QSTR with extended topochemical atom (ETA) indices. 11. Comparative QSAR of acute NSAID cytotoxicity in rat hepatocytes using chemometric tools

Molecular Simulation

Volumn 35, Issue 8, 2009, Pages 648-659

  Roy, Kunal ^a   Ghosh, Gopinath ^a  

^a JADAVPUR UNIVERSITY   (India)

Author keywords

Chemometric tools; ETA; NSAID; QSAR; QSTR

Indexed keywords

CHEMOMETRIC TOOLS; ETA; NSAID; QSAR; QSTR;

PRINCIPAL COMPONENT ANALYSIS; REGRESSION ANALYSIS; SULFUR COMPOUNDS; TOXICITY;

CYTOTOXICITY;

EID: 70449100468     PISSN: 08927022     EISSN: 10290435     Source Type: Journal    
DOI: 10.1080/08927020902744664     Document Type: Article

References (53)

1. D.L. DeWitt, Cox-2-selective inhibitors: the new super aspirins, Mol. Pharmacol. 55 (1999), pp. 625-631.
2. P. Brooks, Use and benefits of nonsteroidal anti-inflammatory drugs, Am. J. Med. 104 (1998), pp. 9S-13S.
3. M.W. James and C.J. Hawkey, Assessment of non-steroidal antiinflammatory drug (NSAID) damage in the human gastrointestinal tract, Br. J. Clin. Pharmacol. 56 (2003), pp. 146-155.
4. U.A. Boelsterli, H.J. Zimmerman, and A. Kretz-Rommel, Idiosyncratic liver toxicity of nonsteroidal antiinflammatory drugs: molecular mechanisms and pathology, Crit. Rev. Toxicol. 25 (1995), pp. 207-235.
5. Y. Pirson and C. van Ypersele de Strihou, Renal side effects of nonsteroidal antiinflammatory drugs: clinical relevance, Am. J. Kidney Dis. 8 (1986), pp. 338-344.
6. S.K. Kulkarni and N.K. Jain, Coxibs: the new super aspirins or unsafe pain killer, Indian J. Pharmacol. 37 (2005), pp. 86-89.
7. K.D. Tripathi, Essentials of Medical Pharmacology, 5th ed., Jaypee Brothers Medical Publishers, New Delhi, 2003, pp. 167-184.
8. J.L. Goldstein, P. Correa, W.W. Zhao, A.M. Burr, R.C. Hubbard, K.M. Verburg, and G.S. Geis, Reduced incidence of gastrodudenal ulcers with celecoxib, a novel cycloxygenase-2 inhibitor, compared to naproxen in patients with arthritis, Am. J. Gastroenterol. 96 (2001), pp. 1019-1027.
9. G.H. Hakimelahi and G.A. Khodarahmi, The identification of toxicophores for the prediction of mutagenicity, hepatotoxicity and cardiotoxicity, J. Iranian Chem. Soc. 2 (2005), pp. 244-267.
10. A.G. Siraki, T. Chevaldina, and P.J. O'Brien, Application of quantitative structure-toxicity relationships for acute NSAID cytotoxicity in rat hepatocytes, Chem.-Biol. Interact. 151 (2005), pp. 177-191.
11. D.F. Lewis, C. Ioannides, and D.V. Parke, A retrospective study of the molecular toxicology of benoxaprofen, Toxicology 65 (1990), pp. 33-47.
12. G.W. Milne, Mathematics as a basis for chemistry, J. Chem. Inf. Comput. Sci. 37 (1997), pp. 639-644.
13. O. Ivanciuc and A.T. Balaban, The graph description of chemical structures, in Topological Indices and Related Descriptors in QSAR and QSPR, J. Devillers and A.T. Balaban, eds., Gordon and Breach Science Publishers, The Netherlands, 1999, pp. 59-167.
14. K. Roy and G. Ghosh, Introduction of extended topochemical atom (ETA) Indices in the valence electron mobile (VEM) environment as tools for QSAR/QSPR studies, Internet Electron. J. Mol. Des. 2 (2003), pp. 599-620, http://www.biochempress.com.
15. K. Roy and G. Ghosh, QSTR with extended topochemical atom indices. 2. Fish toxicity of substituted benzenes, J. Chem. Inf. Comput. Sci. 44 (2004), pp. 559-567.
16. K. Roy and G. Ghosh, QSTR with extended topochemical atom indices. 3. Toxicity of nitrobenzenes to Tetrahymena pyriformis, QSAR Comb. Sci. 23 (2004), pp. 99-108.
