European Journal of Chemistry 2022, 13(3), 319-326 | doi: https://doi.org/10.5155/eurjchem.13.3.319-326.2259 | Get rights and content

Issue cover




Crossmark

  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

QSAR and docking studies of pyrazole analogs as antiproliferative against human colorectal adenocarcinoma cell line HT-29


Hiba Hashim Mahgoub Mohamed (1,*) orcid , Amna Bint Wahab Elrashid Mohammed Hussien (2) orcid , Ahmed Elsadig Mohammed Saeed (3) orcid

(1) Department of Chemistry, College of Science, Sudan University of Science and Technology, Khartoum, 2288, Sudan
(2) College of Animal Production Science and Technology, Sudan University of Science and Technology, Khartoum, 2288, Sudan
(3) Department of Chemistry, College of Science, Sudan University of Science and Technology, Khartoum, 2288, Sudan
(*) Corresponding Author

Received: 10 Mar 2022 | Revised: 21 Apr 2022 | Accepted: 01 Jul 2022 | Published: 30 Sep 2022 | Issue Date: September 2022

Abstract


In-silico quantitative structure-activity relationship (QSAR) study was performed to develop a model on a series of novel pyrazole derivatives containing acetamide moiety which exhibited considerable antiproliferative activity against human colorectal adenocarcinoma cell line HT-29. The model obtained has a correlation coefficient (r) of 0.9693, squared correlation coefficient (r2) of 0.9395 and a leave-one-out (LOO) cross-validation coefficient (Q2) value of 0.8744. The predictive power of the developed model was confirmed by the external validation which has an r2 value of 0.9488. These parameters confirm the stability and robustness of the model to predict the activity of a new designed set of 3,5-dimethyl-pyrazole derivatives (22-36), results indicated that the compounds 26, 31, 35, and 36 showed the strongest antiproliferative activity with (IC50 = 0.182, 0.172, 0.166 and 0.024 μM, respectively) against human colorectal adenocarcinoma cell line HT-29 compared to the reference vemurafenib with (IC50 = 1.52 μM). Molecular docking was performed on the new designed compounds with the human colorectal adenocarcinoma cell line 5JRQ protein. The docking results showed that compounds 26, 31, 35, and 36 have docking affinity of -8.528, -5.932, 23.017 and 18.432 kcal/mol, respectively.


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization between November 15, 2022 and December 28, 2022 (Voucher code: SINGLE2022).

2. Young writers will not be charged for the article processing fee between November 15, 2022 and December 28, 2022 (Voucher code: YOUNG2022).

3. The article processing fee will not be charged from the articles containing a part of the PhD thesis between November 15, 2022 and December 28, 2022 (Voucher code: PhD2022).

4. The article processing fee will not be charged from authors who have at least one publication in the European Journal of Chemistry between November 15, 2022 and December 28, 2022 (Voucher code: (Voucher code: AUTHOR2022).

Editor-in-Chief

European Journal of Chemistry

Keywords


QSAR; HT-29; Pyrazole; Molecular modeling; Antiproliferative activity; Colorectal adenocarcinoma

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.13.3.319-326.2259

Links for Article


| | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 112 times | icon graph PDF Article downloaded 40 times


References


[1]. El Bali, M.; Bakkach, J.; Bennani Mechita, M. Colorectal cancer: From genetic landscape to targeted therapy. J. Oncol. 2021, 2021, 9918116.
https://doi.org/10.1155/2021/9918116

[2]. Sawicki, T.; Ruszkowska, M.; Danielewicz, A.; Niedźwiedzka, E.; Arłukowicz, T.; Przybyłowicz, K. E. A review of colorectal cancer in terms of epidemiology, risk factors, development, symptoms and diagnosis. Cancers (Basel) 2021, 13.
https://doi.org/10.3390/cancers13092025

[3]. Bray, F.; Ferlay, J.; Soerjomataram, I.; Siegel, R. L.; Torre, L. A.; Jemal, A. Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J. Clin. 2018, 68, 394-424.
https://doi.org/10.3322/caac.21492

[4]. Picard, E.; Verschoor, C. P.; Ma, G. W.; Pawelec, G. Relationships between immune landscapes, genetic subtypes and responses to immunotherapy in colorectal cancer. Front. Immunol. 2020, 11, 369.
https://doi.org/10.2307/j.ctv160bt82.12

[5]. You, Y. N.; Lee, L. D.; Deschner, B. W.; Shibata, D. Colorectal cancer in the adolescent and young adult population. JCO Oncol Pract 2020, 16, 19-27.
https://doi.org/10.1200/JOP.19.00153

[6]. Testa, U.; Pelosi, E.; Castelli, G. Colorectal cancer: genetic ab-normalities, tumor progression, tumor heterogeneity, clonal evolution and tumor-initiating cells. Med. Sci. (Basel) 2018, 6.
https://doi.org/10.3390/medsci6020031

[7]. Loke, Y. L.; Chew, M. T.; Ngeow, Y. F.; Lim, W. W. D.; Peh, S. C. Colon carcinogenesis: The interplay between diet and gut Microbiota. Front. Cell. Infect. Microbiol. 2020, 10, 603086.
https://doi.org/10.3389/fcimb.2020.603086

[8]. Vernia, F.; Longo, S.; Stefanelli, G.; Viscido, A.; Latella, G. Dietary factors modulating colorectal carcinogenesis. Nutrients 2021, 13, 143.
https://doi.org/10.3390/nu13010143

