QSAR prediction of the competitive interaction of emerging halogenated pollutants with human transthyretin£

SAR and QSAR in Environmental Research

Volumn 24, Issue 4, 2013, Pages 333-349

  Papa, E ^a   Kovarich, S ^a   Gramatica, P ^a  

^a UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

brominated flame retardants; classification; endocrine disruption; perfluorinated compounds; QSAR; T4 TTR competition

Indexed keywords

ENDOCRINE DISRUPTERS; FLAME RETARDANTS; MOLECULAR GRAPHICS;

BROMINATED FLAME RETARDANTS; COMPETITIVE INTERACTIONS; DATA GAP; ENDOCRINE DISRUPTION; HUMAN TRANSTHYRETIN; PERFLUORINATED COMPOUNDS; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; RELATIVE BINDING; T4-TTR COMPETITION; TRANSTHYRETIN;

COMPUTATIONAL CHEMISTRY;

HALOGENATED HYDROCARBON; POLLUTANT; PREALBUMIN;

ANTAGONISTS AND INHIBITORS; COMPUTER SIMULATION; HUMAN; POLLUTANT; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATISTICAL MODEL; TOXICITY;

COMPUTER SIMULATION; ENVIRONMENTAL POLLUTANTS; HUMANS; HYDROCARBONS, HALOGENATED; MODELS, STATISTICAL; PREALBUMIN; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84891514662     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/1062936X.2013.773374     Document Type: Article

References (47)

