Hexabromocyclododecane enantiomers: Microsomal degradation and patterns of hydroxylated metabolites

Environmental Science and Technology

Volumn 45, Issue 9, 2011, Pages 3938-3944

  Esslinger, Susanne ^a   Becker, Roland ^a   Maul, Ronald ^a   Nehls, Irene ^a  

^a BAM FEDERAL INSTITUTE FOR MATERIALS RESEARCH AND TESTING   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANALYTICAL COLUMNS; FIRST ORDER KINETICS; HALF LIVES; HEXABROMOCYCLODODECANES; HPLC-MS/MS; HYDROXYLATED METABOLITES; IN-VITRO; MUSCLE TISSUES; PHASE I; RAT LIVER MICROSOMES; REVERSED PHASE;

DEGRADATION; ENANTIOMERS; LIVER; METABOLISM; RADIOACTIVITY; TISSUE;

CHIRALITY;

ALPHA HEXABROMOCYCLODODECANE; BETA HEXABROMOCYCLODODECANE; GAMMA HEXABROMOCYCLODODECANE; HEXABROMOCYCLODODECANE; UNCLASSIFIED DRUG;

GADOID; METABOLISM; METABOLITE; MUSCLE; ORGANIC POLLUTANT; PERCIFORM; RODENT; SEABIRD; SEPARATION;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; DEGRADATION; DIHYDROXYLATION; ENANTIOMER; FISH; HALF LIFE TIME; HERRING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; IN VITRO STUDY; ISOMER; LIVER; LIVER MICROSOME; LIVER MICROSOME METABOLISM; MALE; MASS SPECTROMETRY; METABOLITE; MUSCLE TISSUE; NONHUMAN; RAT;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENVIRONMENTAL POLLUTANTS; FLAME RETARDANTS; HYDROCARBONS, BROMINATED; HYDROXYLATION; MALE; MICROSOMES, LIVER; RATS; RATS, SPRAGUE-DAWLEY; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

LARUS ARGENTATUS; POLLACHIUS POLLACHIUS; RATTUS;

EID: 79955538308     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es1039584     Document Type: Article

References (27)

