Estimating stepwise debromination pathways of polybrominated diphenyl ethers with an analogue Markov Chain Monte Carlo algorithm

Chemosphere

Volumn 114, Issue , 2014, Pages 187-194

  Zou, Yonghong ^a,b   Christensen, Erik R ^a   Zheng, Wei ^b   Wei, Hua ^c,d   Li, An ^c  

^a University of Wisconsin Milwaukee   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^d Department of Biological and Environmental Engineering   (United States)

Author keywords

Debromination pathways; Markov Chain Monte Carlo; Polybrominated diphenyl ethers; QSAR; Stochastic processes

Indexed keywords

COMPUTATIONAL CHEMISTRY; ETHERS; EXCITONS; MARKOV CHAINS; MAXIMUM LIKELIHOOD; MONTE CARLO METHODS; ORGANIC POLLUTANTS; RANDOM PROCESSES; STOCHASTIC SYSTEMS;

DEBROMINATION; DECABROMODIPHENYL ETHERS (BDE209); MARKOV CHAIN MONTE CARLO ALGORITHMS; MARKOV CHAIN MONTE-CARLO; MAXIMUM LIKELIHOOD FUNCTION; NATURAL ENVIRONMENTS; POLYBROMINATED DIPHENYL ETHER (PBDES); QSAR;

STOCHASTIC MODELS;

DECABROMODIPHENYL ETHER; ETHER; HEXANE; POLYBROMINATED DIPHENYL ETHER; UNCLASSIFIED DRUG;

ALGORITHM; ALKANE; MARKOV CHAIN; MONTE CARLO ANALYSIS; PBDE; POLLUTANT REMOVAL; REACTION KINETICS; SEPARATION; STOCHASTICITY;

ALGORITHM; ARTICLE; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); DEBROMINATION; LIGHT EXPOSURE; MAXIMUM LIKELIHOOD METHOD; MONTE CARLO METHOD; PROBABILITY; SIMULATION; STATISTICS; SUNLIGHT;

DEBROMINATION PATHWAYS; MARKOV CHAIN MONTE CARLO; POLYBROMINATED DIPHENYL ETHERS; QSAR; STOCHASTIC PROCESSES;

ALGORITHMS; HALOGENATED DIPHENYL ETHERS; HALOGENATION; HEXANES; MARKOV CHAINS; MODELS, CHEMICAL; PHOTOLYSIS; SUNLIGHT;

EID: 84905696145     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2014.04.072     Document Type: Article

References (43)

