Novel hybrids of natural β-elemene bearing isopropanolamine moieties: Synthesis, enhanced anticancer profile, and improved aqueous solubility

Fitoterapia. 2017 Jul:120:117-125. doi: 10.1016/j.fitote.2017.05.002. Epub 2017 May 31.

Abstract

A series of novel β-elemene isopropanolamine derivatives were synthesized and evaluated for their antitumor activity. The results indicated that all of the compounds showed stronger antiproliferative activities than β-elemene as well as improved aqueous solubility. In particular dimer 6q showed the strongest cytotoxicity against four tumor cell lines (SGC-7901, HeLa, U87 and A549) with IC50 values ranging from 4.37 to 10.20μM. Moreover, combination of 6q with cisplatin exhibited a synergistic effect on these cell lines with IC50 values ranging from 1.21 to 2.94μM, and reversed the resistance of A549/DPP cells with an IC50 value of 2.52μM. The mechanism study revealed that 6q caused cell cycle arrest at the G2 phase and induced apoptosis of SGC-7901 cells through a mitochondrial-dependent apoptotic pathway. Further in vivo study in H22 liver cancer xenograft mouse model validated the antitumor activity of 6q with a tumor inhibitory ratio (TIR) of 60.3%, which was higher than that of β-elemene (TIR, 49.1%) at a dose of 60mg/kg. Altogether, the potent antitumor activity of 6qin vitro and in vivo warranted further preclinical investigation for potential anticancer chemotherapy.

Keywords: Antitumor activity; Aqueous solubility; Dimer; Isopropanolamine; β-Elemene.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Cell Cycle Checkpoints / drug effects
  • Cell Line, Tumor
  • Humans
  • Membrane Potential, Mitochondrial
  • Mice
  • Mice, Inbred ICR
  • Mitochondria / drug effects
  • Propanolamines / chemical synthesis
  • Propanolamines / pharmacology*
  • Sesquiterpenes / chemical synthesis
  • Sesquiterpenes / pharmacology*
  • Solubility
  • Xenograft Model Antitumor Assays

Substances

  • Antineoplastic Agents
  • Propanolamines
  • Sesquiterpenes
  • beta-elemene
  • monoisopropanolamine