A quantitative structure–activity relationship approach for assessing toxicity of mixture of organic compounds

References

• M. Karelson, V.S. Lobanov, and A.R. Katritzky, Quantum-chemical descriptors in QSAR/QSPR Studies, Chem. Rev. 96 (1996), pp. 1027–1044.
   PubMed Web of Science ®Google Scholar
• G.F. Yang and X.Q. Huang, Development of quantitative structure-activity relationships and its application in rational drug design, Curr. Pharm. Des. 12 (2006), pp. 4601–4611.
   PubMed Web of Science ®Google Scholar
• L. Zhang, G.F. Hao, Y. Tan, Z. Xi, M.Z. Huang, and G.F. Yang, Bioactive conformation analysis of cyclic imides as protoporphyrinogen oxidase inhibitor by combining DFT calculations, QSAR and molecular dynamic simulations, Bioorg. Med. Chem. 17 (2009), pp. 4935–4942.
   PubMed Web of Science ®Google Scholar
• L. Zhang, J. Wan, and G. Yang, A DFT-based QSARs study of protoporphyrinogen oxidase inhibitors: Phenyl triazolinones, Bioorg. Med. Chem. 12 (2004), pp. 6183–6191.
   PubMed Web of Science ®Google Scholar
• J. Wan, L. Zhang, G. Yang, and C.G. Zhan, Quantitative structure–activity relationship for cyclic imide derivatives of protoporphyrinogen oxidase inhibitors: A study of quantum chemical descriptors from density functional theory, J. Chem. Inf Comput. Sci. 44 (2004), pp. 2099–2105.
   PubMedGoogle Scholar
• Z. Xi, Z. Yu, C. Niu, S. Ban, and G. Yang, Development of a general quantum-chemical descriptor for steric effects: Density functional theory based QSAR study of herbicidal sulfonylurea analogues, J. Comput. Chem. 27 (2006), pp. 1571–1576.
   PubMed Web of Science ®Google Scholar
• R. Parthasarathi, V. Subramanian, D.R. Roy, and P.K. Chattaraj, Electrophilicity index as a possible descriptor of biological activity, Bioorg. Med. Chem. 12 (2004), pp. 5533–5543.
   PubMed Web of Science ®Google Scholar
• J. Padmanabhan, R. Parthasarathi, V. Subramanian, and P.K. Chattaraj, QSPR models for polychlorinated biphenyls: n-Octanol/water partition coefficient, Bioorg. Med. Chem. 14 (2006), pp. 1021–1028.
   PubMed Web of Science ®Google Scholar
• J. Padmanabhan, R. Parthasarathi, V. Subramanian, and P.K. Chattaraj, Group philicity and electrophilicity as possible descriptors for modeling ecotoxicity applied to chlorophenols, Chem. Res. Toxicol. 19 (2006), pp. 356–364.
   PubMed Web of Science ®Google Scholar
• L. Zhang, P.J. Zhou, F. Yang, and Z.D. Wang, Computer-based QSARs for predicting mixture toxicity of benzene and its derivatives, Chemosphere 67 (2007), pp. 396–401.
   PubMed Web of Science ®Google Scholar
• F. Luan, X. Xu, H. Liu, and M.N.D.S. Cordeiro, Prediction of the baseline toxicity of non-polar narcotic chemical mixtures by QSAR approach, Chemosphere 90 (2013), pp. 1980–1986.
   PubMed Web of Science ®Google Scholar
• C.M. Chang, T.H. Lin, Y.S. Chen, C.W. Chang, K.L. Huang, F.W. Wu, W.J. Hsu, M.P. Yu, C. Lin, and M.K. Wang, A quantum chemical approach using classical concepts to characterization and descriptive analysis of various reactions of metal ions and organic compounds, Chemom. Intell. Lab. Syst. 136 (2014), pp. 155–163.
