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Article

Cell Cycle Arrest and Apoptosis-Inducing Ability of Benzimidazole Derivatives: Design, Synthesis, Docking, and Biological Evaluation

by
Syed Nazreen
1,*,
Abdulraheem S. A. Almalki
2,
Serag Eldin I. Elbehairi
3,4,
Ali A. Shati
3,
Mohammad Y. Alfaifi
3,
Ahmed A. Elhenawy
1,5,
Nawaf I. Alsenani
1,
Anas Alfarsi
1,
Abdulrahman Alhadhrami
2,
Esam A. Alqurashi
1 and
Mohammad Mahboob Alam
1,*
1
Department of Chemistry, Faculty of Science, Al-Baha University, Al-Baha 65799, Saudi Arabia
2
Department of Chemistry, Faculty of Science, Taif University, Taif 21974, Saudi Arabia
3
Department of Biology, Faculty of Science, King Khalid University, Abha 61421, Saudi Arabia
4
Cell Culture Laboratory, Egyptian Organization for Biological Products and Vaccines, VACSERA Holding Company, Giza 2311, Egypt
5
Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11884, Egypt
*
Authors to whom correspondence should be addressed.
Molecules 2022, 27(20), 6899; https://doi.org/10.3390/molecules27206899
Submission received: 14 September 2022 / Revised: 2 October 2022 / Accepted: 6 October 2022 / Published: 14 October 2022
(This article belongs to the Section Medicinal Chemistry)
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Abstract

In the current study, new benzimidazole-based 1,3,4-oxadiazole derivatives have been synthesized and characterized by NMR, IR, MS, and elemental analysis. The final compounds were screened for cytotoxicity against MDA-MB-231, SKOV3, and A549 cell lines and EGFR for inhibitory activities. Compounds 10 and 13 were found to be the most active against all the tested cell lines, comparable to doxorubicin, and exhibited significant inhibition on EGFR kinase, with IC50 0.33 and 0.38 μM, respectively, comparable to erlotinib (IC50 0.39 μM). Furthermore, these two compounds effectively suppressed cell cycle progression and induced cell apoptosis in MDA-MB-231, SKOV3, and A549 cell lines. The docking studies revealed that these compounds showed interactions similar to erlotinib at the EGFR site. It can be concluded that the synthesized molecules effectively inhibit EGFR, can arrest the cell cycle, and may trigger apoptosis and therefore, could be used as lead molecules in the development of new anticancer agents targeting EGFR kinase.
Keywords: 1,3,4-oxadiazole; benzimidazole; cell cycle arrest; apoptosis; docking 1,3,4-oxadiazole; benzimidazole; cell cycle arrest; apoptosis; docking

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MDPI and ACS Style

Nazreen, S.; Almalki, A.S.A.; Elbehairi, S.E.I.; Shati, A.A.; Alfaifi, M.Y.; Elhenawy, A.A.; Alsenani, N.I.; Alfarsi, A.; Alhadhrami, A.; Alqurashi, E.A.; et al. Cell Cycle Arrest and Apoptosis-Inducing Ability of Benzimidazole Derivatives: Design, Synthesis, Docking, and Biological Evaluation. Molecules 2022, 27, 6899. https://doi.org/10.3390/molecules27206899

AMA Style

Nazreen S, Almalki ASA, Elbehairi SEI, Shati AA, Alfaifi MY, Elhenawy AA, Alsenani NI, Alfarsi A, Alhadhrami A, Alqurashi EA, et al. Cell Cycle Arrest and Apoptosis-Inducing Ability of Benzimidazole Derivatives: Design, Synthesis, Docking, and Biological Evaluation. Molecules. 2022; 27(20):6899. https://doi.org/10.3390/molecules27206899

Chicago/Turabian Style

Nazreen, Syed, Abdulraheem S. A. Almalki, Serag Eldin I. Elbehairi, Ali A. Shati, Mohammad Y. Alfaifi, Ahmed A. Elhenawy, Nawaf I. Alsenani, Anas Alfarsi, Abdulrahman Alhadhrami, Esam A. Alqurashi, and et al. 2022. "Cell Cycle Arrest and Apoptosis-Inducing Ability of Benzimidazole Derivatives: Design, Synthesis, Docking, and Biological Evaluation" Molecules 27, no. 20: 6899. https://doi.org/10.3390/molecules27206899

APA Style

Nazreen, S., Almalki, A. S. A., Elbehairi, S. E. I., Shati, A. A., Alfaifi, M. Y., Elhenawy, A. A., Alsenani, N. I., Alfarsi, A., Alhadhrami, A., Alqurashi, E. A., & Alam, M. M. (2022). Cell Cycle Arrest and Apoptosis-Inducing Ability of Benzimidazole Derivatives: Design, Synthesis, Docking, and Biological Evaluation. Molecules, 27(20), 6899. https://doi.org/10.3390/molecules27206899

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