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    One-electron reduction of adriamycin and daunomycin: short-term stability of the semiquinones.

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    Authors
    Mukherjee, Tulsi
    Land, Edward J
    Swallow, A John
    Bruce, J M
    Affiliation
    Paterson Institute for Cancer Research, Christie Hospital and Holt Radium Institute, Manchester, England.
    Issue Date
    1989-08-01
    
    Metadata
    Show full item record
    Abstract
    Pulse radiolysis studies of the one-electron reduction of adriamycin have now been extended to daunomycin. The daunomycin semiquinone has a pKa for phenolic dissociation of 2.8 +/- 0.1. Measurement of the one-electron reduction potential using several redox references at pH values within the range pH 6 to 12 indicated no significant difference between the semiquinones of adriamycin and those of daunomycin. A value of E1(7) = -341 +/- 15 mV (vs NHE) fitted the complete set of data for both compounds, with a pKa of the NH+3 group of the sugar moiety of 9.2 +/- 0.1. Measurement of equilibria between the semiquinones and the parent quinones and their fully reduced products showed a maximum semiquinone stability around pH 9. At pH 7 the stability constant is 0.04 for both adriamycin and daunomycin. From the equilibrium and E1 data, the second one-electron and the two-electron reduction potentials have been calculated over the pH range 7 to 12. E2(7) is -260 +/- 15 mV and Em7 is -300 +/- 15 mV for both compounds. The pKa values for the reduced anthracyclines have been calculated from the equilibrium data in the approximate pH range 7-12 to be 8.1 +/- 0.1 and 9.0 +/- 0.2 for the first two hydroxy groups and the two possible combinations for the ionization of the sugar NH+3 groups, with the remaining two hydroxy groups ionizing above pH 14.
    Citation
    One-electron reduction of adriamycin and daunomycin: short-term stability of the semiquinones. 1989, 272 (2):450-8 Arch. Biochem. Biophys.
    Journal
    Archives of Biochemistry and Biophysics
    URI
    http://hdl.handle.net/10541/111003
    DOI
    10.1016/0003-9861(89)90239-7
    PubMed ID
    2751311
    Type
    Article
    Language
    en
    ISSN
    0003-9861
    ae974a485f413a2113503eed53cd6c53
    10.1016/0003-9861(89)90239-7
    Scopus Count
    Collections
    All Paterson Institute for Cancer Research

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