   Web of Science ®Google Scholar
• Z. Lin, H. Yu, D. Wei, G. Wang, J. Feng, and L. Wang, Prediction of mixture toxicity with its total hydrophobicity, Chemosphere 46 (2002), pp. 305–310.
   PubMed Web of Science ®Google Scholar
• Z. Lin, P. Zhong, K. Yin, L. Wang, and H. Yu, Quantification of joint effect for hydrogen bond and development of QSARs for predicting mixture toxicity, Chemosphere 52 (2003), pp. 1199–1208.
   PubMed Web of Science ®Google Scholar
• G. Lu, C. Wang, Z. Tang, and X. Guo, Joint toxicity of aromatic compounds to algae and QSAR study, Ecotoxicology 16 (2007), pp. 485–490.
   PubMed Web of Science ®Google Scholar
• R.G. Pearson, Hard and Soft Acids and Bases, J. Am. Chem. Soc. 85 (1963), pp. 3533–3539.
   Web of Science ®Google Scholar
• R.G. Parr and R.G. Pearson, Absolute hardness: Companion parameter to absolute electronegativity, J. Am. Chem. Soc. 105 (1983), pp. 7512–7516.
   Web of Science ®Google Scholar
• S. Meng, E.G. Wang, and S. Gao, A molecular picture of hydrophilic and hydrophobic interactions from ab initio density functional theory calculations, J. Chem. Phys. 119 (2003), pp. 7617–7620.
   Web of Science ®Google Scholar
• P. Geerlings, F. De Proft, and W. Langenaeker, Conceptual density functional theory, Chem. Rev. 103 (2003), pp. 1793–1874.
   PubMed Web of Science ®Google Scholar
• P.W. Ayers, The physical basis of the hard/soft acid/base principle, Faraday Discuss. 135 (2007), pp. 161–190.
   PubMed Web of Science ®Google Scholar
• P.K. Chattaraj, U. Sarkar, and D.R. Roy, Electrophilicity index, Chem. Rev. 106 (2006), pp. 2065–2091.
   PubMed Web of Science ®Google Scholar
• J.L. Gázquez, A. Cedillo, and A. Vela, Electrodonating and electroaccepting powers, J. Phys. Chem. A 111 (2007), pp. 1966–1970.
   PubMed Web of Science ®Google Scholar
• J.L. Gázquez, Perspectives on the density functional theory of chemical reactivity, J. Mex. Chem. Soc. 52 (2008), pp. 3–10.
   Web of Science ®Google Scholar
• M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. MontgomeryJr., J.E. Peralta, F. Ogliaro, M.J. Bearpark, J. Heyd, E.N. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A.P. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N.J. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox, Gaussian 09 (2009).
   Google Scholar
• R.T. Sanderson, Partial charges on atoms in organic compounds, Science 121 (1955), pp. 207–208.
   PubMed Web of Science ®Google Scholar
• R.S. Mulliken, Electronic population analysis on LCAO–MO molecular wave functions I, J. Chem. Phys. 23 (1955), pp. 1833–1840.
   Web of Science ®Google Scholar
• I.A. Doichinova, R.N. Natcheva, and D.N. Mihailova, QSAR studies of 8-substituted xanthines as adenosine receptor antagonists, Eur. J. Med. Chem. 29 (1994), pp. 133–138.
   Web of Science ®Google Scholar
• R.A. Nyquist, Solvent-induced carbonyl frequency shifts: Cyclopentanone and cyclohexanone, Appl. Spectrosc. 44 (1990), pp. 426–433.
   Web of Science ®Google Scholar
• D.K. Cha, A.A. Kloss, A.C. Tikanen, and W.R. Fawcett, Solvent-induced frequency shifts in the infrared spectrum of acetone in organic solvents, PCCP 1 (1999), pp. 4785–4790.
   Web of Science ®Google Scholar
• J.B.F.N. Engberts, G.R. Famini, A. Perjéssy, and L.Y. Wilson, Solvent effects on C=O stretching frequencies of some 1-substituted 2-pyrrolidinones, J. Phys. Org. Chem. 11 (1998), pp. 261–272.
