Discover the leading compound of 4β-S-(5-fluorobenzoxazole)-4-deoxy-4'-demethylepipodophyllotoxin with millimolar-potency toxicity by modifying the molecule structure of 4'-demethylepipodophyllotoxin

Eur J Med Chem. 2018 Oct 5:158:951-964. doi: 10.1016/j.ejmech.2018.09.022. Epub 2018 Sep 14.

Abstract

4'-Demethylepipodophyllotoxin (DMEP) derivatives are broad-spectrum and potent antitumor leading compound. Because of their unacceptable toxicity, DMEP derivatives often failed in the development of new drug. Until now, there was no report on the millimolar-potency toxicity of DMEP derivatives by modifying the molecule structure of DMEP. For the first time, this work discovered leading compounds with millimolar-potency toxicity by modifying the molecule structure of DMEP. The IC50 value of 4β-S-(5-fluorobenzoxazole-2-)-4-deoxy-4'-demethylepipodophyllotoxin (Compound 2) was around 323.4-2000.9 μM on human healthy cells (i.e., HL-7702, H8, MRC-5 and HMEC), which was significantly reduced by 171-1999 times than podophyllotoxin (1.0-2.6 μM) and 9-80 times than etoposide (21.5-75.4 μM). Compared with the treatment of etoposide, DNA repair proteins HMGB1 and PARK7 were specifically activated and the expression of anti-apoptotic proteins were up-regulated in HL-7702 cells after the treatment of Compound 2. These indicated the toxicity of Compound 2 was synergistically reduced by DNA repair and anti-apoptosis pathway.

Keywords: 4′-demethylepipodophyllotoxin; Anti-Apoptosis pathway; DNA repair; Millimolar-potency toxicity; Toxicity mechanism.

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Cell Line
  • Cell Line, Tumor
  • Drug Design*
  • Halogenation
  • Hep G2 Cells
  • Humans
  • Models, Molecular
  • Neoplasms / drug therapy
  • Neoplasms / metabolism
  • Oxazoles / chemistry
  • Oxazoles / pharmacology
  • Podophyllotoxin / analogs & derivatives*
  • Podophyllotoxin / chemistry
  • Podophyllotoxin / pharmacology

Substances

  • Antineoplastic Agents
  • Oxazoles
  • Podophyllotoxin
  • 4'-demethylepipodophyllotoxin