Application of Wavelet and Genetic Algorithms for QSAR Study on 5-Lipoxygenase Inhibitors and Design New Compounds
DOI:
https://doi.org/10.29356/jmcs.v59i3.36Keywords:
1-phenyl[2H]-tetrahydro-triazine-3-one analogues, genetic algorithms, wavelet transform, QSAR, PLSAbstract
A quantitative structure-activity relationship (QSAR) modeling was carried out for the prediction of inhibitory activity of 1-phenyl[2H]-tetrahydro-triazine-3-one analogues as inhibitors of 5-lipoxygenase. Partial least squares (PLS) algorithm was employed to model the relationships between molecular descriptors and inhibitory activity of molecules using the genetic algorithm (GA) method as variable selection tool. Pre-processing methods such as wavelet transform (WT) were also used to enhance the predictive power of multivariate calibration methods. To evaluate the models applied in this study (PLS, GA-PLS and WT-GA-PLS), the inhibitory activities of several compounds, not included in the modeling procedure, were predicted. The results of models showed high prediction ability with root mean square error of prediction 0.194, 0.161 and 0.140 for PLS, GA-PLS and WT-GA-PLS, respectively. The WT-GA-PLS method was employed to predict the inhibitory activity of the new inhibitor derivatives.Downloads
References
Camargo, A. B.; Marchevsky, E.; Luco, J. M. J. Agric. Food Chem. 2007, 55, 3096-3103. DOI: https://doi.org/10.1021/jf063020e
Zhou, Y. P.; Jiang, J. H.; Lin, W. Q.; Zou, H. Y.; Wu, H. L.; Shen, G. L.; Yu, R. Q. Eur. J. Pharm. Sci. 2006, 28, 344-353. DOI: https://doi.org/10.1016/j.ejps.2006.04.002
Ioele, G.; Luca, M. D.; Oliverio, F.; Ragno, G. Talanta 2009, 79, 1418-1424. DOI: https://doi.org/10.1016/j.talanta.2009.06.009
Cui, W.; Yan, X. Chemomtr. Intell. Lab. Syst. 2009, 98, 130-135. DOI: https://doi.org/10.1016/j.chemolab.2009.05.008
Ghasemi, J. B.; Ahmadi, S. H.; Brown, S. D. Environ. Chem. Lett. 2011, 9, 87-96. DOI: https://doi.org/10.1007/s10311-009-0251-9
Hocking, R. R. Biometrics. 1976, 32, 1-49. DOI: https://doi.org/10.2307/2529336
Shen, Q.; Lu, Q. Z.; Jiang, J. H.; Shen, G. L.; Yu, R. Q. Eur. J. Pharm. Sci. 2003, 20, 63-71. DOI: https://doi.org/10.1016/S0928-0987(03)00170-2
Leardi, R. J. Chemom. 1994, 8, 65-79. DOI: https://doi.org/10.1002/cem.1180080107
Depczynski, U.; Frost, V. J.; Molt, K. Anal. Chim. Acta. 2000, 420, 217-227. DOI: https://doi.org/10.1016/S0003-2670(00)00893-X
Hibbert, D. B. Chemom. Intell. Lab. Syst. 1993, 19, 277-293. DOI: https://doi.org/10.1016/0169-7439(93)80028-G
Leardi, R. J Chemom. 2000, 14, 643-655. DOI: https://doi.org/10.1002/1099-128X(200009/12)14:5/6<643::AID-CEM621>3.0.CO;2-E
Leardi, R. J. Chemom. 2001, 15, 559-569. DOI: https://doi.org/10.1002/cem.651.abs
Ghasemi, J. B.; Niazi, A.; Leardi, R. Talanta 2003, 59, 311-317. DOI: https://doi.org/10.1016/S0039-9140(02)00505-2
Leardi, R.; Boggia, R.; Terrile, M. J. Chemom. 1992, 6, 267-281. DOI: https://doi.org/10.1002/cem.1180060506
Kompany-Zareh, M. Acta Chim Slov. 2003, 50, 259-273.
Narasimhan, B.; Judge, V.; Narang, R.; Ohlan, R.; Ohlan, S. Bioorg. Med. Chem. Lett. 2007, 17, 5836-5845. DOI: https://doi.org/10.1016/j.bmcl.2007.08.037
Hemmateenejad, B.; Safarpour, M. A.; Taghavi, F. J. Mol. Struc. 2003, 635, 183-190. DOI: https://doi.org/10.1016/S0166-1280(03)00418-4
Niazi, A.; Jameh-Bozorghi, S.; Nori-Shargh, D. Turk. J. Chem. 2006, 30, 619-628.
Joreskog, K. G.; Wold, H. System Under Indirect Observations, Amsterdam, North Holland, 1982.
Blessie, A. A.; Nalini, J.; Ramesh, S. C. Int. J. Comput. Sci. Issues. 2011, 8, 449-453.
Kennard, R. W.; Stones, L. A. Technometrics. 1969, 11, 137-148. DOI: https://doi.org/10.1080/00401706.1969.10490666
Daszykowski, M.; Walczak, B.; Massart, D. L. Anal. Chim. Acta. 2002, 468, 91-103. DOI: https://doi.org/10.1016/S0003-2670(02)00651-7
Ahmadi, M.; Shahlaei, M. Res. Pharm. Sci. 2015, 10, 307-325.
Mallat, S. A. Wavelet Tour of Signal Processing, Academic Press, San Diego, 1998. DOI: https://doi.org/10.1016/B978-012466606-1/50008-8
Ghasemi, J. B.; Niazi, A. Talanta 2005, 65, 1168-1173. DOI: https://doi.org/10.1016/j.talanta.2004.08.052
Haaland, D. M.; Thomas, E. V. Anal. Chem. 1988, 60, 1193-1202. DOI: https://doi.org/10.1021/ac00162a020
Niazi, A.; Leardi, R. J. Chemom. 2012, 26, 345-351. DOI: https://doi.org/10.1002/cem.2426
Cherkasov, A.; et al. J. Med. Chem. 2014, 57, 4977-5010. DOI: https://doi.org/10.1021/jm4004285
Tropsha, A. Mol. Inf. 2010, 29, 476-488. DOI: https://doi.org/10.1002/minf.201000061
Tropsha, A.; Gramatica. P.; Vijay, K.G. QSAR. Com. Sci. 2003, 22, 69-77. DOI: https://doi.org/10.1002/qsar.200390007
Golbraikh, A.; Tropsha, A. J. Mol. Graph. Model. 2002, 20, 269-276. DOI: https://doi.org/10.1016/S1093-3263(01)00123-1
Richon, A. B. Drug Discov. Today 2008, 13, 659-664. DOI: https://doi.org/10.1016/j.drudis.2008.03.012
Clark, D. E. Exp. Opin. Drug Discov. 2006, 1, 103-110.
Downloads
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
