Narrow-bore liquid chromatography-tandem mass spectrometry with simultaneous radioactivity monitoring for partially characterizing the biliary metabolites of an arginine fluoroalkyl ketone analog of D-MePhe-Pro-Arg, a potent thrombin inhibitor

J Chromatogr B Biomed Sci Appl. 1997 Jan 24;688(2):281-9. doi: 10.1016/s0378-4347(96)00299-x.

Abstract

Characterizing components eluting from a HPLC column is enhanced when multiple detectors are incorporated in-line. The performance of a system consisting of a combination of two detectors-electrospray ionization mass spectrometry (and tandem mass spectrometry) and radioactivity monitoring, following gradient separation with a 250 x 2.1 mm I.D. (Vydac Protein and Peptide C18, 5 microns, 300 A) column-is evaluated with respect to chromatographic integrity and detection. The HPLC effluent was split (8:1) and a post-column make-up solvent was added to flow directed towards the radioactivity detector containing a solid glass cell. Trifluoracetic acid (0.1%) was added to the make-up flow solvent to prevent silanol interactions from degrading the profile displayed in the 14C trace. A 14C chromatographic peak representing 550 dpm was detected with signal-to-noise ratio of 3. This system was used for rapidly characterizing the biliary metabolites of an arginine fluoroalkyl ketone analog of D-MePhe-Pro-Arg, a potent thrombin inhibitor currently being evaluated as a drug candidate. These metabolites are shown to comprise of mono- and dihydroxylated drug as well as a reduced ketone form of the drug. Combining the radioactivity monitor in-line with the mass spectrometer ensured that all of the major metabolites (as evident from the 14C profile) were characterized by mass spectrometry.

MeSH terms

  • Amino Acid Chloromethyl Ketones / analysis*
  • Amino Acid Chloromethyl Ketones / metabolism
  • Animals
  • Bile / chemistry*
  • Bile / metabolism
  • Carbon Radioisotopes
  • Chromatography, High Pressure Liquid / methods
  • Male
  • Mass Spectrometry
  • Oligopeptides / analysis*
  • Rats
  • Rats, Sprague-Dawley
  • Thrombin / antagonists & inhibitors*

Substances

  • Amino Acid Chloromethyl Ketones
  • Carbon Radioisotopes
  • N-methylphenylalanyl-prolyl-arginine 1,1-difluorobutyl ketone
  • Oligopeptides
  • N-methylphenylalanyl-prolyl-arginine
  • Thrombin