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In Silico Pharmacology

, 5:14 | Cite as

Computational chemistry study of toxicity of some m-tolyl acetate derivatives insecticides and molecular design of structurally related products

  • Nnabuk Okon Eddy
  • Nsikak Bassey Essien
Original Research
  • 18 Downloads

Abstract

Molecular descriptors (including quantum chemical, topological and physicochemical descriptors) were calculated for five m-tolyl derivatives insecticides [namely, carbosulfan (CBS), carbofuran (CBF), isoprocab (IFP), methiocarb (MTC) and isocarbophos (ICP)]. Calculated quantum chemical parameters included the total energy, the electronic energy, the binding energy, the core–core repulsion energy, the heat of formation, the dipole moment and the frontier molecular orbital energies. All the calculated quantum chemical parameters (except dipole moment) exhibited strong correlation with the experimental LD50 values of the studied insecticides (at various Hamiltonians). Calculated topological parameters included the molecular topological index (MTI), polar surface area (PSA), total connectivity (TC), total valence connectivity (TVC), Wiener index (WI), topological diameter (TD) and Balaban index (BI). However, only MTI, PSA, WI and BI exhibited excellent correlation with the toxicological activity of the insecticides. Also among all the calculated physicochemical parameters [logP, surface area (SA), surface volume (SV), hydration energy (EHydr), polarizability (PLZ) and refractivity (RFT)], only SV, EHydr, PLZ and RFT were useful in establishing quantitative structure activity relationship (QSAR). Application of QSAR indicated that the calculated theoretical LD50 values for the studied insecticides displayed excellent correlation with experimentally derived LD50 values. However, best results were obtained from quantum chemical descriptors under modified neglect of atomic overlap (MNDO). The toxicity profile of the insecticides also correlated strongly with ionization energy, electron affinity, global softness and global harness. Reactive sites of each of the insecticides were established using Fukui function, Huckel charges and HOMO/LUMO diagrams. Six new molecules were proposed and their theoretical activities were estimated. The proposed molecules included 2-methyl-2-(methylthio)-2,3-dihydrobenzofuran-7-yl methylcarbamate, O-methyl O-2-((methylaminooxy)carbonyl)phenyl phosphoramidothioate, 2-((methylaminooxy)carbonyl)phenyl methylcarbamate, 2-(1-(methylthio)ethyl)phenyl methylcarbamate, N-methyl-O-(2-(methylthiooxy) benzoyl) hydroxyl amine and 4-methyl naphthalen-2-yl methylcarbamate. Some of the proposed molecules exhibited negative values of LD50 (indicating extreme toxicity) while two of them exhibited values that are comparable to existing insecticides.

Keywords

m-Tolyl acetate insecticides Molecular modeling Quantum, topological and physicochemical descriptors 

