Modeling of the n-octanol/water partition coefficient of a series of PAHs: QSPR model

Year 2024, Volume: 8 Issue: 2, 121 - 127

Youssouf Drıouche , Hamza Haddag , Meriem Ferfar , Laid Bouchaala , Amel Bouakkadia , Amırı Rana , Nabil Bouarra , Samia Alem

https://doi.org/10.32571/ijct.1321749

Abstract

A simple linear model was used to investigate the correlation between the n-octanol/water partition coefficient (kow) of non-substituted fused polycyclic aromatic hydrocarbons (PAHs). Among (74) 3D-geometrically tested descriptors calculated using the Dragon software, volume V turned out to be the best descriptor to model the considered endpoint (with a squared correlation coefficient (R2) of 0.9844 and a standard error of estimation (s) of 0.132 log units). The correlation coefficient cross-validation (Q2) between experimental and predicted log kow for training and test sets was 0.9811 (for training set) and 0.9828 (for test set), respectively.
The reliability of the proposed model was further illustrated using various evaluation techniques: leave-5-out cross-validation, bootstrap, randomization tests, and validation through the test set.

Keywords

Polycyclic aromatic hydrocarbons, log kow, Solute bulk, Simple linear model, QSPR

References

• 1. Touhami, I.; Messadi, D. Enrgy Proced. 2019, 157, 522–532.
• 2. Xu, H.Y.; Zhang, J.Y.; Zou, J.W.; Chen, X.S. J. Mol. Graph. Model. 2008, 26 (7), 1076-1081.
• 3. Touhami, I.; Haddag, H.; Didi, M.; Messadi D. Chromatographia. 2016, 79, 1023–1032.
• 4. Amiri, R.; Messadi, D.; Bouakkadia, A.; lourici, L. Egypt.J.Chem. 2019, 62(9), 1563-1574.
• 5. Katritzky, A.R.; Kuanar, M.; Slavov, S.; Hall, C.D. Chem. Rev. 2010, 110 (10), 5714-5789.
• 6. Li, W.R.; Song, G.B.; Ding G.H.; Gao, H. IOP Conf. Ser.: Earth Environ. Sci. 2020, 612(1), 012044.
• 7. Amiri, R.; Messadi, D.; Bouakkadia, A. J. Serb. Chem. Soc.2020, 85(4), 467-480.
• 8. Mannhold, R.; Van de Waterbeemd, H. J. Comput. Aid. Mol. Des. 2001, 15(4), 337-354.
• 9. Mannhold, R.; Rekker, R.F. Perspect. Drug. Discov. 2000, 18(1), 1-18.
• 10. Ziani, N. ; Amirat, K.; Messadi, D. Rev. Sci. Technol. Synthèses. 2014, 29, 51-58.
• 11. Benfenati, E.; Gini, G.; Piclin, N.; Roncaglioni, A.; Vari, M.R. Chemosphere. 2003, 53(9), 1155-1164.
• 12. Mannhold, R.; Petrauskas, A. QSAR. Comb. Sci. 2003, 22(4), 466-475.
• 13. Klopman, G.; Li, J.K.; Wang, S.; Dimayuge, M. J. Chem. Inf. Comp. Sci. 1994, 34(4), 752-781.
• 14. Netto, A.D.P.; Moreira, J.C.; Dias, A.E.X.O.; Arbilla. G.; Ferreira, L.F.V.; Oliveira, A.S.; Barek, J. Quim. Nova. 2000, 23(6), 765-773.
• 15. Mackay, D.; Shiu, W.V.; Ma, K.C. Illustrated Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals, Vol.3, Lewis, London, 1998.
• 16. HyperchemTM. Release 6.02 for windows. Molecular Modeling system, (2000). (http://www.hyper.com/).
• 17. Todeschini, R.; Consonni, V.; Mauri, A.; Paven, M. (2005) DRAGON Software for the calculation of Molecular Descriptors version 5.3 for Windows, Talete s. r. l., Milano, Italy. (http://www.talete.mi.it/).
• 18. Kennard, R.W.; Stone, L.A. Technometrics. 1996, 11(1), 137-148.
• 19. Todeschini, R.; Ballabio, D.; Consonni, V.; Mauri, A. ; Paven, M. (2004) MobyDigs - version 1.1 - 2009 Copyright TALETE srl. (http://www.talete.mi.it/).
• 20. Bouakkadia, A.; Driouche, Y.; Kertiou, N.; Messadi, D. Int. J. Saf. Secur. Eng. 2020, 10(3), 389-396.
• 21. Driouche, Y.; Messadi, D. J. Serb. Chem. Soc. 2019, 84(4), 405-416.
• 22. Didi, M.; Haddag, H.; Driouche, Y.; Messadi, D. Res. J. Pharm. Biol. Chem. Sci. 2017, 8(4):379-390.
• 23. Bouakkadia, A.; Kertiou, N.; Amiri, R.; Driouche, Y.; Messadi, D. J. Serb. Chem. Soc. 2021, 86(7-8), 673–684.
• 24. Eriksson, L.; Jaworska, J.; Worth, A.; Cronin, M.Mc.; Dowell, R.M.; Gramatica, P. Environ Health Persp. 2003, 111(10):1361-1375.
• 25. Tropscha, A.; Gramatica, P.; Grombar, V.K. QSAR. Comb. Sci. 2003, 22(1), 69-77.
• 26. Kubinyi, H.; Hamprecht, F.A.; Mietzner, T. J. Med. Chem. 1998, 41(14), 2553-2564.
• 27. Golbraikh, A.; Tropsha, A. J. Mol. Graph. Model. 2002, 20(4), 269-276.
• 28. Shen, M.; Béguin, C.; Golbraikh, A.; Stables, J.P.; Kohn, H.; Tropsha, A. J. Med. Chem. 2004, 47(9), 2356-2364.
• 29. Weisberg, S. Applied Linear Regression, 3rd edition. John wiley and sons, Inc., Hoboken, New Jersey, 2005.
• 30. Van de Waterbeemd, H.; Testa, B. The parametrization of lipophilicity and other structural properties in drug design. in: Testa B (Ed.) Advances in Drug Research, vol.16, Academic Press, New York, pp 85-225, 1987.
• 31. Leahy, D.E. J. Pharm. Sci. 1986, 75(7), 629-636.
• 32. Moriguchi, I.; Kanada, Y.; kawatsu, K. Chem. Pharm. Bull. 1976, 24(8), 1799-1806.
• 33. Dadfar, E.; Shafiei, F.; Isfahani, T.M. Curr Comput Aided Drug Des. 2020, 16(3), 207-221.
• 34. Mebarki, F.; Meneceur, S.; Abderrhmane Bouafia, A. Asian J. Research Chem. 2022, 15(6), 443-8.