Synthesis and DNA damaging ability of enediyne-polyamine conjugates

被引:27
作者
Suzuki, I [1 ]
Shigenaga, A [1 ]
Nemoto, H [1 ]
Shibuya, M [1 ]
机构
[1] Univ Tokushima, Fac Pharmaceut Sci, Tokushima 7708505, Japan
关键词
D O I
10.1016/j.tetlet.2003.12.139
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Polyamine-enediyne conjugates were synthesized and exhibited potent DNA damaging ability under physiological conditions. The extent of their activity was shown to depend upon the polyamine length that regulates the DNA binding affinity of the conjugates, and enhanced DNA damaging activities were observed under slightly acidic conditions. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1955 / 1959
页数:5
相关论文
共 28 条
[1]   Asymmetric intercalation of N1-(acridin-9-ylcarbonyl)spermine at homopurine sites of duplex DNA [J].
Blagbrough, IS ;
Taylor, S ;
Carpenter, ML ;
Novoselskiy, V ;
Shamma, T ;
Haworth, IS .
CHEMICAL COMMUNICATIONS, 1998, (08) :929-930
[2]  
BLAGBROUGH IS, 1997, PHARM SCI, V3, P223
[3]   Fused and bridged bi- and tri-cyclic lactams via sequential metallo-azomethine ylide cycloaddition-lactamisation [J].
Blaney, P ;
Grigg, R ;
Rankovic, Z ;
Thornton-Pett, M ;
Xu, J .
TETRAHEDRON, 2002, 58 (09) :1719-1737
[4]   POTENTIAL ANTI-TUMOR AGENTS .28. DEOXYRIBONUCLEIC-ACID POLYINTERCALATING AGENTS [J].
CAIN, BF ;
BAGULEY, BC ;
DENNY, WA .
JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (07) :658-668
[5]   Xylylated dimers of putrescine and polyamines: influence of the polyamine backbone on spermidine transport inhibition [J].
Covassin, L ;
Desjardins, M ;
Soulet, D ;
Charest-Gaudreault, R ;
Audette, M ;
Poulin, R .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (19) :3267-3271
[6]   DNA alkylation sites of nitrogen mustards conjugated to polyamines and their implications for polyamine-DNA interactions [J].
Cullis, PM ;
Merson-Davies, L ;
Sutcliffe, MJ ;
Weaver, R .
CHEMICAL COMMUNICATIONS, 1998, (16) :1699-1700
[7]  
Fujita M, 1998, CHEM PHARM BULL, V46, P631
[8]   Homologation of polyamines in the rapid synthesis of lipospermine conjugates and related lipoplexes [J].
Geall, AJ ;
Blagbrough, IS .
TETRAHEDRON, 2000, 56 (16) :2449-2460
[9]  
Karigiannis G, 2000, EUR J ORG CHEM, V2000, P1841
[10]   Synthesis and antimicrobial activity of squalamine analogue [J].
Kim, HS ;
Choi, BS ;
Kwon, KC ;
Lee, SO ;
Kwak, HJ ;
Lee, CH .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (08) :2059-2065