Quantitative structure activity relationship for the computational prediction of nitrocompounds carcinogenicity

Toxicology

Volumn 220, Issue 1, 2006, Pages 51-62

  Morales, Aliuska Helguera ^a   Pérez, Miguel Ángel Cabrera ^a   Combes, Robert D ^b   González, Maykel Pérez ^a,c  

^a CENTRAL UNIVERSITY OF LAS VILLAS   (Cuba)

^b RUSSELL AND BURCH HOUSE   (United Kingdom)

^c Experimental Sugar Cane Station ^*  (Cuba)

Author keywords

Carcinogenicity; Nitrocompounds; QSAR; Spectral moments; Topological descriptors; TOPS MODE

Indexed keywords

NITRO DERIVATIVE;

ARTICLE; CARCINOGENICITY; CHEMICAL STRUCTURE; CONTROLLED STUDY; MATHEMATICAL ANALYSIS; MATHEMATICAL MODEL; NONHUMAN; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANIMALS; CARCINOGENICITY TESTS; CARCINOGENS; COMPUTATIONAL BIOLOGY; COMPUTER SIMULATION; FORECASTING; MICE; MODELS, THEORETICAL; NITRO COMPOUNDS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RATS;

ANIMALIA; RODENTIA;

EID: 32044437418     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tox.2005.11.024     Document Type: Article

References (34)

