Analyzing toxicity through electrophilicity

Molecular Diversity

Volumn 10, Issue 2, 2006, Pages 119-131

  Roy, D R ^a   Sarkar, U ^a   Chattaraj, P K ^a   Mitra, A ^a   Padmanabhan, J ^a,b   Parthasarathi, R ^b   Subramanian, V ^b   Van Damme, S ^c   Bultinck, P ^c  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

^b CENTRAL LEATHER RESEARCH INSTITUTE   (India)

^c GHENT UNIVERSITY   (Belgium)

Author keywords

Charge transfer; DFT; Electrophilicity; Polychlorinated dibenzofurans; QSAR; Toxicity

Indexed keywords

2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; ALIPHATIC AMINE; AMINOALCOHOL; AROMATIC HYDROCARBON RECEPTOR; FRESH WATER; NUCLEIC ACID BASE; POLYCHLORINATED BIPHENYL; POLYCYCLIC AROMATIC HYDROCARBON; TOXIN;

ANALYTIC METHOD; ARTICLE; BASE PAIRING; BIOLOGICAL ACTIVITY; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); CORRELATION ANALYSIS; DENSITY FUNCTIONAL THEORY; ELECTRON; ELECTRON TRANSPORT; GAS; IC 50; INFORMATION SYSTEM; ISOTOPE LABELING; MATHEMATICAL MODEL; MOLECULAR MODEL; NONHUMAN; PARAMETERS OF MEASUREMENT AND ANALYSIS; PREDICTION; PRIORITY JOURNAL; PROTOZOON; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REGRESSION ANALYSIS; SOLUTION AND SOLUBILITY; STRUCTURE ACTIVITY RELATION; SURFACE CHARGE; TETRAHYMENA PYRIFORMIS; TOXICOLOGY;

ANIMALS; ELECTROCHEMISTRY; ENVIRONMENTAL POLLUTANTS; INHIBITORY CONCENTRATION 50; POLYCHLORINATED BIPHENYLS; POLYCYCLIC HYDROCARBONS, AROMATIC; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTORS, ARYL HYDROCARBON; REGRESSION ANALYSIS; TETRACHLORODIBENZODIOXIN; TETRAHYMENA PYRIFORMIS; TOXICITY TESTS;

EID: 33746266008     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-005-9009-x     Document Type: Article

References (55)

