Cyclometalated Ir(III)-8-oxychinolin complexes acting as red-colored probes for specific mitochondrial imaging and anticancer drugs

Eur J Med Chem. 2020 Apr 15:192:112192. doi: 10.1016/j.ejmech.2020.112192. Epub 2020 Feb 28.

Abstract

A new class of luminescent IrIII antitumor agents, namely, [Ir(CP1)(PY1)2] (Ir-1), [Ir(CP1)(PY2)2] (Ir-2), [Ir(CP1)(PY4)2] (Ir-3), [Ir(CP2)(PY1)2] (Ir-4), [Ir(CP2)(PY4)2] (Ir-5), [Ir(CP3)(PY1)2]⋅CH3OH (Ir-6), [Ir(CP4)(PY4)2]⋅CH3OH (Ir-7), [Ir(CP5)(PY2)2] (Ir-8), [Ir(CP5)(PY4)2]⋅CH3OH (Ir-9), [Ir(CP6)(PY1)2] (Ir-10), [Ir(CP6)(PY2)2]⋅CH3OH (Ir-11), [Ir(CP6)(PY3)2] (Ir-12), [Ir(CP6)(PY41)2] (Ir-13), and [Ir(CP7)(PY1)2] (Ir-14), supported by 8-oxychinolin derivatives and 1-phenylpyrazole ligands was prepared. Compared with SK-OV-3/DDP and HL-7702 cells, the Ir-1-Ir-14 compounds exhibited half maximal inhibitory concentration (IC50) values within the high nanomolar range (50 nM-10.99 μM) in HeLa cells. In addition, Ir-1 and Ir-3 accumulated and stained the mitochondrial inner membrane of HeLa cells with high selectivity and exhibited a high antineoplastic activity in the entire cervical HeLa cells, with IC50 values of 1.22 ± 0.36 μM and 0.05 ± 0.04 μM, respectively. This phenomenon induced mitochondrial dysfunction, suggesting that these cyclometalated IrIII complexes can be potentially used in biomedical imaging and Ir(III)-based anticancer drugs. Furthermore, the high cytotoxicity activity of Ir-3 is correlated with the 1-phenylpyrazole (H-PY4) secondary ligands in the luminescent IrIII antitumor complex.

Keywords: 8-Oxychinolin derivatives; Apoptosis; Luminescent Ir(III) complex; Mitochondrial dysfunction.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Coordination Complexes / chemical synthesis
  • Coordination Complexes / chemistry
  • Coordination Complexes / pharmacology*
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology*
  • HeLa Cells
  • Humans
  • Mitochondria / chemistry*
  • Mitochondria / metabolism
  • Models, Molecular
  • Molecular Structure
  • Optical Imaging

Substances

  • Antineoplastic Agents
  • Coordination Complexes
  • Fluorescent Dyes