Dialkynylpyrenes: Strongly Fluorescent, Environment-Sensitive DNA Building Blocks

被引：61

作者：

Bittermann, Holger ^{[1
]}

Siegemund, Doreen ^{[1
]}

Malinovskii, Vladimir L. ^{[1
]}

Haener, Robert ^{[1
]}

机构：

[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 46期

关键词：

D O I：

10.1021/ja806747h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two isomeric dialkynylpyrene phosphoramidites and their incorporation into oligonucleotides are described. The pyrene units closely resemble the well-known perylene bisimide dye PDI with regard to the ability to self-organize within a DNA duplex. In addition, dialkynylpyrenes exhibit significant monomer and remarkably strong excimer fluorescence. The dialkynylpyrene building blocks are promising candidates for applications in diagnostic toots, such as excimer-based molecular beacons, as well as for novel DNA-based materials with special optical properties.

引用

页码：15285 / +

页数：4

共 46 条

[1] Self-assembly of supramolecular light-harvesting arrays from covalent multi-chromophore peryiene-3,4:9,10-bis(dicarboximide) building blocks [J].

Ahrens, MJ ;

Sinks, LE ;

Rybtchinski, B ;

Liu, WH ;

Jones, BA ;

Giaimo, JM ;

Gusev, AV ;

Goshe, AJ ;

Tiede, DM ;

Wasielewski, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8284-8294

[2] Reversible photoinduced change in molecular ordering of diarylethene derivatives at a solution-HOPG interface [J].

Arai, Ryota ;

Uemura, Shinobu ;

Irie, Masahiro ;

Matsuda, Kenji .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9371-9379

[3] Perylene bisimide dimers as fluorescent "Glue" for DNA and for base-mismatch detection [J].

Baumstark, Daniela ;

Wagenknecht, Hans-Achim .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (14) :2612-2614

[4] Intramolecular excimer formation and delayed fluorescence in sterically constrained pyrene dimers [J].

Benniston, Andrew C. ;

Harriman, Anthony ;

Howell, Sarah L. ;

Sams, Craig A. ;

Zhi, Yong-Gang .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (16) :4665-4674

[5]

Berova N., 2000, CIRCULAR DICHROISM P, P337

[6] Naphthalene- and perylene-based linkers for the stabilization of hairpin triplexes [J].

Bevers, S ;

Schutte, S ;

McLaughlin, LW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (25) :5905-5915

[7] Exciton chirality. (A) origins of and (B) applications from strongly fluorescent dipyrrinone chromophores [J].

Boiadjiev, SE ;

Lightner, DA .

MONATSHEFTE FUR CHEMIE, 2005, 136 (03) :489-508

[8] Highly efficient quenching of excimer fluorescence by perylene diimide in DNA [J].

Bouquin, Nicolas ;

Malinovskii, Vladimir L. ;

Haener, Robert .

CHEMICAL COMMUNICATIONS, 2008, (17) :1974-1976

[9] Beyond exciton theory: A time-dependent DFT and Franck-Condon study of perylene diimide and its chromophoric dimer [J].

Clark, Aurora E. ;

Qin, Changyong ;

Li, Alexander D. Q. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7586-7595

[10] Oligomeric fluorescent labels for DNA [J].

Cuppoletti, A ;

Cho, YJ ;

Park, JS ;

Strässler, C ;

Kool, ET .

BIOCONJUGATE CHEMISTRY, 2005, 16 (03) :528-534

← 1 2 3 4 5 →