Synthesis, characterization of thia-crown ether sugar derivatives and evaluation of their anticancer activity with computational insight
DOI:
https://doi.org/10.5281/zenodo.10267414Keywords:
Anticancer, computationally elucidated, Macrocycles, Thia-crown ether, Molecular docking, Template methodAbstract
Several novel macrocyclic chiral derivatives were prepared and developed by a simple, practical and efficient synthetic protocol for easy access to sugars-linked crown moiety from cheap and easy existing D-glucose in good yields. The structures of macrocyclic chiral derivatives are confirmed by FT-IR, 1HNMR, 13CNMR and mass spectroscopy. The recently produced macrocyclic derivatives underwent assessment for their in vitro anticancer properties against human cells. The investigation involving breast (MCF-7) cancer cell lines and non-cancer cells, specifically the MCF-12A cell line, demonstrated that macrocycles (8, 9, 10, and 11) exhibit potential as anticancer binders. They achieved this by impeding cell migration and proliferation and modulating the expression of crucial anticancer genes, including those associated with breast cancer (MCF-7), p53, mda7, and trail. The anti-proliferative effect of macrocycles on tumour cells was evident, with no observed cytotoxic impact on normal cells. Computational elucidation of the anticancer effect revealed that the binders exhibited a more promising binding affinity, indicating a level below. (BA; -6 kcal/mol) against mitogen-activated protein kinase 8 (3ELJ) comparable to Xeloda. Hence, these outcomes could encourage the researchers to open a new destination toward the synthesis of effective antitumor drugs.
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