BIOTRANSFORMATION; METABOLISM; REACTION KINETICS; RODENT; SALMONID;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; ASSAY; BIOTRANSFORMATION; CELL FRACTIONATION; DEBROMINATION; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; FEMALE; IN VITRO STUDY; ISOMER; KINETICS; LIVER; MALE; METABOLISM; METABOLITE; NONHUMAN; QUALITY CONTROL; RAT; TROUT; ANIMAL; CHEMISTRY; COMPARATIVE STUDY; CYTOLOGY; DRUG EFFECTS; ONCORHYNCHUS MYKISS; SPECIES DIFFERENCE; STEREOISOMERISM;

ANIMALS; BIOTRANSFORMATION; HYDROCARBONS, BROMINATED; IN VITRO TECHNIQUES; KINETICS; LIVER; ONCORHYNCHUS MYKISS; RATS; SPECIES SPECIFICITY; STEREOISOMERISM; SUBCELLULAR FRACTIONS;

EID: 84895523488     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es404644s     Document Type: Article

References (41)

1. BSEF. Bromine Science and Environmental Forum; 2013; www.bsef.com; accessed 4-14-2013.
2. Heeb, N. V.; Schweizer, W. B.; Kohler, M.; Gerecke, A. C. Structure elucidation of hexabromocyclododecanes-A class of compounds with a complex stereochemistry Chemosphere 2005, 61 (1) 65-73
3. KEMI (National Chemicals Inspectorate). Final Draft of the EU Risk Assessment Report on Hexabromocyclododecane; R044-0710-env-hh.doc; R044-0710-env-hh.doc; Sundbyberg, Sweden, 2007.
4. Covaci, A.; Gerecke, A. C.; Law, R. J.; Voorspoels, S.; Kohler, M.; Heeb, N. V.; Leslie, H.; Allchin, C. R.; De Boer, J. Hexabromocyclododecanes (HBCDs) in the environment and humans: A review Environ. Sci. Technol. 2006, 40 (12) 3679-3688
5. Law, R. J.; Herzke, D.; Harrad, S.; Morris, S.; Bersuder, P.; Allchin, C. R. Levels and trends of HBCD and BDEs in the European and Asian environments, with some information for other BFRs Chemosphere 2008, 73 (2) 223-241
6. Marvin, C. H.; Tomy, G. T.; Armitage, J. M.; Arnot, J. A.; McCarty, L.; Covaci, A.; Palace, V. Hexabromocyclododecane: Current understanding of chemistry, environmental fate and toxicology and implications for global management Environ. Sci. Technol. 2011, 45 (20) 8613-8623
7. Roosens, L.; Abdallah, M. A.; Harrad, S.; Neels, H.; Covaci, A. Exposure to hexabromocyclododecanes (HBCDs) via dust ingestion, but not diet, correlates with concentrations in human serum: Preliminary results Environ. Health Perspect. 2009, 117 (11) 1707-1712
8. Abdallah, M. A.; Harrad, S. Tetrabromobisphenol-A, hexabromocyclododecane and its degradation products in UK human milk: Relationship to external exposure Environ. Int. 2011, 37 (2) 443-448
9. Janak, K.; Covaci, A.; Voorspoels, S.; Becher, G. Hexabromocyclododecane in marine species from the Western Scheldt Estuary: Diastereoisomer- and enantiomer-specific accumulation Environ. Sci. Technol. 2005, 39 (7) 1987-1994
10. Janak, K.; Sellstrom, U.; Johansson, A. K.; Becher, G.; de Wit, C. A.; Lindberg, P.; Helander, B. Enantiomer-specific accumulation of hexabromocyclododecanes in eggs of predatory birds Chemosphere 2008, 73 (1 Suppl) S193-200
11. Peck, A. M.; Pugh, R. S.; Moors, A.; Ellisor, M. B.; Porter, B. J.; Becker, P. R.; Kucklick, J. R. Hexabromocyclododecane in white-sided dolphins: Temporal trend and stereoisomer distribution in tissues Environ. Sci. Technol. 2008, 42 (7) 2650-2655
12. Zegers, B. N.; Mets, A.; Van Bommel, R.; Minkenberg, C.; Hamers, T.; Kamstra, J. H.; Pierce, G. J.; Boon, J. P. Levels of hexabromocyclododecane in harbor porpoises and common dolphins from western European seas, with evidence for stereoisomer-specific biotransformation by cytochrome p450 Environ. Sci. Technol. 2005, 39 (7) 2095-2100
