DNA cleavage by the Cu(II) complex of the DNA-intercalating 9-bis(pyridin-2-ylmethyl)aminobenzo[b]quinolizinium.
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)amino receptor 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 (K(b) = 1.9 x 10(4) M(-1)) and exhibits a high selectivity towards complexation of Cu(2+) in water (K(b) = 4.3 x 10(4) M(-1)). This combination of functionalities allows to localize Cu(2+) in close proximity of DNA, where these metal ions induce efficient DNA damage, as shown by the single-strand cleavage of supercoiled plasmid DNA. Notably, the DNA cleavage does not require additional reagents nor light.
Tian
Maoqun
M
University of Siegen, Organic Chemistry II, Adolf-Reichwein-Str. 2, D-57068, Siegen, Germany.
Ihmels
Heiko
H
Brötz
Elke
E
D002942:Circular Dichroism; D056831:Coordination Complexes / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D053837:DNA Cleavage; D004249:DNA Damage; D007364:Intercalating Agents / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
C553996:9-bis(pyridin-2-ylmethyl)aminobenzo(b)quinolizinium; D056831:Coordination Complexes; D007364:Intercalating Agents; D011807:Quinolizines; D003300:Copper; D004247:DNA