Reactivities of flavonoids with different hydroxyl substituents for the cleavage of DNA in the presence of Cu(II)

DNA strand scission reactions of flavonoids in the presence of Cu(II) have been extended by using flavonoids with a variety of patterns of hydroxyl su bstitution. In particular we have examined for the first time a flavonoid ( 7,8-dihydroxyflavone) that lacks the possibility of forming a complex invol ving the oxygen at position 4, By comparing the reactivities of several fla vonoids, including data from the literature, we draw generalizations for th e correlation of structure and activity and present evidence for at least t hree different modes of action of flavonoids as genotoxic agents. Copyright (C) 1999 John Wiley & Sons, Ltd.