Design, synthesis, and biological evaluation of 5-((8-methoxy-2-methylquinolin-4-yl)amino)-1H-indole-2-carbohydrazide derivatives as novel Nur77 modulators

Eur J Med Chem. 2020 Oct 15:204:112608. doi: 10.1016/j.ejmech.2020.112608. Epub 2020 Jul 19.

Abstract

Nur77 is a potential target for the treatment of cancer such as HCC. Herein, we detailed the discovery of a novel series of 5-((8-methoxy-2-methylquinolin-4-yl)amino)-1H-indole-2-carbohydrazide derivatives as potential Nur77 modulators. The studies of antiproliferative activity and Nur77-binding affinity of target compounds resulted in the discovery of a lead candidate (10g), which was a good Nur77 binder (KD = 3.58 ± 0.16 μM) with a broad-spectrum antiproliferative activity against all tested hepatoma cells (IC50 < 2.0 μM) and was low toxic to normal LO2 cells. 10g could up-regulate Nur77 expression and mediate sub-cellular localization of Nur77 to induce apoptosis in hepatocellular carcinoma cell lines, which relied on 10g inducing Nur77-dependent autophagy and endoplasmic reticulum stress as the upstream of apoptosis. Moreover, the in vivo assays verified that 10g significantly inhibited xenograft tumor growth. These results indicate that 10g has the potential to be developed as a novel Nur77-targeting anti-hepatoma drug.

Keywords: Antitumor; Autophagy; ER stress; Indole; Nur77; Quinoline.

MeSH terms

  • Animals
  • Antineoplastic Agents / pharmacology
  • Carcinoma, Hepatocellular / pathology
  • Cell Line, Tumor
  • Drug Design*
  • Humans
  • Hydrazines / chemical synthesis
  • Hydrazines / chemistry*
  • Hydrazines / pharmacology*
  • Kaplan-Meier Estimate
  • Liver Neoplasms / pathology
  • Mice
  • Molecular Docking Simulation
  • Nuclear Receptor Subfamily 4, Group A, Member 1 / drug effects*
  • Nuclear Receptor Subfamily 4, Group A, Member 1 / metabolism
  • Structure-Activity Relationship
  • Xenograft Model Antitumor Assays

Substances

  • Antineoplastic Agents
  • Hydrazines
  • NR4A1 protein, human
  • Nuclear Receptor Subfamily 4, Group A, Member 1
  • carbohydrazide