A perylenedicarboxamide linker for DNA hairpins

被引:28
作者
Lewis, Frederick D. [1 ]
Zhang, Ligang [1 ]
Kelley, Richard F. [1 ]
McCamant, David [1 ]
Wasielewski, Michael R. [1 ]
机构
[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
关键词
fluorescence quenching; electron transfer; hole injection; arenedicarboxamide; circular dichroism;
D O I
10.1016/j.tet.2006.10.089
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis and properties of a perylenediamide diol linker and several DNA hairpins possessing this linker are described. The diol linker absorbs and fluoresces strongly in the visible. Hairpins having poly(dA)-poly(dT) stems have fluorescence quantum yields and decay times similar to those of the linker, indicating that hole injection does not occur from the singlet excited linker into the base pair domain. Fluorescence quenching by dG or dZ bases is observed when these bases are located near the linker. The strong distance dependence of fluorescence quenching is consistent with a superexchange mechanism for electron transfer. Failure to observe formation of the linker anion radical by means of femtosecond time resolved absorption spectroscopy is attributed to fast charge recombination. The properties and behavior of the perylene linker and its hairpins are compared to those of other arenedicarboxamide linkers. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3457 / 3464
页数:8
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