Synthesis and Biological Evaluation of Fangchinoline Derivatives as Anti-Inflammatory Agents through Inactivation of Inflammasome

Molecules. 2019 Mar 23;24(6):1154. doi: 10.3390/molecules24061154.

Abstract

Twenty eight 7-substitued fangchinoline analogues, of which twenty two were novel, were synthesized and evaluated for their effect to inhibit lipopolysaccharide/nigericin (LPS/NIG)-induced IL-1β release at both cell and protein levels at the concentration of 5 μM. Among them, compound 6 exhibited promising inhibitory potency against IL-β activation with an IC50 value of 3.7 μM. Preliminary mechanism study revealed that 6 might target NLRP3 protein, and then block ASC pyroptosome formation with-NLRP3, rather than acting on the activation of the NLRP3 inflammasome (NF-κB and MAPK pathways) or caspase-1 protein. Our current study supported the potential role of compound 6 against IL-β activation, and provided powerful information for developing fangchinoline derivatives into a novel class of anti-inflammatory agents.

Keywords: Anti-inflammatory; IL-1β; NLRP3 inflammasome; fangchinoline.

MeSH terms

  • Anti-Inflammatory Agents / chemical synthesis
  • Anti-Inflammatory Agents / pharmacology*
  • Benzylisoquinolines / chemical synthesis
  • Benzylisoquinolines / pharmacology*
  • Caspase 1 / genetics
  • Cell Line
  • Gene Expression Regulation / drug effects
  • Humans
  • Inflammasomes / drug effects*
  • Inflammasomes / genetics
  • Inflammation / chemically induced
  • Inflammation / drug therapy*
  • Inflammation / genetics
  • Interleukin-1beta / genetics
  • Lipopolysaccharides / toxicity
  • NF-kappa B / genetics
  • NLR Family, Pyrin Domain-Containing 3 Protein / genetics
  • Nigericin / toxicity
  • Transcription Factor RelA / genetics

Substances

  • Anti-Inflammatory Agents
  • Benzylisoquinolines
  • Inflammasomes
  • Interleukin-1beta
  • Lipopolysaccharides
  • NF-kappa B
  • NLR Family, Pyrin Domain-Containing 3 Protein
  • RELA protein, human
  • Transcription Factor RelA
  • fangchinoline
  • Caspase 1
  • Nigericin