QSAR classification models for the screening of the endocrine-disrupting activity of perfluorinated compounds

SAR and QSAR in Environmental Research

Volumn 23, Issue 3-4, 2012, Pages 207-220

  Kovarich, S ^a   Papa, E ^a   Li, J ^b   Gramatica, P ^a  

^a UNIVERSITY OF INSUBRIA   (Italy)

^b LANZHOU UNIVERSITY   (China)

Author keywords

classification; endocrine disruption; perfluorinated compounds; PFCs; QSAR; T4 TTR competition

Indexed keywords

COMPUTATIONAL CHEMISTRY; ENDOCRINE DISRUPTERS; FIRE EXTINGUISHERS; TOXIC MATERIALS; WATER POLLUTION;

CLASSIFICATION MODELS; EMERGING POLLUTANTS; ENDOCRINE DISRUPTING ACTIVITY; ENDOCRINE DISRUPTION; FIRE FIGHTING FOAMS; PERFLUORINATED COMPOUNDS; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; T4-TTR COMPETITION; WATERPROOF FABRICS;

FLAME RETARDANTS;

ANIMALIA;

EID: 84860315462     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/1062936X.2012.657235     Document Type: Article

References (42)

1. Prevedouros, K, Cousins, I, Buck, R and Korzeniowski, A. 2006. Sources, fate and transport of perfluorocarboxylates. Environ. Sci. Technol., 40: 32-44.
2. 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.
3. Giesy, J and Kannan, K. 2001. Global distribution of perfluorooctane sulfonate in wildlife. Environ. Sci. Technol., 35: 1339-1342.
4. Houde, M, Martin, JW, Letcher, RJ, Solomon, KR and Muir, DCG. 2006. Biological monitoring of polyfluoroalkyl substances: A review. Environ. Sci. Technol., 40: 3463-3473.
5. 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.
6. Fromme, H, Tittlemier, SA, Völkel, W, Wilhelm, M and Twardella, D. 2009. Perfluorinated compounds-Exposure assessment for the general population in western countries. Int. J. Hyg. Environ. Health, 212: 239-270.
7. Jensen, AA and Leffers, H. 2008. Emerging endocrine disrupters: Perfluoroalkylated substances. Int. J. Androl., 31: 161-169.
8. 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.
9. Weiss, JM, Andersson, PL, Lamoree, MH, Leonards, PEG, van Leeuwen, SPJ and Hamers, T. 2009. Competitive binding of poly- and perfluorinated compounds to the thyroid hormone transport protein transthyretin. Toxicol. Sci., 109: 206-216.
10. Liu, C, Deng, J, Yu, L, Ramesh, M and Zhou, B. 2010. Endocrine disruption and reproductive impairment in zebrafish by exposure to 8:2 fluorotelomer alcohol. Aquat. Toxicol., 96: 70-76.
11. Bloom, MS, Kannan, K, Spliethoff, HM, Tao, L, Aldous, KM and Vena, JE. 2010. Exploratory assessment of perfluorinated compounds and human thyroid function. Physiol. Behav., 99: 240-245.
12. European Parliament and Council, REACH-Registration, Evaluation, Authorization and Restriction of Chemicals, Off. J. Eur. Union L396 (December 12, 2006) pp. 1-849. Available at: http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2006:396:0001:0849:EN:PDF (Last accessed July 2011)
13. de Escobar, GM, Obregón, MJ and del Rey, FE. 2004. Maternal thyroid hormones early in pregnancy and fetal brain development. Best Pract. Res. Clin. Endocrinol. Metab., 8: 225-248.
14. CADASTER EU-FP7 PROJECT. Available at: www.cadaster.eu (last accessed July 2011)
15. Hamers, T, Kamstra, JH, Sonneveld, E, Murk, AJ, Kester, MHA, Andersson, PL, Legler, J and Brouwer, A. 2006. In vitro profiling of the endocrine-disrupting potency of brominated flame retardants. Toxicol. Sci., 92: 157-173.
16. HYPERCHEM 7.03 for Windows. Hypercube, Inc., Gainesville, Florida, USA, 2002
17. DRAGON 5.5 for Windows, Talete srl, Milan, Italy, 2007
18. Sharaf, MA, Illman, DL and Kowalski, BR. 1986. Chemometrics, New York: Wiley Interscience.
19. Zheng, WF 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.
20. Tropsha, A, Gramatica, P and Gombar, VK. 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.
