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

Abstract

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.

Synthesis, characterization, and anticancer potential of pyrene-appended Schiff base tin(iv) complexes: experimental and computational insights

“…9–17 This has prompted significant research efforts towards the design of organotin( iv ) complexes as potential anticancer agents, aiming to enhance their therapeutic efficacy through selective cytotoxicity against cancer cells. 11–18…”

“…25,28,29 This observation has generated substantial interest in exploring triorganotin( iv ) carboxylates as potential anticancer agents. 12,15–18,30,31 Beyond the choice of organotin compound and its structure, structural modifications to the ligand and the nature of its substituents have been found to significantly influence the antiproliferative activity of organotin( iv ) carboxylates. This opens the door to fine-tuning the biological properties of these compounds.…”

“…6–8 Moreover, organotin compounds have demonstrated potential as cancer chemotherapeutic agents, attributed to their ability to induce apoptosis and their lipophilic nature. 9–17 This has prompted significant research efforts towards the design of organotin( iv ) complexes as potential anticancer agents, aiming to enhance their therapeutic efficacy through selective cytotoxicity against cancer cells. 11–18…”