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Synthesis, molecular docking and antiproliferative activity of upper rim modified Azo Calix[4]arene derivatives

Ali, Yousaf and Eltayeb, Nagla Mustafa and Muhamad Salhimi, Salizawati and Bakhtiar, M. Taher and Abd Hamid, Shafida (2022) Synthesis, molecular docking and antiproliferative activity of upper rim modified Azo Calix[4]arene derivatives. Journal of Inclusion Phenomena and Macrocyclic Chemistry. pp. 873-880. ISSN 1388-3127 E-ISSN 1573-1111 (In Press)

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Azo derivatives of calixarenes are mostly reported for the extraction of transition metal ions and as switchable receptors or sensors for Na+ and K+ ions to mimic the biological Na+/K+ ion pump. Only a few reports describe the drug-like potential of azo calixarenes. The current work is an attempt to explore the anticancer potential of three upper rims modifed azo derivatives of calix[4]arene. Sulfaguanidine (SGC), sulfanilamide (SCM), and 4-amino-2-methylbenzoic acid (COX) groups were linked with calix[4]arene via azo linkage and their antiproliferative efect was evaluated against breast (MCF7 and MDA-MB-231), colon (HCT-116), and lung (A549) cancer cell lines using MTT assay. SGC showed antiproliferative efect on MCF7 and MDA-MB-231 breast cancer cells with IC50 values of 32.2 and 27.3 µM, respectively. SCM exerted an antiproliferative activity against MCF7, MDA-MB-231, and HCT-116 cells with IC50 values of 31.8, 50.1, and 28.03 µM, respectively, while COX did not show an antiproliferative efect against all the tested cell lines. The compounds were docked against Cyclin-Dependent Kinase-2 (CDK2) receptor (PDB ID 1FVT) for their possible interactions followed by in vitro analysis by MTT assay. CDK2 was selected as the target enzyme because of the structural similarities of the synthesized compounds with previously reported CDK2 potential inhibitors. The docking results supported the in vitro results for the two compounds. A proposed scheme for using the azo derivatives of calix[4]arene as prodrugs is suggested for further investigation.

Item Type: Article (Journal)
Uncontrolled Keywords: Calixarenes · Azo calixarenes · Anticancer · Docking · Prodrugs
Subjects: Q Science > QD Chemistry
R Medicine > RM Therapeutics. Pharmacology
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button): Kulliyyah of Science > Department of Chemistry
Kulliyyah of Science
Depositing User: Dr Shafida Abd Hamid
Date Deposited: 29 Nov 2022 11:48
Last Modified: 29 Nov 2022 11:48
URI: http://irep.iium.edu.my/id/eprint/101466

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