Syntheses and copper(II)-dependent DNA photocleavage by acridine and anthracene 1,10-phenanthroline conjugate systems.
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 degrees 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 microM to 0.25 microM, the reverse trend is observed. DNA photocleavage is markedly reduced in the presence of copper(II).
Gude
Lourdes
L
Departamento de Química Orgánica, Universidad de Alcalá, Alcalá de Henares, Madrid, Spain.
Fernández
María-José
MJ
Grant
Kathryn B
KB
Lorente
Antonio
A
D000166:Acridines / Q000737:chemistry*; D000873:Anthracenes / Q000737:chemistry*; D002614:Chelating Agents / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D010618:Phenanthrolines / Q000737:chemistry*; D010777:Photochemistry; D013056:Spectrophotometry, Ultraviolet
D000166:Acridines; D000873:Anthracenes; D002614:Chelating Agents; D010618:Phenanthrolines; D003300:Copper; D004247:DNA; C025205:1,10-phenanthroline