The direct reduction of cytochrome c by some anthraquinone antitumor compounds.
The ability of various anthraquinone antitumor agents to undergo oxidative metabolism with concomitant cytochrome c reduction has been examined. The reduction of cytochrome c by the compounds had enzymatic character and occurred without the formation of oxygen radicals. We have found that the presence of at least two phenolic groups in ring A of the compounds studied was indispensable for their oxidative metabolism. It is suggested that these groups are essential for the binding to cytochrome c. Furthermore, it has been shown that the existence of hydroxy groups in side chains of these compounds augments their interaction with this hemoprotein. On the basis of the results obtained for a series of analogs of mitoxantrone, we can conclude that the structural factor directly responsible for cytochrome c reduction is the primary or secondary amino group of the side chains.
Tarasiuk
J
J
Department of Pharmaceutical Technology and Biochemistry, Technical University of Gdańsk, Poland.
Stefanska
B
B
Borowski
E
E
D000880:Anthraquinones / Q000009:adverse effects / Q000737:chemistry / Q000378:metabolism*; D000970:Antineoplastic Agents / Q000009:adverse effects / Q000737:chemistry / Q000378:metabolism*; D003574:Cytochrome c Group / Q000378:metabolism*; D008942:Mitoxantrone / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D010084:Oxidation-Reduction; D017382:Reactive Oxygen Species / Q000009:adverse effects / Q000378:metabolism; D013329:Structure-Activity Relationship; D013482:Superoxide Dismutase / Q000494:pharmacology
D000880:Anthraquinones; D000970:Antineoplastic Agents; D003574:Cytochrome c Group; D017382:Reactive Oxygen Species; D008942:Mitoxantrone; D013482:Superoxide Dismutase