17. K. Roy and G. Ghosh, QSTR with extended topochemical atom indices. 4. Modeling of the acute toxicity of phenylsulfonyl carboxylates to Vibrio fischeri using principal component factor analysis and principal component regression analysis, QSAR Comb. Sci. 23 (2004), pp. 526-535.
18. K. Roy and G. Ghosh, QSTR with extended topochemical atom indices. Part 5. Modeling of the acute toxicity of phenylsulfonyl carboxylates to Vibrio fischeri using genetic function approximation, Bioorg. Med. Chem. 13 (2005), pp. 1185-1194.
19. K. Roy and G. Ghosh, QSTR with extended topochemical atom (ETA) indices. VI. Acute toxicity of benzene derivatives to tadpoles (Rana japonica), J. Mol. Model. 12 (2006), pp. 306-316.
20. K. Roy and I. Sanyal, QSTR with extended topochemical atom indices. 7. QSAR of substituted benzenes to Saccharomyces cerevisiae, QSAR Comb. Sci. 25 (2006), pp. 359-371.
21. K. Roy and G. Ghosh, QSTR with extended topochemical atom (ETA) indices. 8. QSAR for the inhibition of substituted phenols on germination rate of Cucumis sativus using chemometric tools, QSAR Comb. Sci. 25 (2006), pp. 846-859.
22. K. Roy and G. Ghosh, QSTR with extended topochemical atom (ETA) indices. 9. Comparative QSAR for the toxicity of diverse functional organic compounds to Chlorella vulgaris using chemometric tools, Chemosphere 70 (2007), pp. 1-12.
23. K. Roy, I. Sanyal, and P.P. Roy, QSPR of the bioconcentration factors of nonionic organic compounds in fish using extended topochemical atom (ETA) indices, SAR QSAR Environ. Res. 17 (2006), pp. 563-582.
24. K. Roy, I. Sanyal, and G. Ghosh, QSPR of n-octanol/water partition coefficient of nonionic organic compounds using extended topochemical atom (ETA) indices, QSAR Comb. Sci. 25 (2006), pp. 629-646.
25. D.K. Pal, C. Sengupta, and A.U. De, A new topochemical descriptor (TAU) in molecular connectivity concept: part I-aliphatic compounds, Indian J. Chem. 27B (1988), pp. 734-739.
26. D.K. Pal, C. Sengupta, and A.U. De, Introduction of a novel topochemical index and exploitation of group connectivity concept to achieve predictability in QSAR and RDD, Indian J. Chem. 28B (1989), pp. 261-267.
27. D.K. Pal, M. Sengupta, C. Sengupta, and A.U. De, QSAR with TAU (t) indices: part I-polymethylene primary diamines as amebicidal agents, Indian J. Chem. 29B (1990), pp. 451-454.
28. D.K. Pal, S.K. Purkayastha, C. Sengupta, and A.U. De, Quantitative structure-property relationships with TAU indices: part I-research octane numbers of alkane fuel molecules, Indian J. Chem. 31B (1992), pp. 109-114.
29. K. Roy, D.K. Pal, A.U. De, and C. Sengupta, Comparative QSAR with molecular negentropy molecular connectivity, STIMS and TAU indices: part I. Tadpole narcosis of diverse functional acyclic compounds, Indian J. Chem. 38B (1999), pp. 664-671.
30. K. Roy, D.K. Pal, A.U. De, and C. Sengupta, Comparative QSAR studies with molecular negentropy, molecular connectivity, STIMS and TAU indices. Part II: general anaesthetic activity of aliphatic hydrocarbons, halocarbons and ethers, Indian J. Chem. 40B (2001), pp. 129-135.
31. K. Roy and A. Saha, Comparative QSPR studies with molecular connectivity, molecular negentropy and TAU Indices. Part I: molecular thermochemical properties of diverse functional acyclic compounds, J. Mol. Model. 9 (2003), pp. 259-270.
32. K. Roy and A. Saha, Comparative QSPR studies with molecular connectivity, molecular negentropy and TAU indices. Part 2: lipid- water partition coefficient of diverse functional acyclic compounds, Internet Electron. J. Mol. Des. 2 (2003), pp. 288-305, http://www. biochempress.com.
