Novel naphthalimide hydroperoxide photonucleases: the role of thiocyclic-fused area and the difference in spectra, photochemistry and photobiological activity

Yufang Xu; Xuhong Qian; Wei Yao; Ping Mao; Jingnan Cui

doi:10.1016/j.bmc.2003.09.026

Novel naphthalimide hydroperoxide photonucleases: the role of thiocyclic-fused area and the difference in spectra, photochemistry and photobiological activity

Bioorg Med Chem. 2003 Dec 1;11(24):5427-33. doi: 10.1016/j.bmc.2003.09.026.

Authors

Yufang Xu¹, Xuhong Qian, Wei Yao, Ping Mao, Jingnan Cui

Affiliation

¹ 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.

PMID: 14642587
DOI: 10.1016/j.bmc.2003.09.026

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
DNA / drug effects
DNA / radiation effects
DNA, Superhelical / drug effects
Deoxyribonucleases / chemistry*
Deoxyribonucleases / metabolism
Hydrogen-Ion Concentration
Imides / chemical synthesis
Imides / pharmacology*
Molecular Structure
Naphthalenes / chemical synthesis
Naphthalenes / pharmacology*
Peroxides / chemical synthesis
Peroxides / pharmacology*
Photochemistry
Spectrophotometry, Ultraviolet
Sulfhydryl Compounds / pharmacology*

Substances

DNA, Superhelical
Imides
Naphthalenes
Peroxides
Sulfhydryl Compounds
DNA
Deoxyribonucleases