Antiangiogenic and Anticancer Properties of Bifunctional Ruthenium(II)-p-Cymene Complexes: Influence of Pendant Perfluorous Chains

Mol Pharm. 2015 Aug 3;12(8):3089-96. doi: 10.1021/acs.molpharmaceut.5b00417. Epub 2015 Jul 21.

Abstract

Two bifunctional ruthenium(II)-p-cymene complexes with perfluorinated side chains, attached via pyridine ligands, have been evaluated in a series of in vitro and in vivo assays. Their effects on human endothelial (ECRF24 and HUVEC) cells, noncancerous human embryonic kidney (HEK-293) cells, and various human tumor cells were investigated. The complex with the shorter chain, 1, inhibits the proliferation of the tumor cell lines and ECRF24, whereas 2 selectively inhibits ECRF24 and HUVEC proliferation. Neither inhibits the migration of ECRF24 cells whereas both compounds inhibit sprout formation in HUVEC cells. Using three preclinical models, i.e., vasculature formation in the chorioallantoic membrane (CAM) of the chicken embryo, human A2780 ovarian carcinoma tumors xenografted on the CAM, and human LS174T colorectal adenocarcinoma tumors grown in athymic mice, the angiostatic and anticancer activities of these two complexes were studied. Overall, 1 inhibited tumor growth predominantly through an anticancer effect whereas 2 inhibited tumor growth predominately via an antiangiogenic mechanism.

Keywords: CAM model; antiangiogenesis; bioorganometallic chemistry; colorectal adenocarcinoma; fluorine chemistry; ovarian carcinoma; ruthenium(II)−arene complexes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiogenesis Inhibitors / chemistry
  • Angiogenesis Inhibitors / pharmacology*
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Cell Movement / drug effects
  • Cell Proliferation / drug effects
  • Cells, Cultured
  • Chick Embryo
  • Chorioallantoic Membrane / drug effects
  • Chorioallantoic Membrane / metabolism
  • Colorectal Neoplasms / drug therapy*
  • Colorectal Neoplasms / metabolism
  • Colorectal Neoplasms / pathology
  • Cymenes
  • Drug Screening Assays, Antitumor
  • Endothelium, Vascular / cytology
  • Endothelium, Vascular / drug effects
  • Endothelium, Vascular / metabolism
  • Female
  • HEK293 Cells
  • Humans
  • Immunoenzyme Techniques
  • Mice
  • Models, Molecular
  • Monoterpenes / chemistry*
  • Neovascularization, Pathologic / prevention & control
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology*
  • Ovarian Neoplasms / drug therapy*
  • Ovarian Neoplasms / metabolism
  • Ovarian Neoplasms / pathology
  • Ruthenium / chemistry*
  • Structure-Activity Relationship

Substances

  • Angiogenesis Inhibitors
  • Antineoplastic Agents
  • Cymenes
  • Monoterpenes
  • Organometallic Compounds
  • 4-cymene
  • Ruthenium