Photoinduced DNA cleavage by naphthalimide hydroperoxide-specific strand scission at -GG- site of DNA.
We have prepared a series of naphthalene hydroperoxides (1-3) which possess hydroperoxy group at gamma-position of imide carbonyl. Upon photoirradiation (greater than 350 nm) hydroperoxides (1-3) decomposed with efficient generation of hydroxyl radical, which was confirmed by esr spin trapping technique using dimethylpyrroline oxide as a spin trapper. All these hydroperoxides induced DNA strand scission upon photoirradiation (greater than 350 nm), especially hydroperoxide 3 cleaved plasmid phi X 174 DNA (Form I) to give nicked (Form II) and linear (Form III) DNA even at 1 microM concentration. Further, it was observed that 3 exclusively cleaved DNA at the 5'-G site of -GG-sequence.
Matsugo
S
S
Department of Chemistry, Kobe University of Mercantile Marine, Japan.
Saito
I
I
D001483:Base Sequence; D004247:DNA / Q000187:drug effects* / Q000528:radiation effects; D004278:DNA, Superhelical / Q000737:chemistry / Q000187:drug effects; D004578:Electron Spin Resonance Spectroscopy; D007094:Imides / Q000737:chemistry / Q000494:pharmacology; D008027:Light; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000494:pharmacology*; D010545:Peroxides / Q000737:chemistry / Q000494:pharmacology*
D004278:DNA, Superhelical; D007094:Imides; D009281:Naphthalenes; D010545:Peroxides; D004247:DNA