Research Article
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Year 2023, Volume: 7 Issue: 1, 51 - 61, 15.01.2023

Abstract

Project Number

one

References

  • [1] « Synthesis, biological evaluation and 2D-QSAR analysis of benzoxazoles as antimicrobial agents », Eur. J. Med. Chem., vol. 44, no 2, p. 501‑510, févr. 2009, doi: 10.1016/j.ejmech.2008.04.001.
  • [2] Hu, Y.; Li, C.Y.; Wang, X.M.; Yang, Y.H.; Zhu, H.L. 1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal, Agricultural, and Materials Chemistry. Chem. Rev. 2014, 114, 5572–5610
  • [3] El-Sayed, W.A.; Metwally, M.A.; Nada, D.S. Abdel-Rahman A.A.-H. Synthesis and Antimicrobial Activity of New Substituted 5-(Pyridine-3-yl)-1,3,4-thiadiazoles and Their Sugar Derivatives. J. Heterocycl. Chem. 2013, 50, 194–201.
  • [4] Jordheim, L.P.; Durantel, D.; Zoulim, F.; Dumontet, C. Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases. Nat. Rev. Drug. Disc. 2013, 12, 447–464
  • [5] “Chemical Structure Drawing Software | ACD/ChemSketch.” https://www.acdlabs.com
  • [6] “ChemAxon - Software Solutions and Services for Chemistry & Biology.” https://chemaxon.com
  • [7] Samir Chtita, Majdouline Larif, Mounir Ghamali, Mohammed Bouachrine, Tahar Lakhlifi, Quantitative structure–activity relationship studies of dibenzo[ a , d ]cycloalkenimine derivatives for non-competitive antagonists of N -methyl- d -aspartate based on density functional theory with electronic and topological descriptors . J. Taibah Univ. Sci. 9: 143–154 (2015). https://doi.org/10.1016/j.jtusci.2014.10.006
  • [8] XLSTAT | Logiciel statistique pour Excel. https://www.xlstat.com/fr/.
  • [9] M. Ghamali, Samir Chtita, Rachid Hmamouchi, Azeddine Adad, Mohammed Bouachrine, Tahar Lakhlifi, The inhibitory activity of aldose reductase of flavonoid compounds: Combining DFT and QSAR calculations. J. Taibah Univ. Sci. 10: 534–542 (2016). https://doi.org/10.1016/j.jtusci.2015.09.006
  • [10] Bok-Hee Jung and SoonGohn Kim " A Festival Satisfaction Evaluation Method using Multiple
  • [11] M. Ghamali, et al. QSAR analysis of the toxicity of phenols and thiophenols using MLR and ANN. J. Taibah Univ. Sci. 11: 1–10 (2017).
  • [12] S. Chtita, M. Ghamali, M. Larif, A. Adad, R. Hmammouchi, M. Bouachrine and T. Lakhlifi, Prediction of biological activity of imidazo [1, 2-a] pyrazine derivatives by combining DFT and QSAR results, International Journal of Innovative Research in Science, Engineering and Technology, 2(12): 7951-7962 (2013).
  • [13] Partha Pratim Roy, Somnath Paul, Indrani Mitra, Kunal Roy, On Two Novel Parameters for Validation of Predictive QSAR Models. Molecules 14: 1660–1701 (2009). https://doi.org/10.3390/molecules14051660
  • [14] L. Zhang, H. Zhu, T. I. Oprea, A. Golbraikh, A. Tropsha, QSAR modeling of the blood-brain barrier permeability for diverse organic compounds. Pharm. Res. 25: 1902–1914 (2008). https://doi.org/10.1007/s11095-008-9609-0
  • [15] K. Roy, I. Mitra, S. Kar, P. Kumar Ojha, R. N. Das, H. Kabir, Comparative studies on some metrics for external validation of QSPR models. J. Chem. Inf. Model. 52: 396–408 (2012). https://doi.org/10.1021/ci200520g
  • [16] A. Sankar, « Principal Component Analysis Part 1: The Different Formulations. », Medium, 29 septembre 2021. https://towardsdatascience.com/principal-component-analysis-part-1-the-different-formulations-6508f63a5553 (consulté le 26 juin 2022).
  • [17] Validation of (Q)SAR Models – OECD https://www.oecd.org/chemicalsafety/riskassessment/validationofqsarmodels.html.
  • [18] S. Chtita, A. Aouidate, A. Belhassan, A. Ousaa, A. Idrissi Taourati, B. Elidrissi, M. Ghamali, M. Bouachrine and Tahar Lakhlifi, QSAR study of N -substituted oseltamivir derivatives as potent avian influenza virus H5N1 inhibitors using quantum chemical descriptors and statistical methods. New J. Chem. 44: 1747–1760 (2020). https://doi.org/10.1039/C9NJ04909F
  • [19] A. Aouidate, A. Ghaleb, M. Ghamali, S. Chtita, A. Ousaa, M. Choukrad, A. Sbai, M. Bouachrine, and T. Lakhlifi, QSAR study and rustic ligand-based virtual screening in a search for aminooxadiazole derivatives as PIM1 inhibitors. Chem. Cent. J. 12: 1–12 (2018). https://dx.doi.org/10.1186%2Fs13065-018-0401-x
  • [20] Bok-Hee Jung and SoonGohn Kim " A Festival Satisfaction Evaluation Method using Multiple Regression Analysis "International Journal of Software Engineering and Its Applications Vol.8, No.4 (2014), pp.187-196 http://dx.doi.org/10.14257/ijseia.2014.8.4.20

