A Red-Light-Activated Ruthenium-Caged NAMPT Inhibitor Remains Phototoxic in Hypoxic Cancer Cells

Angew Chem Int Ed Engl. 2017 Sep 11;56(38):11549-11553. doi: 10.1002/anie.201703890. Epub 2017 Aug 9.

Abstract

We describe two water-soluble ruthenium complexes, [1]Cl2 and [2]Cl2 , that photodissociate to release a cytotoxic nicotinamide phosphoribosyltransferase (NAMPT) inhibitor with a low dose (21 J cm-2 ) of red light in an oxygen-independent manner. Using a specific NAMPT activity assay, up to an 18-fold increase in inhibition potency was measured upon red-light activation of [2]Cl2 , while [1]Cl2 was thermally unstable. For the first time, the dark and red-light-induced cytotoxicity of these photocaged compounds could be tested under hypoxia (1 % O2 ). In skin (A431) and lung (A549) cancer cells, a 3- to 4-fold increase in cytotoxicity was found upon red-light irradiation for [2]Cl2 , whether the cells were cultured and irradiated with 1 % or 21 % O2 . These results demonstrate the potential of photoactivated chemotherapy for hypoxic cancer cells, in which classical photodynamic therapy, which relies on oxygen activation, is poorly efficient.

Keywords: anti-tumor agents; hypoxia; photopharmacology; red-light activation; ruthenium.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Cytokines / antagonists & inhibitors*
  • Cytokines / metabolism
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Hypoxia
  • Light*
  • Nicotinamide Phosphoribosyltransferase / antagonists & inhibitors*
  • Nicotinamide Phosphoribosyltransferase / metabolism
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology*
  • Photochemical Processes
  • Photochemotherapy
  • Ruthenium / chemistry
  • Ruthenium / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Cytokines
  • Enzyme Inhibitors
  • Organometallic Compounds
  • Ruthenium
  • Nicotinamide Phosphoribosyltransferase
  • nicotinamide phosphoribosyltransferase, human