Effects of primary metabolites of organophosphate flame retardants on transcriptional activity via human nuclear receptors

Toxicology Letters

Volumn 245, Issue , 2016, Pages 31-39

  Kojima, Hiroyuki ^a   Takeuchi, Shinji ^a   Van den Eede, Nele ^b   Covaci, Adrian ^b  

^a HOKKAIDO INSTITUTE OF PUBLIC HEALTH   (Japan)

^b UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

Flame retardants; Human; Nuclear receptor; Organophosphate; Reporter gene assay; Urinary metabolite

Indexed keywords

CELL NUCLEUS RECEPTOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; FLAME RETARDANT; GLUCOCORTICOID RECEPTOR ANTAGONIST; ORGANOPHOSPHATE; ORGANOPHOSPHATE FLAME RETARDANT; PREGNANE X RECEPTOR; UNCLASSIFIED DRUG; ANDROGEN RECEPTOR; BETA GALACTOSIDASE; CELL RECEPTOR; GLUCOCORTICOID RECEPTOR; ORGANOPHOSPHORUS COMPOUND; STEROID RECEPTOR;

ARTICLE; CHEMICAL STRUCTURE; CHO CELL LINE; CONTROLLED STUDY; ENZYME ACTIVITY; HUMAN; METABOLITE; PRIORITY JOURNAL; REPORTER GENE; TRANSACTIVATION ASSAY; AGONISTS; ANIMAL; ANTAGONISTS AND INHIBITORS; BIOTRANSFORMATION; CRICETULUS; DRUG EFFECTS; GENETICS; HAMSTER; METABOLISM; PLASMID; STRUCTURE ACTIVITY RELATION; TRANSCRIPTION INITIATION; URINE;

ANIMALS; BETA-GALACTOSIDASE; BIOTRANSFORMATION; CHO CELLS; CRICETINAE; CRICETULUS; ESTROGEN RECEPTOR BETA; FLAME RETARDANTS; GENES, REPORTER; HUMANS; ORGANOPHOSPHORUS COMPOUNDS; PLASMIDS; RECEPTORS, ANDROGEN; RECEPTORS, CYTOPLASMIC AND NUCLEAR; RECEPTORS, GLUCOCORTICOID; RECEPTORS, STEROID; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSCRIPTIONAL ACTIVATION;

EID: 84955476824     PISSN: 03784274     EISSN: 18793169     Source Type: Journal    
DOI: 10.1016/j.toxlet.2016.01.004     Document Type: Article

References (45)

