Probabilistic neural network multiple classifier system for predicting the genotoxicity of quinolone and quinoline derivatives

Chemical Research in Toxicology

Volumn 18, Issue 3, 2005, Pages 428-440

  He, Linnan ^a   Jurs, Peter C ^a   Kreatsoulas, Constantine ^b   Custer, Laura L ^b   Durham, Stephen K ^b   Pearl, Greg M ^b  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 ETHYL 4 HYDROXY 1,2 DIHYDROQUINOLIN 2 ONE; 2 (4 METHYLPHENYL) 4 QUINOLINECARBOXAMIDE; 2 ISOPROPYL 4 PHENYLQUINOLINE; 2 PHENYLQUINOLIN 4 YLAMINE; 2 PHENYLQUINOLINE DERIVATIVE; 2 PYRIDIN 4 YLQUINOLINE 4 CARBOXYLIC ACID; 4 (4 CHLORO 3 METHYLPHENOXY) 2 METHYLQUINOLINE; 4 (4 METHOXYPHENOXY) 2 METHYLQUINOLINE; 8 QUINOLINESULFONIC ACID; CARBOSTYRIL DERIVATIVE; CHLOROQUINE; CLINAFLOXACIN; ENOXACIN; GATIFLOXACIN; GEMIFLOXACIN; GREPAFLOXACIN; HYDROQUINIDINE 4 METHYL 2 QUINOLYL ETHER; HYDROQUININE; LEVOFLOXACIN; MOXIFLOXACIN; N PHENETHYLQUINOLINE 6 CARBOXAMIDE; NORFLOXACIN; OFLOXACIN; QUINOLINE DERIVATIVE; QUINOLONE DERIVATIVE; SPARFLOXACIN; TOSUFLOXACIN; TRIBROMOQUINALDINE; TROVAFLOXACIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACCURACY; ARTICLE; ARTIFICIAL NEURAL NETWORK; CARCINOGENICITY; GENOTOXICITY; MUTAGENICITY; NONHUMAN; PROBABILISTIC NEURAL NETWORK; PROBABILITY; QUALITATIVE ANALYSIS; SALMONELLA TYPHIMURIUM;

ANIMALS; MUTAGENESIS; MUTAGENICITY TESTS; MUTAGENS; NEURAL NETWORKS (COMPUTER); QUINOLONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 15344347473     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049742m     Document Type: Article

References (60)