1. Dreyer, A., Weinberg, I., Temme, C. and Ebinghaus, R. 2009. Polyfluorinated compounds in the atmosphere of the Atlantic and southern oceans: Evidence for a global distribution. Environ. Sci. Technol., 43: 6507 - 6514.
2. Houde, M., Martin, J.W., Letcher, R.J., Solomon, K.R. and Muir, D.C.G. 2006. Biological monitoring of polyfluoroalkyl substances: A review. Environ. Sci. Technol., 40: 3463 - 3473.
3. Lau, C., Anitole, K., Hodes, C., Lai, D., Pfahles-Hutchens, A. and Seed, J. 2007. Perfluoroalkyl acids: A review of monitoring and toxicological findings. Toxicol. Sci., 99: 366 - 394.
4. de Wit, C.A. 2002. An overview of brominated flame retardants in the environment. Chemosphere, 46: 583 - 624.
5. Law, R.J., Herzke, D., Harrad, S., Morris, S., Bersuder, P. and Allchin, C.R. 2008. Levels and trends of HBCD and BDEs in the European and Asian environments, with some information for other BFRs. Chemosphere, 73: 223 - 241.
6. Jensen, A.A. and Leffers, H. 2008. Emerging endocrine disrupters: Perfluoroalkylated substances. Int. J. Androl., 31: 161 - 169.
7. Shi, Z., Zhang, H., Ding, L., Feng, Y., Xu, M. and Dai, J. 2009. The effect of perfluorododecanonic acid on endocrine status, sex hormones and expression of steroidogenic genes in pubertal female rats. Rep. Toxicol., 27: 352 - 359.
8. Weiss, J.M., Andersson, P.L., Lamoree, M.H., Leonards, P.E.G., van Leeuwen, S.P.J. and Hamers, T. 2009. Competitive binding of poly- and perfluorinated compounds to the thyroid hormone transport protein transthyretin. Toxicol. Sci., 109: 206 - 216.
9. Meerts, I.A.T.M., van Zanden, J.J., Luijks, E.A.C., van Leeuwen-Bol, I., Marsh, G., Jakobsson, E., Bergman, A. and Brouwer, A. 2000. Potent competitive interactions of some brominated flame retardants and related compounds with human transthyretin in vitro. Toxicol. Sci., 56: 95 - 104.
10. Lilienthal, H., Hack, A., Roth-Harer, A., Grande, S.W. and Talsness, C.E. 2006. Effects of developmental exposure to 2,2,4,4,5-pentabromodiphenyl ether (PBDE-99) on sex steroids, sexual development, and sexually dimorphic behavior in rats. Environ. Health Perspect., 114: 194 - 201.
11. Hamers, T., Kamstra, J.H., Sonneveld, E., Murk, A.J., Kester, M.H.A., Andersson, P.L., Legler, J. and Brouwer, A. 2006. In vitro profiling of the endocrine-disrupting potency of brominated flame retardants. Toxicol. Sci., 92: 157 - 173.
12. Morreale de Escobar, G., Obregón, M.J. and Escobar del Rey, F. 2004. Role of thyroid hormone during early brain development. Eur. J. Endocrinol., 151: U25 - U37.
13. Gutshall, D.M., Pilcher, G.D. and Langley, A.E. 1989. Mechanism of the serum thyroid hormone lowering effect of perfluoro-n-decanoic acid (PFDA) in rats. J. Toxicol. Environ. Health, 28: 53 - 65.
14. Lau, C., Anitole, K., Hodes, C., Lai, D., Pfahles-Hutchens, A. and Seed, J. 2007. Perfluoroalkyl acids: A review of monitoring and toxicological findings. Toxicol. Sci., 99: 366 - 394.
15. Chang, S.-C., Thibodeaux, J.R., Eastvold, M.L., Ehresman, D.J., Bjork, J.A., Froehlich, J.W., Lau, C., Singh, R.J., Wallace, K.B. and Butenhoff, J.L. 2008. Thyroid hormone status and pituitary function in adult rats given oral doses of perfluorooctane sulfonate (PFOS). Toxicology, 243: 330 - 339.
16. Ucán-Marin, F., Arukwe, A., Mortensen, A.S., Gabrielsen, G.W. and Letcher, R.J. 2010. Recombinant albumin and transthyretin transport proteins from two gull species and human: chlorinated and brominated contaminant binding and thyroid hormones. Environ. Sci. Technol., 44: 497 - 504.
17. Kovarich, S., Papa, E., Li, J. and Gramatica, P. 2012. QSAR classification models for the screening of the endocrine-disrupting activity of perfluorinated compounds. SAR QSAR Environ. Res., 23: 207 - 220.
18. CADASTER FP7 PROJECT; available at http://www.cadaster.eu.
19. Organisation for Economic Co-operation and Development (OECD). 2004. OECD Principles for the Validation, for Regulatory Purposes, of (Quantitative) Structure-Activity Relationship Models, Paris: OECD.
20. Hamers, T., Kamstra, J.H., Sonneveld, E., Murk, A.J., Visser, T.J., Van Velzen, M.J.M., Brouwer, A. and Bergman, A. 2008. Biotransformation of brominated flame retardants into potentially endocrine-disrupting metabolites, with special attention to 2,2,4,4-tetrabromodiphenyl ether (BDE-47). Mol. Nutr. Food Res., 52: 284 - 298.
21. Kovarich, S., Papa, E. and Gramatica, P. 2011. QSAR classification models for the prediction of endocrine disrupting activity of brominated flame retardants. J. Haz. Mater., 190: 106 - 112.
22. Papa, E., Kovarich, S. and Gramatica, P. 2010. QSAR modeling and prediction of the endocrine disrupting potencies of brominated flame retardants. Chem. Res. Toxicol., 23: 946 - 954.
