Ring-Substituted 1-Hydroxynaphthalene-2-Carboxanilides Inhibit Proliferation and Trigger Mitochondria-Mediated Apoptosis

Int J Mol Sci. 2020 May 12;21(10):3416. doi: 10.3390/ijms21103416.

Abstract

Ring-substituted 1-hydroxynaphthalene-2-carboxanilides were previously investigated for their antimycobacterial properties. In our study, we have shown their antiproliferative and cell death-inducing effects in cancer cell lines. Cell proliferation and viability were assessed by WST-1 assay and a dye exclusion test, respectively. Cell cycle distribution, phosphatidylserine externalization, levels of reactive oxygen or nitrogen species (RONS), mitochondrial membrane depolarization, and release of cytochrome c were estimated by flow cytometry. Levels of regulatory proteins were determined by Western blotting. Our data suggest that the ability to inhibit the proliferation of THP-1 or MCF-7 cells might be referred to meta- or para-substituted derivatives with electron-withdrawing groups -F, -Br, or -CF3 at anilide moiety. This effect was accompanied by accumulation of cells in G1 phase. Compound 10 also induced apoptosis in THP-1 cells in association with a loss of mitochondrial membrane potential and production of mitochondrial superoxide. Our study provides a new insight into the action of salicylanilide derivatives, hydroxynaphthalene carboxamides, in cancer cells. Thus, their structure merits further investigation as a model moiety of new small-molecule compounds with potential anticancer properties.

Keywords: antiproliferative effect; apoptosis; cell cycle; hydroxynaphthalene carboxamides; salicylanilides.

MeSH terms

  • Anilides / chemistry
  • Anilides / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Apoptosis / drug effects*
  • Cell Cycle / drug effects
  • Cell Proliferation / drug effects*
  • Cell Survival / drug effects
  • Humans
  • MCF-7 Cells
  • Membrane Potential, Mitochondrial / drug effects
  • Mitochondria / drug effects*
  • Mitochondria / metabolism
  • Molecular Structure
  • Naphthols / chemistry*
  • Reactive Oxygen Species / metabolism
  • Salicylanilides / chemistry
  • Salicylanilides / pharmacology
  • Structure-Activity Relationship
  • Superoxides / metabolism
  • THP-1 Cells

Substances

  • Anilides
  • Antineoplastic Agents
  • Naphthols
  • Reactive Oxygen Species
  • Salicylanilides
  • Superoxides
  • salicylanilide