One-electron reduction of adriamycin: Properties of the semiquinone

Pulse radiolysis of aqueous solutions containing adriamycin and redox indicators of known one-electron reduction potential ( E 1) shows that its E 1 at pH 7 is −328 mV (vs NHE). The variation E 1 with pH in the range 6–12 shows that the net charge on the semiquinone at pH 7 is zero. As well as the p...

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Veröffentlicht in:	Arch. Biochem. Biophys.; (United States) 1983-08, Vol.225 (1), p.116-121
Hauptverfasser:	Land, Edward J., Mukherjee, Tulsi, Swallow, A.John, Bruce, J.Malcolm
Format:	Artikel
Sprache:	eng
Schlagworte:	400400 - Electrochemistry 400600 - Radiation Chemistry ANTI-INFECTIVE AGENTS ANTIBIOTICS ANTINEOPLASTIC DRUGS Benzoquinones Chemical Phenomena CHEMICAL RADIATION EFFECTS CHEMISTRY DOXORUBICIN DRUGS ELECTRIC POTENTIAL ELECTROCHEMISTRY Electrons INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY Mathematics Models, Chemical Oxidation-Reduction Quinones RADIATION CHEMISTRY RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY RADIATION EFFECTS
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Zusammenfassung:	Pulse radiolysis of aqueous solutions containing adriamycin and redox indicators of known one-electron reduction potential ( E 1) shows that its E 1 at pH 7 is −328 mV (vs NHE). The variation E 1 with pH in the range 6–12 shows that the net charge on the semiquinone at pH 7 is zero. As well as the p K a values of 2.9 and ≥ 14 established independently, the semiquinone has a p K a close to 9.2. The new data enable the structure and likely reactivity of the semiquinone to be specified.
ISSN:	0003-9861 1096-0384
DOI:	10.1016/0003-9861(83)90013-9