Discovery of a potent and orally bioavailable benzolactam-derived inhibitor of Polo-like kinase 1 (MLN0905)

J Med Chem. 2012 Jan 12;55(1):197-208. doi: 10.1021/jm2011172. Epub 2011 Dec 5.

Abstract

This article describes the discovery of a series of potent inhibitors of Polo-like kinase 1 (PLK1). Optimization of this benzolactam-derived chemical series produced an orally bioavailable inhibitor of PLK1 (12c, MLN0905). In vivo pharmacokinetic-pharmacodynamic experiments demonstrated prolonged mitotic arrest after oral administration of 12c to tumor bearing nude mice. A subsequent efficacy study in nude mice achieved tumor growth inhibition or regression in a human colon tumor (HT29) xenograft model.

MeSH terms

  • Administration, Oral
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology
  • Benzazepines / chemical synthesis*
  • Benzazepines / pharmacokinetics
  • Benzazepines / pharmacology
  • Biological Availability
  • Cell Cycle Proteins / antagonists & inhibitors*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Humans
  • Lactams / chemical synthesis*
  • Lactams / pharmacokinetics
  • Lactams / pharmacology
  • Mice
  • Mice, Nude
  • Mitosis
  • Models, Molecular
  • Neoplasm Transplantation
  • Polo-Like Kinase 1
  • Protein Conformation
  • Protein Serine-Threonine Kinases / antagonists & inhibitors*
  • Proto-Oncogene Proteins / antagonists & inhibitors*
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship
  • Thiones / chemical synthesis*
  • Thiones / pharmacokinetics
  • Thiones / pharmacology
  • Transplantation, Heterologous

Substances

  • 9-trifluoromethyl-2-((5-(3-(dimethylamino)propyl)-2-methylpyridin-3-yl)amino)-5,7-dihydro-6H-pyrimido(5,4-d)(1)benzazepine-6-thione
  • Antineoplastic Agents
  • Benzazepines
  • Cell Cycle Proteins
  • Lactams
  • Proto-Oncogene Proteins
  • Thiones
  • Protein Serine-Threonine Kinases

Associated data

  • PDB/3THB