Lee, Yean Kee and Nurhaliza, Wati Mekzali and Cheok, Wui Chee and Iskandar, Abdullah and Nurshamimi, Nor Rashid and Vannajan, Sanghiran Lee and Rozana, Othman and Najihah, Mohd Hashim and Chin, Fei Chee (2024) Design, synthesis and anticolorectal cancer activity of 2- bromoalkoxyanthraquinones. In: The 16th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-16), 01-04 December 2023, National University of Singapore, Singapore.
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Abstract
The impact of alkoxy chain length and the presence of a 1-hydroxy group in synthesised 2-bromoalkoxyanthraquinones was evaluated against HCT116, HT29, and CCD841 CoN cell lines. Molecular docking was employed to elucidate the interactions between these compounds and potential p53 and KRAS targets. Results indicated that 2-bromoalkoxyanthraquinones with the 1-hydroxy group exhibited greater anticancer activity compared to their counterparts. Specifically, compound 6b bearing C3 alkoxy chain displayed the most promising antiproliferation activity against HCT116 cells (IC50 = 3.83 ± 0.05 μM) and demonstrated high selectivity for HCT116 over CCD841 CoN cells (SI = 45.47). Molecular docking analysis revealed additional hydrogen bonds between the 1-hydroxy group of 6b and the proteins. Compound 6b also exhibited adequate lipophilicity (cLogP = 3.27) and ligand efficiency metrics (LE = 0.34; LLE = 2.15) within the acceptable range for an initial hit. This study underscores the potential of the 1-hydroxy group and a short alkoxy chain in enhancing the anti-colorectal cancer activity of 2-bromoalkoxyanthraquinones. Further optimisation should be possible for compound 6b as a potential therapeutic agent against colorectal cancer.
| Item Type: | Conference or Workshop Item (Paper) |
|---|---|
| Funders: | UNSPECIFIED |
| Additional Information: | Conference paper |
| Uncontrolled Keywords: | Anticolorectal cancer; Hydroxy group; Antiproliferation activity; Hydrogen; Therapeutic agent |
| Subjects: | Q Science > Q Science (General) Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry |
| Depositing User: | Mr. Mohd Safri |
| Date Deposited: | 26 Jun 2024 01:51 |
| Last Modified: | 26 Jun 2024 01:51 |
| URI: | http://eprints.um.edu.my/id/eprint/45060 |
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