[9]. Barnes, J. L.; Zubair, M.; John, K.; Poirier, M. C.; Martin, F. L. Carcinogens and DNA damage. Biochem. Soc. Trans. 2018, 46, 1213-1224.
https://doi.org/10.1042/BST20180519

[10]. Basu, A. K. DNA damage, Mutagenesis and cancer. Int. J. Mol. Sci. 2018, 19.
https://doi.org/10.3390/ijms19040970

[11]. Mármol, I.; Sánchez-de-Diego, C.; Pradilla Dieste, A.; Cerrada, E.; Rodriguez Yoldi, M. J. Colorectal carcinoma: A general overview and future perspectives in colorectal cancer. Int. J. Mol. Sci. 2017, 18, 197.
https://doi.org/10.3390/ijms18010197

[12]. Naim, M. J.; Alam, O.; Nawaz, F.; Alam, M. J.; Alam, P. Current status of pyrazole and its biological activities. J. Pharm. Bioallied Sci. 2016, 8, 2-17.
https://doi.org/10.4103/0975-7406.171694

[13]. Alsayari, A.; Asiri, Y. I.; Muhsinah, A. B.; Hassan, M. Z. Anticolon cancer properties of pyrazole derivatives acting through xanthine oxidase inhibition. J. Oncol. 2021, 2021, 5691982.
https://doi.org/10.1155/2021/5691982

[14]. Aziz, H.; Zahoor, A. F.; Ahmad, S. Pyrazole bearing molecules as bioactive scaffolds: A review. J. Chil. Chem. Soc. 2020, 65, 4746-4753.
https://doi.org/10.4067/S0717-97072020000104746

[15]. Karrouchi, K.; Radi, S.; Ramli, Y.; Taoufik, J.; Mabkhot, Y. N.; Al-Aizari, F. A.; Ansar, M. Synthesis and pharmacological activities of pyrazole derivatives: A review. Molecules 2018, 23, 134.
https://doi.org/10.3390/molecules23010134

[16]. Halder, A. K.; Moura, A. S.; Cordeiro, M. N. D. S. QSAR modelling: a therapeutic patent review 2010-present. Expert Opin. Ther. Pat. 2018, 28, 467-476.
https://doi.org/10.1080/13543776.2018.1475560

[17]. Kausar, S.; Falcao, A. O. An automated framework for QSAR model building. J. Cheminform. 2018, 10, 1.
https://doi.org/10.1186/s13321-017-0256-5

[18]. Muhammad, U.; Uzairu, A.; Ebuka Arthur, D. Review on: quantitative structure activity relationship (QSAR) modeling. J. Anal. Pharm. Res. 2018, 7, 240-242.
https://doi.org/10.15406/japlr.2018.07.00232

[19]. Wang, C.-R.; Wang, Z.-F.; Shi, L.; Wang, Z.-C.; Zhu, H.-L. Design, synthesis, and biological evaluation of pyrazole derivatives containing acetamide bond as potential BRAF V600E inhibitors. Bioorg. Med. Chem. Lett. 2018, 28, 2382-2390.
https://doi.org/10.1016/j.bmcl.2018.06.028

[20]. ACD/ChemSketch, version 14.01, Advanced Chemistry Development, Inc. (ACD/Labs), Toronto, ON, Canada, www.acdlabs.com (accessed June 2, 2022).

[21]. Molecular Operating Environment (MOE), 2009.10 Chemical Computing Group ULC, 1010 Sherbooke St. West, Suite #910, Montreal, QC, Canada, H3A 2R7, 2022.

[22]. Berman, H. M.; Henrick, K.; Nakamura, H. Announcing the worldwide Protein Data Bank Nature Structural Biology 10 (12): 980, 2003, https://www.rcsb.org/structure/5JRQ (accessed June 2, 2022).
https://doi.org/10.1038/nsb1203-980


How to cite


Mohamed, H.; Hussien, A.; Saeed, A. Eur. J. Chem. 2022, 13(3), 319-326. doi:10.5155/eurjchem.13.3.319-326.2259
Mohamed, H.; Hussien, A.; Saeed, A. QSAR and docking studies of pyrazole analogs as antiproliferative against human colorectal adenocarcinoma cell line HT-29. Eur. J. Chem. 2022, 13(3), 319-326. doi:10.5155/eurjchem.13.3.319-326.2259
Mohamed, H., Hussien, A., & Saeed, A. (2022). QSAR and docking studies of pyrazole analogs as antiproliferative against human colorectal adenocarcinoma cell line HT-29. European Journal of Chemistry, 13(3), 319-326. doi:10.5155/eurjchem.13.3.319-326.2259
Mohamed, Hiba, Amna Bint Wahab Elrashid Mohammed Hussien, & Ahmed Elsadig Mohammed Saeed. "QSAR and docking studies of pyrazole analogs as antiproliferative against human colorectal adenocarcinoma cell line HT-29." European Journal of Chemistry [Online], 13.3 (2022): 319-326. Web. 3 Dec. 2022
Mohamed, Hiba, Hussien, Amna, AND Saeed, Ahmed. "QSAR and docking studies of pyrazole analogs as antiproliferative against human colorectal adenocarcinoma cell line HT-29" European Journal of Chemistry [Online], Volume 13 Number 3 (30 September 2022)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.13.3.319-326.2259


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2022, 13(3), 319-326 | doi: https://doi.org/10.5155/eurjchem.13.3.319-326.2259 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c) 2022 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).



© Copyright 2010 - 2022  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2022 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.