Novel naphthalimide hydroperoxide photonucleases: the role of thiocyclic-fused area and the difference in spectra, photochemistry and photobiological activity.
Novel five- and six-membered thiocyclic-fused naphthalimide hydroperoxides (7, 8) as photonucleases were designed, synthesized via unusual isomerization in Pschorr cyclization and photooxygenation. The five-membered 7 was able to induce single-strand nicks in duplex DNA pH independently (7.0-8.5) at 0.5 microM under 366 nm, while the six-membered 8 could photonick the duplex DNA pH dependently (7.0-8.5) at 5 microM under 450 nm and showed 'time-controlled' photo-bioactivity. Their thiocycles and the angular conjugated plane have contributions to their binding affinity with DNA and photocleaving efficiency.
Xu
Yufang
Y
Shanghai Key Lab. of Chemical Biology, Institute of Pesticides Pharmaceuticals, East China University of Science and Technology, PO Box 544, 130Meilong Road, Shanghai 200237, China.
Qian
Xuhong
X
Yao
Wei
W
Mao
Ping
P
Cui
Jingnan
J
D003500:Cyclization; D004247:DNA / Q000187:drug effects / Q000528:radiation effects; D004278:DNA, Superhelical / Q000187:drug effects; D003851:Deoxyribonucleases / Q000737:chemistry* / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D007094:Imides / Q000138:chemical synthesis / Q000494:pharmacology*; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis / Q000494:pharmacology*; D010545:Peroxides / Q000138:chemical synthesis / Q000494:pharmacology*; D010777:Photochemistry; D013056:Spectrophotometry, Ultraviolet; D013438:Sulfhydryl Compounds / Q000494:pharmacology*
D004278:DNA, Superhelical; D007094:Imides; D009281:Naphthalenes; D010545:Peroxides; D013438:Sulfhydryl Compounds; D004247:DNA; D003851:Deoxyribonucleases