A comprehensive QSAR treatment of the genotoxicity of heteroaromatic and aromatic amines

Quantitative Structure-Activity Relationships

Volumn 18, Issue 1, 1999, Pages 03-10

  Maran, Uko ^a   Karelson, Mati ^a   Katritzky, Alan R ^b  

^a UNIVERSITY OF TARTU   (Estonia)

^b University of Florida ^*  (United States)

Author keywords

Ames test; Genotoxicity; QSAR; Quantum chemical descriptors; Theoretical descriptors

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; COMPUTATIONAL CHEMISTRY; HYDROGEN BONDS; QUANTUM CHEMISTRY;

AMES TEST; AROMATIC AMINES; DESCRIPTORS; GENOTOXICITIES; HETEROAROMATICS; MUTAGENIC ACTIVITY; QSAR; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; QUANTUM CHEMICAL DESCRIPTORS; THEORETICAL DESCRIPTOR;

AMINES;

AROMATIC AMINE;

ARTICLE; CHEMICAL STRUCTURE; GENOTOXICITY; MOLECULAR MODEL; MUTAGENIC ACTIVITY; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 0033043476     PISSN: 09318771     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3838(199901)18:1<03::aid-qsar3>3.0.co;2-p     Document Type: Article

References (56)

1. Hansch, C., Hoekman, D., Leo, A., Zhang, L., and Li, P., The expanding role of quantitative structure-activity relationships (QSAR) in toxicology. Toxicol. Lett. 79, 45-53 (1995).
2. Basak, S. C., Bertelsen, S., and Grunwald, G. D., Use of graph theoretic parameters in risk assessment of chemicals. Toxicol. Lett. 79, 239-250 (1995).
3. Frierson, M. R., Klopman, G., and Rosenkrantz, H. S., Structure-activity relationships among mutagens and carcinogens: A review. Environ. Mutagen. 8, 283-327 (1986).
4. Benigni, R., Andreoli, C., and Giuliani, A., Quantitative structure-activity relationships: principles, and applications to mutagenicity and carcinogenicity. Mut. Res. 221, 197-216 (1989).
5. Benigni, R., and Giuliani, A., Quantitative structure-activity relationship (QSAR) studies of mutagens and carcinogens. Med. Res. Rev. 16, 267-284 (1996).
6. Cornin, M. T. D., and Dearden, J. C., QSAR in toxicology. 3. Prediction of chronic toxicities. Quant. Struct.-Act. Relat. 14, 329-334 (1995).
7. McCann, J., Choi, E., Yamasaki, E., and Ames, B. N., Detection of carcinogens as mutagens in the Salmonella/ microsome test: Assay of 300 chemicals. Proc. Nat Acad. Sci. USA 72, 5135-5319 (1975).
8. Zakrzewski, S. F., Principles of Environmental Toxicology. ACS, Washington 1991.
9. Soderman, J. V., CRC Handbook of Identified Carcinogens and Noncarcinogens: Carcinogenicity and Mutagenicity Database. CRC Press, Boca Raton, Florida 1982.
10. McCann, J., and Ames, B. N., The Salmonella/microsome mutagenicity test: Predictive value of animal carcinogenicity. in: Hiatt, H. H., Watson, J. D., and Winsten, J. A., (Ed.) Origins of Human Cancer: Book C, Human Risk Assessment, Cold Spring Harbor Laboratory 1977, pp. 1431-1450.
11. Ames, B. N., Identifying environmental chemicals causing mutations and cancer. Science 204, 587-593 (1979).
12. Hansch, C., and Fujita, T., ρ-σ-π analysis. A method for the correlation of biological activity and chemical structure. J. Am. Chem. Soc. 86, 1616-1626 (1964).
13. Poso, A., Wright, A., and Gynther, J., An empirical and theoretical study on mechanism of mutagenic activity of hydrazine compounds. Mut. Res. 332, 63-71 (1995).
14. Venger, B. H., Hansch, C., Hatheway, G. J., and Amrein, Y. U., Ames Test of 1-(X-phenyl)-3,3-dialkyltriazenes. A quantitative structure-activity study. J. Med. Chem., 22, 473-476 (1979).
15. Tuppurainen, K., QSAR approach to molecular mutagenicity. A survey and case study: MX compounds. J. Mol. Struct. (Theochem) 306, 49-56 (1994).
16. Hooberman, B. H., Chakraborty, P. K., and Sinsheimer, J. E., Quantitative structure-activity relationships for the mutagenicity of propylene oxides with Salmonella. Mut. Res. 299, 85-93 (1993).
