[논문]Novel nickel(II), palladium(II), and platinum(II) complexes having a pyrrolyl-iminophosphine (PNN) pincer: Synthesis, crystal structures, and cytotoxic activity

Kim, Youngwon; Lee, Jinwook; Son, You-Hwa; Choi, Sang-Un; Alam, Mahboob; Park, Soonheum

doi:10.1016/j.jinorgbio.2020.111015

[해외논문] Novel nickel(II), palladium(II), and platinum(II) complexes having a pyrrolyl-iminophosphine (PNN) pincer: Synthesis, crystal structures, and cytotoxic activity

Journal of inorganic biochemistry, v.205, 2020년, pp.111015 -

Kim, Youngwon (Department of Advanced Materials Chemistry, Dongguk University) , Lee, Jinwook (Department of Advanced Materials Chemistry, Dongguk University) , Son, You-Hwa (Center for Drug Discovery Technology, Korea Research Institute of Chemical Technology) , Choi, Sang-Un (Center for Drug Discovery Technology, Korea Research Institute of Chemical Technology) , Alam, Mahboob (Division of Chemistry and Biotechnology, Dongguk University) , Park, Soonheum (Department of Advanced Materials Chemistry, Dongguk University)

Abstract ▼ AI-Helper

Abstract A pyrrolyl-iminophosphine (PNNH) which would act as a potential terdentate ligand has been prepared by Schiff base reaction. Complexes [M(PNN)X] (M = Ni; X = Cl (1), Pd; X = Cl (2), Br (3), I (4), M = Pt; X = Cl (5)) were prepared. The title complexes were characterized by various spectroscopic (IR, 1H, 13C, and 31P NMR) and elemental analyses. The molecular structures of 1, 2, and 5 have been established by single-crystal X-ray crystallography, demonstrating a distorted square planar geometry comprising two 5-membered metallacyclic rings. Complexes 1 and 2 were found to crystallize in the orthorhombic while complex 5 crystallizes in the monoclinic. Cytotoxicities of the complexes along with PNNH were evaluated against A549 (lung), SK-OV-3 (ovarian), SM-MEL-2 (skin), and HCT15 (colon) human cancer cell lines by sulforhodamine B assay. Notably, the palladium(II) complex (2) shows the highest activity. Apoptosis activity along with the caspase inhibitor Z-VAD (Z-Val-Ala-Asp-fluoromethyl ketone) assay of 2 and 5 against A549 and HCT15 cancer cell lines were investigated to learn a mechanistic pathway for the observed cytotoxicity, practically eliminating an apoptotic cell-death route. Complexes 2 and 5 were studied to DNA cleavage assay and molecular docking simulation. The DNA (pcDNA3.0) cleavage experiment evaluates complex 5 interacting with DNA, more effectively, in comparison to complex 2. Molecular docking simulation of 2 and 5 toward DNA and GRP78 (glucose-regulated protein 78) was performed to predict binding sites of ligand-receptors and a plausible mechanistic aspect of metallodrug-action. Highlights Novel nickel-triad complexes having pyrrolyl-iminophosphine (PNN) have been prepared. Single crystal X-ray studies on Ni(II), Pd(II), and Pt(II) complexes with PNN ligand Cytotoxicity of the title complexes against human cancer cell lines was evaluated. Apoptosis, pan-caspase inhibitor effect (Z-VAD) and DNA cleavage were investigated. Molecular docking simulation was performed to determine the probable binding modes. Graphical abstract Complexes M(PNN)X (M = Ni, Pd, Pt; PNN = PPh2(CH2)2N=CHC4H3N) were prepared and characterized. Cytotoxicities of the complexes were evaluated against human cancer cell lines. Apoptosis activity along with Z-VAD (Z-Val-Ala-Asp-fluoromethyl-ketone), and DNA cleavage assays of 2 and 5 were investigated followed by molecular docking simulation. [DISPLAY OMISSION]

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