1. Andersson P.L., Oberg K., Orn U. Chemical characterization of brominated flame retardants and identification of structurally representative compounds. SETAC Environ. Toxicol. Chem. 2006, 25:1275-1282.
2. Bartoszynski R., Niewiadomska-Bugaj M. Markov Chains. Probability and Statistical Inference 2008, 103-124. John Wiley & Sons, Inc., Hoboken, New Jersey. second ed. R. Bartoszynski, M. Niewiadomska-Bugaj (Eds.).
3. Bastos P.M., Eriksson J., Vidarson J., Bergman Å. Oxidative transformation of polybrominated diphenyl ether congeners (PBDEs) and of hydroxylated PBDEs (OH-PBDEs). Environ Sci. Pollut. Res. 2008, 15:606-613.
4. Bezares-Cruz J., Jafvert C.T., Hua I. Solar photodecomposition of decabromodiphenyl ether: products and quantum yield. Environ. Sci. Technol. 2004, 38:4149-4156.
5. Bzdusek P.A., Christensen E.R., Lee C.M., Pakdeesusuk U., Freedman D.L. PCB congeners and dechlorination in sediments of Lake Hartwell, South Carolina, determined from cores collected in 1987 and 1998. Environ. Sci. Technol. 2006, 40:109-119.
6. Bzdusek P.A., Lu J., Christensen E.R. PCB congeners and dechlorination in sediments of Sheboygan River, Wisconsin, determined by matrix factorization. Environ. Sci. Technol. 2006, 40:120-129.
7. Chen Y., Zhou S., Li Q. Mathematical modeling of degradation for bulk-erosive polymers: applications in tissue engineering scaffolds and drug delivery systems. Acta Biomater. 2011, 7:1140-1149.
8. Christiansson A., Eriksson J., Teclechiel D., Bergman A. Identification and quantification of products formed via photolysis of decabromodiphenyl ether. Environ. Sci. Pollut. Res. 2009, 16:312-321.
9. Darnerud P.O. Toxic effects of brominated flame retardants in man and in wildlife. Environ. Int. 2003, 29:841-853.
10. Davis E.F., Stapleton H.M. Photodegradation pathways of nonabrominated diphenyl ethers, 2-ethylhexyltetrabromobenzoate and di(2-ethylhexyl)tetrabromophthalate: identifying potential markers of photodegradation. Environ. Sci. Technol. 2009, 43:5739-5746.
11. Eriksson J., Green N., Marsh G., Bergman A. Photochemical decomposition of 15 polybrominated diphenyl ether congeners in methanol/water. Environ. Sci. Technol. 2004, 38:3119-3125.
12. Fang L., Huang J., Yu G., Li X. Quantitative structure-property relationship studies for direct photolysis rate constants and quantum yields of polybrominated diphenyl ethers in hexane and methanol. Ecotoxicol. Environ. Safety 2009, 72:1587-1593.
13. He J., Robrock K.R., Alvarez-Cohen L. Microbial reductive debromination of polybrominated diphenyl ethers (PBDEs). Environ. Sci. Technol. 2006, 40:4429-4434.
14. Heimstad E.S., Bastos P.M., Eriksson J., Bergman K., Harju M. Quantitative structure - photodegradation relationships of polybrominated diphenyl ethers, phenoxyphenols and selected organochlorines. Chemosphere 2009, 77:914-921.
15. Hites R.A. Polybrominated diphenyl ethers in the environment and in people: a meta-analysis of concentrations. Environ. Sci. Technol. 2004, 38(4):945-2481.
16. Hu J., Eriksson L., Bergman A., Jakobsson E., Kolehmainen E., Knuutinen J., Suontamo R., Wei X. Molecular orbital studies on brominated diphenyl ethers. Part II-reactivity and quantitative structure-activity (property) relationships. Chemosphere 2005, 59:1043-1057.
17. Hughes A.S., Vanbriesen J.M., Small M.J. Identification of structural properties associated with polychlorinated biphenyl dechlorination processes. Environ. Sci. Technol. 2010, 44:2842-2848.
18. Imamoglu, I., 2001.PCB sources and degradation in river sediments determined by receptor modeling. PhD Thesis. University of Wisconsin - Milwaukee, Milwaukee, WI.
19. Imamoglu I., Li K., Christensen E.R. PCB congener patterns and dechlorination in dated sediments from Ashtabula River, Ohio, USA. SETAC Environ. Toxicol. Chem. 2002, 21:2283-2291.
20. Imamoglu I., Li K., Christensen E.R., McMullin J.K. Sources and dechlorination of polychlorinated biphenyl congeners in the sediments of Fox River, Wisconsin. Environ. Sci. Technol. 2004, 38:2574-2583.
21. La Guardia M.J., Hale R.C., Harvey E. Detailed polybrominated diphenyl ether (PBDE) congener composition of the widely used penta-, octa- and deca-PBDE technical flame-retardant mixture. Environ. Sci. Technol. 2006, 40:6247-6254.