Cytotoxic activity of new thioglycosides against Escherichia coli: 2DQSAR study by Multiple Linear Regression method

Year 2023, Volume: 7 Issue: 1, 51 - 61, 15.01.2023

Abstract

The main objective of our study is the modeling of the cytotoxic activity of a series of 17 compounds derived
from new thioglycosides of the arylamino-1, 3,4-thiadiazole and glycosyl-1, 3,4-thiadiazole-triazole
conjugates against Escherichia coli using 2D-QSAR and some statistical tools (Principal Component Analysis
(PCA), Multiple Linear Regression (MLR), This study consists of three main steps: Data set selection,
molecular descriptor generation, construction and validation of predictive models for the studied activity. To
build and validate our QSAR model, the dataset was divided into two sets: 17 molecules constitute the training
set and the remaining 4 molecules constitute the test set. The division of the data set was done by random
selection. The training set and the test set were validated separately using internal and external tests, such as
the y-randomization and Golbraikh and Trouphsa model validation criteria. The model is validated with the
high values of R2
, R2
test and Q2
cv (R2= 0.731, R2
adj =0.641 and Q2
cv=0.51, R2
test =0.666, MSE=0.003).

Supporting Institution

Meknès

Project Number

one

Thanks

Thank you for your consideration of this manuscript.

