Photo-induced DNA cleavage reaction characteristics of propargylic sulfones possessing anthraquinone chromophore.
DNA cleavage potency of propargylic sulfones possessing anthraquinone chromophore 1 under UV-irradiation was evaluated in comparison with the dark reaction. 1 showed inefficient DNA cleavage activity, while having considerably strong DNA binding ability. This result is accounted for by spatial conditions that the activated alkylating allenic site of intercalated 1 could not effectively approach to DNA bases, most probably guanine moiety, and thereby led to insufficient DNA strand cleavage. In contrast, the DNA cleavage activity of 1 was notably enhanced upon UV-irradiation (lambda(ex)=365 nm) followed by incubation. Under UV-irradiation, further DNA cleavage were occurred primary at 5'-G of GG steps within DNA. A DNA cleavage mechanism for 1, by which photo-induced one-electron oxidation of 5'-G of GG steps may occur along with ordinary alkylation, has been proposed.
Haruna
Ken-ichi
K
Department of Energy and Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
Tanabe
Kazuhito
K
Ishii
Atsushi
A
Dai
Wei-Min
WM
Min-Dai
Wei
W
Hatta
Hiroshi
H
Nishimoto
Sei-ichi
S
D000478:Alkylation; D000818:Animals; D000880:Anthraquinones / Q000737:chemistry*; D004247:DNA / Q000737:chemistry* / Q000528:radiation effects; D008297:Male; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010777:Photochemistry; D012474:Salmon; D013094:Spermatozoa / Q000737:chemistry; D013450:Sulfones / Q000737:chemistry*; D014466:Ultraviolet Rays
D000880:Anthraquinones; D013450:Sulfones; D004247:DNA