17. Treiff, N. M., Biagi, G. L., Ramanujam, V. M. S., Connor, T. H., Cantelli-Forti, G., Guerra, M. C., Bunce III, H., and Legator, M. S., Aromatic amines and acetamines in Salmonella typhimurium TA98 and TA100: A quantitative structure-activity relation study. J. Mol. Tox. 2, 53-65 (1989).
18. Ferguson, L. R., and Denny, W. A., Potential antitumor agents. 33. Quantitative structure-activity relationships for mutagenic activity and antitumor activity of substituted 4′-(9-acridinylamino)methanesulfonaniline dericatives. J. Med. Chem. 23, 269-274 (1980).
19. Shusterman, A. J., Predicting chemical mutagenicity by using quantitative structure-activity relationships. in: Finley, J. W., Robinson, S. F., and Armstrong, D. J., (Ed.) Food Safety Assessment, ACS, Washington 1992, pp. 181-190.
20. Lewis, D. F. V., and Parke, D. V., The genotoxicity of benzanthracenes: a quantitative structure-activity study. Mut. Res. 328, 207-214 (1995).
21. Debnath, A. K., Compadre, R. L. L., Debnath, D., Shusterman, A. J., and Hansch, C., Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity. J. Med. Chem. 34, 786-797 (1991).
22. Debnath, A. K., Debnath, G., Shusterman, A. J., and Hansch, C., A QSAR investigation of the role of hydrophobicity in regulating mutagenicity in the Ames test: 1. Mutagenicity of aromatic and heteroaromatic amines in Salmonella typhimurium TA98 and TA100. Environ. Mol. Mutagen. 19, 37-52 (1992).
23. Dednath, A. K., Hanch, C., Kim, K. H., and Martin, Y. C., Mechanistic interpretation of the genotoxicity of nitrofurans (antibacterial agents) using quantitative structure-activity relationships and comparative molecular field analysis J. Med. Chem. 36, 1007-1016 (1993).
24. Basak, S. C., Grunwald, G. D., and Niemi, G. J., Use of graphic-theoretic and geometrical molecular descriptors ir structure-activity relationships. in: Balaban A. T., (Ed.), From Chemical Topology to Three-Dimensional Geometry, Plenum Press, New York 1997, pp. 73-116.
25. Debnath, A. K., Debnath, D., Shusterman, A. J., and Hansch, C., Quantitative structure-activity relationship investigation of the role of hydrophobicity in regulating mutagenicity ir the Ames test: 2. Mutagenicity of aromatic and heteroaromatic nitro compounds in Salmonella typhimurium TA100. Environ. Mol. Mutagen. 19, 53-70 (1992).
26. Debnath, A. K., Compadre, R. L. L., and Hanch, C., Mutagenicity of quinolines in Salmonella typhimurium TA100. A QSAR study based on hydrophobicity and molecular orbital determinants. Mut. Res. 280, 55-65 (1992).
27. Tuppurainen, K., and Lötjönen, S., On the mutagenicity of MX compounds. Mut. Res. 287, 235-241 (1993).
28. Tuppurainen, K., Lötjönen, S., Laatikainen, R., and Vartiainen, T., Structural and electronic properties of MX compounds related to TA100 mutagenicity. A semi-empirical molecular orbital QSAR study. Mut. Res. 266, 181-188 (1992).
29. Tuppurainen, K., Lötjönen, S., Laatikainen, R., Vartiainen, T., Maran, U., Strandberg, M., and Tamm, T., About the mutagenicity of chlorine-substituted furanones and halopropenals. A QSAR study using molecular orbital indices. Mut. Res. 247, 97-102 (1991).
30. Debnath, A. K., Shusterman, A. J., Lopez de Compadre, R. L., and Hansch, C., The importance of the hydrophobic interaction in the mutagenicity of organic compounds. Mut. Res. 305, 63-73 (1994).
31. Karelson, M., Lobanov, V. S., and Katritzky, A. R., Quantum-chemical descriptors in QSAR/QSPR studies. Chem. Rev. 96, 1027-1043 (1996).
32. Katritzky, A. R., Mu, L., Lobanov, V. S., and Karelson, M., Correlation of boiling points with molecular structure. 1. A training set of 298 diverse organics and test set of 9 simple inorganics. J. Phys. Chem. 100, 10400-10407 (1996).
33. Katritzky, A. R., Maran, U., Lobanov, V., and Karelson, M., Prediction of melting points for the substituted benzenes: A QSPR approach. J. Chem. Inf. Comput. Sci. 37, 913-919 (1997).
