Enhancement of fluorescence quenching and exciplex formation in DNA major groove by double incorporation of modified fluorescent deoxyuridines

被引：4

作者：

Tanaka, Makiko ^{[1
,2
]}

Oguma, Kazuhiro ^{[1
,2
]}

Saito, Yoshio ^{[1
]}

Saito, Isao ^{[2
]}

机构：

[1] Nihon Univ, Sch Engn, Dept Chem Biol & Appl Chem, Koriyama, Fukushima 9638642, Japan

[2] Nihon Univ, Sch Engn, NEWCAT Inst, Koriyama, Fukushima 9638642, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 12期

关键词：

DNA; Major groove; Modified nucleoside; Ethynyl linker; Exciplex; SUPRAMOLECULAR SCAFFOLD; HELICAL ARRANGEMENT; DUPLEX FORMATION; ENERGY-TRANSFER; PYRENE; OLIGONUCLEOTIDES; STABILIZATION;

D O I：

10.1016/j.bmcl.2012.04.067

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

5-(1-Naphthalenylethynyl)-2'-deoxyuridine (U-N) and 5-[(4-cyano-1-naphthalenyl) ethynyl]-2'-deoxyuridine (U-CN) were synthesized and incorporated into oligodeoxynucleotides. Fluorescence emissions of modified duplexes containing double U-N were efficiently quenched depending upon the sequence pattern of the naphthalenes in DNA major groove, as compared to the duplex possessing single U-N. When one of the naphthalene moieties has a cyano substituent, the exciplex emission from the chromophores in DNA major groove was observed at longer wavelength. (C) 2012 Elsevier Ltd. All rights reserved.

引用

收藏

页码：4103 / 4105

页数：3

相关论文

共 21 条

[11] Accumulation of Fluorophores into DNA Duplexes To Mimic the Properties of Quantum Dots [J].

Kashida, Hiromu ;

Sekiguchi, Koji ;

Liang, Xingguo ;

Asanuma, Hiroyuki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) :6223-6230

[12] Helical arrangement of interstrand stacked pyrenes in a DNA framework [J].

Malinovskii, Vladimir L. ;

Samain, Florent ;

Haener, Robert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (24) :4464-4467

[13] Structure-sensitive and self-assembled helical pyrene array based on DNA architecture [J].

Mayer-Enthart, Elke ;

Wagenknecht, Hans-Achim .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (20) :3372-3375

[14] Pyrene-zipper array assembled via RNA duplex formation [J].

Nakamura, Mitsunobu ;

Murakami, Yohei ;

Sasa, Kazuhiro ;

Hayashi, Haruhisa ;

Yamana, Kazushige .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (22) :6904-+

[15] Duplex Stabilization and Energy Transfer in Zipper Porphyrin-DNA [J].

Nguyen, ThaoNguyen ;

Brewer, Ashley ;

Stulz, Eugen .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (11) :1974-1977

[16] DNA-templated assembly of dyes and extended π-conjugated systems [J].

Ruiz-Carretero, Amparo ;

Janssen, Pim G. A. ;

Kaeser, Adrien ;

Schenning, Albertus P. H. J. .

CHEMICAL COMMUNICATIONS, 2011, 47 (15) :4340-4347

[17] Self-duplex formation of an APy-substituted oligodeoxyadenylate and its unique fluorescence [J].

Seo, Young Jun ;

Rhee, Hanju ;

Joo, Taiha ;

Kim, Byeang Hyean .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (16) :5244-5247

[18] Stabilization of DNA duplex by 2-substituted adenine as a minor groove modifier [J].

Tanaka, Makiko ;

Kozakai, Ryota ;

Saito, Yoshio ;

Saito, Isao .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (23) :7021-7024

[19] Ultrafast energy transfer and structural dynamics in DNA [J].

Trifonov, A ;

Raytchev, M ;

Buchvarov, I ;

Rist, M ;

Barbaric, J ;

Wagenknecht, HA ;

Fiebig, T .

JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (41) :19490-19495

[20] DNA as a supramolecular framework for the helical arrangements of chromophores: towards photoactive DNA-based nanomaterials [J].

Varghese, Reji ;

Wagenknecht, Hans-Achim .

CHEMICAL COMMUNICATIONS, 2009, (19) :2615-2624