N-aroyloxylthioxo-naphthalimides as DNA photocleavers of aroyloxyl oxygen radicals: synthesis, evaluation, and substituents' effect.
Novel N-Aroyloxylthioxo-naphthalimides as highly efficient 'time-resolved' DNA photocleavers of aroyloxyl radicals type were designed and synthesized. The substituents at the aroyloxyl moiety have an important and unusual influence on the DNA photocleavage, and DNA photodamages of the compounds were unusually not depended on the electronic effects of substituents on the corresponding oxygen-centered radicals. With AM1 semi-empirical quantum calculation, it was found that their photocleaving activities were correlated with the densities of electron clouds on the N-O bonds in the triplet state. N-(m-Dichloro-benzoyloxy)-thioxo-naphthalimide could photodamage DNA effectively at less than the concentration of 2 microM.
Xu
Yufang
Y
Shanghai Key Laboratory of Chemical Biology, Institute of Pesticides & Pharmaceuticals, East China University of Science and Technology, Shanghai 200237, China.
Huang
Xiayu
X
Qian
Xuhong
X
Yao
Wei
W
D004247:DNA / Q000187:drug effects* / Q000528:radiation effects; D004353:Drug Evaluation, Preclinical; D005609:Free Radicals; D007094:Imides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010100:Oxygen / Q000737:chemistry*; D010777:Photochemistry; D013057:Spectrum Analysis
D005609:Free Radicals; D007094:Imides; D004247:DNA; D010100:Oxygen