New evidence for toxicity of polybrominated diphenyl ethers: DNA adduct formation from quinone metabolites

Environmental Science and Technology

Volumn 45, Issue 24, 2011, Pages 10720-10727

  Lai, Yongquan ^a   Lu, Minghua ^a   Gao, Xiang ^a   Wu, Hanzhi ^a   Cai, Zongwei ^a  

^a HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE ATOMS; DEOXYGUANOSINE (DG); DNA ADDUCTS; ELECTRON-DEFICIENT; ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY; IN-VITRO; IN-VIVO; MICHAEL ADDITIONS; POLYBROMINATED DIPHENYL ETHERS; QUINONE RINGS; REDUCTIVE CYCLIZATION; TYPE II;

ADDITION REACTIONS; BENZENE; BIOMOLECULES; BROMINE; DNA; ELECTROSPRAY IONIZATION; ETHERS; MASS SPECTROMETRY; METABOLISM; METABOLITES; TOXICITY;

ORGANIC POLLUTANTS;

(BROMO )1 HYDROPEROXY BENZENE; AMIDE; BENZENE DERIVATIVE; BROMINE; POLYBROMINATED DIPHENYL ETHER; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

AMMONIA; BENZENE; BROMINE; CHEMICAL BINDING; DNA; MASS SPECTROMETRY; METABOLITE; PBDE; TOXICOLOGY;

ANIMAL CELL; ARTICLE; ATOM; CYCLIZATION; DNA ADDUCT; DNA BINDING; ELECTRON; MICHAEL ADDITION; MOLECULAR MECHANICS; NONHUMAN; RAT; SUBSTITUTION REACTION;

BENZOQUINONES; DNA ADDUCTS; ENVIRONMENTAL POLLUTANTS; FLAME RETARDANTS; HALOGENATED DIPHENYL ETHERS; RISK ASSESSMENT; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TOXICITY TESTS;

EID: 83455187024     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es203068f     Document Type: Article

References (31)

