New benzimidazole-2-urea derivates as tubulin inhibitors

Bioorg Med Chem Lett. 2014 Sep 1;24(17):4250-3. doi: 10.1016/j.bmcl.2014.07.035. Epub 2014 Jul 17.

Abstract

Emerging drug resistance and other drawbacks limit tubulin inhibitors' therapeutic applications and developing novel tubulin inhibitors still attracts intensive efforts. We describe the discovery and structure-activity relationship study of a series of benzimidazole-2-urea derivatives as novel β tubulin inhibitors. The representative compound 6o potently suppressed the proliferation of a panel of human cancer cells (NCI-H460, Colo205, K562, A431, HepG2, Hela, MDA-MB-435S) with IC50 values of 0.040, 0.050, 0.006, 0.026, 1.774, 0.452 and 0.052 μM, respectively. Compound 6o obviously inhibited NCI-H460 spindles formation and induced cell cycle arrest at G2/M phase at 0.10 μM. Computational study suggested that 6o interacts with β tubulin in a novel binding mode. Our results suggested that benzimidazole-2-urea derivatives might be promising tubulin inhibitors with novel binding mode for further development.

Keywords: Ant-cancer; Benzimidazole-2-urea derivates; Cell cycle arrest; Microtubule; Tubulin inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Benzimidazoles / chemical synthesis
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology*
  • Cell Cycle Checkpoints / drug effects
  • Cell Division / drug effects
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • G2 Phase / drug effects
  • HeLa Cells
  • Hep G2 Cells
  • Humans
  • K562 Cells
  • Methylurea Compounds / chemical synthesis
  • Methylurea Compounds / chemistry
  • Methylurea Compounds / pharmacology*
  • Models, Molecular
  • Molecular Structure
  • Structure-Activity Relationship
  • Tubulin / metabolism*
  • Tubulin Modulators / chemical synthesis
  • Tubulin Modulators / chemistry*
  • Tubulin Modulators / pharmacology*

Substances

  • Antineoplastic Agents
  • Benzimidazoles
  • Methylurea Compounds
  • Tubulin
  • Tubulin Modulators