Syntheses and copper(ii)-dependent DNA photocleavage by acridine and anthracene 1,10-phenanthroline conjugate systems

Abstract

We report the syntheses and characterization of a series of compounds based on 1,10-phenanthroline covalently tethered, at the 2 and 9 positions, to either two benzene, naphthalene, acridine or anthracene chromophores. The acridine and anthracene derivatives are shown to efficiently cleave pUC19 plasmid DNA upon irradiation with ultraviolet light (pH = 7.0, 22 °C, 350 nm). Furthermore, photocleavage levels are markedly increased by the addition of Cu²⁺ to the DNA photolysis reactions. Interestingly, when the concentrations of the anthracene compounds are lowered from 35 µM to 0.25 µM, the reverse trend is observed. DNA photocleavage is markedly reduced in the presence of copper(II).