Design, synthesis and cytotoxicity of BODIPY FL labelled triterpenoids

Eur J Med Chem. 2020 Jan 1:185:111858. doi: 10.1016/j.ejmech.2019.111858. Epub 2019 Nov 6.

Abstract

Several triterpenoid acids (betulinic, oleanolic, ursolic, glycyrrhetinic) and triterpene betulin were used as starting material to synthesize BODIPY FL adducts, and these compounds were screened for their cytotoxic activity employing several human tumor cell lines. The cytotoxicity of the compounds strongly depended on the chosen spacer between the triterpenoid core and the BODIPY FL unit. Thus, 3-O-acetyl-betulinic acid derived BODIPY FL conjugate holding an ethylendiamine spacer was cytotoxic for human breast adenocarcinoma cells MCF7 but not cytotoxic for all other cell lines.

Keywords: BODIPY FL; Betulinic acid; Cytotoxicity; Glycyrrhetinic acid; Oleanolic acid; Triterpenoids; Ursolic acid.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Boron Compounds / chemical synthesis
  • Boron Compounds / chemistry
  • Boron Compounds / pharmacology*
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Drug Screening Assays, Antitumor
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology*
  • Humans
  • MCF-7 Cells
  • Molecular Structure
  • Structure-Activity Relationship
  • Triterpenes / chemistry
  • Triterpenes / pharmacology*

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Antineoplastic Agents
  • Boron Compounds
  • Fluorescent Dyes
  • Triterpenes