1. Lohray, B. B., Baskaran, S., Rao, B. S., Mallesham, B., Bharath, K. S. N., Yadi Reddy, B., Venkateswarlu, S., Ashok Sadhukhan, K., Sitaram Kumar, M., and Sarnaik, H. M. (1998) Novel quinolone derivatives as potent antibacterials. Bioorg. Med. Chem. Lett. 8 (5), 525-528.
2. Cohen, M. A., Huband, M. D., Mailloux, G. B., Yoder, S. L., Roland, G. E., and Heife, C. L. (1991) In vitro antibacterial activities of the fluoroquinolones PD 117596, PD 124816, and PD 127391. Diagn. Microbiol. Infect. Dis. 14 (3), 245-258.
3. Jefferson, E. A., Swayze, E. E., Osgood, S. A., Miyaji, A., Risen, L. M., and Blyn, L. B. (2003) Antibacterial activity of quinolone-macrocycle conjugates. Bioorg. Med. Chem. Lett. 13 (10), 1635-1638.
4. Appelbaum, P. C., and Hunter, P. A. (2000) The fluoroquinolone antibacterials: past, present and future perspectives. Int. J. Antimicrob. Agents 16 (1), 5-15.
5. Bush, K., and Macielag, M. (2000) New approaches in the treatment of bacterial infections. Curr. Opin. Chem. Biol. 4 (4), 433-439.
6. Mäkinen, M., Forbes, P. D., and Stenbäck, F. (1997) Quinolone antibacterials: A new class of photochemical carcinogens. J. Photochem. Photobiol. B 37 (3), 182-187.
7. Lescher, G. Y., Froelich, E. D., Gruet, M. D., Bailey, J. H., and Brundage, R. P. (1962) 1,8-Naphthyridine derivatives. A new class of chemotherapeutic agents. J. Med. Pharm. Chem. 5, 1063-1068.
8. Aylward, J. M. (1993) Hydroxychloroquine and chloroquine: Assessing the risk of retinal toxicity. J. Am. Optom. Assoc. 64, 787-797.
9. Bernstein, H. N., Zvaifler, N., Rubin, M., and Mansour, A. M. (1963) Ocular deposition of chloroquine. Invest. Ophthalmol. Vision Sci. 2 (4), 384-392.
10. Bataille, L., Rahier, J., and Geubel, A. (2002) Delayed and prolonged cholestatic hepatitis with ductopenia after long-term ciprofloxacin therapy for Crohn's disease. J. Hepatol. 37 (5), 696-699.
11. U.S. Environmental Protection Agency (U.S. EPA) (1985) Health and Environmental Effects Profile for Quinoline, Environmental Criteria and Assessment Office, EPA, Cincinnati, OH.
12. LaVoie, E. J., Defauw, J., and Fearly, M., et al. (1991) Genotoxicity of fluoroquinolines and methylquinolines. Carcinogenesis 12, 217-220.
13. Siporin, C. (1989) The evolution of fluorinated quinolones: Pharmacology, microbiological activity, clinical uses, and toxicities. Anna. Rev. Microbiol. 43, 601-627.
14. Takahashi, K., Kamiya, M., and Sengoku, Y., et al. (1988) Deprivation of the mutagenicity property of quinoline: Inhibition of mutagenic metabolism by fluorine substitution. Chem. Pharm. Bull. 36 (11), 4630-4633.
15. Saeki, K., Takahashi, K., and Kawazoe, Y. (1993) Metabolism of mutagenicity deprived 3-fluoroquinoline: Comparison with mutagenic quinoline. Biol. Pharm. Bull. 16 (3), 232-234.
16. Jurs, P. C., Chou, J. T., and Yuan, M. (1979) Computer-Assisted Drug Design (Olson, E. C., and Christofferson, R. E., Eds.) American Chemical Society, Washington, DC.
17. Stuper, A. J., Brugger, W. E., and Jurs, P. C. (1979) Computer-Assisted Studies of Chemical Structure and Biologial Function, Wiley, New York.
18. He, L., Jurs, P. C., Custer, L. L., Durham, S. K., and Pearl, G. M. (2003) Predicting the genotoxicity of polycyclic aromatic compounds from molecular structure with different classifiers. Chem. Res. Toxicol. 16 (12), 1567-1580.
19. Wessel, M. D., and Jurs, P. C. (1995) Prediction of normal boiling points for a diverse set of industrially important organic compounds from molecular structure. J. Chem. Inf. Comput. Sci. 15, 841-850.
20. Mitchell, B. E., and Jurs, P. C. (1998) Prediction of aqueous solubility of organic compounds from molecular structure. J. Chem. Inf. Comput. Sci. 38, 489-496.
21. Mattioni, B. E., and Jurs, P. C. (2000) Development of quantitative structure-activity relationship, classification models for a set of carbonic anhydrase inhibitors. J. Chem. Inf. Comput. Sci. 42 (1), 94-102.
22. Patankar, S. J., and Jurs, P. C. (2002) Prediction of glycine/NMDA receptor antagonist inhibition from molecular structure. J. Chem. Inf. Comput. Sci. 42 (5), 1053-1068.
23. Quillardet, P., and Hofnung, M. (1993) The SOS chromotest: A review. Mutat. Res. 297 (3), 235-279.
24. Hofnung, M., and Quillardet, P. (1998) The SOS chromotest, a colorimetric assay based on the primary cellular responses to genotoxic agents. Ann. N. Y. Acad. Sci. 534, 817-825.
25. Gudas, L. J., and Pardee, A. B. (1976) DNA synthesis inhibition, the induction of protein X in Escherichia coli. J. Mol. Biol. 101, 459-477.
26. Engle, L. J., Manes, S. H., and Drlica, K. (1982) Differential effects of antibiotics inhibiting gyrase. J. Bacteriol. 149, 92-98.
27. Benbrook, D. M., and Miller, R. V. (1986) Effects of norfloxacin on DNA metabolism in Pseudomonas aeruginosa. Agents Chemother. 29, 1-6.
