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Articles

Monte Carlo QSAR models for predicting organophosphate inhibition of acetycholinesterase

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Pages 449-460 | Received 04 Mar 2015, Accepted 27 Apr 2015, Published online: 04 Jun 2015

References

  • B. Eskenazi, A. Bradman, and R. Castorina, Exposures of children to organophosphate pesticides and their potential adverse health effects, Environ. Health Persp. 107(Suppl. 3) (1999), pp. 409–419.
  • M. Eddleston, N.A. Buckley, P. Eyer, and A.H. Dawson, Management of acute organophosphorus pesticide poisoning, Lancet 371 (2008), pp. 597–607.
  • J. Jeyaratnam, Acute pesticide poisoning: A major global health problem, World Health Stat. Q. 43 (1990), pp. 139–144.
  • T.C. Marrs, Organophosphate poisoning, Pharmacol. Therapeut. 58 (1993), pp. 51–66.
  • N.B. Munro, K.R. Ambrose, and A.P. Watson, Toxicity of the organophosphate chemical warfare agents GA, GB, and VX: Implications for public protection, Environ. Health Persp. 102 (1994), pp. 18–38.
  • U. Sharma and S. Singh, Insect vectors of Leishmania: Distribution, physiology and their control, J. Vector Dis. 45 (2008), pp. 255–272.
  • R.P. Penilla, A.D. Rodríguez, J. Hemingway, J.L. Torres, J.I. Arredondo-Jiménez, and M.H. Rodríguez, Resistance management strategies in malaria vector mosquito control. Baseline data for a large-scale field trial against Anopheles albimanus in Mexico, Med. Vet. Entomol. 12 (1998), pp. 217–233.
  • T.R. Fukuto, Mechanism of action of organophosphorus and carbamate insecticides, Environ. Health Persp. 87 (1990), pp. 245–254.
  • B.E. Mileson, J.E. Chambers, W.L. Chen, W. Dettbarn, M. Ehrich, A.T. Eldefrawi, D.W. Gaylor, K. Hamernik, E. Hodgson, A.G. Karczmar, S. Padilla, C.N. Pope, R.J. Richardson, D.R. Saunders, L.P. Sheets, L.G. Sultatos, and K.B. Wallace, Common mechanism of toxicity: A case study of organophosphorus pesticides, Toxicol. Sci. 41 (1998), pp. 8–20.
  • J.B. Knaak, C.C. Dary, F. Power, C.B. Thompson, and J.N. Blancato, Physicochemical and biological data for the development of predictive organophosphorus pesticide QSARs and PBPK/PD models for human risk assessment, Crit. Rev. Toxicol. 34 (2004), pp. 143–207.
  • C.D. Ruark, C.E. Hack, P.J. Robinson, P.E. Anderson, and J.M. Gearhart, Quantitative structure–activity relationships for organophosphates binding to acetylcholinesterase, Arch. Toxicol. 87 (2013), pp. 281–289.
  • L. Eriksson, J. Jaworska, A.P. Worth, M.T.D. Cronin, R.M. McDowell, and P. Gramatica, Methods for reliability and uncertainty assessment and for the applicability evaluations of classification and regression-based QSARs, Environ. Health Persp. 111 (2003), pp. 1361–1375.
  • A.R. Katritzky, R. Petrukhin, D. Tatham, S.C. Basak, E. Benfenati, M. Karelson, and U. Maran, Interpretation of quantitative structure property and activity relationships, J. Chem. Inf. Comp. Sci. 41 (2001), pp. 679–685.
  • M. Karelson, V.S. Lobanov, and A.R. Katritzky, Quantum-chemical descriptors in QSAR/QSPR studies, Chem. Rev. 96 (1996), pp. 1027–1043.
  • A. Goulon, T. Picot, A. Duprat, and G. Dreyfus, Predicting activities without computing descriptors: Graph machines for QSAR, SAR QSAR Environ. Res. 18 (2007), pp. 141–153.
  • O. Ivanciuc, QSAR comparative study of Wiener descriptors for weighted molecular graphs, J. Chem. Inf. Model. 40 (2000), pp. 1412–1422.
  • O. Ivanciuc, Chemical graphs, molecular matrices and topological indices in chemoinformatics and quantitative structure-activity relationships, Curr. Comput. Aided Drug Des. 9 (2013), pp. 153–163.
  • H. González-Díaz, F. Prado-Prado, and F.M. Ubeira, Predicting antimicrobial drugs and targets with the MARCH-INSIDE approach, Curr. Top. Med. Chem. 8 (2008), pp. 1676–1690.
  • A.A. Toropov and E. Benfenati, SMILES as an alternative to the graph in QSAR modelling of bee toxicity, Comput. Biol. Chem. 31 (2007), pp. 57–60.