13. Huhtala, S.; Schultz, E.; Nakari, T.; MacInnis, G.; Marvin, C.; Alaee, M. Analysis of hexabromocyclododecanes and their hydroxy metabolites from in vitro and environmental samples by LCMSMS Organohalogen Compd. 2006, 86, 1987-1990
14. Abdallah, M. A.; Ibarra, C.; Neels, H.; Harrad, S.; Covaci, A. Comparative evaluation of liquid chromatography-mass spectrometry versus gas chromatography-mass spectrometry for the determination of hexabromocyclododecanes and their degradation products in indoor dust J. Chromatogr. A 2008, 1190 (1-2) 333-341
15. Brandsma, S. H.; van der Ven, L. T. M.; de Boer, J.; Leonards, P. E. G. Identification of hydroxylated metabolites of hexabromocyclododecane in wildlife and 28-days exposed Wistar rats Environ. Sci. Technol. 2009, 43 (15) 6058-6063
16. Esslinger, S.; Becker, R.; Maul, R.; Nehls, I. Hexabromocyclododecane enantiomers: Microsomal degradation and patterns of hydroxylated metabolites Environ. Sci. Technol. 2011, 45 (9) 3938-3944
17. Hakk, H.; Szabo, D. T.; Huwe, J.; Diliberto, J.; Birnbaum, L. S. Novel and distinct metabolites identified following a single oral dose of alpha- or gamma-hexabromocyclododecane in mice Environ. Sci. Technol. 2012, 46 (24) 13494-13503
18. Barnes, B. R.; Marklund, S.; Steiler, T. L.; Walter, M.; Hjalm, G.; Amarger, V.; Mahlapuu, M.; Leng, Y.; Johansson, C.; Galuska, D.; Lindgren, K.; Abrink, M.; Stapleton, D.; Zierath, J. R.; Andersson, L. The 5′-AMP-activated protein kinase gamma 3 isoform has a key role in carbohydrate and lipid metabolism in glycolytic skeletal muscle J. Biol. Chem. 2004, 279 (37) 38441-38447
19. Soldatow, V. Y.; LeCluyse, E. L.; Griffith, L. G.; Rusyn, I. In vitro models for liver toxicity testing Toxicol. Res. 2013, 2 (1) 23-39
20. Johanning, K.; Hancock, G.; Escher, B.; Adekola, A.; Bernhard, M. J.; Cowan-Ellsberry, C.; Domoradzki, J.; Dyer, S.; Eickhoff, C.; Embry, M.; Erhardt, S.; Fitzsimmons, P.; Halder, M.; Hill, J.; Holden, D.; Johnson, R.; Rutishauser, S.; Segner, H.; Schultz, I.; Nichols, J. Assessment of metabolic stability using the rainbow trout (Oncorhynchus mykiss) liver S9 fraction. Curr. Protoc. Toxicol. 2012, Ch. 14, Unit 14, 10, pp 1-28; 10.1002/0471140856. tx1410s53.
21. Tang, L.; Zhou, J.; Yang, C. H.; Xia, B. J.; Hu, M.; Liu, Z. Q. Systematic studies of sulfation and glucuronidation of 12 flavonoids in the mouse liver S9 fraction reveal both unique and shared positional preferences J. Agric. Food Chem. 2012, 60 (12) 3223-3233
22. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 1976, 72, 248-254
23. Uchea, C. The utility of trout hepatic cells in the prediction of xenobiotic bioaccumulation and environmental persistence. Ph.D. Thesis. University of Birmingham. 2013, http://etheses.bham.ac.uk/4313/.
24. Abdallah, M. A.; Harrad, S.; Covaci, A. Hexabromocyclododecanes and tetrabromobisphenol-A in indoor air and dust in Birmingham, U.K: Implications for human exposure Environ. Sci. Technol. 2008, 42 (18) 6855-6861
25. Harrad, S.; Abdallah, M. A.; Covaci, A. Causes of variability in concentrations and diastereomer patterns of hexabromocyclododecanes in indoor dust Environ. Int. 2009, 35 (3) 573-579
26. Keller, J. M.; Stapleton, H. M.; Heltsley, R.; Peck, A.; Kucklick, J. R.; Schantz, M.; Wise, S. A. SRMs available from NIST for the analysis of brominated flame retardants; Poster presented at BFR2007; Amsterdam, The Netherlands, 2007.
