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

مقال فى مجلة

2023

In this study, we report the synthesis and comprehensive characterization of two novel pyreneappended
Schiff base organotin(IV) compounds, trimethylstannyl (E)-4-((pyren-1-ylmethylene)amino)-
benzoate (1) and triphenylstannyl (E)-4-((pyren-1-ylmethylene)amino)benzoate (2). They were
synthesized through the condensation of trimethylstannyl 4-aminobenzoate or triphenylstannyl
4-aminobenzoate with 1-pyrenealdehyde in toluene. The characterization included elemental analysis,
infrared spectroscopy, 1H, 13C, and 119Sn NMR, and ESI-MS. The crystal structure of compound 1 was
elucidated through single crystal X-ray diffraction analysis. The interaction of compounds 1 and 2 with
calf thymus DNA (CT DNA) was investigated using absorption and fluorescence spectroscopic
techniques. The calculated binding constants (Kb) unveiled a notably stronger binding propensity of
compound 2 compared to 1. Furthermore, the in vitro cytotoxicity assays of these compounds were
performed against human lung (A549) cancer cell lines, which revealed concentration-dependent
cytotoxic effects, with 2 exhibiting a higher cytotoxicity than 1. Moreover, the scratch assay
demonstrated the ability of both compounds to inhibit cancer cell migration, with 2 displaying stronger
inhibitory effects. Furthermore, gene expression studies showed that both compounds downregulated
the expression of MMP-2 and TGF-b genes, indicating their potential in modulating critical signaling
pathways in cancer cells. Molecular docking simulations provided insights into the binding interactions
of these compounds with MMP-2 and TGF-b, further supporting their potential as inhibitors of cancerrelated
proteins. Overall, our findings highlight the promising anticancer properties of these novel
pyrene-appended Schiff base compounds, with 2 showing particular potency. This research provides an
insight into the development of potential chemotherapeutic agents targeting cancer cell proliferation,
migration, and signalling pathways.