Steric effect on the nuclease activity of Cu(II) complexes with aminoquinoline derivatives.
Three copper(II) complexes of aminoquinoline derivatives, l-glycine-N'-8-quinolylamide (L1), l-alanine-N'-8-quinolylamide (L2), and N-(8-quinolyl) pyridine-2-carboxamide (L3) have been shown to cleave plasmid DNA pBR322 and pUC18 with or without the presence of H(2)O(2)/ascorbate. Crystallographic data reveal that the Cu(II) coordination plane in [Cu(L1)(Ac)(H(2)O)] (1) and [Cu(L2)(Ac)] (2) is nearly co-planar with the quinoline ring. The cleavage activity follows the order of complex 1>complex 2>complex 3, which is in agreement with the reverse order of the steric hindrance of the amino-substituent of the ligands. The presence of the standard radical scavengers does not have a clear effect on the cleavage efficiency of the Cu(II) complexes, suggesting the reactive species leading to DNA damage could be DNA-bound copper-centered radicals rather than the free diffusible ones.
Shao
Ying
Y
State Key Laboratory of Coordination Chemistry, Coordination Chemistry Institute, Nanjing University, 210093 Nanjing, PR China.
Zhang
Junyong
J
Tu
Chao
C
Dai
Chunhui
C
Xu
Qiang
Q
Guo
Zijian
Z
D000634:Aminoquinolines / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004247:DNA / Q000737:chemistry; D004249:DNA Damage; D016166:Free Radical Scavengers / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D010957:Plasmids / Q000187:drug effects; D012260:Ribonucleases / Q000737:chemistry / Q000187:drug effects*
D000634:Aminoquinolines; D016166:Free Radical Scavengers; D009942:Organometallic Compounds; D003300:Copper; D004247:DNA; D012260:Ribonucleases