Separatory determination of diastereomeric ibuprofen glucuronides in human urine by liquid chromatography/electrospray ionization-mass spectrometry

✍ Scribed by Shigeo Ikegawa; Naoaki Murao; Junji Oohashi; Junichi Goto

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 80 KB
• Volume: 12
• Category: Article
• ISSN: 0269-3879
• DOI: 10.1002/(sici)1099-0801(199811/12)12:6<317::aid-bmc752>3.0.co;2-t

✦ Synopsis

A method for the separatory determination of diastereomeric isomers of glucuronic acid conjugates of ibuprofen having a carboxyl group at the chiral center by liquid chromatography (LC)/electrospray ionization (ESI)-mass spectrometry (MS) has been developed. The authentic specimens of acyl glucuronides of R(À)-and S()-ibuprofen were chemically synthesized by the Mitsunobu reaction. In the ESI mode, the glucuronides were characterized by an abundant quasi-molecular ion [M-H] À , and the formation of the negative ion was markedly influenced by a drift voltage. The resolution of diastereomeric isomers was achieved on a Develosil ODS-HG-5 column with 20 mM ammonium acetate (pH 5.0):acetonitrile (5:2, v/v) as a mobile phase where diastereomers were monitored with a corresponding quasi-molecular ion. After oral administration of racemic ibuprofen, a preferential excretion of (S)-ibuprofen glucuronide into the urine was observed.