1. Alaee, M.; Arias, P.; Sjodin, A.; Bergman, A. An overview of commercially used bromi-nated flame retardants, their applications, their use patterns in different countries/regions and possible modes of release Environ. Int. 2003, 29, 683-689 (Pubitemid 37337114)
2. 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, 3679-3688 (Pubitemid 43902361)
3. de Wit, C. A.; Herzke, D.; Vorkamp, K. Brominated flame retardants in the Arctic environment-Trends and new candidates Sci. Total Environ. 2010, 408, 2885-2918
4. Law, R. J.; Allchin, C. R.; de Boer, J.; Covaci, A.; Herzke, D.; Lepom, P.; Morris, S.; Tronczynski, J.; de Wit, C. A. Levels and trends of brominated flame retardants in the European environment Chemosphere 2006, 64, 187-208 (Pubitemid 43841888)
5. Becher, G. The stereochemistry of 1,2,5,6,9,10-hexabromocyclododecane and its graphic representation Chemosphere 2005, 58, 989-991 (Pubitemid 40091713)
6. Heeb, N. V.; Schweizer, W. B.; Kohler, M.; Gerecke, A. C. Structure elucidation of hexabromocyclododecanes-A class of compounds with a complex stereochemistry Chemos-phere 2005, 61, 65-73 (Pubitemid 41266913)
7. Peled, M.; Scharia, R.; Sondack, D. Thermal Rearrangement of Hexabromocyclododecane (HBCD); Elsevier: New York, 1995; p 92 - 99.
8. Arsenault, G.; Konstantinov, A.; Marvin, C. H.; MacInnis, G.; McAlees, A.; McCrindle, R.; Riddell, N.; Tomy, G. T.; Yeo, B. Synthesis of the two minor isomers, delta- and epsilon-1,2,5,6,9,10-hexabromocyclododecane, present in commercial hexabromocyclododecane Chemosphere 2007, 68, 887-892 (Pubitemid 46602504)
9. Tomy, G. T.; Pleskach, K.; Oswald, T.; Halldorson, T.; Helm, P. A.; Macinnis, G.; Marvin, C. H. Enantioselective bioaccumulation of hexabromocyclododecane and congener-specific accumulation of brominated diphenyl ethers in an eastern Canadian Arctic marine food web Environ. Sci. Technol. 2008, 42, 3634-3639 (Pubitemid 351694072)
10. Janák, K.; Sellstrom, U.; Johansson, A. K.; Becher, G.; de Wit, C. A.; Lindberg, P.; He-lander, B. Enantiomer-specific accumulation of hexabromocyclododecanes in eggs of predatory birds Chemosphere 2008, 73, S193-S200
11. Janák, K.; Covaci, A.; Voorspoels, S.; Becher, G. Hexabromocyclododecane in marine species from the Western Scheldt Estuary: Diastereoisomer- and enantiomer-specific ac-cumulation Environ. Sci. Technol. 2005, 39, 1987-1994 (Pubitemid 40490281)
12. Köppen, R.; Becker, R.; Esslinger, S.; Nehls, I. Enantiomer-specific analysis of hexabro-mocyclododecane in fish from Etnefjorden (Norway) Chemosphere 2010, 80, 1241-1245
13. Esslinger, S.; Becker, R.; Jung, C.; Schröter-Kermani, C.; Bremser, W.; Nehls, I. Temporal trend (1988-2008) of hexabromocyclododecane enantiomers in herring gull eggs from the German coastal region Chemosphere 2011, 83, 161-167
14. He, M. J.; Luo, X. J.; Yu, L. H.; Liu, J. A.; Zhang, X. L.; Chen, S. J.; Chen, D.; Mai, B. X. Tetrabromobisphenol-A and Hexabromocyclododecane in birds from an E-waste region in South China: Influence of diet on diastereoisomer- and enantiomer-specific dis-tribution and trophodynamics Environ. Sci. Technol. 2010, 44, 5748-5754
15. 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, 2095-2100 (Pubitemid 40490295)
16. 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 LC-MS/MS Organohalogen Compd. 2006, 68, 1987-1990
17. Szabo, D. T.; Diliberto, J. J.; Hakk, H.; Huwe, J. K.; Birnbaum, L. S. Toxicokinetics of the flame retardant hexabromocyclododecane gamma: effect of dose, timing, route, repeated exposure, effect of dose, timing, route, repeated exposure, and metabolism Toxicol. Sci. 2010, 117, 282-293
18. Abdallah, M. A. E.; Harrad, S. Personal exposure to HBCDs and its degradation products via ingestion of indoor dust Environ. Int. 2009, 35, 870-876
19. Hiebl, J.; Vetter, W. Detection of hexabromocyclododecane and its metabolite pentabro-mocyclododecene in chicken egg and fish from the official food control J. Agr. Food Chem. 2007, 55, 3319-3324 (Pubitemid 46806541)
20. Harrad, S.; Abdallah, M. A. E.; 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, 9077-9083
21. 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, 6058-6063
22. Esslinger, S.; Becker, R.; Muller-Belecke, A.; Bremser, W.; Jung, C.; Nehls, I. HBCD stereoisomer pattern in mirror carps following dietary exposure to pure gamma-HBCD enantiomers J. Agric. Food Chem. 2010, 58, 9705-9710
23. Koeppen, R.; Becker, R.; Emmerling, F.; Jung, C.; Nehls, I. Enantioselective preparative HPLC separation of the HBCD-Stereoisomers from the technical product and their absolute structure elucidation using X-ray crystallography Chirality 2007, 19, 214-222
24. Umweltbundesamt, German Environmental Specimen Bank-Standard Operating Proce-dures 2009. http://www.umweltprobenbank.de/en/documents/10022 (accessed March 15, 2009, ].
25. 2002/657/EC, COMMISSION DECISION 2002/657/EC implementing Council Directive 96/23/EC concerning the performance of analytical methods and the interpretation of re-sults. Off. J. Eur. 2002; L 221: 8-36.
26. Hunziker, R. W.; Gonsior, S.; MacGregor, J. A.; Desjardins, D.; Ariano, J.; Friederich, U. Fate and effect of hexabromocyclododecane in the environment Organohalogen Compd. 2004, 66, 2300-2305
27. Arnot, J.; McCarty, L.; Armitage, J.; Toose-Reid, L.; Wania, F.; Cousins, I. An evaluation of hexabromocyclododecane (HBCD) for Persistent Organic Pollutant (POP) properties and the potential for adverse effects in the Environment, p. 98. European Brominated Flame Retardant Industry Panel (EBFRIP), May 26, 2009, submitted, http://www.unece.org/env/documents/2009/EB/wg5/wgsr45/ Informal%20docs/An%20evaluation%20of%20hexabromocyclododecane-Final%20report. pdf (accessed March 2, 2011)