The activity of thiosemicarbazones is closely related to the parent aldehyde or ketone group, metal chelation ability, and terminal amino substitution. Metal complexes of thiosemicarbazones that bind and cleave DNA under certain physiological conditions are likely to be good candidates for therapeutical agents in medicinal applications. Fluorene-2-carboxaldehyde thiosemicarbazones (L1 and L2) were prepared by the condensation reaction (1:1) of fluorene-2-carboxaldehyde with substituted thiosemicarbazide in the presence of ethanol and a few drops of glacial acetic acid. These further reacted with CuCl2.2H2O for complexation in a chloroform-methanol mixture under an inert atmosphere. The newly synthesized ligands (L1 and L2) and their Copper (II) complexes were exposed to spectral and structural characterization (FT-IR, UV-Visible, 1H and 13C NMR, HRMS and EPR). The interactions of the Cu (II) complexes and their ligands with calf thymus DNA (CT DNA) were examined by UV–Visible and fluorescence spectroscopy measurements, which implied that the complexes bound to CT DNA via intercalation, and complexes and ligands showed a higher binding affinity. The protein binding interaction of the complexes was observed by fluorescence and absorption techniques, which intimate that the complexes could bind effectively with bovine serum albumin (BSA). Synchronous fluorescence titrations showed the changes in the conformations of the protein micro-regions (tryptophan and tyrosine). Molecular docking studies of the ligands and complexes were also done with cytochrome P450 1A1(CYP1A1) protein and it gave insight into the binding potential of the complexes theoretically. In addition to this, in silico pharmacokinetic pieces of information were carried out to predict the absorption, distribution, metabolism, and elimination (ADME) properties of the targeted ligands, and their corresponding metal complexes were determined by using the Swiss ADME tool and all of these studies indicate the promising role of the synthesized ligands and complexes in bioactivities.

DNA/protein binding, molecular docking and ADME studies of fluorene-2-carboxaldehyde thiosemicarbazones and its copper complexes

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