Effect of a conjugated acridine moiety on the binding and reactivity of Cu(II)[9-acridinylmethyl-1,4,7-triazacyclononane] with DNA.
The DNA binding orientation and dynamic behavior of Cu(II) complexes of 1,4,7-triazacyclononane ([9]aneN(3)), 1, and an acridine conjugate, 2, were investigated by DNA fiber EPR (EPR=electron paramagnetic resonance) spectroscopy. Crystal and molecular structure of 2 were determined by X-ray diffraction. It has been shown that 1 binds to DNA in two different modes at room temperature; one species is rapidly rotating and the other is immobilized randomly on the DNA. The introduction of acridine to [9]aneN(3) fixed the [Cu([9]aneN(3))](2+) moiety of 2 in two different environments on the DNA: the g(mid R:mid R:) axis of one species (g( parallel)=2.26) is aligned perpendicularly to the DNA fiber axis whereas that of the other (g( parallel)=2.24) aligns<90 degrees with the DNA fiber axis. The different DNA binding structures of 1 and 2 are reflected also in their different efficiencies of DNA cleavage; 2 was found to be more effective both in oxidative and hydrolytic cleavage reactions.
Hirohama
Tomoya
T
Department of Applied Chemistry, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, 112-8551 Tokyo, Japan.
Arii
Hidekazu
H
Chikira
Makoto
M
D000166:Acridines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000818:Animals; D010584:Bacteriophage phi X 174; D002417:Cattle; D004247:DNA / Q000737:chemistry* / Q000187:drug effects; D004279:DNA, Viral / Q000737:chemistry / Q000187:drug effects; D004578:Electron Spin Resonance Spectroscopy; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D012474:Salmon; D013737:Testis; D013950:Thymus Gland
D000166:Acridines; C504263:Cu(II)(9-acridinylmethyl-1,4,7-triazacyclononane); D004279:DNA, Viral; D009942:Organometallic Compounds; D004247:DNA