Synthesis, Crystallographic Structure, Theoretical Analysis, Molecular Docking Studies, and Biological Activity Evaluation of Binuclear Ru(II)-1-Naphthylhydrazine Complex

Abstract

Ruthenium(II)–arene complexes have gained significant research interest due to their possible application in cancer therapy. In this contribution two new complexes are described, namely [{RuCl(η6-p-cymene)}2(μ-Cl)(μ-1-N,N’-naphthyl)]X (X = Cl, 1; PF6, 2), which were fully characterized by IR, NMR, and elemental microanalysis. Furthermore, the structure of 2 in the solid state was determined by a single crystal X-ray crystallographic study, confirming the composition of the crystals as 2·2MeOH. The Hirshfeld surface analysis was employed for the investigation of interactions that govern the crystal structure of 2·2MeOH. The structural data for 2 out of 2·2MeOH was used for the theoretical analysis of the cationic part [{RuCl(η6-p-cymene)}2(μ-Cl)(μ-1-N,N´-naphthyl)]+ (2a) which is common to both 1 and 2. The density functional theory, at B3LYP/6-31+G(d,p) basis set for H, C, N, and Cl atoms and LanL2DZ for Ru ions, was used for the optimization of the 2a structure. The natural bond orbital and quantum theory of atoms in molecules analyses were employed to quantify the intramolecular interactions. The reproduction of experimental IR and NMR spectra proved the applicability of the chosen level of theory. The binding of 1 to bovine serum albumin was examined by spectrofluorimetry and molecular docking, with complementary results obtained. Compound 1 acted as a radical scavenger towards DPPH• and HO• radicals, along with high activity towards cancer prostate and colon cell lines.

Ru(II)‐Nitrophenylhydrazine/Chlorophenylhydrazine Complexes: Nanoarchitectonics, Biological Evaluation and In silico Study

“…[32,33] Medium bands between 1500 and 1000 cm À 1 can be assigned to bending vibrations of p-cymene and benzene rings. [31] The same region of spectra of 2 contains a strong band at 1646 cm À 1 (L2•HCl: 1603 cm À 1 ) that belongs to the same mixed mode of bending vibrations. The shift between 1665 and 1646 cm À 1 is due to chlorine's weak positive resonant effect.…”

“…These values are similar to previously crystallographically determined for binuclear Ru(II)-naphthylhydrazine complex with bridging chlorido ligand. [31] The differences between crystalographic and optimized structures are due to the overall system relaxation during optimization. When bond angles are concerned, the change of substituents does not induce significant changes in the spatial arrangement of ligands around Ru(II).…”

“…[36] These vibrations are essential to distinguish between the terminal and bridging Cl ligands. [31]…”

Evaluation of Some Benzo[g]Quinazoline Derivatives as Antiviral Agents against Human Rotavirus Wa Strain: Biological Screening and Docking Study

“…The Molecular Operating Environment (MOE) was created with the intention of studying molecular docking and 3D/2D structures [ 20 , 31 , 36 ]. We used the MOE-Dock docking program, and the MOE-implemented ligplot to visualize the protein-ligand interaction.…”

Exploring the cytotoxicity of dinuclear Ru(ii) p-cymene complexes appended N,N′-bis(4-substituted benzoyl)hydrazines: insights into the mechanism of apoptotic cell death

“…They observed that the binuclear complexes cause cytotoxicity via the p53 pathway and decrease the invasion ability of breast cancer cells. 21 Two binuclear ruthenium arene complexes with a naphthylhydrazyl ligand have been synthesized and examined for their stability, BSA binding affinity, and cytotoxic activity against prostate PC-3 and colon HT-29 cancer cells by Eichhorn et al 22 Fig. 2 depicts the structures of some previously reported binuclear arene ruthenium complexes.…”