Novel indolo-sophoridinic scaffold as Topo I inhibitors: Design, synthesis and biological evaluation as anticancer agents

Eur J Med Chem. 2018 Aug 5:156:479-492. doi: 10.1016/j.ejmech.2018.07.028. Epub 2018 Jul 17.

Abstract

Based on the mechanism of action, novel scaffolds as Topo I inhibitors bearing indole and sophoridinine were designed. Preliminary docking study revealed that some molecules among the designed series possessed promising Topo I inhibitor properties. Subsequently, thirty new compounds were synthesized and characterized by 1H NMR, 13C NMR, and Mass spectral analyses. The compounds were then screened for their antiproliferative and enzymatic inhibitory activities. The results affirmed the consistency between docking and activities and the rationality of the design strategy. Furthermore, compound 10b was chosen as a representative compound to test its anticancer effects in vitro and in vivo. The results showed that 10b caused prominent S phase cell cycle arrest and significantly suppressed tumor growth in HepG2 cell derived mouse model. These findings present a promising series of lead molecules which can serve as potential Topo I inhibitors for the treatment of cancer and a theoretical basis for structural modifications.

Keywords: Anticancer activities; Binding mode; Enzymatic activity; Indolo-sophoridinic Topo I inhibitors; Molecular docking.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Antineoplastic Agents / therapeutic use
  • Cell Cycle Checkpoints / drug effects
  • Cell Proliferation / drug effects
  • Drug Design
  • Female
  • Hep G2 Cells
  • Humans
  • Indoles / chemistry*
  • Indoles / pharmacology*
  • Indoles / therapeutic use
  • Liver Neoplasms / drug therapy
  • Liver Neoplasms / metabolism
  • Liver Neoplasms / pathology
  • Mice
  • Mice, Inbred BALB C
  • Molecular Docking Simulation
  • Structure-Activity Relationship
  • Topoisomerase I Inhibitors / chemistry*
  • Topoisomerase I Inhibitors / pharmacology*
  • Topoisomerase I Inhibitors / therapeutic use

Substances

  • Antineoplastic Agents
  • Indoles
  • Topoisomerase I Inhibitors