28. Stewart, J. P. P. (1990) MOPAC: A semiempirical molecular orbital program. J. Comput.-Aided Mol. Des. 4, 1-105.
29. Stewart, J. P. P. MOPAC 6.0, Quantum Chemistry Program Exchange, Program 455, Indiana University, Bloomington.
30. Dewar, M. J. S., Zoebisch, E. G., Healy, E. F., and Steward, J. P. P. (1985) AM1: A new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107, 3902-3909.
31. Kier, L. B., and Hall, L. H. (1986) Molecular Connectivity in Structure-Activity Analysis, Research Studies Press Ltd., John Wiley & Sons, New York.
32. Balaban, A. T. (1982) Highly discriminating distance-based topological index. Chem. Phys. Lett. 89, 399-404.
33. Madan, A. K., Gupta, S., and Singh, M. (1999) Superpendentic index: A novel highly discriminating topological descriptor for predicting biological activity. J. Chem. Inf. Comput. Sci. 39, 9.
34. Kier, L. B., and Hall, L. H. (2000) Intermodular accessibility: The meaning of molecular connectivity. J. Chem. Inf. Comput. Sci. 40, 792-795.
35. Rohrbaugh, R. H., and Jurs, P. C. (1987) Molecular shape, the prediction of high-performance liquid chromatographic retention indexes of polycyclic aromatic hydrocarbons. Anal. Chem. 59, 1048-1054.
36. Goldstein, H. (1950) Classical Mechanics, pp 144-156, Addison-Wesley, Reading, MA.
37. Pearlman, R. S. (1980) Molecular Surface Area and Volumes and Their Use in Structure/Activity Relationships (Yalkowsky, S. H., Sinkula, A. A., and Valvani, S. C., Eds.) Marcel Dekker, New York.
38. Stouch, T. R., and Jurs, P. C. (1986) A simple method for the representation, quantification, and comparison of the volumes and shapes of chemical compounds. J. Chem. Inf. Comput. Sci. 26, 4-12.
39. Katritzky, A. R., Mu, L., Lobanov, V. S., and Karelson, M. (1996) Correlation of boiling points with molecular structure. 1. A training set of 298 diverse organics and a test set of 9 simple organics. J. Phys. Chem. 100, 10400-10407.
40. Dixo, S. L., and Jurs, P. C. (1992) Atomic charge calculations for quantitative structure-property relationships. J. Comput. Chem. 18, 492-504.
41. Abraham, R. J., and Smith, P. E. (1987) Charge calculations in molecular mechanics IV: A general method for conjugated systems. J. Comput. Chem. 13, 288-297.
42. Stanton, D. T., and Jurs, P. C. (1990) Development and use of charged partial surface area structural descriptors in computer-assisted quantitative structure-property relationship studies. Anal. Chem. 62, 2323-2329.
43. Vinogradov, S. N., and Linnell, R. H. (1971) Hydrogen Bonding, Van Nostrand Reinhold, New York.
44. Brain Mattioni's Thesis. (2003) Pennsylvania State University.
45. Russell, C. J., Dixon, S. L., and Jurs, P. C. (1992) Computer assisted study of the relationship between molecular structure, Henry's law constant. Anal. Chem. 64, 1350.
46. Sutter, J. M., Dixon, S. L., and Jurs, P. C. (1995) Automated descriptor selection for quantitative structure-activity relationships using generalized simulated annealing. J. Chem. Inf. Comput. Sci. 35, 77-84.
47. Luke, B. T. (1994) Evolutionary programming applied to the development of quantitative structure-activity relationships and quantitative structure-property relationships. J. Chem. Inf. Comput. Sci. 34, 1279-1287.
48. Specht, D. F. (1990) Probabilistc neural networks. Neural Networks 3, 109-118.
49. Wasserman, P. D. (1993) Advanced Methods in Neural Networks, Chapter 3, pp 35-55, Van Nostrand Reinhold, New York.
50. Parzen, E. (1962) On estimation of a probability density function and mode. Ann. Math. Statist. 33, 1065-1076.
51. Kittle, Roli, J. F., Eds. (2002) Third International Workshop on Multiple Classifier Systems, Cagliari, Italy, Springer, New York.
52. Dietterich, T. (2000) Ensemble methods in machine learning. Proc. First Int. Workshop Multiple Classifier Systems, 1-15.
53. Breiman, L. (1996) Bagging predictors. Machine Learning 24 (2), 123-140.
54. Breiman, L. (1999) Pasting small votes for classification in large database and on-line. Machine Learning 36 (1-2), 85-103.
55. Dietterich, T. (2000) An experimental comparison of three methods for constructing ensembles of decision trees: Bagging, boosting, and randomization. Machine Learning 40 (2), 139-158.
56. Breiman, L. (2001) Random forests. Machine Learning 45 (1), 5-32.
57. Sharma, V., Goswami, R., and Madan, A. K. (1997) Eccentric connectivity index: A novel highly discriminating topological descriptor for structure-property and structure-activity studies. J. Chem. Inf. Comput. Sci. 37, 273-282.
58. Gupta, S., Singh, M., and Madan, A. K. (1999) Superpendentic index: A novel topological descriptor for predicting biological activity. J. Chem. Inf. Comput. Sci. 39, 272-277.
59. Goldstein, H. (1950) Classical Mechanics, Addison-Wesley, Reading, MA.
60. Kier, L. B., and Hall, L. H. (1990) An electrotopological-state index for atoms in molecules. Pharm. Res. 7, 801-807.