References

  • [1] « Synthesis, biological evaluation and 2D-QSAR analysis of benzoxazoles as antimicrobial agents », Eur. J. Med. Chem., vol. 44, no 2, p. 501‑510, févr. 2009, doi: 10.1016/j.ejmech.2008.04.001.
  • [2] Hu, Y.; Li, C.Y.; Wang, X.M.; Yang, Y.H.; Zhu, H.L. 1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal, Agricultural, and Materials Chemistry. Chem. Rev. 2014, 114, 5572–5610
  • [3] El-Sayed, W.A.; Metwally, M.A.; Nada, D.S. Abdel-Rahman A.A.-H. Synthesis and Antimicrobial Activity of New Substituted 5-(Pyridine-3-yl)-1,3,4-thiadiazoles and Their Sugar Derivatives. J. Heterocycl. Chem. 2013, 50, 194–201.
  • [4] Jordheim, L.P.; Durantel, D.; Zoulim, F.; Dumontet, C. Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases. Nat. Rev. Drug. Disc. 2013, 12, 447–464
  • [5] “Chemical Structure Drawing Software | ACD/ChemSketch.” https://www.acdlabs.com
  • [6] “ChemAxon - Software Solutions and Services for Chemistry & Biology.” https://chemaxon.com
  • [7] Samir Chtita, Majdouline Larif, Mounir Ghamali, Mohammed Bouachrine, Tahar Lakhlifi, Quantitative structure–activity relationship studies of dibenzo[ a , d ]cycloalkenimine derivatives for non-competitive antagonists of N -methyl- d -aspartate based on density functional theory with electronic and topological descriptors . J. Taibah Univ. Sci. 9: 143–154 (2015). https://doi.org/10.1016/j.jtusci.2014.10.006
  • [8] XLSTAT | Logiciel statistique pour Excel. https://www.xlstat.com/fr/.
  • [9] M. Ghamali, Samir Chtita, Rachid Hmamouchi, Azeddine Adad, Mohammed Bouachrine, Tahar Lakhlifi, The inhibitory activity of aldose reductase of flavonoid compounds: Combining DFT and QSAR calculations. J. Taibah Univ. Sci. 10: 534–542 (2016). https://doi.org/10.1016/j.jtusci.2015.09.006
  • [10] Bok-Hee Jung and SoonGohn Kim " A Festival Satisfaction Evaluation Method using Multiple
  • [11] M. Ghamali, et al. QSAR analysis of the toxicity of phenols and thiophenols using MLR and ANN. J. Taibah Univ. Sci. 11: 1–10 (2017).
  • [12] S. Chtita, M. Ghamali, M. Larif, A. Adad, R. Hmammouchi, M. Bouachrine and T. Lakhlifi, Prediction of biological activity of imidazo [1, 2-a] pyrazine derivatives by combining DFT and QSAR results, International Journal of Innovative Research in Science, Engineering and Technology, 2(12): 7951-7962 (2013).
  • [13] Partha Pratim Roy, Somnath Paul, Indrani Mitra, Kunal Roy, On Two Novel Parameters for Validation of Predictive QSAR Models. Molecules 14: 1660–1701 (2009). https://doi.org/10.3390/molecules14051660
  • [14] L. Zhang, H. Zhu, T. I. Oprea, A. Golbraikh, A. Tropsha, QSAR modeling of the blood-brain barrier permeability for diverse organic compounds. Pharm. Res. 25: 1902–1914 (2008). https://doi.org/10.1007/s11095-008-9609-0
  • [15] K. Roy, I. Mitra, S. Kar, P. Kumar Ojha, R. N. Das, H. Kabir, Comparative studies on some metrics for external validation of QSPR models. J. Chem. Inf. Model. 52: 396–408 (2012). https://doi.org/10.1021/ci200520g
  • [16] A. Sankar, « Principal Component Analysis Part 1: The Different Formulations. », Medium, 29 septembre 2021. https://towardsdatascience.com/principal-component-analysis-part-1-the-different-formulations-6508f63a5553 (consulté le 26 juin 2022).
  • [17] Validation of (Q)SAR Models – OECD https://www.oecd.org/chemicalsafety/riskassessment/validationofqsarmodels.html.
  • [18] S. Chtita, A. Aouidate, A. Belhassan, A. Ousaa, A. Idrissi Taourati, B. Elidrissi, M. Ghamali, M. Bouachrine and Tahar Lakhlifi, QSAR study of N -substituted oseltamivir derivatives as potent avian influenza virus H5N1 inhibitors using quantum chemical descriptors and statistical methods. New J. Chem. 44: 1747–1760 (2020). https://doi.org/10.1039/C9NJ04909F
  • [19] A. Aouidate, A. Ghaleb, M. Ghamali, S. Chtita, A. Ousaa, M. Choukrad, A. Sbai, M. Bouachrine, and T. Lakhlifi, QSAR study and rustic ligand-based virtual screening in a search for aminooxadiazole derivatives as PIM1 inhibitors. Chem. Cent. J. 12: 1–12 (2018). https://dx.doi.org/10.1186%2Fs13065-018-0401-x
  • [20] Bok-Hee Jung and SoonGohn Kim " A Festival Satisfaction Evaluation Method using Multiple Regression Analysis "International Journal of Software Engineering and Its Applications Vol.8, No.4 (2014), pp.187-196 http://dx.doi.org/10.14257/ijseia.2014.8.4.20
There are 20 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Research Article
Authors