References

  1. Ameh PO, Eddy NO (2016) Theoretical and experimental studies on the corrosion inhibition potentials of 3-nitrobenzoic acid for mild steel in 0.1 M H2SO4. Cogent Chem 2:1253904CrossRefGoogle Scholar
  2. Barbosa S, Hastings MI (2012) The importance of modelling the spread of insecticide resistance in a heterogeneous environment: the example of adding synergists to bed nets. Malar J.  https://doi.org/10.1186/1475-2875-11-258 Google Scholar
  3. Borget F, Chiavassa T, Allouche A, Aycard JP (2001) Experimental and quantum study of adsorption of ozone on amorphous water ice film. J Phys Chem B 105(2):449–454CrossRefGoogle Scholar
  4. Eddy NO (2010) Theoretical study on some amino acids and their potential activity as corrosion inhibitors for mild steel in HCl. Mol Simul 35(5):354–363CrossRefGoogle Scholar
  5. Eddy NO (2011) Experimental and theoretical studies on some amino acids and their potential activity as inhibitors for the corrosion of mild steel, Part 2. J Adv Res 2:35–47CrossRefGoogle Scholar
  6. Eddy NO, Ita BI (2011a) Experimental and theoretical studies on the inhibition potentials of some derivatives of cyclopenta-1,3-diene for the corrosion of mild steel in HCl solutions. Int J Quantum Chem 111(14):3456–3473Google Scholar
  7. Eddy NO, Ita BI (2011b) Theoretical and experimental studies on the inhibition potentials of aromatic oxaldehydes for the corrosion of mild steel in 0.1 M HCl. J Mol Model 17:633–647CrossRefPubMedGoogle Scholar
  8. Eddy NO, Momoh-Yahaya H, Oguzie EE (2015) Theoretical and experimental studies on the corrosion inhibition potentials of some purines for aluminum in 0.1 M HCl. J Adv Res 6:203–216CrossRefPubMedGoogle Scholar
  9. Gao W, Wang W, Farahani R (2016) Topological indices study of molecular structure in anticancer drugs. J Chem.  https://doi.org/10.1155/2016/3216327 Google Scholar
  10. Garcia GC, Ruiz IL, Gomez-Nieto MA (2005) From Wiener index to molecules. Chem Inform Mod 45(2):231–238CrossRefGoogle Scholar
  11. Gomez-Jeria JS, Ojeda-Vergara M, Donoso-Espinoza C (1995) Quantum chemical structure activity relationship in carbamat e insecticides. Mol Eng 5(4):391–401CrossRefGoogle Scholar
  12. Husarova V, Ostatnikova D (2013) Monosodium glutamate toxic effects and their implication for human intake: a review. JMED Res.  https://doi.org/10.5171/2013.608765 Google Scholar
  13. Iwamura H, Nishimura K, Fujita T (1985) Quantitative structure-activity relationships of insecticides and plant growth regulators: comparative studies toward understanding the molecular mechanism of action. Environ Health Perspect 61:307–320CrossRefPubMedPubMedCentralGoogle Scholar
  14. Jian L, Yanging G, Shibin S, Xiaoping R, Jie S, Zongde W (2014) Synthesis and quantitative structure-activity relationship (QSAR) studies of novel rosin-based diamide insecticides. RSC Adv 4:58190–58199CrossRefGoogle Scholar
  15. Karabunarliev S, Mekenyan OG, Karcher W, Russom CL, Bradbury SP (1996) Quantum-chemical Descriptors for Estimating the Acute Toxicity of Substituted Benzenes to the Guppy (Poecilia reticulata) and Fathead Minnow (Pimephales promelas). Mol Inform 15(4):311–320Google Scholar
  16. Kard B, Shelton K, Luper C (2014) Toxicity of pesticides Pesticide applicator certification series. Oklahoma cooperation extension services EPP-7457-8. Available from: http://pods.dasnr.okstate.edu/docushare/dsweb/Get/Document-3591/EPP-7457web.pdf
  17. Kier LB, Hall LH (2002) The meaning of molecular connectivity: a bimolecular accessibility model. Croat Chem Acta 75(2):371–382Google Scholar
  18. Lorenz ES (2006) Pesticide safety fact sheel: toxicity of pesticide. Pennsylvania University, ‎PhiladelphiaGoogle Scholar
  19. Musa AY, Jalgham RTT, Mohamad AB (2012) Molecular dynamic and quantum chemical calculations for phthalazine derivatives as corrosion inhibitors for mild steel in 1 M HCl. Corros Sci 56:176–183CrossRefGoogle Scholar
  20. Naik PK, Singh T, Singh H (2009) Quantitative structure-activity relationship (QSAR) for insecticides: development of predictive in vivo insecticide activity models. SAR/QSAR Environ Res 20(5–6):551–556Google Scholar
  21. Naik PK, Alam A, Malhotra A, Rizvi O (2010) Molecular modeling and structure-activity relationship of podophyllotoxin and its congeners. J Biomol Screen 15(5):528–540CrossRefPubMedGoogle Scholar
  22. Nikolić S, Trinajstić N, Mihadlid Z (1993) Molecular topological index: an extension to heterosystems. J Math Chem 12(1):251–264CrossRefGoogle Scholar
  23. Pandith AH, Giri S, Chattaraj PK (2010) A comparative study of two quantum chemical descriptors in predicting toxicity of aliphatic compounds towards tetrahymena pyriformis. Org Chem Int.  https://doi.org/10.1155/2010/545087 Google Scholar
  24. Prasanna S, Doerksen RJ (2009) Topological polar surface area: a useful descriptor in 2D-QSAR. Curr Med Chem 16(1):21–41CrossRefPubMedGoogle Scholar
  25. Schaftenaa G, de Vilieg J (2012) Quantum mechanical polar surface area. J Comput Aided Des 26(3):311–318CrossRefGoogle Scholar
  26. Tanii H (1994) Structure-activity relationships of organic solvents and related chemicals. Sangyo Igaku 36(5):299–313CrossRefPubMedGoogle Scholar
  27. Todeschini R, Consonni V (2000) Handbook of molecular descriptors. Methods and principles in medicinal chemistry, vol 11. Wiley, New YorkCrossRefGoogle Scholar
  28. Usha T, Tripathi P, Pande V, Middha SK (2013) Molecular docking and quantum mechanical studies on pelargonidin-3-glucoside as renoprotective ACE inhibitor. Comput Biol.  https://doi.org/10.1155/2013/428378 Google Scholar
  29. Vikas R (2015) Exploring the role of quantum chemical descriptors in modeling acute toxicity of diverse chemicals to Daphnia magna. J Mol Graph Mod 61:89–101CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2017

Authors and Affiliations

  1. 1.Federal University LokojaLokojaNigeria
  2. 2.Department of ChemistryAkwa Ibom State PolytechnicIkot OsuruaNigeria

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