2D/3D-QSAR comparative study on mutagenicity of nitroaromatics

Science in China, Series B: Chemistry

Volumn 48, Issue 3, 2005, Pages 246-252

  Wang, Xiaodong ^a   Lin, Zhifen ^b   Yin, Daqiang ^a   Liu, Shushen ^a   Wang, Liansheng ^a  

^a NANJING UNIVERSITY   (China)

^b SOUTH CHINA SEA INSTITUTE OF OCEANOLOGY   (China)

Author keywords

3D QSAR; CoMFA; Mechanism; Mutagenicity; Nitroaromatics

Indexed keywords

CARCINOGENS; ENVIRONMENTAL ENGINEERING; MOLECULAR STRUCTURE; MUTAGENESIS; ORGANIC COMPOUNDS; TOXICITY;

COMPARATIVE MOLECULAR FIELD ANALYSIS (COMFA); MOLECULAR ORBITAL THEORY; MUTAGENICITY; NITROAROMATICS; ORGANIC POLLUTANTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS (QSARS);

TOXIC MATERIALS;

EID: 21444448435     PISSN: 10069291     EISSN: None     Source Type: Journal    
DOI: 10.1360/04yb0077     Document Type: Article

References (20)

1. Wang, L. S., Quantitative Structure-Activity Relationships of Organic Pollutants (in Chinese), Beijing: Environmental Science Press of China, 1993.
2. Wang, X. D., Structure-activity Relationships of Selected Organic Pollutants (in Chinese), Nanjing: Doctoral Thesis of Nanjing University, 2002.
3. Hadley, W. M., A review of the literature on enzymatic reduction of nitrocompounds, Springfield: LMF-104 UC 48 National Tech. Inform. Serv., U.S. Department of Commerce, 1983, 1-20.
4. Rosenkranz, H. S., Mermelstein, R., The genotoxicity, metabolism and carcinogenicity of nitrated polycyclic aromatic hydrocarbons, J. Environ. Sci. Health., 1985, C3: 221-272.
5. Fu, P. P., Metabolism of nitro-PAHs, Drug Metab. Rev., 1990, 22: 209-268.
6. Maro, D. M., Ames, B. N., Revised methods for the S. typhimurium mutagenicity test, Mut. Res., 1983, 113: 173-215.
7. Zeiger, E., Carcinogenicity of mutagens: Predictive capability of the Salmonella mutagenesis assay for rodent carcinogenicity, Cancer Res., 1987, 47: 1287-1296.
8. Hansch, C., Leo, A., Hoekman, D., Exploring QSAR. Hydrophobic, Electronic, and Steric Constants, Washington, D. C: American Chemical Society, 1995, 219-304.
9. Zeiger, E., Ashby, J., Bakale, G. et al., Prediction of Salmonella mutagenicity, Mutagenesis, 1996, 11: 471-484.
10. Rosenkranz, H. S., Klopman, G, The structural basis of the mutagenicity of chemicals in Salmonlla typhimurium: The national Toxicology Program Database, Mut. Res., 1990, 228: 51-80.
11. Cramer III, R. D., Patterson, D. E., Bunce, J. D., Comparative molecular field analysis (CoMFA), Effect of shape on binding of steroids to carrier proteins, J. Am. Chem. Soc., 1989, 110: 5959-5967.
12. Waller, C. L., McKinney, J. D., Three-dimensional quantitative structure-Activity relationships of dioxins and dioxin-like compounds: Model validation and Ah receptor characterization, Chem. Res. Toxicol., 1995, 8: 847-858.
13. Debnath, A. K., Lopez de Compadre, R. L., Debnath, G. et al., Structure-activity relationships of mutagenic aromatic heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity, J. Med. Chem., 1991, 34: 786-797.
14. Fu, P. P., Ni, Y., Zhang, Y. et al., Effect of orientations of nitro substituent on the bacterial mutagenicity of dinitrobenzo[e]pyrenes, Mut. Res., 1989, 225: 121-125.
15. You, Z., Brezzell, M. D., Das, S. K. et al., Ortho substituent effects on the in vitro and in vivo genotoxicity of benzidine derivatives, Mut. Res., 1993, 319: 19-30.
16. Hooberman, B. H., Brezzell, M. D., Das, S. K. et al., Substituent effects on the genotoxicity of 4-nitrostilbene derivatives, Mut. Res., 1994, 341: 57-69.
17. Watanabe, M., Nohmi, T., Ishidate, M. Jr., New tester strains of Salmonella typhimurium highly sensitive to mutagenic nitroarenes, Biochem. Biophys. Res. Commun., 1987, 147: 974-979.
18. McFarland, J. W., On the parabolic relationship between drug potency and hydrophobicity, J. Med. Chem., 1970, 13: 1092-1196.
19. Basak, S. C., Grunwald, G. D., Predicting mutagenicity of chemicals using topological and quantum chemicals parameters: A similarity based study, Chemosphere, 1995, 31: 2529-2546.
20. Toropov, A. A., Toropova, A. P., Prediction of heteroaromatic amine mutagenicity by means of correlation weighting of atomic orbital graphs of local invariants, J. Mol. Struct. (Theochem)., 2001, 538: 287-293.