Esterase inhibitors as ester-containing drug stabilizers and their hydrolytic products: potential contributors to the matrix effects on bioanalysis by liquid chromatography/tandem mass spectrometry

Rapid Commun Mass Spectrom. 2012 Jun 15;26(11):1291-304. doi: 10.1002/rcm.6230.

Abstract

Rationale: Esterase inhibitors are widely used to stabilize ester-containing drugs in biological matrices for quantitative liquid chromatography/tandem mass spectrometry (LC/MS/MS) assays. These co-existing inhibitors could cause matrix effects on bioanalysis and jeopardize the assay performance. We therefore developed an LC/MS/MS methodology to monitor the fate of inhibitors and evaluate their matrix effects, which is described in this study.

Methods: Human plasma containing 20 mM of diisopropylfluorophosphate (DFP), paraoxon, eserine, phenylmethylsulfonyl fluoride (PMSF) or 2-thenoyltrifluoroacetone (TTFA) was extracted by liquid-liquid extraction (LLE) and analyzed by an LC/MS/MS assay for BMS-068645 (a model drug) with additional pre-optimized selected reaction monitoring (SRM) transitions using positive/negative electrospray ionization (ESI) mode for each inhibitor. Hydrolytic products were characterized by product ion or neutral loss scan LC/MS/MS analysis. The matrix effect contribution from each inhibitor was evaluated by post-column infusion of BMS-068645.

Results: In the extracted samples by LLE, SRM chromatograms revealed the presence of paraoxon, eserine and TTFA with peak intensity of >2.50E08. Three DFP hydrolytic products, diisopropyl phosphate (DP), triisopropyl phosphate (TP) and DP dimer, and one PMSF hydrolytic product, phenymethanesulfonic acid (PMSA), were identified in the extracted samples. In post-column infusion profiles, ion suppression or enhancement was observed in the retention time regions of eserine (~10% suppression), paraoxon (~70% enhancement) and DP dimer (~20% suppression).

Conclusions: The SRM transitions described here make it possible to directly monitor the inhibitors and their hydrolytic products. In combination with post-column infusion, this methodology provides a powerful tool to routinely monitor the matrix effects-causing inhibitors, so that their matrix effects on the bioanalysis can be evaluated and minimized.

MeSH terms

  • Alkynes / blood
  • Alkynes / chemistry
  • Blood Chemical Analysis / methods*
  • Blood Chemical Analysis / standards
  • Chromatography, Liquid / methods*
  • Drug Stability
  • Enzyme Inhibitors / blood
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / metabolism
  • Esterases / antagonists & inhibitors*
  • Humans
  • Hydrolysis
  • Isoflurophate / blood
  • Isoflurophate / chemistry
  • Isoflurophate / metabolism
  • Models, Chemical
  • Paraoxon / blood
  • Paraoxon / chemistry
  • Paraoxon / metabolism
  • Phenylmethylsulfonyl Fluoride / blood
  • Phenylmethylsulfonyl Fluoride / chemistry
  • Phenylmethylsulfonyl Fluoride / metabolism
  • Physostigmine / blood
  • Physostigmine / chemistry
  • Physostigmine / metabolism
  • Purine Nucleosides / blood
  • Purine Nucleosides / chemistry
  • Tandem Mass Spectrometry / methods*
  • Thenoyltrifluoroacetone / analysis
  • Thenoyltrifluoroacetone / chemistry
  • Thenoyltrifluoroacetone / metabolism

Substances

  • Alkynes
  • BMS-068645
  • Enzyme Inhibitors
  • Purine Nucleosides
  • Isoflurophate
  • Thenoyltrifluoroacetone
  • Phenylmethylsulfonyl Fluoride
  • Physostigmine
  • Esterases
  • Paraoxon