Anthracene appended organotin (IV) compounds: Synthesis, structure elucidation and their cytotoxicity against A549 and RBL cancer cell lines

مقال فى مجلة

2023

Two new anthracene Schiff base triorganotin (IV) compounds trimethylstannyl

(E)-4-((anthracen-9-ylmethylene)amino)benzoate (1) and triphenylstannyl(E)-

4-((anthracen-9-ylmethylene)amino)benzoate (2) were synthesized by mixing

trimethylstannyl (or triphenylstannyl) 4-aminobenzoate and 9-anthraldehyde

in anhydrous toluene under refluxing conditions. Elemental analysis, FT-IR,

1H-NMR, 119Sn NMR and ESI-MS were used to determine the composition of

the compounds. X-ray diffraction analyses revealed the structural details of the

compounds. The in vitro cytotoxicity assessment of these compunds was

screened against human A-549 (lung carcinoma) and rat RBL (leukemia) cancer

cell lines. Both compounds displayed a pronounced in vitro cytotoxic effect

on the subjected cancer cell lines. Notably, the proliferation of A-549 cells

experienced substantial inhibition in the presence of compound 2. The mode

of interaction with Hsp90 and NF-κB p65 proteins responsible for cancer propagation

was also assessed by molecular docking. Compounds 1 and 2 bind to

the Hsp90 protein with binding energies of
307.65 and
373.45 kcal/mol,

respectively, while to NF-κB p65 protein the binding energies are of
329.35

and
395.35 kcal/mol, in the same order. Compound 2 exhibited a significantly

high binding affinity to NF-κB p65 and Hsp90 proteins validating our

experimental findings from the in vitro experiments.