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Chemical Compound Review:

HBCD 1,2,5,6,9,10- hexabromocyclododecane

Synonyms: AGN-PC-007VUG, CHEMBL375298, ACMC-1BN89, AG-L-22912, ANW-27232, ...

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High impact information on HSDB 6110

In a previous study the biodegradation of hexabromocyclododecane (HBCD) was reported to occur under realistic environmental concentrations in soils and freshwater aquatic sediments with biotransformation half-lives ranging from approximately 2 days to 2 months [1].
The extent of bioaccumulation of hexabromocyclododecane (HBCD) isomers (alpha, beta, and gamma) was determined in the Lake Ontario pelagic food web using liquid chromatography tandem mass spectrometry (LC/MS/MS) [2].
Occurrence and bioavailability of polybrominated diphenyl ethers and hexabromocyclododecane in sediment and fish from the Cinca River, a tributary of the Ebro River (Spain) [3].
Neurotoxicity of the pentabrominated diphenyl ether mixture, DE-71, and hexabromocyclododecane (HBCD) in rat cerebellar granule cells in vitro [4].
T(3)-induced tail tip regression was antagonized by 2,2',3,3',4,4',5,5',6-nona brominated diphenyl ether (BDE206) and potentiated by hexabromocyclododecane (HBCD) in a concentration dependent manner, which was consistent with results obtained with a in vitro T(3)-dependent proliferation bioassay termed the T-screen [5].

Biological context of HSDB 6110

Levels of hexabromocyclododecane in harbor porpoises and common dolphins from western European seas, with evidence for stereoisomer-specific biotransformation by cytochrome p450 [6].
The levels in the peregrine falcon are similar to those found earlier in the Baltic region [Lindberg, P., Sellstrom, U., Haggberg, L., de Wit, C.A., 2004. Higher brominated diphenyl ethers and hexabromocyclododecane found in eggs of peregrine falcons (Falco peregrinus) breeding in Sweden. Environmental Science & Technology. 38 (1), 93-96] [7].
Disruption of thyroid hormone-mediated Xenopus laevis tadpole tail tip regression by hexabromocyclododecane (HBCD) and 2,2',3,3',4,4',5,5',6-nona brominated diphenyl ether (BDE206) [5].

Anatomical context of HSDB 6110

In this study, polychlorinated biphenyls (PCBs), some organochlorinated pesticides (OCPs), polybrominated diphenyl ethers (PBDEs), and hexabromocyclododecane (HBCD) were analyzed in yolk sac of European shag (Phalacrocorax aristotelis) hatchlings from an island situated on the coast of Mid-Norway [8].

Associations of HSDB 6110 with other chemical compounds

Tetrabromobisphenol A (TBBPA) and hexabromocyclododecane diastereoisomers (alpha-, beta/-, and gamma-HBCD) were investigated in effluents from sewage treatment works, landfill leachates, sediments, and food web organisms of the North Sea basin [9].
In this study, a screening of selected biomarkers in juvenile rainbow trout (Oncorhynchus mykiss) and feral eelpout (Zoarces viviparus) was performed after exposure to hexabromocyclododecane (HBCDD) and tetrabromobisphenol A (TBBPA) [10].
Biomagnification of polybrominated diphenyl ether and hexabromocyclododecane flame retardants in the polar bear food chain in Svalbard, Norway [11].

Analytical, diagnostic and therapeutic context of HSDB 6110

Congener-specific analysis of hexabromocyclododecane by high-performance liquid chromatography/electrospray tandem mass spectrometry [12].
Investigation of hexabromocyclododecane thermal degradation pathways by gas chromatography/mass spectrometry [13].

