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Chemical Compound Review:

CHEMBL150098 2,3,4,5-tetrabromo-6-(3,5- dibromo-2...

Synonyms: CHEBI:348085, NSC-364753, AC1L7PIZ, NSC364753, 80246-27-1, ...

Sonne, C. et al., Schecter, A. et al., Rattner, B.A. et al., Zhou, T. et al., Streets, S.S. et al., et al.

Rattner, McGowan, Golden, Hatfield, Toschik, Lukei, Hale, Schmitz-Afonso, Rice, Staskal, Diliberto, Birnbaum, Boon, Lewis, Tjoen-A-Choy, Allchin, Law, De Boer, Ten Hallers-Tjabbes, Zegers, Schecter, P??pke, Harris, Tung, Musumba, Olson, Birnbaum, Shelver, Keum, Kim, Rutherford, Hakk, Bergman, Li, Fuglei, Bustnes, Hop, Mørk, Björnfoth, van Bavel, Schecter, Pavuk, Päpke, Ryan, Birnbaum, Rosen, Kodavanti, Ward, Ludewig, Robertson, Birnbaum, Sjödin, Jones, Focant, Lapeza, Wang, McGahee, Zhang, Turner, Slazyk, Needham, Patterson, Staskal, Hakk, Bauer, Diliberto, Birnbaum, de la Fuente, Manzanaro, Martín, de Quesada, Reymundo, Luengo, Gago, Stapleton, Dodder, Kucklick, Reddy, Schantz, Becker, Gulland, Porter, Wise, Schecter, Johnson-Welch, Tung, Harris, P??pke, Rosen, Kuiper, Bergman, Vos, van den Berg, Beineke, Siebert, M??ller, Baumg??rtner, Fernlöf, Gadhasson, Pödra, Darnerud, Thuvander,

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Disease relevance of NSC364753

Polybrominated diphenyl ether (PBDE) congeners are constituents of flame retardants, and there is growing concern regarding their persistence, bioaccumulation, and toxicity [1].
Our primary goal was to detect possible changes in bone mineral content (osteopenia) due to elevated exposure to organochlorine [polychlorinated biphenyls (PCBs), dichlorodiphenyl trichloroethane (DDT) and its metabolites, chlordanes (CHLs), dieldrin, hexacyclohexanes, hexachlorobenzene] and polybrominated diphenyl ether (PBDE) compounds [2].
In an age-controlled statistical analysis of covariance, increases in glomerular mesangial deposits and interstitial fibrosis were significantly (p < 0.05) correlated with polybrominated diphenyl ether (sigmaPBDE) concentrations in subadults [3].

High impact information on NSC364753

In this study, a polybrominated diphenyl ether (1) naturally occurring in a marine sponge was found to inhibit recombinant human ALR2 with an IC(50) of 6.4 microM [4].
Retrospective time-trend study of polybrominated diphenyl ether and polybrominated and polychlorinated biphenyl levels in human serum from the United States [5].
No previous reports exist on polybrominated diphenyl ether (PBDE) congeners in human milk from individual U.S. mothers [6].
This reflects suspected debromination of BDE-99 in the food web of Lake Michigan. A regression of the log of the bioaccumulation factor (BAF) and the log of the octanol-water partition coefficent (K(OW)) indicated a positive relationship for both PCB congeners and PBDE congeners [7].
Toxicokinetics of polybrominated diphenyl ether congeners 47, 99, 100, and 153 in mice [8].

Biological context of NSC364753

Quantitative structure-activity relationship models for prediction of the toxicity of polybrominated diphenyl ether congeners [9].
Levels of polybrominated diphenyl ether (PBDE) flame retardants in animals representing different trophic levels of the North Sea food Web [10].
Polybrominated diphenyl ether (PBDE) body burdens in North America are 20 times that of Europeans and some "high accumulation" individuals have burdens up to 1-2 orders of magnitude higher than median values, the reasons for which are not known [11].
Polybrominated diphenyl ether (PBDE) effects in rat neuronal cultures: 14C-PBDE accumulation, biological effects, and structure-activity relationships [12].
The objective of the current study was to characterize the effects of DE-71 (a commercial polybrominated diphenyl ether mixture containing mostly tetra- and penta-bromodiphenyl ethers) on thyroid hormones and hepatic enzyme activity in offspring, following perinatal maternal exposure [13].

