Horseradish peroxidase/hydrogen peroxide-catalyzed oxidation of VP16-213. Identification of a new metabolite

Massimo Broggini, Cosmo Rossi, Emilio Benfenati, Maurizio D'Incalci, Roberto Fanelli, Pierluigi Gariboldi

Research output: Contribution to journalArticlepeer-review

Abstract

VP16 was submitted to oxidation catalyzed by horseradish peroxidase (HRP) and H2O2 in phosphate buffer (pH 7.0). The product of the reaction, which has a high performance liquid chromatographic (HPLC) retention time different from the previously known metabolites of VP16, was identified as 1,2,3,4-tetradehydro-VP16 by 1H-NMR and mass spectrometry (MS) analysis. It was found to result from the loss of four hydrogens and the formation of an aromatic ring (ring B of VP16). This new product retains, in the 4′ position of the E ring of VP16, the hydroxy group which is crucial for the antitumoral activity of podophyllotoxin derivatives. The reaction was linear in a wide range of VP16 concentrations and was dependent on the concomitant presence of peroxidase and H2O2.

Original languageEnglish
Pages (from-to)215-224
Number of pages10
JournalChemico-Biological Interactions
Volume55
Issue numberC
DOIs
Publication statusPublished - 1985

Keywords

  • Horseradish peroxidase
  • Nuclear magnetic resonance
  • VP16 oxidation
  • VP16-metabolism

ASJC Scopus subject areas

  • Toxicology

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