Novel 2-aminothiazonaphthalimides as visible light activatable photonucleases: effects of intercalation, heterocyclic-fused area and side chains.
A new family of 2-aminothiazonaphthalimides with different side chains as novel intercalative and visible light activatable photonucleases, was designed, synthesized and quantitatively evaluated. The order of their photocleaving abilities was parallel to that of their intercalative properties. The compound with linear heterocyclic-fused chromophore could intercalate into and photocleave DNA more efficiently than the one with angular heterocyclic-fused chromophore. B(2), the most efficient compound, caused obvious DNA damage at 1 microM. Mechanism experiment showed that superoxide anion was involved.
Li
Zhigang
Z
State Key Laboratory of Fine Chemicals, Dalian University of Technology, PO Box 158, Zhongshan Road, Dalian 116012, China.
Yang
Qing
Q
Qian
Xuhong
X
D004249:DNA Damage / Q000187:drug effects / Q000528:radiation effects; D003851:Deoxyribonucleases / Q000737:chemistry* / Q000378:metabolism; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000494:pharmacology; D007364:Intercalating Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D008027:Light; D009690:Nucleic Acid Conformation / Q000187:drug effects; D010782:Photolysis; D010797:Phthalimides / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000737:chemistry; D013844:Thiazoles / Q000737:chemistry*
D006576:Heterocyclic Compounds, 4 or More Rings; D007364:Intercalating Agents; D010797:Phthalimides; D013844:Thiazoles; D013481:Superoxides; C031363:2-aminothiazoline; D003851:Deoxyribonucleases