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Hydroxymethylfurfural: an enemy or a friendly xenobiotic? A bioanalytical approach

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Abstract

Hydroxymethylfurfural (HMF), a well-known heterocyclic Maillard reaction product, has often been studied for its potential toxic, mutagenic, and carcinogenic effects. Recent clinical studies, however, have strongly suggested that HMF might have exciting antitumor potential. We report on the development and validation of a bioanalytical assay for HMF that could be suitable as a basis for pharmacokinetic models in cancer patients. Two strategies were tested, i.e., direct and indirect methodologies. A direct isocratic LC determination at 283 nm was designed. Two indirect attempts involved derivatization coupled to HPLC-UV. It was possible to resolve the stereoisomers of the HMF derivative, and factors influencing their equilibrium ratio are discussed. HMF was extracted from the biomatrix by solid-phase extraction using different cartridges. A comparative study was made of the implemented methods as well as the extraction protocols. Both indirect assays proved to be more sensitive and were used to assess HMF quantitatively in human plasma. However, the newly introduced derivatization conditions led to the highest sensitivity with a LOD (S/N ratio = 3) of at least 2 pmol analyte on column. The assay selectivity was satisfactory in pre- and post-dose real samples. The mean recoveries of the assays were 79% and 89%, with acceptable accuracies and reproducibilities.

Schematic representation of hydroxymethylfurfural (HMF) in human plasma

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Acknowledgments

We are very grateful to C.Y.L. Pharmazeutika Gmbh especially Ch. Buecherl and P. Moser for the partial financial support of this work.

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Authors and Affiliations

  1. Institute of Pharmaceutical Sciences, Pharmaceutical Chemistry, University of Graz, Schubertstraβe 1, 8010, Graz, Austria

    K. Michail, O. Kunert & R. Wintersteiger

  2. Faculty of Pharmacy-Pharmaceutical Chemistry, University of Alexandria, Alexandria, Egypt

    K. Michail

  3. Department of Thoracic and Hyperbaric Surgery, Medical University of Graz, Graz, Austria

    V. Matzi & A. Maier

  4. Department of Urology, Medical University of Vienna, Vienna, Austria

    R. Herwig

  5. Institute of Physiological Chemistry, Medical University of Graz, Graz, Austria

    J. Greilberger

  6. Department of Biomedical Research, Medical University of Graz, Graz, Austria

    H. Juan

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  1. K. Michail
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  2. V. Matzi
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Correspondence to R. Wintersteiger.

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Michail, K., Matzi, V., Maier, A. et al. Hydroxymethylfurfural: an enemy or a friendly xenobiotic? A bioanalytical approach. Anal Bioanal Chem 387, 2801–2814 (2007). https://doi.org/10.1007/s00216-007-1121-6

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  • DOI: https://doi.org/10.1007/s00216-007-1121-6

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