Synthesis, crystal structure and anticancer activity of the complex chlorido(η2-ethylene)(quinolin-8-olato-κ2N,O)platinum(II) by experimental and theoretical methods

Abstract

The complex [Pt(C9H6NO)Cl(C2H4)], (I), was synthesized and structurally characterized by ESI mass spectrometry, IR, NMR spectroscopy, DFT calculations and X-ray diffraction. The results showed that the deprotonated 8-hydroxyquinoline (C9H6NO) coordinates with the PtII atom via the N and O atoms while the ethylene coordinates in the η2 manner and in the trans position compared to the coordinating N atom. The crystal packing is characterized by C—H...O, C—H...π, Cl...π and Pt...π interactions. Complex (I) showed high selective activity against Lu-1 and Hep-G2 cell lines with IC50 values of 0.8 and 0.4 µM, respectively, 54 and 33-fold more active than cisplatin. In particular, complex (I) is about 10 times less toxic to normal cells (HEK-293) than cancer cells Lu-1 and Hep-G2. Furthermore, the reaction of complex (I) with guanine at the N7 position was proposed and investigated using the DFT method. The results indicated that replacement of the ethylene ligand with guanine is thermodynamically more favorable than the Cl ligand and that the reaction occurs via two consecutive steps, namely the replacement of ethylene with H2O and the water with the guanine molecule.

Keywords

• platinum(ii) complex
• crystal structure
• anticancer activity
• 8-hydroxyquinoline
• dft