N-aroyloxynaphthalimides as novel highly efficient DNA photocleavers:: substituent effects

被引:14
作者
Qian, XH [1 ]
Yao, W
Chen, G
Huang, XY
Mao, P
机构
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China
[2] E China Univ Sci & Technol, Inst Pesticides & Pharmaceut, Shanghai 200237, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0040-4039(01)01214-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel DNA photocleaver family of N-benzovloxythioxonaphthalimides. which show improved DNA intercalation and photocleaving activity compared with their oxo- counterparts, were synthesized and evaluated. The substituents on the benzene ring of the benzoyloxy moiety have an important and unusual influence on the DNA photocleaving activity. N-(p-Methoxylbenzovloxy)thioxonaphthalimide is able to photocleave DNA at low concentration (5 muM) with 'time-resolved' and pH independent properties. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6175 / 6178
页数:4
相关论文
共 18 条
[1]   SEQUENCE-SPECIFIC DOUBLE-STRAND CLEAVAGE OF DNA BY FE BLEOMYCIN .1. THE DETECTION OF SEQUENCE-SPECIFIC DOUBLE-STRAND BREAKS USING HAIRPIN OLIGONUCLEOTIDES [J].
ABSALON, MJ ;
KOZARICH, JW ;
STUBBE, J .
BIOCHEMISTRY, 1995, 34 (06) :2065-2075
[2]   N-HYDROXYPYRIDINETHIONES AS PHOTOCHEMICAL HYDROXYL RADICAL SOURCES FOR OXIDATIVE DNA-DAMAGE [J].
ADAM, W ;
BALLMAIER, D ;
EPE, B ;
GRIMM, GN ;
SAHAMOLLER, CR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (19) :2156-2158
[3]   PHOTOCHEMISTRY OF N-HYDROXYPYRIDINE-2 THIONE DERIVATIVES - INVOLVEMENT OF THE 2-PYRIDYLTHIYL RADICAL IN THE RADICAL-CHAIN REACTION-MECHANISM [J].
AVELINE, BM ;
KOCHEVAR, IE ;
REDMOND, RW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (38) :9699-9708
[4]  
BOIVIN J, 1992, B SOC CHIM FR, V129, P145
[5]   SUPEROXIDE AND HYDROGEN-PEROXIDE IN RELATION TO MAMMALIAN-CELL PROLIFERATION [J].
BURDON, RH .
FREE RADICAL BIOLOGY AND MEDICINE, 1995, 18 (04) :775-794
[6]   Homolytic cleavage energies of R-H bonds centered on carbon atoms of high electronegativity:: First general observations of O-type variation on C-HBDEs and the implication for the governing factors leading to the distinct O/S patterns of radical substituent effects [J].
Cheng, JP ;
Liu, B ;
Zhao, YY ;
Wen, Z ;
Sun, YK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) :9987-9992
[7]   FLUORESCENCE STUDIES ON THE INTERACTION OF FUROCOUMARINS WITH DNA IN THE DARK [J].
GUPTA, M ;
ALI, R .
JOURNAL OF BIOCHEMISTRY, 1984, 95 (05) :1253-1257
[8]   CALICHEAMICIN-DNA COMPLEXES - WARHEAD ALIGNMENT AND SACCHARIDE RECOGNITION OF THE MINOR-GROOVE [J].
IKEMOTO, N ;
KUMAR, RA ;
LING, TT ;
ELLESTAD, GA ;
DANISHEFSKY, SJ ;
PATEL, DJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (23) :10506-10510
[9]   DESIGNED ENEDIYNES - A NEW CLASS OF DNA-CLEAVING MOLECULES WITH POTENT AND SELECTIVE ANTICANCER ACTIVITY [J].
NICOLAOU, KC ;
DAI, WM ;
TSAY, SC ;
ESTEVEZ, VA ;
WRASIDLO, W .
SCIENCE, 1992, 256 (5060) :1172-1178
[10]  
Qian X. H., 2000, J CHEM SOC P2, P715, DOI DOI 10.1039/A908787G