Dual activity of indolin-2-ones containing an arylidene motif: DNA and BSA interaction

Abstract

Applying a multistep approach, novel indolin-2-ones (IND) that possess an arylidene motif have been synthesized. Eight compounds were chosen for different biological tests (antimicrobial and cytotoxicity). IND containing 2-thienyl (4h) fragment have been found to exhibit good antimicrobial activity against B. cereus. Molecules that have 3-aminophenyl (4d) or 2-pyridyl (4g) groups have shown the best antifungal activities against all tested fungi. These compounds have also been noticed as promising pharmaceuticals against MCF-7 cancer cell lines. Experimental outcomes from the investigation of the interaction of 4d with DNA implied its moderate binding to DNA (K_SV = 1.35 × 10⁴ and 3.05 × 10⁴ M⁻¹ for EB and Hoechst binder, respectively). However, considerably stronger binding of 4d to BSA has been evidenced (K_a = 6.1 × 10⁶ M⁻¹). In summary, IND that contains m-aminobenzylidene fragment (4d) exhibits a good dual biological activity making it a promising candidate for further investigation in the drug discovery sector.