21. Gramatica, P. 2007. Principles of QSAR models validation: Internal and external. QSAR Comb. Sci., 26: 694-701.
22. Cooper, JA, Saracci, R and Cole, P. 1979. Describing the validity of carcinogen screening tests. Brit. J. Cancer, 39: 87-89.
23. Eriksson, L, Jaworska, J, Worth, AP, Cronin, MTD, McDowell, RM 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.
24. Kovarich, S, Papa, E and Gramatica, P. 2011. QSAR classification models for the prediction of endocrine disrupting activity of brominated flame retardants. J. Hazard. Mat., 190: 106-112.
25. Li, J and Gramatica, P. 2010. Classification and virtual screening of androgen receptor antagonists. J. Chem. Inf. Model., 50: 861-874.
26. 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.
27. Hamers, T, Kamstra, JH, Sonneveld, E, Murk, AJ, Visser, TJ, Van Velzen, MJM, 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.
28. Vinggaard, AM, Niemelä, J, Wedebye, EB and Jensen, GE. 2008. Screening of 397 chemicals and development of a quantitative structure-activity relationship model for androgen receptor antagonism. Chem. Res. Toxicol., 21: 813-823.
29. METI, Ministry of Economy Trade and Industry, Japan, Current status of testing methods development for endocrine disrupters, in 6th Meeting of the Task Force on Endocrine Disrupters Testing and Assessment (EDTA), 24-25 June 2002, Tokyo, Japan
30. database, EDKB. http://www.fda.gov/ScienceResearch/BioinformaticsTools/EndocrineDisruptorKnowledgebase/ucm135074.htm (last accessed July 2011)
31. 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.
32. Peterson, SA, Klabunde, T, Lashuel, HA, Purkey, H, Sacchettini, JC and Kelly, JW. 1998. Inhibiting transthyretin conformational changes that lead to amyloid fibril formation. Proc. Natl. Acad. Sci. U S A, 95: 12956-12960.
33. Maras, M, Vanparys, C, Muylle, F, Robbens, J, Berger, U, Barber, JL, Blust, R and De Coen, W. 2006. Estrogen-like properties of fluorotelomer alcohols as revealed by MCF-7 breast cancer cell proliferation. Environ. Health Perspect., 114: 100-105.
34. Liu, C, Du, Y and Zhou, B. 2007. Evaluation of estrogenic activities and mechanism of action of perfluorinated chemicals determined by vitellogenin induction in primary cultured tilapia hepatocytes. Aquat. Toxicol., 85: 267-277.
35. Shi, L, Fang, H, Tong, W, Wu, J, Perkins, R, Blair, RM, Branham, WS, Dial, SL, Moland, CL and Sheehan, DM. 2001. QSAR models using a large diverse set of estrogens. J. Chem. Inf. Comput. Sci., 41: 186-195.
36. Shi, L, Tong, W, Fang, H, Xie, Q, Hong, H, Perkins, R, Wu, J, Tu, M, Blair, R, Branham, WS, Waller, C, Walker, J and Sheehan, DM. 2002. An integrated "4-phase" approach for setting endocrine disruptor screening priorities - phase I and II predictions of estrogen receptor binding affinity. SAR QSAR Environ. Res., 13: 69-88.
37. Serafimova, R, Todorov, M, Nedelcheva, D, Pavlov, T, Akahori, Y, Nakai, M and Mekenyan, O. 2007. QSAR and mechanistic interpretation of estrogen receptor binding. SAR QSAR Environ. Res., 18: 389-421.
38. 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.
39. Jensen, GE, Niemelä, JR, Wedebye, EB and Nikolov, NG. 2008. QSAR models for reproductive toxicity and endocrine disruption in regulatory use-a preliminary investigation. SAR QSAR Environ. Res., 19: 631-641.
40. Ji, L, Wang, X, Qin, L, Luo, S and Wang, L. 2009. Predicting the androgenicity of structurally diverse compounds from molecular structure using different classifiers. QSAR Comb. Sci., 28: 542-550.
41. Torodov, M, Mombelli, E, Aït-Aïssa, S and Mekenyan, O. 2011. Androgen receptor binding affinity: A QSAR evaluation. SAR QSAR Environ. Res., 22: 265-291.
42. validation, OECD principles for the. for regulatory purposes, of (quantitative) structure-activity relationship models. Available at: http://www.oecd.org/dataoecd/33/37/37849783.pdf (last accessed July 2011)