Synthesis, molecular docking study and anticancer activity of novel 1,3,4-oxadiazole derivatives as potential tubulin inhibitors
The current study reports on the synthesis and anticancer efficacy of novel oxadiazole derivatives (8a-f) as tubulin polymerization inhibitors. NMR, mass, and elemental studies were used to confirm the newly produced compounds. In contrast to the conventional medicine colchicine, compounds 8e and 8f...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2023-02-01
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| Series: | Heliyon |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844023006679 |
| _version_ | 1811161787366637568 |
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| author | Tarek A. Yousef Abdulrahman G. Alhamzani Mortaga M. Abou-Krisha G. Kanthimathi M.S. Raghu K. Yogesh Kumar M.K. Prashanth Byong-Hun Jeon |
| author_facet | Tarek A. Yousef Abdulrahman G. Alhamzani Mortaga M. Abou-Krisha G. Kanthimathi M.S. Raghu K. Yogesh Kumar M.K. Prashanth Byong-Hun Jeon |
| author_sort | Tarek A. Yousef |
| collection | DOAJ |
| description | The current study reports on the synthesis and anticancer efficacy of novel oxadiazole derivatives (8a-f) as tubulin polymerization inhibitors. NMR, mass, and elemental studies were used to confirm the newly produced compounds. In contrast to the conventional medicine colchicine, compounds 8e and 8f demonstrated stronger sensitivity and improved IC50 values in the range of 3.19–8.21 μM against breast MCF-7, colorectal HCT116, and liver HepG2 cancer cell lines. The target compounds were tested for enzymatic activity against the tubulin enzyme. Compounds 8e and 8f were shown to have the most effective inhibitory action among the new compounds, with IC50 values of 7.95 and 9.81 nM, respectively. As compared to the reference drug, molecular docking investigations of the developed compounds revealed the crucial hydrogen bonding in addition to the hydrophobic interaction at the binding site, assisting in the prediction of the structural requirements for the found anticancer activity. These findings indicate that the 1,3,4-oxadizole scaffold has the potential for future research into new anticancer medicines. |
| first_indexed | 2024-04-10T06:19:57Z |
| format | Article |
| id | doaj.art-d18d1f59136c496187e4bedf4713f874 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-04-10T06:19:57Z |
| publishDate | 2023-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-d18d1f59136c496187e4bedf4713f8742023-03-02T05:01:39ZengElsevierHeliyon2405-84402023-02-0192e13460Synthesis, molecular docking study and anticancer activity of novel 1,3,4-oxadiazole derivatives as potential tubulin inhibitorsTarek A. Yousef0Abdulrahman G. Alhamzani1Mortaga M. Abou-Krisha2G. Kanthimathi3M.S. Raghu4K. Yogesh Kumar5M.K. Prashanth6Byong-Hun Jeon7College of Science, Chemistry Department, Imam Mohammad Ibn Saud Islamic University, Riyadh 11623, Saudi Arabia; Department of Toxic and Narcotic Drug, Forensic Medicine, Mansoura Laboratory, Medicolegal Organization, Ministry of Justice, EgyptCollege of Science, Chemistry Department, Imam Mohammad Ibn Saud Islamic University, Riyadh 11623, Saudi ArabiaCollege of Science, Chemistry Department, Imam Mohammad Ibn Saud Islamic University, Riyadh 11623, Saudi Arabia; Department of Chemistry, South Valley University, Qena, 83523, EgyptDepartment of Chemistry, Ramco Institute of Technology, Rajapalayam, Tamilnadu, 626117, IndiaDepartment of Chemistry, New Horizon College of Engineering, Bengaluru 560 103, IndiaDepartment of Chemistry, Faculty of Engineering and Technology, Jain University, Ramanagara, 562 112, IndiaDepartment of Chemistry, B N M Institute of Technology, Bengaluru 560 070, India; Corresponding author.Department of Earth Resources and Environmental Engineering, Hanyang University, 222, Wangsimni-ro, Seongdong-gu, Seoul, 04763, Republic of Korea; Corresponding author. Department of Earth Resources and Environmental Engineering, Hanyang University, 222, Wangsimni-ro, Seongdong-gu, Seoul, 04763, Republic of Korea.The current study reports on the synthesis and anticancer efficacy of novel oxadiazole derivatives (8a-f) as tubulin polymerization inhibitors. NMR, mass, and elemental studies were used to confirm the newly produced compounds. In contrast to the conventional medicine colchicine, compounds 8e and 8f demonstrated stronger sensitivity and improved IC50 values in the range of 3.19–8.21 μM against breast MCF-7, colorectal HCT116, and liver HepG2 cancer cell lines. The target compounds were tested for enzymatic activity against the tubulin enzyme. Compounds 8e and 8f were shown to have the most effective inhibitory action among the new compounds, with IC50 values of 7.95 and 9.81 nM, respectively. As compared to the reference drug, molecular docking investigations of the developed compounds revealed the crucial hydrogen bonding in addition to the hydrophobic interaction at the binding site, assisting in the prediction of the structural requirements for the found anticancer activity. These findings indicate that the 1,3,4-oxadizole scaffold has the potential for future research into new anticancer medicines.http://www.sciencedirect.com/science/article/pii/S24058440230066791,3,4-OxadiazoleAnticancerTubulin inhibitorsMolecular docking |
| spellingShingle | Tarek A. Yousef Abdulrahman G. Alhamzani Mortaga M. Abou-Krisha G. Kanthimathi M.S. Raghu K. Yogesh Kumar M.K. Prashanth Byong-Hun Jeon Synthesis, molecular docking study and anticancer activity of novel 1,3,4-oxadiazole derivatives as potential tubulin inhibitors Heliyon 1,3,4-Oxadiazole Anticancer Tubulin inhibitors Molecular docking |
| title | Synthesis, molecular docking study and anticancer activity of novel 1,3,4-oxadiazole derivatives as potential tubulin inhibitors |
| title_full | Synthesis, molecular docking study and anticancer activity of novel 1,3,4-oxadiazole derivatives as potential tubulin inhibitors |
| title_fullStr | Synthesis, molecular docking study and anticancer activity of novel 1,3,4-oxadiazole derivatives as potential tubulin inhibitors |
| title_full_unstemmed | Synthesis, molecular docking study and anticancer activity of novel 1,3,4-oxadiazole derivatives as potential tubulin inhibitors |
| title_short | Synthesis, molecular docking study and anticancer activity of novel 1,3,4-oxadiazole derivatives as potential tubulin inhibitors |
| title_sort | synthesis molecular docking study and anticancer activity of novel 1 3 4 oxadiazole derivatives as potential tubulin inhibitors |
| topic | 1,3,4-Oxadiazole Anticancer Tubulin inhibitors Molecular docking |
| url | http://www.sciencedirect.com/science/article/pii/S2405844023006679 |
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