33. K. Roy and A. Saha, QSPR with TAU indices: water solubility of diverse functional acyclic compounds, Internet Electron. J. Mol. Des. 2 (2003), pp. 475-491, http://www.biochempress.com.
34. K. Roy, S. Chakroborty, C.C. Ghosh, and A. Saha, QSPR with TAU indices: molar thermochemical properties of diverse functional acyclic compounds, J. Indian Chem. Soc. 81 (2004), pp. 115-125.
35. K. Roy and A. Saha, QSPR with TAU indices: boiling points of sulfides and thiols, Indian J. Chem. 43A (2004), pp. 1369-1376.
36. K. Roy and A. Saha, QSPR with TAU indices: molar refractivity of diverse functional acyclic compounds, Indian J. Chem. 44B (2005), pp. 1693-1707.
37. K. Roy and A. Saha, QSPR with TAU indices: part 5. Liquid heat capacity of diverse functional organic compounds, J. Indian Chem. Soc. 83 (2006), pp. 351-355.
38. The GW-BASIC programs RRR98, KRETA1, KRETA2, KRPRES1 and KRPRES2 were developed by Kunal Roy and standardized using known data sets.
39. Cerius 2 version 4.10 is a product of Accelrys Inc., San Diego, CA, USA, http://www.accelrys.com/cerius2
40. P.J. Lewi, Multivariate data analysis in structure activity relationships, in Drug Design, E.J. Ariens, ed., 10, Academic Press, New York, 1980, pp. 307-342.
41. R. Franke and A. Gruska, Principal component and factor analysis, in Chemometric Methods in Molecular Design, H. van de Waterbeemd, ed., 2, VCH, Weinheim, 1995, pp. 113-163.
42. R.B. Darlington, Regression and Linear Models, McGraw-Hill, New York, 1990.
43. S. Wold, PLS for multivariate linear modeling, in Chemometric Methods in Molecular Design, H. van de Waterbeemd, ed., VCH, Weinheim, 1995, pp. 195-218.
44. G.M. Sperandio da Silva, C.M. Sant'Anna, and E. Barreiro, A novel 3D-QSAR comparative molecular field analysis (CoMFA) model of imidazole and quinazolinone functionalized p38 MAP kinase inhibitors, Bioorg. Med. Chem. 12 (2004), pp. 3159-3166.
45. S.S. Kulkarni and V.M. Kulkarni, Three-dimensional quantitative structure-activity relationship of interleukin 1-beta converting enzyme inhibitors: a comparative molecular field analysis study, J. Med. Chem. 42 (1999), pp. 373-380.
46. Y. Fan, L.M. Shi, K.W. Kohn, Y. Pommier, and J.N. Weinstein, Quantitative structure-antitumor activity relationships of camptothecin analogues: cluster analysis and genetic algorithm-based studies, J. Med. Chem. 44 (2001), pp. 3254-3263.
47. D. Rogers and A.J. Hopfinger, Application of genetic function approximation to quantitative structure-activity relationships and quantitative structure-property relationships, J. Chem. Inf. Comput. Sci. 34 (1994), pp. 854-866.
48. W.J. Dunn III and D. Rogers, Genetic partial least squares in QSAR, in Genetic Algorithms in Molecular Modeling, J. Devillers, ed., Academic Press, London, 1996, pp. 109-130.
49. K. Hasegawa, Y. Miyashita, and K. Funatsu, GA strategy for variable selection in QSAR studies: GA based PLS analysis of calcium channel antagonists, J. Chem. Inf. Comput. Sci. 37 (1997), pp. 306-310.
50. SPSS is statistical software of SPSS Inc., USA.
51. MINITAB is a statistical software of MINITAB Inc., USA.
52. G.W. Snedecor and W.G. Cochran, Statistical Methods, Oxford and IBH Publishing Co. Pvt. Ltd, New Delhi, 1967, pp. 381-418.
53. A.K. Debnath, Quantitative structure-activity relationship (QSAR): a versatile tool in drug design, in Combinatorial Library Design and Evaluation, A.K. Ghose and V.N. Viswanadhan, eds., Marcel Dekker, Inc., New York, 2001, pp. 73-129.