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

来源：

TETRAHEDRON | 2007年 / 63卷 / 17期

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

页码：3457 / 3464

页数：8

共 57 条

[41] PHOTOPHYSICS OF 2'-DEOXYURIDINE (DU) NUCLEOSIDES COVALENTLY SUBSTITUTED WITH EITHER 1-PYRENYL OR 1-PYRENOYL - OBSERVATION OF PYRENE-TO-NUCLEOSIDE CHARGE-TRANSFER EMISSION IN 5-(1-PYRENYL)-DU
NETZEL, TL
ZHAO, M
NAFISI, K
HEADRICK, J
SIGMAN, MS
EATON, BE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (36) : 9119 - 9128
[42] STRUCTURE AND DYNAMICS OF A FLUORESCENT DNA OLIGOMER CONTAINING THE ECORI RECOGNITION SEQUENCE - FLUORESCENCE, MOLECULAR-DYNAMICS, AND NMR-STUDIES
NORDLUND, TM
ANDERSSON, S
NILSSON, L
RIGLER, R
GRASLUND, A
MCLAUGHLIN, LW
[J]. BIOCHEMISTRY, 1989, 28 (23) : 9095 - 9103
[43] DNA charge transport: Conformationally gated hopping through stacked domains
O'Neill, MA
Barton, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (37) : 11471 - 11483
[44] Pyrene-labeled base-discriminating fluorescent DNA probes for homogeneous SNP typing
Okamoto, A
Kanatani, K
Saito, I
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (15) : 4820 - 4827
[45] STRUCTURAL OPTIMIZATION OF NON-NUCLEOTIDE LOOP REPLACEMENTS FOR DUPLEX AND TRIPLEX DNAS
RUMNEY, S
KOOL, ET
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) : 5635 - 5646
[46] CONTROL OF FOLDING AND BINDING OF OLIGONUCLEOTIDES BY USE OF A NONNUCLEOTIDE LINKER
SALUNKHE, M
WU, TF
LETSINGER, RL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) : 8768 - 8772
[47] INTRAMOLECULAR PHOTOCHEMICAL ELECTRON-TRANSFER .4. SINGLET AND TRIPLET MECHANISMS OF ELECTRON-TRANSFER IN A COVALENTLY LINKED PORPHYRIN-AMIDE-QUINONE MOLECULE
SCHMIDT, JA
MCINTOSH, AR
WEEDON, AC
BOLTON, JR
CONNOLLY, JS
HURLEY, JK
WASIELEWSKI, MR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) : 1733 - 1740
[48] Nucleobase-specific quenching of fluorescent dyes .1. Nucleobase one-electron redox potentials and their correlation with static and dynamic quenching efficiencies
Seidel, CAM
Schulz, A
Sauer, MHM
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (13) : 5541 - 5553
[49] Ultrafast intermolecular electron transfer dynamics: Perylene in electron-accepting micellar medium
Singh, AK
Mondal, JA
Ramakrishma, G
Ghosh, HN
Bandyopadhyay, T
Palit, DK
[J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (09) : 4014 - 4023
[50] SJOEBACK R, 1995, SPECTROCHIM ACTA A, V51, pL7

← 1 2 3 4 5 6 →