Inhibition of DNA cross-linking by mitomycin C by peroxidase-mediated oxidation of mitomycin C hydroquinone

J Biol Chem. 2001 Sep 14;276(37):34445-52. doi: 10.1074/jbc.M104263200. Epub 2001 Jul 16.

Abstract

Mitomycin C requires reductive activation to cross-link DNA and express anticancer activity. Reduction of mitomycin C (40 microm) by sodium borohydride (200 microm) in 20 mm Tris-HCl, 1 mm EDTA at 37 degrees C, pH 7.4, gives a 50-60% yield of the reactive intermediate mitomycin C hydroquinone. The hydroquinone decays with first order kinetics or pseudo first order kinetics with a t(12) of approximately 15 s under these conditions. The cross-linking of T7 DNA in this system followed matching kinetics, with the conversion of mitomycin C hydroquinone to leuco-aziridinomitosene appearing to be the rate-determining step. Several peroxidases were found to oxidize mitomycin C hydroquinone to mitomycin C and to block DNA cross-linking to various degrees. Concentrations of the various peroxidases that largely blocked DNA cross-linking, regenerated 10-70% mitomycin C from the reduced material. Thus, significant quantities of products other than mitomycin C were produced by the peroxidase-mediated oxidation of mitomycin C hydroquinone or products derived therefrom. Variations in the sensitivity of cells to mitomycin C have been attributed to differing levels of activating enzymes, export pumps, and DNA repair. Mitomycin C hydroquinone-oxidizing enzymes give rise to a new mechanism by which oxic/hypoxic toxicity differentials and resistance can occur.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Borohydrides / pharmacology
  • Chromatography, High Pressure Liquid
  • DNA / metabolism*
  • Hydroquinones / metabolism*
  • Mitomycin / metabolism*
  • Oxidation-Reduction
  • Peroxidases / physiology*

Substances

  • Borohydrides
  • Hydroquinones
  • Mitomycin
  • sodium borohydride
  • DNA
  • Peroxidases
  • hydroquinone