27. Hiebl, J.; Vetter, W. Detection of hexabromocyclododecane and its metabolite pentabromocyclododecene in chicken egg and fish from the official food control J. Agric. Food Chem. 2007, 55 (9) 3319-3324
28. Benedict, R. T.; Stapleton, H. M.; Letcher, R. J.; Mitchelmore, C. L. Debromination of polybrominated diphenyl ether-99 (BDE-99) in carp (Cyprinus carpio) microflora and microsomes Chemosphere 2007, 69 (6) 987-993
29. Butt, C. M.; Wang, D.; Stapleton, H. M. Halogenated phenolic contaminants inhibit the in vitro activity of the thyroid regulating deiodinases in human liver Toxicol. Sci. 2011, 124 (2) 339-347
30. Szabo, D. T.; Richardson, V. M.; Ross, D. G.; Diliberto, J. J.; Kodavanti, P. R. S.; Birnbaum, L. S. Effects of perinatal PBDE Exposure on hepatic phase I, phase II, phase III, and deiodinase 1 gene expression involved in thyroid hormone metabolism in male rat pups Toxicol. Sci. 2009, 107 (1) 27-39
31. Harrad, S.; Abdallah, M. A.; Rose, N. L.; Turner, S. D.; Davidson, T. A. Current-use brominated flame retardants in water, sediment, and fish from English lakes Environ. Sci. Technol. 2009, 43 (24) 9077-9083
32. Abdallah, M. A.; Tilston, E.; Harrad, S.; Collins, C. In vitro assessment of the bioaccessibility of brominated flame retardants in indoor dust using a colon extended model of the human gastrointestinal tract J. Environ. Monit. 2012, 14 (12) 3276-3283
33. Haukas, M.; Mariussen, E.; Ruus, A.; Tollefsen, K. E. Accumulation and disposition of hexabromocyclododecane (HBCD) in juvenile rainbow trout (Oncorhynchus mykiss) Aquat. Toxicol. 2009, 95 (2) 144-151
34. Koenig, S.; Fernandez, P.; Sole, M. Differences in cytochrome P450 enzyme activities between fish and crustacea: Relationship with the bioaccumulation patterns of polychlorobiphenyls (PCBs) Aquat. Toxicol. 2012, 108, 11-17
35. Roberts, S. C.; Noyes, P. D.; Gallagher, E. P.; Stapleton, H. M. Species-specific differences and structure-activity relationships in the debromination of PBDE congeners in three fish species Environ. Sci. Technol. 2011, 45 (5) 1999-2005
36. Roberts, S. C.; Macaulay, L. J.; Stapleton, H. M. In vitro metabolism of the brominated flame retardants 2-ethylhexyl-2,3,4,5-tetrabromobenzoate (TBB) and bis(2-ethylhexyl) 2,3,4,5-tetrabromophthalate (TBPH) in human and rat tissues Chem. Res. Toxicol. 2012, 25 (7) 1435-1441
37. Bearr, J. S.; Mitchelmore, C. L.; Roberts, S. C.; Stapleton, H. M. Species specific differences in the in vitro metabolism of the flame retardant mixture, Firemaster (R) BZ-54 Aquat. Toxicol. 2012, 124, 41-47
38. van der Ven, L. T.; van de Kuil, T.; Leonards, P. E.; Slob, W.; Lilienthal, H.; Litens, S.; Herlin, M.; Hakansson, H.; Canton, R. F.; van den Berg, M.; Visser, T. J.; van Loveren, H.; Vos, J. G.; Piersma, A. H. Endocrine effects of hexabromocyclododecane (HBCD) in a one-generation reproduction study in Wistar rats Toxicol. Lett. 2009, 185 (1) 51-62
39. Germer, S.; Piersma, A. H.; van der Ven, L.; Kamyschnikow, A.; Fery, Y.; Schmitz, H. J.; Schrenk, D. Subacute effects of the brominated flame retardants hexabromocyclododecane and tetrabromobisphenol A on hepatic cytochrome P450 levels in rats Toxicology 2006, 218 (2-3) 229-236
40. Germer, S.; van der Ven, L.; Piersma, A. H.; Schrenk, D. Effect of hexabromocyclododecane (HBCDD), a flame retardant, on expression of cytochrome P450 enzymes in rat liver Naunyn-Schmiedebergs Arch. Pharmacol. 2005, 371, R109-R109
41. Darnerud, P. O. Toxic effects of brominated flame retardants in man and in wildlife Environ. Int. 2003, 29 (6) 841-853