The coordination of copper(II) to 1-hydroxy-4-(glycyl-histidyl-lysine)-anthraquinone; a synthetic model of anthraquinone anti-cancer drugs.
Results are reported of a pH-metric and spectroscopic (CD and ESR) study of the complexes formed between the pseudo-peptide 1-hydroxy-4-(Gly-His-Lys)-anthraquinone (Q-GHK) since, when complexed to copper ions, Q-GHK has been shown to be very effective in promoting the formation of free radicals and inducing DNA cleavage. Q-GHK forms very stable complexes with copper, the major species being bonded to three nitrogen donors in the coordination plane: an imidazole-N of the His residue and the peptide nitrogens of the Gly and His residues. This species is probably stabilized through bonding of the fourth planar coordination site of Cu(II) to the 9-anthraquinone oxygen. At high Q-GHK:copper ratios a second Q-GHK molecule is coordinated through its imidazole-N donor.
Pettit
L D
LD
School of Chemistry, The University, Leeds, United Kingdom.
Ueda
J
J
Morier-Teissier
E
E
Helbecque
N
N
Bernier
J L
JL
Henichart
J P
JP
Kozlowski
H
H
D000880:Anthraquinones / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry*; D002413:Cations, Divalent; D002942:Circular Dichroism; D003300:Copper / Q000737:chemistry*; D004578:Electron Spin Resonance Spectroscopy; D006863:Hydrogen-Ion Concentration; D008942:Mitoxantrone / Q000031:analogs & derivatives* / Q000737:chemistry
D000880:Anthraquinones; D000970:Antineoplastic Agents; D002413:Cations, Divalent; C075335:4-(glycyl-histidyl-lysine)-1-hydroxyanthraquinone; D003300:Copper; D008942:Mitoxantrone