Quantitative structure activity relationship (QSAR) for toxicity of chlorophenols on L929 cells in vitro

Chemosphere

Volumn 64, Issue 10, 2006, Pages 1619-1626

  Liu, Xiaohua ^a   Chen, Jiangning ^a   Yu, Hongxia ^a   Zhao, Jinsong ^a   Giesy, John P ^a,b,c   Wang, Xiaorong ^a  

^a NANJING UNIVERSITY   (China)

^b National Food Safety and Toxicology Center   (United States)

^c CITY UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

2D QSAR; CoMFA; CoMSIA; Mechanism; Time dependent toxicity

Indexed keywords

HYDROPHOBICITY; MATHEMATICAL MODELS; MOLECULAR STRUCTURE; REGRESSION ANALYSIS; TOXICITY;

2D-QSAR; COMPARATIVE MOLECULAR FIELD ANALYSIS (COMFA); COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS (COMSIA); MECHANISM; TIME-DEPENDENT TOXICITY;

PHENOLS;

CHLOROPHENOL; OCTANOL; WATER;

HYDROPHOBICITY; MATHEMATICAL MODELS; MOLECULAR STRUCTURE; PHENOLS; REGRESSION ANALYSIS; TOXICITY;

CHLOROPHENOL; QUANTITATIVE ANALYSIS; TOXICITY;

ANIMAL CELL; ARTICLE; CELL STRAIN L 929; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; CORRELATION ANALYSIS; CYTOTOXICITY; DISSOCIATION CONSTANT; HYDROPHOBICITY; LC 50; LIPOPHILICITY; MOUSE; NONHUMAN; PARTITION COEFFICIENT; PHYSICAL CHEMISTRY; PREDICTION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REGRESSION ANALYSIS;

EID: 33746022389     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2006.04.091     Document Type: Article

References (25)

1. Beltrame P., Beltrame P.L., and Carniti P. Inhibiting action of chloro and nitrophenols on biodegradation of phenol: a structure-toxicity relationship. Chemosphere 13 (1984) 3-9
2. Carstens C.P., Blum J.K., and Witte I. The role of hydroxyl radicals in tetrachloro-hydroquinone induced DNA strand break formation in PM2 DNA and human fibroblasts. Chem. Biol. Interact. 74 (1990) 305-314
3. Dahlhaus M., Almstadt E., and Appel K.E. The pentachlorophenol metabolite tetrachloro-p-hydroquinone induces the formation of 8-hydroxy-2-deoxyguanosine in liver DNA of male B6C3F1 mice. Toxicol. Lett. 74 (1994) 265-274
4. Dahlhaus M., Almstadt E., Henschke P., Luttgert S., and Appel K.E. Induction of 8-hydroxy-2-deoxyguanosine and single strand breaks in DNA of V79 cells by tetrachloro-phydroquinone. Mutat. Res. 329 (1995) 29-36
5. Dahlhaus M., Almstadt E., Henachke P., Luttgert S., and Appel K.E. Oxidative DNA lesions in V79 cells mediated by pentachlorophenol metabolites. Arch. Toxicol. 70 (1996) 457-460
6. Dercova K., et al. Biodegradation and bioremediation of pentachlorophenol. Chemicke Listy 10 (2003) 991-1002
7. Ehrlich W. The effect of pentachlorophenol and its metabolite tetrachlorohydroquinone on cell growth and the induction of DNA damage in Chinese hamster ovary cells. Mutat. Res. 244 (1990) 299-302
8. Emanuele A., Cinzia B., et al. Quantitative structure-activity relationship for the toxicity of chlorophenols to mammalian submitochondrial particles. Chemosphere 38 10 (1999) 2281-2292
9. Fent K., and Hunn J. Cytotoxicity of organic environmental chemicals to fish liver cells (PLHC-1). Biochim. Biophys. Anta. 205 (1996) 1-6
10. IARC, 1991. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans: Occupational Exposures in Insecticide Application, and Some Pesticides, Lyon, vol. 53, pp. 371-402.
11. Jansson K., and Jansson V. Induction of mutation in V79 Chinese hamster cells by tetrachlorohydroquinone, a metabolite of pentachlorophenol. Mutat. Res. 260 (1991) 83-87
12. Jansson K., and Jansson V. Induction of micronuclei in V79 Chinese hamster cells by tetrachlorohydroquinone, a metabolite of pentachlorophenol. Mutat. Res. 279 (1992) 205-208
13. Jiang J., Chen J.N., Yu H.X., Zhang F., Zhang J.F., and Wang L.S. Quantitative structure activity relationship and toxicity mechanisms of chlorophenols on cells in vitro. Chin. Sci. Bull. 49 (2004) 987-989
14. Juhl U., Witte I., and Butte W. Metabolism of pentachlorophenol to tetrachloro-hydroquinone by human liver homogenate. Bull. Environ. Contam. Toxicol. 35 (1985) 596-601
15. Liu Y., and Yu H.X. Three-dimensional quantitative structure activity relationship (3D-QSAR) analysis for in vitro toxicity of chlorophenols to HepG2 cells. Chemosphere 60 6 (2005) 791-795
16. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65 (1983) 55-63
17. Renner G., and Mucke W. Transformations of pentachlorophenol Part I: Metabolism in animals and man. Toxicol. Environ. Chem. 11 (1986) 9-29
18. Rvanel P., Taillander G., Tissut M., and Benoit-Guyod J.L. Effects of chlorophenols on isolated plant mitochondria activities: a QSAR study. Ecotoxical. Environ. Safety 9 (1985) 300-320
19. Saito H., Sudo M., et al. In vitro cytotoxicity of chlorophenols to goldfish GF-Scale (GFS) cells and quantitative structure-activity relationships. Environ. Toxicol. Chem. 10 (1991) 235-241
20. Seiler J.P. Pentachlorophenol. Mutat. Res. 257 (1991) 27-47
21. Shannon R.D., Boarman G.D., Dietrich A.M., and Bevan D.R. Mitochondrial response to chlorophenols as a short-term toxicity assay. Environ. Toxicol. Chem. 10 (1991) 57-66
22. Taillandier G., Domard M., and Boucherie A. QSAR at series aromatiques: propositions de parameters steriques. Farmaco-Edizione Scientifica 38 (1983) 473-487
23. Van Ommen B., Adang A., Muller F., and Van Bladeren P.J. The microsomal metabolism of pentachlorophenol and its covalent binding to protein and DNA. Chem. Biol. Interact. 60 (1986) 1-11
24. Wang Y.J., Ho Y.S., Chu S.W., et al. Induction of glutathione depletion, p53 protein accumulation and cellular transformation by tetrachlorohydroquinone, a toxic metabolite of pentachlorophenol. Chem. Biol. Interact. 105 (1997) 1-16
25. Witte I., Juhl U., and Butte W. DNA-damaging properties and cytotoxicity in human fibroblasts of tetrachlorohydroquinone, a pentachlorophenol metabolite. Mutat. Res. 145 (1985) 71-75