Synthesis and structural elucidation of novel Bis-chalcone dyes: solvent/media effects, DNA binding, and molecular docking with their anticancer efficacy.

In the present research, we have successfully synthesized and characterized two novel Bis-chalcones, namely 3-(4-(dimethylamino)benzylidene)pentane-2,4-dione (DBPD) and 3-(3-(4-dimethylamino)phenyl)allylidene)pentane-2,4-dione (DPAPD). Their photophysical properties were studied in a series of solvents. UV–Vis absorption spectra are insensitive to solvent polarity whereas the fluorescence spectra in the same solvent set show an important solvatochromic effect leading to large Stokes shifts. Linear solvation energy relations were employed to correlate the position of fluorescence spectra maxima with microscopic empirical solvent parameters. This study indicates that important intramolecular charge transfer, ICT, takes place during the excitation process. Furthermore, we extended our investigations to encompass absorption and fluorescence behaviors in mixed water-EtOH environments, allowing us to gauge microenvironmental polarity. DFT method with B3LYP/6-311⁺⁺G(d,p) basis set has been used to analyze DBPD and DPAPD computationally, and to determine the most stable structure and the nature of the molecular orbitals, which are essential to understand the binding feature of the compounds. The experimental data from NMR, UV–Vis and FTIR were compared with the theoretical calculations of electronic and conformational properties. Moreover, the QTAIM (RDG) topological analysis was applied to both compounds using Multiwfn software. Also, we delved into the determination of binding constants and the assessment of micellar properties, including polarity and critical micelle concentration. The dynamic interactions between the investigated dyes and CT-DNA were investigated using electronic absorption and emission techniques. In the closing phases of our research, we delved into the exploration of the potential antitumor activity exhibited by the synthesized compounds. Moreover, the docking binding affinity of investigated compounds toward CT-DNA and tumors protein were estimated by the Schrödinger suite software. [ABSTRACT FROM AUTHOR]