1. L.M. Ball, M.J. Kohan, J.P. Inmon, L.D. Claxton, and J. Lewtas Metabolism of 1-nitro[14C]pyrene in vivo in the rat and mutagenicity of urinary metabolites Carcinogenesis 5 1984 1557 1564
2. R. Benigni, G. Alessandro, R. Franke, and A. Gruska Quantitative structure-activity relationships of mutagenic and carcinogenic aromatic amines Chem. Rev. 100 2000 3697 3714
3. R. Benigni, and A. Giuliani Putting the predictive toxicology challenge into perspective: reflections on the results Bioinformatics 19 2003 1194 1200
4. R.D. Combes The in vivo relevance of in vitro genotoxicity assays incorporating enzyme activation systems G.G. Gibson Progress in Drug Metabolism 13 1992 Taylor and Francis Limited London 295 321
5. R.D. Combes Detection of nongenotoxic carcinogens: major barriers to replacement of the rodent bioassay? L.F.M. van Zutphen M. Balls Animal Alternative, Welfare and Ethics 1997 Elsevier Amsterdam 627 634
6. Dearden, J.C., Barratt, M.D., Benigni, R., Bristol, D.W., Combes, R.D., Cronin, M.T.D., Judson, P.N., Payne, M.P., Richard, A.M., Tich_, M., Worth, A.P., Yourick, J.J. (1997) The development and validation of expert systems for predicting toxicity. The Report and Recommendations of ECVAM Workshop 24. ATLA, 25, pp. 223-252.
7. deBethizy, J.D., Hayes, J.R. (1994) Metabolism. In: Wallace Hayes A., A Determinant of Toxicity. Principles and Methods of Toxicology, New York, pp. 59-100.
8. K. El-Bayoumy, A. Rivenson, B. Johnson, J. DiBello, P. Little, and S.S. Hecht Comparative tumorigenicity of 1-nitropyrene, 1-nitrosopyrene, and 1-aminopyrene administered by gavage to Sprague-Dawley rats Cancer Res. 48 1988 4256 4260
9. E. Estrada Spectral moments of edge adjacency matrix in molecular graph. 1. Definition and application to the prediction of physical properties of alkanes J. Chem. Inf. Comp. Sci. 36 1996 844 849
10. E. Estrada Spectral moments of edge adjacency matrix in molecular graph. 2. Molecules containing heteroatoms and QSAR applications J. Chem. Inf. Comp. Sci. 37 1997 320 328
11. E. Estrada On the topological sub-structural molecular design (TOSS-MODE) in QSPR/QSAR and drug design research SAR QSAR Environ. Res. 11 2000 55 73
12. E. Estrada, E. Uriarte, Y. Gutierrez, and H. González Quantitative structure-toxicity relationships using TOPS-MODE. 3. Structural factors influencing the permeability of commercial solvents through living human skin SAR QSAR Environ. Res. 14 2003 145 163
13. J. Gallagher, U. Heinrich, M. George, L. Hendee, D.H. Phillips, and J. Lewtas Formation of DNA adducts in rat lung following chronic inhalation of diesel emissions, carbon black and titanium dioxide particles Carcinogenesis 15 1994 1291 1299
14. R. García-Domenech, and J.V. Julián-Ortiz Antimicrobial activity characterization in a heterogeneous group of compounds J. Chem. Inf. Comp. Sci. 38 1998 445 449
15. L.S. Gold, N.B. Manley, T.H. Slone, and L. Rohrbach Supplement to the Carcinogenic Potency Database (CPDB): results of animal bioassays published in the general literature in 1993-1994 and by the National Toxicology Program in 1995-1996 Environ. Health Persp. Suppl. 107 Suppl. 4 1999 527 602
16. L.S. Gold, and E. Zeiger Handbook of Carcinogenic Potency and Genotoxicity Databases 1997 CRC Press Boca Roca, FL
17. M.P. González, A. Morales, and H. González A TOPS-MODE approach to predict permeability coefficients Polymer 45 2004 2073 2079
18. M.P. González, A. Morales, R. Molina, and J. García A topological sub-structural approach of the mutagenic activity in dental monomers. 1. Aromatic epoxides Polymer 45 2004 2773 2779
19. M.P. González, A.H. Morales, and M.A. Cabrera Quantitative structure-activity relationship to predict toxicological properties of benzene derivative compounds Bioorgan. Med. Chem. 13 2005 1775 1781
20. E. Gottmann, S. Kramer, B. Pfahringer, and Ch. Helma Data quality in predictive toxicology: reproducibility of rodent carcinogenicity experiments Environ. Health Perspect 109 2001 1 11
21. Gutiérrez, Y., Estrada, E. (2002). MODESLAB 1.0 (Molecular DEScriptors LABoratory) for Windows. Universidad de Santiago de Compostela, España.
22. N.A. Helsby, S.J. Wheeler, F.B. Pruijn, B.D. Palmer, S. Yang, W.A. Denny, and W.R. Wilson Effect of nitroreduction on the alkylating reactivity and cytotoxicity of the 2. 4 Dinitrobenzamide-5-aziridine CB 1954 and the Corresponding Nitrogen Mustard SN 23862: distinct mechanisms of bioreductive activation Chem. Res. Toxicol. 16 2003 469 478
23. M. Kaneko, K. Morimura, T. Nishikawa, H. Wanibuchi, N. Takada, H. Osugi, H. Kinoshita, and S. Fukushima Different genetic alterations in rat forestomach tumors induced by genotoxic and non-genotoxic carcinogens Carcinogenesis 23 2002 1729 1735
24. J.C. Louis Predicting carcinogenicity early: the latest in silico solution Biosilico 1 2003 115 116
25. D.R. McCalla Mutagenicity of nitrofuran derivatives: review Environ. Mutagenesis 5 1983 745 765
26. A.H. Morales, M.P. González, and J. Rieumont TOPS-MODE approach to predict mutagenicity in dental monomers Polymer 45 2004 2045 2050
27. A.H. Morales, M.A. Cabrera, R.D. Combes, and M.P. González The prediction of carcinogenicity from molecular structure Curr. Comp. Aided Drug Desig. 3 2005 237 255
28. A.H. Morales, M.A. Cabrera, M.P. González, R.R. Molina, and H. González-Díaz A topological substructural approach applied to the computational prediction of rodent carcinogenicity Bioorgan. Med. Chem. 13 2005 2477 2488
29. R. Ramos-de Armas, H. Gonzalez-Díaz, R.R. Molina, M.P. Gonzalez, and E. Uriarte Stochastic-based descriptors studying peptides biological properties: modeling the bitter tasting threshold of dipeptides Bioorgan. Med. Chem. 12 2004 4815 4822
30. M. Randić Orthogonal molecular descriptors New J. Chem. 15 1991 517 525
31. Stewar, J.J.P. (1990). MOPAC manual, 6th ed., p. 189, Frank J. Seiler Research Laboratory, US Air Force academy, Colorado Springs, CO.
32. R. Todeschini V. Consonni Handbook of Molecular Descriptors (Methods and Principles in Medicinal Chemistry) 2000 Wiley-VCH Weinheim
33. Todeschini, R., Consonni, V., Pavan. M. (2002) Dragon. Software version 2.1.
34. H. Tokiwa, and Y. Ohnishi Mutagenicity and carcinogenicity of nitroarenes and their sources in the environment Crit. Rev. Toxicol. 17 1986 23 60