References

Biodegradation and product identification of [14C]hexabromocyclododecane in wastewater sludge and freshwater aquatic sediment. Davis, J.W., Gonsior, S.J., Markham, D.A., Friederich, U., Hunziker, R.W., Ariano, J.M. Environ. Sci. Technol. (2006) [Pubmed]
Biomagnification of alpha- and gamma-hexabromocyclododecane isomers in a Lake Ontario food web. Tomy, G.T., Budakowski, W., Halldorson, T., Whittle, D.M., Keir, M.J., Marvin, C., MacInnis, G., Alaee, M. Environ. Sci. Technol. (2004) [Pubmed]
Occurrence and bioavailability of polybrominated diphenyl ethers and hexabromocyclododecane in sediment and fish from the Cinca River, a tributary of the Ebro River (Spain). Eljarrat, E., de la Cal, A., Raldua, D., Duran, C., Barceló, D. Environ. Sci. Technol. (2004) [Pubmed]
Neurotoxicity of the pentabrominated diphenyl ether mixture, DE-71, and hexabromocyclododecane (HBCD) in rat cerebellar granule cells in vitro. Reistad, T., Fonnum, F., Mariussen, E. Arch. Toxicol. (2006) [Pubmed]
Disruption of thyroid hormone-mediated Xenopus laevis tadpole tail tip regression by hexabromocyclododecane (HBCD) and 2,2',3,3',4,4',5,5',6-nona brominated diphenyl ether (BDE206). Schriks, M., Zvinavashe, E., David Furlow, J., Murk, A.J. Chemosphere (2006) [Pubmed]
Levels of hexabromocyclododecane in harbor porpoises and common dolphins from western European seas, with evidence for stereoisomer-specific biotransformation by cytochrome p450. Zegers, B.N., Mets, A., Van Bommel, R., Minkenberg, C., Hamers, T., Kamstra, J.H., Pierce, G.J., Boon, J.P. Environ. Sci. Technol. (2005) [Pubmed]
Brominated flame retardants and other organobromines in Norwegian predatory bird eggs. Herzke, D., Berger, U., Kallenborn, R., Nygård, T., Vetter, W. Chemosphere (2005) [Pubmed]
Exposure and effects of persistent organic pollutants in European shag (Phalacrocorax aristotelis) hatchlings from the coast of Norway. Murvoll, K.M., Skaare, J.U., Anderssen, E., Jenssen, B.M. Environ. Toxicol. Chem. (2006) [Pubmed]
Distribution and fate of HBCD and TBBPA brominated flame retardants in North Sea estuaries and aquatic food webs. Morris, S., Allchin, C.R., Zegers, B.N., Haftka, J.J., Boon, J.P., Belpaire, C., Leonards, P.E., Van Leeuwen, S.P., De Boer, J. Environ. Sci. Technol. (2004) [Pubmed]
Effects of the brominated flame retardants hexabromocyclododecane (HBCDD), and tetrabromobisphenol A (TBBPA), on hepatic enzymes and other biomarkers in juvenile rainbow trout and feral eelpout. Ronisz, D., Finne, E.F., Karlsson, H., Förlin, L. Aquat. Toxicol. (2004) [Pubmed]
Biomagnification of polybrominated diphenyl ether and hexabromocyclododecane flame retardants in the polar bear food chain in Svalbard, Norway. Sørmo, E.G., Salmer, M.P., Jenssen, B.M., Hop, H., Baek, K., Kovacs, K.M., Lydersen, C., Falk-Petersen, S., Gabrielsen, G.W., Lie, E., Skaare, J.U. Environ. Toxicol. Chem. (2006) [Pubmed]
Congener-specific analysis of hexabromocyclododecane by high-performance liquid chromatography/electrospray tandem mass spectrometry. Budakowski, W., Tomy, G. Rapid Commun. Mass Spectrom. (2003) [Pubmed]
Investigation of hexabromocyclododecane thermal degradation pathways by gas chromatography/mass spectrometry. Barontini, F., Cozzani, V., Cuzzola, A., Petarca, L. Rapid Commun. Mass Spectrom. (2001) [Pubmed]

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