34. Katritzky, A. R., Ignatchenko, E. S., Barcock, R. A., Lobanov, V. S., and Karelson, M., Prediction of gas chromatographic retention times and response factors using a general quantitative structure-property relationship treatment. Anal. Chem. 66, 1799-1807 (1994).
35. Katritzky, A. R., Rachwal, P., Law, K. W., Karelson, M., and Lobanov, V. S., Prediction of polymer glass transition temperatures using a general quantitative structure-property relationship treatment. J. Chem. Inf. Comput. Sci. 36, 879-884 (1996).
36. Huibers, P. D. T., Lobanov, V. S., Katritzky, A. R., Shah, D. O., and Karelson, M., Prediction of critical micelle concentration using a quantitative structure-property relationship approeach. I. Nonionic surfactants. Langmuir 12, 1462-1470 (1996).
37. PCMODEL, Molecular modelling package. Serena Software, Bloomington 1992.
38. Stewart, J. J. P., MOPAC Program Package. QCPE 1989, No 455.
39. Dewar, M. J. S., Zoebisch, E. G., Healy, E. F., and Stewart, J. J. P., AMI: A new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107, 3902-3909 (1985).
40. Baker, J., An algorithm for the location of transition states. J. Comput. Chem. 7, 385-395 (1986).
41. Stewart, J. J. P., Optimization of parameters for semi-empirical methods I: Method. J. Comput. Chem. 10, 209-220 (1989).
42. Katritzky, A. R., Lobanov, V. S., and Karelson, M., QSPR: The correlation and quantitative prediction of chemical and physical properties from structure. Chem. Soc. Rev. 24, 279-287 (1995).
43. Katritzky, A. R., Lobanov, V. S., and Karelson, M., CODESSA: Reference manual (version 2.0), Gainesville, Florida 1994.
44. Rohrbaugh, R. H., and Jurs, P. C., Descriptions of molecular shape applied in studies of structure-activity and structure-property relationships. Anal. Chim. Acta. 199, 99-109 (1987).
45. Stankevich, M. I., Stankevich, I. V., and Zefirov, N. S., Topological indices in organic chemistry. Russ. Chem. Rev. 57, 191-208 (1988).
46. Kier, L. B., and Hall, L. H. Molecular Connectivity in Chemistry and Drug Research., Academic Press, New York 1976, pp. 27-39.
47. Kier, L. B., and Hall, L. H. Molecular Connectivity in Structure-Activity Analysis. Research Studies Press, Letchworth 1986.
48. Randic, M., On characterization of molecular branching. J. Am. Chem. Soc. 97, 6609-6615 (1975).
49. Wiener, H., Structural determination of paraffin boiling points. J. Am. Chem. Soc. 69, 17-20 (1947).
50. Zefirov, N. S., Kirpichenok, M. A., Izmailov, F. F., and Trofimov, M. I., Scheme for the calculation of the electronegativities of atoms in a molecule in the framework of Sanderson's principle. Dokl. Akad. Nauk SSSR 296, 883-887 (1987).
51. Kirpichenok, M. A., and Zefirov, N. S., Electronegativity and molecular geometry. I. General principles of the method and analysis of the effect of short-range electrostatic interactions on bond lengths in organic molecules. Zh. Org. Khim. 23, 607-623 (1987).
52. Stanton, D. T., and Jurs, P. C., Development and use of charged partial surface area structural descriptors in computer-assisted quantitative structure-property relationship studies. Anal. Chem. 62, 2323-2329 (1990).
53. Stanton, D. T., Egolf, L. M., Jurs, P. C., and Hicks, M. G., Computer-assisted prediction of normal boiling points of pyrans and pyrroles. J. Chem. Inf. Comput. Sci. 32, 306-316 (1992).
54. Draper, N. R., and Smith, H., Applied Regression Analysis., Wiley, New York 1966.
55. Kurtz, H. A., Stewart, J. J. P., and Dieter, K. M., Calculation of the nonlinear optical properties of molecules. J. Comput. Chem. 11, 82-87 (1990).
56. Pullman, A., and Pullman, B., Electronic structure and carcinogenic activity of some aromatic molecules. Adv. Cancer Res. 3, 117-169 (1955).