Anatomical context of NSC364753

Identification of hydroxylated polybrominated diphenyl ether metabolites in blood plasma from polybrominated diphenyl ether exposed rats [14].
Several antibodies were developed for the polybrominated diphenyl ether flame retardant BDE-47 (1), often found in the highest concentration in human milk, plasma, and adipose tissue [15].
Toxicological analysis revealed an association between elevated body burdens of environmental contaminants, such as polychlorinated biphenyls (PCB) and polybrominated diphenyl ether (PBDE) and lymphoid depletion in thymus and spleen of these whales [16].
Polybrominated diphenyl ether (PBDE) levels in livers of U.S. human fetuses and newborns [17].
Some polybrominated diphenyl ether (PBDE) flame retardants with wide environmental distribution inhibit TCDD-induced EROD activity in primary cultured carp (Cyprinus carpio) hepatocytes [18].

Associations of NSC364753 with other chemical compounds

Polybrominated diphenyl ether (PBDE)-induced alterations in vitamin A and thyroid hormone concentrations in the rat during lactation and early postnatal development [19].
Adipose tissues from 20 arctic foxes (Alopex lagopus) of both sexes from Svalbard were analysed for polybrominated diphenyl ether (PBDE), polychlorinated biphenyl (PCB), p,p'-dichlorodiphenyltrichloroethane (DDE), chlordane, and hexachlorobenzene (HCB) concentrations [20].
Concentrations of p,p'-DDE and many other organochlorine pesticides or metabolites, total PCBs, some arylhydrocarbon receptor-active PCB congeners and polybrominated diphenyl ether congeners, and perfluorooctanesulfonate were often greater in sample eggs from regions of concern compared to the reference site [21].
In addition, HBCD concentrations appear to be increasing in California sea lion populations, whereas PBDE concentrations, between 1993 and 2003, were highly variable [22].
Additionally, 11 polybrominated diphenyl ether (PBDE) congeners were measured in the human milk samples. p,p'-DDT and its major metabolite, p,p'-DDE, together with HCB, were found in all milk and serum samples [23].

Gene context of NSC364753

2,2',4,4'-Tetrabromodiphenyl ether (BDE 47) is the major polybrominated diphenyl ether (PBDE) found in environmental samples and human tissue despite its small contribution to global production and usage [24].
Lack of effects of some individual polybrominated diphenyl ether (PBDE) and polychlorinated biphenyl (PCB) congeners on human lymphocyte functions in vitro [25].

Analytical, diagnostic and therapeutic context of NSC364753

ObjectivesOur objectives in this study were to expand a previously reported U.S. market basket survey using a larger sample size and to estimate levels of PBDE intake from food for the U.S. general population by sex and age.MethodsWe measured concentrations of 13 polybrominated diphenyl ether (PBDE) congeners in food in 62 food samples [26].

