Synthesis and biological evaluation of oleanolic acid derivatives with electrophilic warheads as antitumor agents

Future Med Chem. 2023 May;15(9):769-790. doi: 10.4155/fmc-2023-0041. Epub 2023 May 25.

Abstract

Aim: The oleanolic acid derivatives containing electrophilic warheads were synthesized, and their antitumor activities were investigated. Materials & methods: The cytotoxicity of compounds against tumor cells were determined by the MTT method. The antitumor effects of compounds 27a, Y03 and Y04 were evaluated in vitro through a wound-healing assay, apoptosis and cell circle analysis, and cellular reactive oxide species determination. The levels of related proteins in MCF-7 cells treated with Y03 was determined through Western blot analysis. Results & conclusion: Compounds 27a, Y03 and Y04 displayed high cytotoxicity against breast cancer cells and inhibited cell migration, induced apoptosis, arrest cell circle at G0/G1 and promoted cellular reactive oxide species generation. The antitumor mechanism involved inhibition of Akt/mTOR and induction of ferroptosis.

Keywords: antitumor; apoptosis induction; electrophilic warheads; ferroptosis induction; inhibition of Akt/mTOR pathway; inhibition of GPX4; oleanolic acid derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents* / pharmacology
  • Apoptosis
  • Cell Line, Tumor
  • Cell Proliferation
  • Humans
  • MCF-7 Cells
  • Oleanolic Acid* / pharmacology

Substances

  • Oleanolic Acid
  • Antineoplastic Agents