(P)-helicene displays chiral selection in binding to Z-DNA

被引:207
作者
Xu, Y
Zhang, YX
Sugiyama, H
Umano, T
Osuga, H
Tanaka, K [1 ]
机构
[1] Tokyo Med & Dent Univ, Inst Biomat & Bioengn, Chiyoda Ku, Tokyo 1010062, Japan
[2] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto, Japan
[3] Wakayama Univ, Fac Syst Engn, Dept Mat Sci & Chem, Wakayama 6408510, Japan
关键词
D O I
10.1021/ja0499748
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantiomeric helicenes of (P)-A and (M)-A were synthesized. The binding of the helicenes to B- and Z-DNA was studied quantitatively by CD, equilibrium dialysis, and fluorescence spectroscopy. Enantiomeric (P)-A not only bound selectively to Z-DNA but also effectively converted the B-DNA conformation to Z-DNA. The enantioselectivity of the helicenes offers a new route for the rational design of inhibitors of biological functions that may depend on Z-DNA. Copyright © 2004 American Chemical Society.
引用
收藏
页码:6566 / 6567
页数:2
相关论文
共 18 条
[11]  
Norden B, 1996, MET IONS BIOL SYST, V33, P177
[12]  
Perry, 1999, Expert Opin Investig Drugs, V8, P1981, DOI 10.1517/13543784.8.12.1981
[13]   Allosteric, chiral-selective drug binding to DNA [J].
Qu, XG ;
Trent, JO ;
Fokt, I ;
Priebe, W ;
Chaires, JB .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (22) :12032-12037
[14]   Z-DNA: the long road to biological function [J].
Rich, A ;
Zhang, SG .
NATURE REVIEWS GENETICS, 2003, 4 (07) :566-572
[15]   THE CHEMISTRY AND BIOLOGY OF LEFT-HANDED Z-DNA [J].
RICH, A ;
NORDHEIM, A ;
WANG, AHJ .
ANNUAL REVIEW OF BIOCHEMISTRY, 1984, 53 :791-846
[16]   Structure of the DLM-1-Z-DNA complex reveals a conserved family of Z-DNA-binding proteins [J].
Schwartz, T ;
Behlke, J ;
Lowenhaupt, K ;
Heinemann, U ;
Rich, A .
NATURE STRUCTURAL BIOLOGY, 2001, 8 (09) :761-765
[17]   Crystal structure of the Zα domain of the human editing enzyme ADAR1 bound to left-handed Z-DNA [J].
Schwartz, T ;
Rould, MA ;
Lowenhaupt, K ;
Herbert, A ;
Rich, A .
SCIENCE, 1999, 284 (5421) :1841-1845
[18]   Synthesis, structure and thermodynamic properties of 8-methylguanine-containing oligonucleotides: Z-DNA under physiological salt conditions [J].
Sugiyama, H ;
Kawai, K ;
Matsunaga, A ;
Fujimoto, K ;
Saito, I ;
Robinson, H ;
Wang, AHJ .
NUCLEIC ACIDS RESEARCH, 1996, 24 (07) :1272-1278