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

• Published in: Applied organometallic chemistry 2023-10, Vol.37 (10), p.n/a
• Main Authors: Paul, Anup, Khan, Rais Ahmad, Shaik, Gouse M., Shaik, Jilani P., Rai, Avdhesh K., Guedes da Silva, M. Fátima C., Pombeiro, Armando J. L.
• Format: Article
• Language: English
• Subjects: Anthracene; Benzoates; Binding energy; Cancer; Chemical analysis; Chemistry; crystal structures; Cytotoxicity; docking; Imines; Leukemia; Molecular docking; NMR; Nuclear magnetic resonance; Proteins; Refluxing; Toluene; Toxicity; Triorganotin(IV)
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.7232

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. In vitro, cytotoxicity evaluation of two new anthracene Schiff base triorganotin(IV) compounds are reported. Molecular docking studies suggest their interaction with Hsp90 and NF‐κB p65 proteins. One of the compounds demonstrates a notable inhibitory effect on the proliferation of A‐549 (lung carcinoma) cells, and has a strong affinity for those proteins.