Oxime esters of anthraquinone as photo-induced DNA-cleaving agents for single- and double-strand scissions

被引：28
作者：
Hwu, JR
Tsay, SC
Hong, SC
Leu, YJ
Liu, CF
Chou, SSP [1 ]
机构：
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
[2] Fu Jen Catholic Univ, Dept Chem, Taipei 24205, Taiwan
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 14期
关键词：
anthraquinone; DNA cleavage; photolysis; radicals;
D O I：
10.1016/S0040-4039(03)00375-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Anthraquinone-O-9-(4-cyanobenzoyl)oxime (13) with binding constant of 4.49x 10(4) M-1 exhibited single-strand scission of DNA at the concentration of 10 muM and double-strand scission at 50 muM upon UV irradiation. (C) 2003 Published by Elsevier Science Ltd.
引用
收藏
页码：2957 / 2960
页数：4
相关论文
共 25 条
[1]   SPECTROSCOPIC AND KINETIC CHARACTERISTICS OF AROYLOXYL RADICALS .2. BENZOYLOXYL AND RING-SUBSTITUTED AROYLOXYL RADICALS [J].
CHATEAUNEUF, J ;
LUSZTYK, J ;
INGOLD, KU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (09) :2886-2893
[2]   DNA cleavage potency, cytotoxicity, and mechanism of action of a novel class of enediyne prodrugs [J].
Dai, WM ;
Lai, KW ;
Wu, AX ;
Hamaguchi, W ;
Lee, MYH ;
Zhou, L ;
Ishii, A ;
Nishimoto, S .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (04) :758-761
[3]   UVA light-induced DNA cleavage by isomeric methylbenz[a]anthracenes [J].
Dong, S ;
Fu, PP ;
Shirsat, RN ;
Hwang, HM ;
Leszczynski, J ;
Yu, H .
CHEMICAL RESEARCH IN TOXICOLOGY, 2002, 15 (03) :400-407
[4]   INTERACTIONS OF ANTITUMOR DRUGS WITH NATURAL DNA - H-1-NMR STUDY OF BINDING MODE AND KINETICS [J].
FEIGON, J ;
DENNY, WA ;
LEUPIN, W ;
KEARNS, DR .
JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (04) :450-465
[5]   Three-dimensional structure and reactivity of a photochemical cleavage agent bound to DNA [J].
Gasper, SM ;
Armitage, B ;
Shui, XQ ;
Hu, GG ;
Yu, CJ ;
Schuster, GB ;
Williams, LD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (48) :12402-12409
[6]   ARYL RADICAL ADDITIONS TO ALDEHYDES AND OXIME ETHERS - THE TANDEM ENEDIYNE-RADICAL CYCLIZATION [J].
GRISSOM, JW ;
KLINGBERG, D .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6559-6564
[7]   THE BENZOYLOXY RADICAL - ATTEMPTED PHOTOCHEMICAL GENERATION FOR KINETIC-STUDIES AND SOME RELATIVE RATE CONSTANTS [J].
GROSSI, L ;
LUSZTYK, J ;
INGOLD, KU .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5882-5885
[8]   ELECTRON-PARAMAGNETIC-RESONANCE STUDIES OF THE REACTION OF ARYL RADICALS WITH NUCLEIC-ACIDS AND THEIR COMPONENTS [J].
HAZLEWOOD, C ;
DAVIES, MJ ;
GILBERT, BC ;
PACKER, JE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (12) :2167-2174
[9]  
HURLEY LH, 1996, ADV DNA SEQUENCE SPE, V2
[10]   Development of arylhydrazines and diphenyl arylhydrazidophosphates as photo-induced DNA-cleaving agents [J].
Hwu, JR ;
Yau, CS ;
Tsai, FY ;
Tsay, SC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (17) :2451-2453
123