Novel ATP-competitive kinesin spindle protein inhibitors

J Med Chem. 2007 Oct 4;50(20):4939-52. doi: 10.1021/jm070435y. Epub 2007 Aug 29.

Abstract

Kinesin spindle protein (KSP), an ATPase responsible for spindle pole separation during mitosis that is present only in proliferating cells, has become a novel and attractive anticancer target with potential for reduced side effects compared to currently available therapies. We report herein the discovery of the first known ATP-competitive inhibitors of KSP, which display a unique activity profile as compared to the known loop 5 (L5) allosteric KSP inhibitors that are currently under clinical evaluation. Optimization of this series led to the identification of biphenyl sulfamide 20, a potent KSP inhibitor with in vitro antiproliferative activity against human cells with either wild-type KSP (HCT116) or mutant KSP (HCT116 D130V). In a murine xenograft model with HCT116 D130V tumors, 20 showed significant antitumor activity following intraperitoneal dosing, providing in vivo proof-of-principle of the efficacy of an ATP-competitive KSP inhibitor versus tumors that are resistant to the other known KSP inhibitors.

MeSH terms

  • Adenosine Triphosphate / metabolism*
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology
  • Biphenyl Compounds / chemical synthesis*
  • Biphenyl Compounds / pharmacokinetics
  • Biphenyl Compounds / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Screening Assays, Antitumor
  • Female
  • Humans
  • Kinesins / antagonists & inhibitors*
  • Kinesins / genetics
  • Mice
  • Mice, Nude
  • Mutation
  • Neoplasm Transplantation
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / pharmacokinetics
  • Sulfonamides / pharmacology

Substances

  • Antineoplastic Agents
  • Biphenyl Compounds
  • KIF11 protein, human
  • N-(4'-(trifluoromethyl)-4-biphenylyl)sulfamide
  • Sulfonamides
  • Adenosine Triphosphate
  • Kinesins