Electrochemical reduction of the iodinated contrast medium iomeprol: iodine mass balance and identification of transformation products

  • Christian Zwiener
  • Thomas Glauner
  • Jochen Sturm
  • Michael Wörner
  • Fritz H. Frimmel
Original Paper

DOI: 10.1007/s00216-009-3098-9

Cite this article as:
Zwiener, C., Glauner, T., Sturm, J. et al. Anal Bioanal Chem (2009) 395: 1885. doi:10.1007/s00216-009-3098-9

Abstract

Potentiostatic-controlled electrochemical reduction of iomeprol was used to deiodinate iomeprol (IMP), a representative of the iodinated X-ray contrast media. The reduction process was followed by product analysis with liquid chromatography-electrospray ionization-tandem mass spectrometry and ion chromatography-inductively coupled plasma-mass spectrometry. The identification is mainly based on the interpretation of the mass fragmentation. The product analysis showed a rather selective deiodination process with the successive occurrence of IMP-I, IMP-2I, IMP-3I, and a transformation product (TP), respectively. The TP was formed from IMP-3I by a further cleavage of an amide bond and release of a (C = O)CHOH group from the side chain of IMP. The iodine mass balance on the basis of IMP and iodide showed a gap of about 26% at the beginning of the electrolysis process which could be completely closed by taking the intermediates IMP-I and IMP-2I into consideration. This means that the major intermediates and the TPs were considered and that the reduction process is a rather selective one to remove organically bound iodine from X-ray contrast media. An attractive application area would be the electrochemical deiodination of X-ray contrast media in urine of patients or hospital effluents.

Mass fragmentation of iomeprol and its deiodination products

Keywords

Electrolysis Cathodic dehalogenation Iodine mass balance Mass-spectrometric fragmentation 

Copyright information

© Springer-Verlag 2009

Authors and Affiliations

  • Christian Zwiener
    • 1
  • Thomas Glauner
    • 1
  • Jochen Sturm
    • 2
    • 3
  • Michael Wörner
    • 3
  • Fritz H. Frimmel
    • 1
  1. 1.Engler-Bunte-Institut, Chair of Water ChemistryUniversität Karlsruhe (TH)KarlsruheGermany
  2. 2.Daimler AGStuttgartGermany
  3. 3.Institute of Process Engineering in Life Sciences, Chair of Biomolecular Separation EngineeringUniversity of Karlsruhe (TH)KarlsruheGermany