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Related Experiment Videos

Autocatalytic quinone methide formation from mitomycin c.

D M Peterson, J Fisher

    Biochemistry
    |July 15, 1986
    PubMed
    Summary
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    Mitomycin C undergoes reductive activation via an autocatalytic pathway initiated by NADPH and the Old Yellow enzyme. This process generates mitosene products through a pH-dependent quinone methide intermediate.

    Area of Science:

    • Biochemistry
    • Enzymology
    • Chemical Biology

    Background:

    • Mitomycin C is an anticancer agent activated by reduction.
    • Understanding its activation mechanism is crucial for drug development.

    Purpose of the Study:

    • To elucidate the mechanism of Mitomycin C reductive activation by NADPH and the Old Yellow enzyme.
    • To investigate the role of pH and intermediates in the reaction pathway.

    Main Methods:

    • Anaerobic enzymatic reactions with Mitomycin C, NADPH, and Old Yellow enzyme.
    • Kinetic analysis and mathematical modeling.
    • Product identification and characterization.

    Main Results:

    • Mitomycin C is converted to cis- and trans-1-hydroxy-2,7-diaminomitosenes at pH 8.0 via a quinone methide intermediate.

    Related Experiment Videos

  • At pH 6.5, 2,7-diaminomitosene is the major product, formed by reaction with H+.
  • The reaction proceeds via an autocatalytic pathway initiated by the enzyme and NADPH, and propagated by mitosene hydroquinones.

    • Conclusions:

    • The reductive activation of Mitomycin C involves a pH-dependent quinone methide intermediate.
    • An autocatalytic pathway, potentially dominant in vitro, is initiated by NADPH and the Old Yellow enzyme.
    • Oxidation of mitosene hydroquinones may be essential for stable adduct formation in vivo.