22. Lee L.K., Ding C., Yang K.-L., He J. Complete debromination of tetra- and penta-brominated diphenyl ethers by a coculture consisting of Dehalococcoides and Desulfovibrio species. Environ. Sci. Technol. 2011, 45:8475-8482.
23. McDonald T.A. A perspective on the potential health risks of PBDEs. Chemosphere 2002, 46:745-755.
24. Metropolis N., Rosenbluth A.W., Rosenbluth M.N., Teller A.H., Teller E. Equation of state calculations by fast computing machines. J. Chem. Phys. 1953, 21:1087-1092.
25. Niu J.F., Shen Z.Y., Yang Z.F., Long X.X., Yu G. Quantitative structure-property relationship on photodegradation of polybrominated diphenyl ethers. Chemosphere 2006, 64:658-665.
26. Oliveira R.F., Terrin A., Di Benedetto G., Cannon R.C., Koh W., Kim M., Zaccolo M., Blackwell K.T. The role of type 4 phosphodiesterases in generating microdomains of cAMP: large scale stochastic simulations. PLoS ONE 2010, 5:e11725.
27. Petrov P.P., Miller W. Kinetic Monte Carlo simulation of the wetting layer in Stranski-Krastanov heteroepitaxial growth. Comput. Mater. Sci. 2012, 60:176-180.
28. Press W.H., Teukolsky S.A., Vetterling W.T., Flannery B.P. Modeling of data. Numerical Recipes in C the Art of Scientific Computing 2002, 657-666. Cambridge University Press, New York. second ed. W.H. Press, S.A. Teukolsky, W.T. Vetterling, B.P. Flannery (Eds.).
29. Ribeiro A.S., Dai X., Yli-Harja O. Variability of the distribution of differentiation pathway choices regulated by a multipotent delayed stochastic switch. J. Theor. Biol. 2009, 260:66-76.
30. Robrock K.R., Korytar P., Alvarez-Cohen L. Pathways for the anaerobic microbial debromination of polybrominated diphenyl ethers. Environ. Sci. Technol. 2008, 42:2845-2852.
31. Subbian E., Yabuta Y., Shinde U.P. Folding pathway mediated by an intramolecular chaperone: intrinsically unstructured propeptide modulates stochastic activation of subtilisin. J. Mol. Biol. 2005, 347:367-383.
32. Suh Y.W., Buettner G.R., Venkataraman S., Treimer S.E., Robertson L.W., Ludewig G. UVA/B-induced formation of free radicals from decabromodiphenyl ether. Environ. Sci. Technol. 2009, 43:2581-2588.
33. Tokarz J.A., Ahn M.Y., Leng J., Filley T.R., Nies L. Reductive debromination of polybrominated diphenyl ethers in anaerobic sediment and a biomimetic system. Environ. Sci. Technol. 2008, 42:1157-1164.
34. USEPA, 2009. Polybrominated diphenyl ethers (PBDEs) action plan. USEPA, (accessed on 1.04.11). http://www.epa.gov/opptintr/existingchemicals/pubs/pbdes_ap_2009_1230_final.pdf.
35. Vinu R., Levine S.E., Wang L., Broadbelt L.J. Detailed mechanistic modeling of poly(styrene peroxide) pyrolysis using kinetic Monte Carlo simulation. Chem. Eng. Sci. 2012, 69:456-471.
36. Wang S., Hao C., Gao Z., Chen J., Qiu J. Effects of excited-state structures and properties on photochemical degradation of polybrominated diphenyl ethers: a TDDFT study. Chemosphere 2012, 88:33-38.
37. Wei H., Yang R., Li A., Christensen E.R., Rockne K.J. Gas chromatographic retention of 180 polybrominated diphenyl ethers and prediction of relative retention under various operational conditions. J. Chromatography A 2010, 1217:2964-2972.
38. Wei H., Dassanayake P.S., Li A. Parametric evaluation for programmable temperature vaporization large volume injection in gas chromatographic analysis of polybrominated diphenyl ethers. Int. J. Environ. Anal. Chem. 2010, 90:535-547.
39. Wei H., Zou Y.H., Li A., Christensen E.R., Rockne K.J. Photolytic debromination pathway of polybrominated diphenyl ethers in hexane by sunlight. Environ. Pollut. 2013, 174:194-200.
40. Wei H., Zhang S., Wang Y., Wang Ying, Li A., Negrusz A., Yu Gang Dependence of mass spectrometric fragmentation on the bromine substitution pattern of polybrominated diphenyl ethers. J. Am. Soc. Mass Spect. 2014.
41. Zeng X., Simonich S.L., Robrock K.R., Korytar P., Alvarez-Cohen L., Barofsky D.F. Development and validation of a congener-specific photodegradation model for polybrominated diphenyl ethers. SETAC Environ. Toxicol. Chem. 2008, 27:2427-2435.
42. Zhuang Y., Jin L., Luthy R.G. Kinetics and pathways for the debromination of polybrominated diphenyl ethers by bimetallic and nanoscale zerovalent iron: effects of particle properties and catalyst. Chemosphere 2012, 89:426-432.
43. Zou, Y.H., 2011. PCB and PBDE sources and degradation in aquatic sediments determined by positive matrix factorization. PhD Thesis. University of Wisconsin - Milwaukee, Milwaukee, WI.