1. Valters, K.; Li, H. X.; Alaee, M.; DSa, I.; Marsh, G.; Bergman, A.; Letcher, R. J. Polybrominated diphenyl ethers and hydroxylated and methoxylated brominated and chlorinated analogues in the plasma of fish from the Detroit River Environ. Sci. Technol. 2005, 39 (15) 5612-5619 (Pubitemid 41098393)
2. Alaee, M.; Arias, P.; Sjodin, A.; Bergman, A. An overview of commercially used brominated flame retardants, their applications, their use patterns in different countries/regions and possible modes of release Environ. Int. 2003, 29 (6) 683-689 (Pubitemid 37337114)
3. Qiu, X. H.; Bigsby, R. M.; Hites, R. A. Hydroxylated metabolites of polybrominated diphenyl ethers in human blood samples from the United States Environ. Health Perspect. 2009, 117 (1) 93-98
4. de Wit, C. A. An overview of brominated flame retardants in the environment Chemosphere 2002, 46 (5) 583-624 (Pubitemid 34304081)
5. Wan, Y.; Wiseman, S.; Chang, H.; Zhang, X. W.; Jones, P. D.; Hecker, M.; Kannan, K.; Tanabe, S.; Hu, J. Y.; Lam, M. H. W.; Giesy, J. P. Origin of hydroxylated brominated diphenyl ethers: natural compounds or man-made flame retardants Environ. Sci. Technol. 2009, 43 (19) 7536-7542
6. Hites, R. A. Polybrominated diphenyl ethers in the environment and in people: A meta-analysis of concentrations Environ. Sci. Technol. 2004, 38 (4) 945-956 (Pubitemid 38228706)
7. Vonderheide, A. P. A review of the challenges in the chemical analysis of the polybrominated diphenyl ethers Microchem. J. 2009, 92 (1) 49-57
8. Chen, G. S.; Konstantinov, A. D.; Chittim, B. G.; Joyce, E. M.; Bols, N. C.; Bunce, N. J. Synthesis of polybrominated diphenyl ethers and their capacity to induce CYP1A by the Ah receptor mediated pathway Environ. Sci. Technol. 2001, 35 (18) 3749-3756 (Pubitemid 32868423)
9. Sanders, J. M.; Burka, L. T.; Smith, C. S.; Black, W.; James, R.; Cunningham, M. L. Differential expression of CYP1A, 2B, and 3A genes in the F344 rat following exposure to a polybrominated diphenyl ether mixture or individual components Toxicol. Sci. 2005, 88 (1) 127-133 (Pubitemid 41548754)
10. Pacyniak, E. K.; Cheng, X. G.; Cunningham, M. L.; Crofton, K.; Klaassen, C. D.; Guo, G. L. The flame retardants, polybrominated diphenyl ethers, are pregnane X receptor activators Toxicol. Sci. 2007, 97 (1) 94-102 (Pubitemid 47072159)
11. Orn, U.; Klasson-Wehler, E. Metabolism of 2,2′,4,4′- tetrabromodiphenyl ether in rat and mouse Xenobiotica 1998, 28 (2) 199-211 (Pubitemid 28102455)
12. Sandholm, A.; Emanuelsson, B. M.; Wehler, E. K. Bioavailability and half-life of decabromodiphenyl ether (BDE-209) in rat Xenobiotica 2003, 33 (11) 1149-1158 (Pubitemid 37500171)
13. Malmberg, T.; Athanasiadou, M.; Marsh, G.; Brandt, I.; Bergmant, A. Identification of hydroxylated polybrominated diphenyl ether metabolites in blood plasma from polybrominated diphenyl ether exposed rats Environ. Sci. Technol. 2005, 39 (14) 5342-5348 (Pubitemid 41003755)
14. Stapleton, H. M.; Letcher, R. J.; Baker, J. E. Debromination of polybrominated diphenyl ether congeners BDE 99 and BDE 183 in the intestinal tract of the common carp (Cyprinus carpio) Environ. Sci. Technol. 2004, 38 (4) 1054-1061 (Pubitemid 38228719)
15. Hakk, H.; Huwe, J.; Low, M.; Rutherford, D.; Larsen, G. Tissue disposition, excretion and metabolism of 2,2′,4,4′,6- pentabromodiphenyl ether (BDE-100) in male Sprague-Dawley rats Xenobiotica 2006, 36 (1) 79-94
16. Hakk, H.; Larsen, G.; Klasson-Wehler, E. Tissue disposition, excretion and metabolism of 2,2′,4,4′,5-pentabromodiphenyl ether (BDE-99) in the male Sprague-Dawley rat Xenobiotica 2002, 32 (5) 369-382 (Pubitemid 34624632)
17. Qiu, X. H.; Mercado-Feliciano, M.; Bigsby, R. M.; Hites, R. A. Measurement of polybrominated diphenyl ethers and metabolites in mouse plasma after exposure to a commercial pentabromodiphenyl ether mixture Environ. Health Perspect. 2007, 115 (7) 1052-1058 (Pubitemid 47317072)
18. Lupton, S. J.; McGarrigle, B. P.; Olson, J. R.; Wood, T. D.; Aga, D. S. Human liver microsome-mediated metabolism of brominated diphenyl ethers 47, 99, and 153 and identification of their major metabolites Chem. Res. Toxicol. 2009, 22 (11) 1802-1809
19. Yu, Z. Q.; Zheng, K. W.; Ren, G. F.; Zheng, Y. Y.; Ma, S. T.; Peng, P. G.; Wu, M. H.; Sheng, G. Y.; Fu, J. M. Identification of hydroxylated octa- and nona-bromodiphenyl ethers in human serum from electronic waste dismantling workers Environ. Sci. Technol. 2010, 44 (10) 3979-3985
20. Bolton, J. L.; Trush, M. A.; Penning, T. M.; Dryhurst, G.; Monks, T. J. Role of quinones in toxicology Chem. Res. Toxicol. 2000, 13 (3) 135-160 (Pubitemid 30169958)
21. Zhao, S. X.; Narang, A.; Ding, X. X.; Eadon, G. Characterization and quantitative analysis of DNA adducts formed from lower chlorinated PCB-derived quinones Chem. Res. Toxicol. 2004, 17 (4) 502-511 (Pubitemid 38506984)
22. Zhao, S.; Narang, A.; Gierthy, J.; Eadon, G. Detection and characterization of DNA adducts formed from metabolites of the fungicide ortho-phenylphenol J. Agric. Food Chem. 2002, 50 (11) 3351-3358 (Pubitemid 34533646)
23. Meerts, I. A. T. M.; van Zanden, J. J.; Luijks, E. A. C.; van Leeuwen-Bol, I.; Marsh, G.; Jakobsson, E.; Bergman, A.; Brouwer, A. Potent competitive interactions of some brominated flame retardants and related compounds with human transthyretin in vitro Toxicol. Sci. 2000, 56 (1) 95-104 (Pubitemid 30441468)
24. Crain, P. F. Preparation and enzymatic hydrolysis of DNA and RNA for mass spectrometry Methods Enzymol. 1990, 193, 782-790
25. Embrechts, J.; Lemiere, F.; Van Dongen, W.; Esmans, E. L.; Buytaert, P.; Van Marck, E.; Kockx, M.; Makar, A. Detection of estrogen DNA-adducts in human breast tumor tissue and healthy tissue by combined nano LC-nano ES tandem mass spectrometry J. Am. Soc. Mass Spectrom. 2003, 14 (5) 482-491 (Pubitemid 36871629)
26. Lai, Y. Q.; Lu, M. H.; Lin, S. H.; Wu, H. Z.; Cai, Z. W. Electrospray ionization tandem mass spectrometric characterization of DNA adducts formed by bromobenzoquinones Rapid Commun. Mass Spectrom. 2011, 25 (19) 2943-2950
27. McLean, M. R.; Robertson, L. W.; Gupta, R. C. Detection of PCB adducts by the P-32-Postlabeling technique Chem. Res. Toxicol. 1996, 9 (1) 165-171
28. Oakley, G. G.; Robertson, L. W.; Gupta, R. C. Analysis of polychlorinated biphenyl-DNA adducts by P-32-postlabeling Carcinogenesis 1996, 17 (1) 109-114
29. Jowa, L.; Witz, G.; Snyder, R.; Winkle, S.; Kalf, G. F. Synthesis and characterization of deoxyguanosine-benzoquinone adducts J. Appl. Toxicol. 1990, 10 (1) 47-54 (Pubitemid 20200274)
30. Hallgren, S.; Darnerud, P. O. Polybrominated diphenyl ethers (PBDEs), polychlorinated biphenyls (PCBs) and chlorinated paraffins (CPs) in rats-testing interactions and mechanisms for thyroid hormone effects Toxicology 2002, 177 (2-3) 227-243 (Pubitemid 34804309)
31. Wan, Y.; Choi, K.; Kim, S.; Ji, K.; Chang, H.; Wiseman, S.; Jones, P. D.; Khim, J. S.; Park, S.; Park, J.; Lam, M. H. W.; Giesy, J. P. Hydroxylated polybrominated diphenyl ethers and bisphenol A in pregnant women and their matching fetuses: Placental transfer and potential risks Environ. Sci. Technol. 2010, 44 (13) 5233-5239