Hassan Badaouı

Yassıne Koubı This is me 0000-0002-2483-5307

Youness Moukhlıss This is me 0000-0002-1347-7639

Khalil El Khatabi 0000-0001-8669-9657

Mohamed Ouabane This is me 0000-0002-1081-5225

M'barek Choukrad This is me 0000-0001-7215-3020

Mohammed Aziz Ajana 0000-0003-4409-2202

Abdelouahid Sbai 0000-0002-7140-9853

Tahar Lakhlıfı 0000-0001-6707-9057

Mohammed Bouachrıne 0000-0002-8901-047X

Project Number one
Early Pub Date August 15, 2022
Publication Date January 15, 2023
Submission Date March 28, 2022
Published in Issue Year 2023 Volume: 7 Issue: 1

Cite

APA Badaouı, H., Koubı, Y., Moukhlıss, Y., El Khatabi, K., et al. (2023). Cytotoxic activity of new thioglycosides against Escherichia coli: 2DQSAR study by Multiple Linear Regression method. Turkish Computational and Theoretical Chemistry, 7(1), 51-61. https://doi.org/10.33435/tcandtc.1093987
AMA Badaouı H, Koubı Y, Moukhlıss Y, El Khatabi K, Ouabane M, Choukrad M, Ajana MA, Sbai A, Lakhlıfı T, Bouachrıne M. Cytotoxic activity of new thioglycosides against Escherichia coli: 2DQSAR study by Multiple Linear Regression method. Turkish Comp Theo Chem (TC&TC). January 2023;7(1):51-61. doi:10.33435/tcandtc.1093987
Chicago Badaouı, Hassan, Yassıne Koubı, Youness Moukhlıss, Khalil El Khatabi, Mohamed Ouabane, M’barek Choukrad, Mohammed Aziz Ajana, Abdelouahid Sbai, Tahar Lakhlıfı, and Mohammed Bouachrıne. “Cytotoxic Activity of New Thioglycosides Against Escherichia Coli: 2DQSAR Study by Multiple Linear Regression Method”. Turkish Computational and Theoretical Chemistry 7, no. 1 (January 2023): 51-61. https://doi.org/10.33435/tcandtc.1093987.
EndNote Badaouı H, Koubı Y, Moukhlıss Y, El Khatabi K, Ouabane M, Choukrad M, Ajana MA, Sbai A, Lakhlıfı T, Bouachrıne M (January 1, 2023) Cytotoxic activity of new thioglycosides against Escherichia coli: 2DQSAR study by Multiple Linear Regression method. Turkish Computational and Theoretical Chemistry 7 1 51–61.
IEEE H. Badaouı, “Cytotoxic activity of new thioglycosides against Escherichia coli: 2DQSAR study by Multiple Linear Regression method”, Turkish Comp Theo Chem (TC&TC), vol. 7, no. 1, pp. 51–61, 2023, doi: 10.33435/tcandtc.1093987.
ISNAD Badaouı, Hassan et al. “Cytotoxic Activity of New Thioglycosides Against Escherichia Coli: 2DQSAR Study by Multiple Linear Regression Method”. Turkish Computational and Theoretical Chemistry 7/1 (January 2023), 51-61. https://doi.org/10.33435/tcandtc.1093987.
JAMA Badaouı H, Koubı Y, Moukhlıss Y, El Khatabi K, Ouabane M, Choukrad M, Ajana MA, Sbai A, Lakhlıfı T, Bouachrıne M. Cytotoxic activity of new thioglycosides against Escherichia coli: 2DQSAR study by Multiple Linear Regression method. Turkish Comp Theo Chem (TC&TC). 2023;7:51–61.
MLA Badaouı, Hassan et al. “Cytotoxic Activity of New Thioglycosides Against Escherichia Coli: 2DQSAR Study by Multiple Linear Regression Method”. Turkish Computational and Theoretical Chemistry, vol. 7, no. 1, 2023, pp. 51-61, doi:10.33435/tcandtc.1093987.
Vancouver Badaouı H, Koubı Y, Moukhlıss Y, El Khatabi K, Ouabane M, Choukrad M, Ajana MA, Sbai A, Lakhlıfı T, Bouachrıne M. Cytotoxic activity of new thioglycosides against Escherichia coli: 2DQSAR study by Multiple Linear Regression method. Turkish Comp Theo Chem (TC&TC). 2023;7(1):51-6.

Journal Full Title: Turkish Computational and Theoretical Chemistry


Journal Abbreviated Title: Turkish Comp Theo Chem (TC&TC)