Design, semi-synthesis and bioevaluation of koumine-like derivatives as potential antitumor agents in vitro and in vivo

Future Med Chem. 2024;16(14):1413-1428. doi: 10.1080/17568919.2024.2350878. Epub 2024 May 29.

Abstract

Aims: Five series of novel koumine-like compounds were designed, semi-synthesized and systematically evaluated for antitumor activities.Methods: All compounds were evaluated for antiproliferative activity against four human cancer cell lines, including HT-29, HCT-116, HCT-15 and Caco-2.Results: Most compounds exhibited much higher antiproliferation activities (IC50 <10 μM) than koumine. Two selected compounds A4 and C5 showed comparable antitumor effects to 5-FU in vivo, as well as better safety profiles. Further studies suggested that A4 and C5 could arrest HT-29 cell cycle in G2 phase and raise reactive oxygen species level, thus inducing cell apoptosis related to Erk MAPK and NF-κB signaling pathways inhibition.Conclusion: These results will greatly promote the druggability study of these koumine-like compounds.

Keywords: Koumine; antitumor; structural modification; structure and activity relationship.

Plain language summary

[Box: see text].

MeSH terms

  • Animals
  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Apoptosis* / drug effects
  • Cell Line, Tumor
  • Cell Proliferation* / drug effects
  • Dioxolanes / chemical synthesis
  • Dioxolanes / chemistry
  • Dioxolanes / pharmacology
  • Drug Design*
  • Drug Screening Assays, Antitumor*
  • Humans
  • Indole Alkaloids
  • Mice
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors
  • NF-kappa B / metabolism
  • Reactive Oxygen Species / metabolism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • koumine
  • Reactive Oxygen Species
  • Dioxolanes
  • NF-kappa B
  • Indole Alkaloids