References

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Is bone mineral composition disrupted by organochlorines in east Greenland polar bears (Ursus maritimus)? Sonne, C., Dietz, R., Born, E.W., Riget, F.F., Kirkegaard, M., Hyldstrup, L., Letcher, R.J., Muir, D.C. Environ. Health Perspect. (2004) [Pubmed]
Are organohalogen contaminants a cofactor in the development of renal lesions in east Greenland polar bears (Ursus maritimus)? Sonne, C., Dietz, R., Leifsson, P.S., Born, E.W., Kirkegaard, M., Letcher, R.J., Muir, D.C., Riget, F.E., Hyldstrup, L. Environ. Toxicol. Chem. (2006) [Pubmed]
Synthesis, activity, and molecular modeling studies of novel human aldose reductase inhibitors based on a marine natural product. de la Fuente, J.A., Manzanaro, S., Martín, M.J., de Quesada, T.G., Reymundo, I., Luengo, S.M., Gago, F. J. Med. Chem. (2003) [Pubmed]
Retrospective time-trend study of polybrominated diphenyl ether and polybrominated and polychlorinated biphenyl levels in human serum from the United States. Sjödin, A., Jones, R.S., Focant, J.F., Lapeza, C., Wang, R.Y., McGahee, E.E., Zhang, Y., Turner, W.E., Slazyk, B., Needham, L.L., Patterson, D.G. Environ. Health Perspect. (2004) [Pubmed]
Polybrominated diphenyl ethers (PBDEs) in U.S. mothers' milk. Schecter, A., Pavuk, M., Päpke, O., Ryan, J.J., Birnbaum, L., Rosen, R. Environ. Health Perspect. (2003) [Pubmed]
Partitioning and bioaccumulation of PBDEs and PCBs in Lake Michigan. Streets, S.S., Henderson, S.A., Stoner, A.D., Carlson, D.L., Simcik, M.F., Swackhamer, D.L. Environ. Sci. Technol. (2006) [Pubmed]
Toxicokinetics of polybrominated diphenyl ether congeners 47, 99, 100, and 153 in mice. Staskal, D.F., Hakk, H., Bauer, D., Diliberto, J.J., Birnbaum, L.S. Toxicol. Sci. (2006) [Pubmed]
Quantitative structure-activity relationship models for prediction of the toxicity of polybrominated diphenyl ether congeners. Wang, Y., Liu, H., Zhao, C., Liu, H., Cai, Z., Jiang, G. Environ. Sci. Technol. (2005) [Pubmed]
Levels of polybrominated diphenyl ether (PBDE) flame retardants in animals representing different trophic levels of the North Sea food Web. Boon, J.P., Lewis, W.E., Tjoen-A-Choy, M.R., Allchin, C.R., Law, R.J., De Boer, J., Ten Hallers-Tjabbes, C.C., Zegers, B.N. Environ. Sci. Technol. (2002) [Pubmed]
Is house dust the missing exposure pathway for PBDEs? An analysis of the urban fate and human exposure to PBDEs. Jones-Otazo, H.A., Clarke, J.P., Diamond, M.L., Archbold, J.A., Ferguson, G., Harner, T., Richardson, G.M., Ryan, J.J., Wilford, B. Environ. Sci. Technol. (2005) [Pubmed]
Polybrominated diphenyl ether (PBDE) effects in rat neuronal cultures: 14C-PBDE accumulation, biological effects, and structure-activity relationships. Kodavanti, P.R., Ward, T.R., Ludewig, G., Robertson, L.W., Birnbaum, L.S. Toxicol. Sci. (2005) [Pubmed]
Developmental exposure to brominated diphenyl ethers results in thyroid hormone disruption. Zhou, T., Taylor, M.M., DeVito, M.J., Crofton, K.M. Toxicol. Sci. (2002) [Pubmed]
Identification of hydroxylated polybrominated diphenyl ether metabolites in blood plasma from polybrominated diphenyl ether exposed rats. Malmberg, T., Athanasiadou, M., Marsh, G., Brandt, I., Bergman, A. Environ. Sci. Technol. (2005) [Pubmed]
Hapten syntheses and antibody generation for the development of a polybrominated flame retardant ELISA. Shelver, W.L., Keum, Y.S., Kim, H.J., Rutherford, D., Hakk, H.H., Bergman, A., Li, Q.X. J. Agric. Food Chem. (2005) [Pubmed]
Increased blood interleukin-10 mRNA levels in diseased free-ranging harbor porpoises (Phocoena phocoena). Beineke, A., Siebert, U., M??ller, G., Baumg??rtner, W. Vet. Immunol. Immunopathol. (2007) [Pubmed]
Polybrominated diphenyl ether (PBDE) levels in livers of U.S. human fetuses and newborns. Schecter, A., Johnson-Welch, S., Tung, K.C., Harris, T.R., P??pke, O., Rosen, R. J. Toxicol. Environ. Health Part A (2007) [Pubmed]
Some polybrominated diphenyl ether (PBDE) flame retardants with wide environmental distribution inhibit TCDD-induced EROD activity in primary cultured carp (Cyprinus carpio) hepatocytes. Kuiper, R.V., Bergman, A., Vos, J.G., van den Berg, M. Aquat. Toxicol. (2004) [Pubmed]
Polybrominated diphenyl ether (PBDE)-induced alterations in vitamin A and thyroid hormone concentrations in the rat during lactation and early postnatal development. Ellis-Hutchings, R.G., Cherr, G.N., Hanna, L.A., Keen, C.L. Toxicol. Appl. Pharmacol. (2006) [Pubmed]
Environmental contaminants in arctic foxes (Alopex lagopus) in Svalbard: Relationships with feeding ecology and body condition. Fuglei, E., Bustnes, J.O., Hop, H., Mørk, T., Björnfoth, H., van Bavel, B. Environ. Pollut. (2007) [Pubmed]
Contaminant exposure and reproductive success of ospreys (Pandion haliaetus) nesting in Chesapeake Bay regions of concern. Rattner, B.A., McGowan, P.C., Golden, N.H., Hatfield, J.S., Toschik, P.C., Lukei, R.F., Hale, R.C., Schmitz-Afonso, I., Rice, C.P. Arch. Environ. Contam. Toxicol. (2004) [Pubmed]
Determination of HBCD, PBDEs and MeO-BDEs in California sea lions (Zalophus californianus) stranded between 1993 and 2003. Stapleton, H.M., Dodder, N.G., Kucklick, J.R., Reddy, C.M., Schantz, M.M., Becker, P.R., Gulland, F., Porter, B.J., Wise, S.A. Mar. Pollut. Bull. (2006) [Pubmed]
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