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The synthesis and the investigation of the Cu(II)-binding, the DNA-binding, and the DNA-damaging properties of a conjugate between the benzo[b]quinolizinium ion and the bis(pyridin-2-ylmethyl)aminoreceptor are presented. Photometric and fluorimetric titrations as well as CD spectroscopic analysis reveal that the 9-bis(pyridin-2-ylmethyl)aminobenzo[b]quinolizinium ligand intercalates into DNA (Kb = 1.9 × 104 M−1) and exhibits a high selectivity towards complexation of Cu2+ in water (Kb = 4.3 × 104 M−1). This combination of functionalities allows to localize Cu2+ in close proximity of DNA, where these metal ions induce efficient DNA damage, as shown by the single-strand cleavage of supercoiled plasmidDNA. Notably, the DNA cleavage does not require additional reagents nor light.
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