   Web of Science ®Google Scholar
• W. Yang and W.J. Mortier, The use of global and local molecular parameters for the analysis of the gas-phase basicity of amines, J. Am. Chem. Soc. 108 (1986), pp. 5708–5711.
   PubMed Web of Science ®Google Scholar
• W. Yang and R.G. Parr, Hardness, softness, and the fukui function in the electronic theory of metals and catalysis, Proc. Nat. Acad. Sci. USA 82 (1985), pp. 6723–6726.
   PubMed Web of Science ®Google Scholar
• A. Pedretti, L. Villa, and G. Vistoli, Atom-type description language: A universal language to recognize atom types implemented in the VEGA program, Theor. Chem. Acc. 109 (2003), pp. 229–232.
   Web of Science ®Google Scholar
• B. Lee and F.M. Richards, The interpretation of protein structures: Estimation of static accessibility, J. Mol. Biol. 55 (1971), pp. 379–400.
   PubMed Web of Science ®Google Scholar
• F.M. Richards, Areas, Volumes, Packing, and Protein Structure, Annu. Rev. Biophys. Bio. 6 (1977), pp. 151–176.
   PubMedGoogle Scholar
• K. Palm, K. Luthman, A.-L. Unge, G. Strandlund, and P. Artursson, Correlation of drug absorption with molecular surface properties, J. Pharm. Sci. 85 (1996), pp. 32–39.
   PubMed Web of Science ®Google Scholar
• H. Huang, X. Wang, Y. Shao, D. Chen, X. Dai, and L. Wang, QSAR for prediction of joint toxicity of substituted phenols to tadpoles (Rana japonica), Bull. Environ. Contam. Toxicol. 71 (2003), pp. 1124–1130.
   PubMed Web of Science ®Google Scholar
• G.H. Lu, C. Wang, P.F. Wang, and Z.Y. Chen, Joint toxicity evaluation and QSAR modeling of aromatic amines and phenols to bacteria, Bull. Environ. Contam. Toxicol. 83 (2009), pp. 8–14.
   PubMed Web of Science ®Google Scholar
• C. Wang, G. Lu, Z. Tang, and X. Guo, Quantitative structure-activity relationships for joint toxicity of substituted phenols and anilines to Scenedesmus obliquus, J. Environ. Sci. 20 (2008), pp. 115–119.
   Web of Science ®Google Scholar
• A.P. Toropova, A.A. Toropov, E. Benfenati, G. Gini, D. Leszczynska, and J. Leszczynski, CORAL: Models of toxicity of binary mixtures, Chemom. Intell. Lab. Syst. 119 (2012), pp. 39–43.
   Web of Science ®Google Scholar
• R.M. Bethea, B.S. Duran, and T.L. Boullion, Statistical Methods for Engineers and Scientists, Marcel Dekker, New York, NY, 1995.
   Google Scholar
• D.A. Belesley, E. Kuh, and R.E. Welsh, Regression Diagnostics, Wiley, New York, NY, 1980.
   Google Scholar
• A. Golbraikh and A. Tropsha, Beware of q2!, J. Molec. Graph. Model. 20 (2002), pp. 269–276.
   PubMed Web of Science ®Google Scholar
• A. Tropsha, P. Gramatica, and V.K. Gombar, The importance of being earnest: Validation is the absolute essential for successful application and interpretation of QSPR models, QSAR. Comb. Sci. 22 (2003), pp. 69–77.
   Google Scholar
• H.Y. Shen, X.L. Shao, H. Xu, J. Li, and S.D. Pan, In vitro study of DNA interaction with trichlorobenzenes by spectroscopic and voltammetric techniques, Int. J. Electrochem. Sci. 6 (2011), pp. 532–547.
   Web of Science ®Google Scholar