1. Abdallah M.A., Zhang J., Pawar G., Viant M.R., Chipman J.K., D'Silva K., Bromirski M., Harrad S. High-resolution mass spectrometry provides novel insights into products of human metabolism of organophosphate and brominated flame retardants. Anal. Bioanal. Chem. 2015, 407:1871-1883.
2. Ali N., Van den Eede N., Dirtu A.C., Neels H., Covaci A. Assessment of human exposure to indoor organic contaminants via dust ingestion in Pakistan. Indoor Air 2012, 22:200-211.
3. Arulmozhiraja S., Shiraishi F., Okumura T., Iida M., Takigami H., Edmonds J.S., Morita M. Structural requirements for the interaction of 91 hydroxylated polychlorinated biphenyls with estrogen and thyroid hormone receptors. Toxicol. Sci. 2005, 84:49-62.
4. Ballesteros-Gómez A., Van den Eede N., Covaci A. In vitro human metabolism of the flame retardant resorcinol bis(diphenylphosphate) (RDP). Environ. Sci. Techol. 2015, 49:3897-3904.
5. Belcher S.M., Cookman C.J., Patisaul H.B., Stapleton H.M. In vitro assessment of human nuclear hormone receptor activity and cytotoxicity of the flame retardant mixture FM 550 and its triarylphosphate and brominated components. Toxicol. Lett. 2014, 228:93-102.
6. Butt C.M., Congleton J., Hoffman K., Fang M., Stapleton H.M. Metabolites of organophosphate flame retardants and 2-ethylhexyl tetrabromobenzoate in urine from paired mothers and toddlers. Environ. Sci. Technol. 2014, 48:10432-10438.
7. Carignan C.C., McClean M.D., Cooper E.M., Watkins D.J., Fraser A.J., Heiger-Bernays W., Stapleton H.M., Webster T.F. Predictors of tris(1,3-dichloro-2-propyl) phosphate metabolite in the urine of office workers. Environ. Int. 2013, 55:56-61.
8. Cooper E.M., Covaci A., van Nuijs A.L., Webster T.F., Stapleton H.M. Analysis of the flame retardant metabolites bis(1,3-dichloro-2-propyl) phosphate (BDCPP) and diphenyl phosphate (DPP) in urine using liquid chromatography-tandem mass spectrometry. Anal. Bioanal. Chem. 2011, 401:2123-2132.
9. Dodson R.E., Van den Eede N., Covaci A., Perovich L.J., Brody J.G., Rudel R.A. Urinary biomonitoring of phosphate flame retardants: levels in California adults and recommendations for future studies. Environ. Sci. Technol. 2014, 48:13625-13633.
10. Fang M., Webster T.F., Ferguson P.L., Stapleton H.M. Characterizing the peroxisome proliferator-activated receptor (PPARγ) ligand binding potential of several major flame retardants, their metabolites, and chemical mixtures in house dust. Environ. Health Perspect. 2015, 123:166-172.
11. Fang M., Webster T.F., Stapleton H.M. Activation of human peroxisome proliferator-activated nuclear receptors (PPARγ1) by semi-volatile compounds (SVOCs) and chemical mixtures in indoor dust. Environ. Sci. Technol. 2015, 49:10057-10064.
12. Hartmann P.C., Burgi D., Giger W. Organophosphate flame retardants and plasticizers in indoor air. Chemosphere 2004, 57:781-787.
13. Hoffman K., Daniels J.L., Stapleton H.M. Urinary metabolites of organophosphate flame retardants and their variability in pregnant women. Environ. Int. 2014, 63:169-172.
14. Kitamura S., Jinno N., Suzuki T., Sugihara K., Ohta S., Kuroki H., Fujimoto N. Thyroid hormone-like and estrogenic activity of hydroxylated PCBs in cell culture. Toxicology 2005, 208:377-387.
15. Kojima H., Sata F., Takeuchi S., Sueyoshi T., Nagai T. Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays. Toxicology 2011, 280:77-87.
16. Kojima H., Takeuchi S., Uramaru N., Sugihara K., Yoshida T., Kitamura S. Nuclear hormone receptor activity of polybrominated diphenyl ethers and their hydroxylated and methoxylated metabolites in transactivation assays using Chinese hamster ovary cells. Environ. Health Perspect. 2009, 117:1210-1218.
17. Kojima H., Takeuchi S., Itoh T., Iida M., Kobayashi S., Yoshida T. In vitro endocrine disruption potential of organophosphate flame retardants via human nuclear receptors. Toxicology 2013, 314:76-83.
18. Lynn R.K., Wong K., Garviegould C., Kennish J.M. Disposition of the flame-retardant, tris(1,3-dichloro-2-propyl) phosphate, in the rat. Drug Metab. Dispos. 1981, 9:434-441.
19. Marklund A., Andersson B., Haglund P. Screening of organophosphorus compounds and their distribution in various indoor environments. Chemosphere 2003, 53:1137-1146.
20. McKenna N.J., Lanz R.B., O'Malley B.W. Nuclear receptor coregulators: cellular and molecular biology. Endocr. Rev. 1999, 20:321-344.
21. Meeker J.D., Cooper E.M., Stapleton H.M., Hauser R. Urinary metabolites of organophosphate flame retardants: temporal variability and correlations with house dust concentrations. Environ. Health Perspect. 2013, 121:580-585.
22. Meeker J.D., Stapleton H.M. House dust concentrations of organophosphate flame retardants in relation to hormone levels and semen quality parameters. Environ. Health Perspect. 2010, 118:318-323.