1. Parr, R.G. and Yang, W., Density Functional theory of Atoms and Molecules (Oxford University Press: New York) (1989).
2. Chermette, H., Chemical reactivity indexes in density functional theory, J. Comp. Chem., 20 (1999) 129-154.
3. Geerlings, P., De Proft, F. and Langenaeker, W., Conceptual density functional theory, Chem. Rev., 103 (2003) 1793-1874.
4. Chattaraj, P.K., Nath, S. and Maiti, B., "Reactivity descriptors" in Computational Medicinal Chemistry and Drug Discovery. Eds., Tollenaere, J., Bultinck, P., Winter, H. D., and Langenaeker, W. (Marcel Dekker: New York), Chapter 11, 2003, pp. 295-322.
5. Karelson, M., "Quantum-Chemical descriptors in QSAR" in Computational medicinal chemistry and drug discovery. Eds., Tollenaere, J., Bultinck, P., Winter, H. D., and Langenaeker, W. (Marcel Dekker: New York), Chapter 11, 2004, pp. 641-668.
6. Parr, R.G., Szentpaly, L.V. and Liu, S., Electrophilicity index, J. Am. Chem. Soc., 121 (1999) 1922-1924.
7. Maynard, A.T. and Covell, D.G., Reactivity of zinc finger cores: Analysis of protein packing and electrostatic screening, J. Am. Chem. Soc., 123 (2001) 1047-1058.
8. Chattaraj, P.K., Maiti, B. and Sarkar, U., Philicity: A unified treatment of chemical reactivity and selectivity, J. Phys. Chem. A., 107 (2003) 4973-4975.
9. Thanikaivelan, P., Subramanian, V., Raghava Rao, J. and Nair, B.U., Application of quantum chemical descriptor in quantitative structure activity and structure property relationship, Chem. Phys. Lett., 323 (2000) 59-70.
10. Parthasarathi, R., Subramanian, V., Roy, D.R. and Chattaraj, P.K., Electrophilicity index as a possible descriptor of biological activity, Bioorg. Med. Chem., 12 (2004) 5533-5543.
11. Parthasarathi, R., Padmanabhan, J., Subramanian, V., Maiti, B. and Chattaraj, P.K., Chemical reactivity profiles of two selected polychlorinated biphenyls, J. Phys. Chem. A., 107 (2003) 10346-10352.
12. Parthasarathi, R., Padmanabhan, J., Subramanian, V., Maiti, B. and Chattaraj, P.K., Toxicity analysis of 33′44′5 - pentachloro biphenyl through chemical reactivity and selectivity profiles, Current Sci., 86 (2004) 535-542.
13. Parthasarathi, R., Padmanabhan, J., Subramanian, V., Sarkar, U., Maiti, B. and Chattaraj, P.K., Toxicity analysis of benzidine through chemical reactivity and selectivity profiles: A DFT approach, Internet Electron J. Mol. Des., 2 (2003) 798-813.
14. Bailey and Love's 'Short Practice of Surgery', Russell, R.C.G., Williums, N.S., Bulstrode, C., J.K. (eds.), 23rd Edition (Arnold: London), 2000, pp. 1227-1228.
15. Walker, M.K. and Peterson, R.E., Potencies of polychlorinated dibenzo-p-dioxin, dibenzofuran, and biphenyl congeners, relative to 2,3,7,8-tetrachlorodibenzo-p-dioxin, for producing early life stage mortality in rainbow trout (Oncorhynchus mykiss), Aquat. Toxicol, 21 (1991) 219-237.
16. Zabel, E.W., Cook, P.M. and Peterson, R.E., Toxic equivalency factors of polychlorinated dibenzo-p-dioxin, dibenzofuran and biphenyl congeners based on early life stage mortality in rainbow trout (Oncorhynchus mykiss), Aquat. Toxicol., 31 (1995) 315-328.
17. Hutzinger, O., Blumich, M.J., Berg, M.V.D. and Olie, K., Sources and fate of PCDDs and PCDFs: an overview, Chemosphere, 14 (1985) 581-600.
18. Olie, K., Vermeulen, P.L. and Hutzinger, O., Chlorodibenzo-p-dioxins and chlorodibenzofurans are trace components of fly ash and flue gas of some municipal incinerators in the Netherlands, Chemosphere, 6 (1977) 455-459.
19. Marklund, S., Rappe, C., Tsyklind, M. and Egebäck, K.E., Identification of polychlorinated dibenzofurans and dioxins in exhausts from cars run on leaded gasoline, Chemosphere, 16 (1987) 29-36.
20. Lohmann, R. and Jones, K.C., Dioxins and furans in air and deposition: A review of levels, behaviour and processes, Sci. Total Environ., 219 (1998) 53-81.
21. Safe, S.H., Polychlorinated biphenyls (PCBs): Environmental impact, biochemical and toxic responses, and implications for risk assessment, Crit. Rev. Toxicol., 24 (1994) 87-149.
22. Van den Berg, M., Birnbaum, L., Bosveld, A.T., Brunstrom, B., Cook, P., Feeley, M., Giesy, J.P., Hanberg, A., Hasegawa, R., Kennedy, S.W., Kubiak, T., Larsen, J.C., van Leeuwen, F.X., Liem, A.K., Nolt, C., Peterson, R.E., Poellinger, L., Safe, S., Schrenk, D., Tillitt, D., Tysklind, M., Younes, M., Waern, F. and Zacharewski, T., Toxic equivalency factors (TEFs) for PCBs, PCDDs, PCDFs for humans and wildlife, Environ. Health. Perspet., 106 (1998) 775-792.
