A Cancer-Selective Zinc Ionophore Inspired by the Natural Product Naamidine A

ACS Chem Biol. 2019 Jan 18;14(1):106-117. doi: 10.1021/acschembio.8b00977. Epub 2019 Jan 8.

Abstract

We present data demonstrating the natural product mimic, zinaamidole A (ZNA), is a modulator of metal ion homeostasis causing cancer-selective cell death by specifically inducing cellular Zn2+-uptake in transformed cells. ZNA's cancer selectivity was evaluated using metastatic, patient-derived breast cancer cells, established human breast cancer cell lines, and three-dimensional organoid models derived from normal and transformed mouse mammary glands. Structural analysis of ZNA demonstrated that the compound interacts with zinc through the N2-acyl-2-aminoimidazole core. Combination treatment with ZnSO4 strongly potentiated ZNA's cancer-specific cell death mechanism, an effect that was not observed with other transition metals. We show that Zn2+-dyshomeostasis induced by ZNA is unique and markedly more selective than other known Zn2+-interacting compounds such as clioquinol. The in vivo bioactivity of ZNA was also assessed and revealed that tumor-bearing mice treated with ZNA had improved survival outcomes. Collectively, these data demonstrate that the N2-acyl-2-aminoimidazole core of ZNA represents a powerful chemotype to induce cell death in cancer cells concurrently with a disruption in zinc homeostasis.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Cell Proliferation / drug effects
  • Female
  • Humans
  • Imidazoles / pharmacology*
  • Ionophores / metabolism
  • Ionophores / pharmacology*
  • Mice
  • Zinc / metabolism*

Substances

  • Imidazoles
  • Ionophores
  • naamidine A
  • Zinc