Ketocoumarin-based Potential Biomaterial: Crystal structure, BSA binding, Zebrafish Toxicity, Anticancer Activity and Swiss-ADME Evaluation

Coumarin-based derivatives have significant potential for the development of novel antibiotics and anticancer drugs. In this study, we used the 3,3’-carbonyl bis(7-diethylamino)-2H-chromen-2-one (ketocoumarin, KC), which was derived from 4-diethylaminosalicyaldehyde and dimethyl 1,3-acetonedicarboxylate using a simple reflux method. The structure of KC was verified by combining FT-IR and NMR spectroscopic data with single-crystal X-ray crystallographic analysis. The crystal structure of KC is orthorhombic, space group Pbca. The binding interactions between BSA and KC were examined using absorption and fluorescence spectroscopy. Stern-Volmer analysis demonstrated strong binding affinity, indicating that the quenching mechanism is predominantly static. The quenching constant and the binding constant were calculated to be 1.09×1014 M −1 s−1 and 1.15×104 M−1, respectively. Molecular docking studies further supported these results, revealing strong binding affinities between BSA and KC via hydrogen bonding and electrostatic interactions. The anticancer activity was evaluated against A549 lung cancer cells, showing moderate cytotoxicity with an IC50 of 107 µM, compared to cisplatin (12 µM). Fluorescence microscopy confirmed apoptosis induction in treated cells using AO/PI staining. Additionally, antimicrobial assays showed that KC exhibits stronger antibacterial and antifungal activity against B. substilis, S. aureus, E. coli, and C. albicans. Zebrafish assays revealed efficient uptake and organ-specific localization of KC in larvae, supporting its potential for use in pharmacokinetic, biodistribution, and early developmental toxicity studies. Swiss-ADME analysis further predicted favourable physicochemical and biophysical properties. Overall, KC shows promise as a multifunctional molecule for various biological applications.