Determination of the glucuronide metabolite of ON 013100, a benzylstyrylsulfone antineoplastic drug, in colon cancer cells using LC/MS/MS

J Pharm Biomed Anal. 2013 Mar 5:75:138-44. doi: 10.1016/j.jpba.2012.11.022. Epub 2012 Nov 23.

Abstract

ON 013100, (E)-2,4,6-trimethoxystyryl-3-hydroxy-4-methoxybenzyl sulfone, is a potent kinase inhibitor whose phosphate form is in Phase I clinical trials in lymphoma and acute lymphoid leukemia. The objectives were to: (a) investigate the possible presence of the glucuronide metabolite of the drug in two representative colon cancer cell lines, a drug resistant (colo-205) and a drug sensitive (colo-320); (b) quantify the glucuronide metabolite and the unchanged drug in the cells after treatment with ON 013100. The glucuronide was synthesized and a selective LC/MS/MS method was developed and validated for the characterization and quantification of the metabolite. The glucuronide metabolite (570.6 Da) was found in the drug-resistant cells upon a 1h incubation with ON 013100 (20 μg/ml). After treatment with the drug, the concentration of the metabolite gradually decreased from 0.84 μg/ml at 0 h through 0.21 μg/ml at 6h to below detection limit of 8.0 ng/ml at 9 h. No glucuronide metabolite was detected in the drug-sensitive cells. The concentrations of intact ON 013100 in the drug-resistant cells gradually decreased from 0.41 μg/ml (0 h) to 0.06 μg/ml (9 h). The corresponding concentrations of the intact drug in the drug-sensitive cells were from 2.88 μg/ml to 0.94 μg/ml.

Publication types

  • Research Support, Non-U.S. Gov't
  • Validation Study

MeSH terms

  • Antineoplastic Agents / analysis
  • Antineoplastic Agents / metabolism*
  • Antineoplastic Agents / pharmacology
  • Benzyl Compounds / analysis
  • Benzyl Compounds / metabolism*
  • Benzyl Compounds / pharmacology
  • Cell Line, Tumor
  • Chromatography, High Pressure Liquid
  • Colonic Neoplasms / drug therapy
  • Colonic Neoplasms / metabolism*
  • Drug Resistance, Neoplasm
  • Glucuronides / analysis*
  • Glucuronides / chemistry
  • Glucuronides / metabolism
  • Humans
  • Kinetics
  • Limit of Detection
  • Metabolic Detoxication, Phase I
  • Molecular Weight
  • Protein Kinase Inhibitors / analysis
  • Protein Kinase Inhibitors / metabolism*
  • Protein Kinase Inhibitors / pharmacology
  • Spectrometry, Mass, Electrospray Ionization
  • Stereoisomerism
  • Styrenes / analysis
  • Styrenes / metabolism*
  • Styrenes / pharmacology
  • Sulfones
  • Tandem Mass Spectrometry

Substances

  • Antineoplastic Agents
  • Benzyl Compounds
  • Glucuronides
  • ON013100
  • Protein Kinase Inhibitors
  • Styrenes
  • Sulfones