Lead optimization-hit expansion of new asymmetrical pyridinium/quinolinium compounds as choline kinase α1 inhibitors

Future Med Chem. 2018 Aug 1;10(15):1769-1786. doi: 10.4155/fmc-2018-0059. Epub 2018 Jul 25.

Abstract

Aim: Choline kinase α inhibitors represent one of the newest classes of cytotoxic drugs for cancer treatment, since aberrant choline metabolism is a characteristic shared by many human cancers.

Results: Here, we present a new class of asymmetrical pyridinium/quinolinium derivatives developed and designed based on drug optimization.

Conclusion: Among all compounds described here, compound 8, bearing a 7-chloro-4N-methyl-p-chloroaniline quinolinium moiety, exhibited the greatest inhibitory activity at the enzyme (IC50 = 0.29 μM) and antiproliferative activity in cellular assays (GI50 = 0.29-0.92 μM). Specifically, compound 8 strongly induces a cell-cycle arrest in G1 phase, but it does not significantly induce apoptosis while causing senescence in the MDA-MB-231 cell line.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line
  • Cell Proliferation / drug effects
  • Choline Kinase / antagonists & inhibitors*
  • Choline Kinase / metabolism
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Pyridinium Compounds / chemical synthesis
  • Pyridinium Compounds / chemistry
  • Pyridinium Compounds / pharmacology*
  • Quinolinium Compounds / chemical synthesis
  • Quinolinium Compounds / chemistry
  • Quinolinium Compounds / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Protein Kinase Inhibitors
  • Pyridinium Compounds
  • Quinolinium Compounds
  • CHKA protein, human
  • Choline Kinase