23. European Parliament, Regulation (EC) No 1907/2006 of the European Parliament and of the Council of 18 December 2006 concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH) establishing a European Chemicals Agency, amending Directive 1999/45/EC and repealing Council Regulation (EEC) No 793/93 and Commission Regulation (EC) No 1488/94 as well as Council Directive 76/769/EEC and Commission Directives 91/155/EEC, 93/67/EEC, 93/105/EC and 2000/21/EC, Off. J. Eur. Union L396 (2006), pp. 1-849.
24. HYPERCHEM 7.03 for Windows. Hypercube, Inc., Gainesville, FL, USA, 2002.
25. DRAGON 5.5 for Windows, Talete srl, Milan, Italy, 2007.
26. Tropsha, A., Gramatica, P. and Gombar, V.K. 2003. The importance of being Earnest: Validation is the absolute essential for successful application and interpretation of QSPR models. QSAR Comb. Sci., 22: 69 - 77.
27. Gramatica, P. 2007. Principles of QSAR models validation: internal and external. QSAR Comb. Sci., 26: 694 - 701.
28. Ballabio, D. and Todeschini, R. 2008. " Multivariate Classification for Qualitative Analysis ". In Infrared Spectroscopy for Food Quality Analysis and Control, Edited by: Sun, Da-Wen. 83 - 104. Amsterdam and London: Elsevier.
29. Sharaf, M.A., Illman, D.L. and Kowalski, B.R. 1986. Chemometrics, New York: Wiley Interscience.
30. Zheng, W.F. and Tropsha, A. 2000. Novel variable selection quantitative structure-property relationship approach based on the k-nearest-neighbor principle. J. Chem. Inform. Comput. Sci., 40: 185 - 194.
31. N. Chirico, E. Papa, S. Kovarich, S. Cassani, and P. Gramatica, QSARINS (software for QSAR model development and validation). University of Insubria, Varese, Italy; software available at http://www.qsar.it.
32. Todeschini, R., Maiocchi, A. and Consonni, V. 1999. The K correlation index: Theory development and its application in chemometrics. Chemom. Intell. Lab., 46: 13 - 29.
33. Shi, L.M., Fang, H., Tong, W., Wu, J., Perkins, R., Blair, R.M., Branham, W.S., Dial, S.L., Moland, C.L. and Sheehan, D.M. 2001. QSAR models using a large diverse set of estrogens. J. Chem. Inf. Comput. Sci., 41: 186 - 195.
34. Schüürmann, G., Ebert, R.U., Chen, J., Wang, B. and Kühne, R. 2008. External validation and prediction employing the predictive squared correlation coefficient. Test set activity mean vs. Training set activity mean. J. Chem. Inf. Model., 48: 2140 - 2145.
35. Consonni, V., Ballabio, D. and Todeschini, R. 2010. Evaluation of model predictive ability by external validation techniques. J. Chemom., 24: 194 - 201.
36. Chirico, N. and Gramatica, P. 2011. Real external predictivity of QSAR models: How to evaluate it? Comparison of different validation criteria and proposal of using the concordance correlation coefficient. J. Chem. Inf. Model., 51: 2320 - 2335.
37. Eriksson, L., Jaworska, J., Worth, A.P., Cronin, M.T.D., McDowell, R.M. and Gramatica, P. 2003. Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs. Environ. Health Perspect., 111: 1361 - 1375.
38. Atkinson, A.C. 1985. Plots, Transformations and Regression, Oxford: Clarendon Press.
39. Consonni, V., Todeschini, R. and Pavan, M. 2002. Structure/response correlations and similarity/diversity analysis by GETAWAY descriptors. 1. Theory of the novel 3D molecular descriptors. J. Chem. Inform. Comput. Sci., 42: 682 - 692.
40. Pike, A.C.W., Brzozowski, A.M. and Hubbard, R.E. 2000. A structural biologist's view of the oestrogen receptor. J. Steroid Biochem. Mol. Biol., 74: 261 - 268.
41. Liu, H., Papa, E., Walker, J.D. and Gramatica, P. 2007. In silico screening of estrogen-like chemicals based on different nonlinear classification models. J. Mol. Graph. Model, 26: 135 - 144.
42. Roncaglioni, A., Piclin, N., Pintore, M. and Benfenati, E. 2008. Binary classification models for endocrine disrupter effects mediated through the estrogen receptor. SAR QSAR Environ. Res., 19: 697 - 733.
43. Li, J. and Gramatica, P. 2010. QSAR classification of estrogen receptor binders and pre-screening of potential pleiotropic EDCs. SAR QSAR Environ. Res., 21: 657 - 669.
44. Harju, M., Hamers, T., Kamstra, J.H., Sonneveld, E., Boon, J.P., Tysklind, M. and Andersson, P.L. 2007. Quantitative structure activity relationship modeling on in vitro endocrine effects and metabolic stability involving 26 selected brominated flame retardants. Environ. Toxicol. Chem., 26: 816 - 826.
45. Marchesini, G.R., Meimaridou, A., Haasnoot, W., Meulenberg, E., Albertus, F., Mizuguchi, M., Takeuchi, M., Irth, H. and Murk, A.J. 2008. Biosensor discovery of thyroxine transport disrupting chemicals. Tox. Appl. Pharmacol., 232: 150 - 160.
46. Ucán-Marín, F., Arukwe, A., Mortensen, A., Gabrielsen, G.W., Fox, G.A. and Letcher, R.J. 2009. Recombinant transthyretin purification and competitive binding with organohalogen compounds in two gull species (Larus argentatus and Larus hyperboreus). Toxicol. Sci., 107: 440 - 450.
47. Peterson, S.A., Klabunde, T., Lashuel, H.A., Purkey, H., Sacchettini, J.C. and Kelly, J.W. 1998. Inhibiting transthyretin conformational changes that lead to amyloid fibril formation. Proc. Natl. Acad. Sci. U. S. A., 95: 12956 - 12960.