23. Nomeir A.A., Kato S., Matthews H.B. The metabolism and disposition of tris(1,3-dichloro-2-propyl) phosphate (Fyrol FR-2) in the rat. Toxicol. Appl. Pharmacol. 1981, 57:401-413.
24. ® 550: effects on adipogenesis and osteogenesis in vitro. Environ. Health Perspect. 2014, 122:1225-1232.
25. Reemtsma T., Quintana J.B., Rodil R., Garcia-Lopez M., Rodriguez I. Organophosphorus flame retardants and plasticizers in water and air I. Occurrence and fate. Trends Anal. Chem. 2008, 27:727-737.
26. Reemtsma T., Lingott J., Roegler S. Determination of 14 monoalkyl phosphates, dialkyl phosphates and dialkyl thiophosphates by LC-MS/MS in human urinary samples. Sci. Total Environ. 2011, 409:1990-1993.
27. Sasaki K., Suzuki T., Takeda M., Uchiyama M. Metabolism of phosphoric acid triester by rat liver homogenate. Bull. Environ. Contam. Toxicol. 1984, 33:281-288.
28. Schindler B.K., Förster K., Angerer J. Determination of human urinary organophosphate flame retardant metabolites by solid-phase extraction and gas chromatography-tandem mass spectrometry. J. Chromatogr. B 2009, 877:375-381.
29. Stapleton H.M., Sharma S., Getzinger G., Ferguson P.L., Gabriel M., Webster T.F., et al. Novel and high volume use flame retardants in US couches reflective of the 2005 PentaBDE phase out. Environ. Sci. Technol. 2012, 46:13432-13439.
30. Stapleton H.M., Klosterhaus S., Eagle S., Fuh J., Meeker J.D., Blum A., Webster T.F. Detection of organophosphate flame retardants in furniture foam and US house dust. Environ. Sci. Technol. 2009, 43:7490-7495.
31. Su G., Crump D., Letcher R.J., Kennedy S.W. Rapid in vitro metabolism of the flame retardant triphenyl phosphate and effects on cytotoxicity and mRNA expression in chicken embryonic hepatocytes. Environ. Sci. Technol. 2014, 48:13511-13519.
32. Su G., Letcher R.J., Crump D., Gooden D.M., Stapleton H.M. In vitro metabolism of the flame retardant triphenyl phosphate in chicken embryonic hepatocytes and the importance of the hydroxylation pathway. Environ. Sci. Technol. Lett. 2015, 2:100-104.
33. Suzuki G., Tue N.M., Malarvannan G., Sudaryanto A., Takahashi S., Tanabe S., Sakai S., Brouwer A., Uramaru N., Kitamura S., Takigami H. Similarities in the endocrine-disrupting potencies of indoor dust and flame retardants by using human osteosarcoma (U2OS) cell-based reporter gene assays. Environ. Sci. Technol. 2013, 47:2898-2908.
34. Tajima S., Araki A., Kawai T., Tsuboi T., Ait Bamai Y., Yoshioka E., Kanazawa A., Cong S., Kishi R. Detection and intake assessment of organophosphate flame retardants in house dust in Japanese dwellings. Sci. Total Environ. 2014, 478:190-199.
35. Takeuchi S., Iida M., Kobayashi S., Jin K., Matsuda T., Kojima H. Differential effects of phthalate esters on transcriptional activities via human estrogen receptors α and β, and androgen receptor. Toxicology 2005, 210:223-233.
36. Takeuchi S., Shiraishi F., Kitamura S., Kuroki H., Jin K., Kojima H. Characterization of steroid hormone receptor activities in 100 hydroxylated polychlorinated biphenyls, including congeners identified in humans. Toxicology 2011, 289:112-121.
37. Takigami H., Suzuki G., Hirai Y., Ishikawa Y., Sunami M., Sakai S. Flame retardants in indoor dust and air of a hotel in Japan. Environ. Int. 2009, 35:688-693.
38. van der Veen I., de Boer J. Phosphorus flame retardants: Properties, production, environmental occurrence, toxicity and analysis. Chemoshere 2012, 88:1119-1153.
39. Van den Eede N., Dirtu A.C., Neels H., Covaci A. Analytical developments and preliminary assessment of human exposure to organophosphate flame retardants from indoor dust. Environ Int. 2011, 37:454-461.
40. Van den Eede N., Maho W., Erratico C., Neels H., Covaci A. First insights in the metabolism of phosphate flame retardants and plasticizers using human liver fractions. Toxicol. Lett. 2013, 223:9-15.
41. Van den Eede N., Neels H., Jorens P.G., Covaci A. Analysis of organophosphate flame retardant diester metabolites in human urine by liquid chromatography electrospray ionisation tandem mass spectrometry. J. Chromatogr. A 2013, 1303:48-53.
42. Van den Eede N., Erratico C., Exarchou V., Maho W., Neels H., Covaci A. In vitro biotransformation of tris(2-butoxyethyl) phosphate (TBOEP) in human liver and serum. Toxicol. Appl. Pharmacol. 2015, 284:246-253.
43. Van den Eede N., Heffernan A.L., Aylward L.L., Hobson P., Neels H., Mueller J.F., Covaci A. Age as a determinant of phosphate flame retardant exposure of the Australian population and identification of novel urinary PFR metabolites. Environ. Int. 2015, 74:1-8.
44. WHO Flame retardants: tris(chloropropyl) phosphate and tris(2-chloroethyl) phosphate. Environmental Health Criteria 1998, World Health Organization, Geneva, pp. 209.
45. WHO Flame retardants: tris(2-butoxyethyl) phosphate and tris(2-ethylhexyl) phosphate. Environmental Health Criteria 2000, World Health Organization, Geneva, pp. 218.