23. Oakley, G.G., Devanaboyina, U.S., Robertson, L.W. and Gupta, R.C., Oxidative DNA damage induced by activation of polychlorinated biphenyls (PCBs): Implications for PCB-Induced oxidative stress in breast cancer, Chem. Res. Toxicol, 9 (1996) 1285-1292.
24. Erickson, M.D., Analytical Chemistry of PCBs (Butterworth Publishers, Boston) (1986).
25. Silberhorn, E.M., Glauert, H.P. and Robertson, L.W., Carcinogenicity of polyhalogenated biphenyls: PCBs and PBBs, Crit. Rev. Toxicol., 20 (1990) 439-496.
26. Miller, G., Sontum, S. and Crosby, D.G., Electron-acceptor properties of chlorinated dibenzo-p-dioxins, Bull. Environ. Contam. Toxicol, 18 (1977) 611-616.
27. Poland, A., Palen, D., and Glover, E., Tumour promotion by TCDD in skin of HRS/J hairless mice, Nature, 300 (1982) 271-273.
28. Waller, C.L. and McKinney, J.D., Three-dimensional quantitative structure-activity relationships of dioxins and dioxin-like compounds: Model validation and ah receptor characterization, Chem. Res. Toxicol. 8 (1995) 847-858.
29. Schultz, T.W., Tetratox: Tetrahymena pyriformis population growth impairment endpoint-a surrogate for fish lethality, Toxicol, Methods, 7 (1997) 289-309.
30. Pearson, R.G., Chemical hardness - Applications from molecules to solids (VCH-Wiley: Weinheim) (1997).
31. Parr, R.G., Donnelly, R.A., Levy, M. and Palke, W.E., Electronegativity: The density functional viewpoint, J. Chem. Phys., 68 (1978) 3801-3807.
32. Parr, R.G. and Yang, W., Density functional approach to the frontier-electron theory of chemical reactivity, J. Am. Chem. Soc., 106 (1984) 4049.
33. Fukui, K., Role of Frontier Orbitals in Chemical Reactions, Science, 218 (1987) 747-754.
34. Yang, W. and Mortier, W.J., The use of global and local molecular parameters for the analysis of the gas-phase basicity of amines, J. Am. Chem. Soc., 108 (1986) 5708-5711.
35. 2CO, J. Mol. Struct. (Theochem), 163 (1988) 305.
36. Cioslowski, J., Martinov, M. and Mixon, S.T., Atomic Fukui indexes from the topological theory of atoms in molecules applied to Hartree-Fock and correlated electron densities, J. Phys. Chem, 97 (1993) 10948-10951.
37. Parr, R.G. and Pearson, R.G., Absolute hardness: Companion parameter to absolute electronegativity, J. Am. Chem. Soc., 105 (1983) 7512-7516.
38. Sanderson, R. T., An interpretation of bond lengths and a classification of bonds, Science, 114 (1951) 670.
39. Espinosa, A., Frontera, A., García, R., Soler, M.A. and Tárraga, A., Electrophilic behavior of 3-methyl-2-methylthio-1,3,4- thiadiazolium salts: A multimodal theoretical approach, ARKIVOC, (ix) (2005) 415-437.
40. Becke, A.D., Density-functional exchange-energy approximation with correct asymptotic behavior, Phys. Rev. A., 38 (1998) 3098-3100.
41. Hariharan, P. C. and Pople, J. A., Theor. Chim. Acta., 28 (1973) 213.
42. Lee, C., Yang, W. and Parr, R.G., Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B., 37 (1988) 785-789.
43. Gaussian 03 & Gaussian 98, Revision B.03; Gaussian, Inc.: Pittsburgh, PA.
44. Mulliken, R. S., Electronic population analysis on LCAO-MO molecular wave functions, I, J. Chem. Phys., 23 (1955) 1833-1840.
45. Reed, A.E. and Weinhold, F., Natural bond orbital analysis of near-Hartree-Fock water dimmer, J Chem Phys., 78 (1983) 4066-4073.
46. Reed, A.E., Weinstock, R.B. and Weinhold, F., Natural population analysis, J. Chem. Phys., 83 (1985) 735-746.
47. Hirshfeld, F.L., Bonded-atom fragments for describing molecular charge densities, Theor. Chim. Acta., 44 (1977) 129-138.
48. 3, Accelrys, Inc. San Diego, California.
49. MATLAB, The Math Works (Inc.: Natick, U.S.A), (1999).
50. Pecka, J. and Ponec, R., Simple analytical method for evaluation of statistical importance of correlations in QSAR studies, J. Math. Chem., 27 (2000) 13-22.
51. Basak, S.C., Chertian, J., Natarajan, R.; Private communication.
52. Arulmozhiraja, S. and Morita, M., Structure-activity relationships for the toxicity of polychlorinated dibenzofurans: Approach through density functional theory-based descriptors, Chem. Res. Toxicol., 17 (2004) 348-356.
53. Tysklind, M., Tillitt, D., Eriksson, L., Lundgren, K. and Rappe, C., A toxic equivalency factor scale for polychlorinated dibenzofurans, Fundam. Appl. Toxicol., 22 (1994) 277-285.
54. Roy, D.R., Parthasarathi, R., Maiti, B., Subramanian, V. and Chattaraj, P.K., Electrophilicity as a possible descriptor for toxicity prediction, Bioorg. Med. Chem., 13 (2005) 3405-3412.
55. Hawkins, D.M., Basak, S.C. and Mills, D., Assessing model fit by cross-validation, J. Chem. Inf. Comput. Sci., 43 (2003) 579-586.