  • A.A. Toropov and E. Benfenati, Additive SMILES-based optimal descriptors in QSAR modelling bee toxicity: Using rare SMILES attributes to define the applicability domain, Bioorgan. Med. Chem. 16 (2008), pp. 4801–4809.
  • A.A. Toropov, A.P. Toropova, and I. Raska Jr., QSPR modeling of octanol/water partition coefficient for vitamins by optimal descriptors calculated with SMILES, Eur. J. Med. Chem. 43 (2008), pp. 714–740.
  • A.A. Toropov, A.P. Toropova, A. Lombardo, A. Roncaglioni, E. Benfenati, and G. Gini, CORAL: Building up the model for bioconcentration factor and defining its applicability domain, Eur. J. Med. Chem. 46 (2011), pp. 1400–1403.
  • A.M. Veselinović, J.B. Milosavljević, A.A. Toropov, and G.M. Nikolić, SMILES-based QSAR models for arylpiperazines as high-affinity 5-HT1A receptor ligands using CORAL, Eur. J. Pharm. Sci. 48 (2013), pp. 532–541.
  • A.M. Veselinović, J.B. Milosavljević, A.A. Toropov, and G.M. Nikolić, SMILES-based QSAR models for the calcium channel antagonistic effect of 1,4-dihydropyridines, Arch. Pharm. 346 (2013), pp. 134–139.
  • A.P. Toropova, A.A. Toropov, J.B. Veselinović, F.N. Miljković, and A.M. Veselinović, QSAR models for HEPT derivates as NNRTI inhibitors based on Monte Carlo method, Eur. J. Med. Chem. 77 (2014), pp. 298–305.
  • R.S. Yang, R.S. Thomas, D.L. Gustafson, J. Campain, S.A. Benjamin, and H.J. Verhaar, Approaches to developing alternative and predictive toxicology based on PBPK/PD and QSAR modeling, Environ. Health Persp. 106 (1998), pp. 1385–1393.
  • N.M. O’Boyle, M. Banck, C.A. James, C. Morley, T. Vandermeersch, and G.R. Hutchison, Open Babel: An Open chemical toolbox, J. Cheminform. 3 (2011), art. no. 33.
  • P.K. Ojha and K. Roy, Comparative QSARs for antimalarial endochins: Importance of descriptor-thinning and noise reduction prior to feature selection, Chemom. Intell. Lab. Sys. 109 (2011), pp. 146–161.
  • A.P. Toropova, A.A. Toropov, E. Benfenati, D. Leszczynska, and J. Leszczynski, QSAR model as a random event: A case of rat toxicity, Bioorgan. Med. Chem. 23 (2015), pp. 1223–1230.
  • A.A. Toropov, A.P. Toropova, and E. Benfenati, SMILES-based optimal descriptors: QSAR modeling of carcinogenicity by balance of correlations with ideal slopes, Eur. J. Med. Chem. 45 (2010), pp. 3581–3587.
  • K. Roy, On some aspects of validation of predictive quantitative structure activity relationship models, Expert. Opin. Drug Discov. 2 (2007), pp. 1567–1577.
  • P.P. Roy, J.T. Leonard, and K. Roy, Exploring the impact of the size of training sets for the development of predictive QSAR models, Chemometr. Intell. Lab. 90 (2008), pp. 31–42.
  • A. Golbraikh and A. Tropsha, Beware of q2!, J. Mol. Graph. Model. 20 (2002), pp. 269–276.
  • P.P. Roy and K. Roy, QSAR studies of CYP2D6 inhibitor aryloxypropanolamines using 2D and 3D descriptors, Chem. Biol. Drug Des. 73 (2009), pp. 442–455.
  • P.K. Ojha, I. Mitra, R.N. Das, and K. Roy, Further exploring rm2 metrics for validation of QSPR models, Chemometr. Intell. Lab. 107 (2011), pp. 194–205.
  • P. Gramatica, Principles of QSAR models validation: Internal and external, QSAR Comb. Sci. 26 (2007), pp. 694–701.
  • S. Wold, M. Sjostrom, and L. Eriksson, PLS-regression: A basic tool of chemometrics, Chemometr. Intell. Lab. 58 (2001), pp. 109–130.
  • K. Roy, P. Chakraborty, I. Mitra, P.K. Ojha, S. Kar, and R.N. Das, Some case studies on application of ‘rm2’ metrics for judging quality of quantitative structure–activity relationship predictions: Emphasis on scaling of response data, J. Comput. Chem. 34 (2013), pp. 1071–1082.
  • OECD, Guidance document on the validation of (quantitative) structure–activity relationships [(Q)SAR] models, ENV/JM/MONO(2007(2), Organisation for Economic Co-operation and Development, Paris, 2007.
  • S.E. Kunz and D.H. Kemp, Insecticides and acaricides: Resistance and environmental impact, Rev. Sci. Tech. OIE 13 (1994), pp. 1249–1286.

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