2. Academic Validation
  3. Rhodamine B conjugates of triterpenoic acids are cytotoxic mitocans even at nanomolar concentrations

Rhodamine B conjugates of triterpenoic acids are cytotoxic mitocans even at nanomolar concentrations

  • Eur J Med Chem. 2017 Feb 15:127:1-9. doi: 10.1016/j.ejmech.2016.12.040.
Sven Sommerwerk 1,  Lucie Heller 1,  Christoph Kerzig 1,  Annemarie E Kramell 1,  René Csuk 2
Affiliations

Affiliations

  • 1 Martin-Luther University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany.
  • 2 Martin-Luther University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany. Electronic address: rene.csuk@chemie.uni-halle.de.
PMID: 28033541 DOI: 10.1016/j.ejmech.2016.12.040
Abstract

Triterpenoic acids 1-6 exhibited very low or no cytotoxicity at all, but their corresponding 2,3-di-O-acetyl-piperazinyl amides 13-18 showed low EC50 values for several human tumor cell lines. Their cytotoxicity, however, was also high for the non-malignant mouse fibroblasts NIH 3T3. A significant improvement was achieved by preparing the rhodamine B derivatives 19-24. While rhodamine B is not cytotoxic (up to a concentration of 30μM - cut-off of the assay), the triterpenoid piperazine-spacered rhodamine B derivatives were cytotoxic in nano-molar concentration. Compound 24 (a diacetylated maslinic acid derivative) was most toxic for several human tumor cell lines but less toxic for mouse fibroblasts NIH 3T3. Staining and double-staining experiments revealed 24 to act as a mitocan.

Keywords

Betulinic acid; Cytotoxicity; Glycyrrhetinic acid; Maslinic acid; Mitocan; Oleanolic acid; Platanic acid; Rhodamine B; Triterpenes; Ursolic acid.

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