DNA as a supramolecular framework for the helical arrangements of chromophores: towards photoactive DNA-based nanomaterials

被引:128
作者
Varghese, Reji [1 ]
Wagenknecht, Hans-Achim [1 ]
机构
[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany
关键词
INTERSTRAND-STACKING; NUCLEIC-ACID; C-NUCLEOSIDES; PORPHYRIN ARRAYS; H-AGGREGATION; PYRENE-ARRAY; DUPLEX DNA; FLUORESCENT; ANALOGS; DYES;
D O I
10.1039/b821728a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Nucleic acids have been emerging as supramolecular structural scaffolds for the helical organization of chromophores in the creation of functional nanomaterials mainly because of the their unique structural features and synthetic accessibility. A large number of chromophores have been successfully incorporated into DNA or RNA as C-nucleosides, as base surrogates or as modified sugars using solid phase phosphoramidite chemistry. Moreover, multiple incorporations yield the helical organization of the chromophores inside or outside the DNA or RNA double helix depending upon the conjugation of the chromophores. Significant photophysical interactions are observed in the chromophore stacks resulting in unique optical properties that are significantly different from the monomer properties. In this feature article, multichromophore labelled nucleic acids are reviewed with special emphasis on the self-assembly induced modulation of the optical properties.
引用
收藏
页码:2615 / 2624
页数:10
相关论文
共 73 条
[41]   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
[42]   Helical self-assembled chromophore clusters based on DNA-like architecture [J].
Mayer-Enthart, Elke ;
Wagner, Clemens ;
Barbaric, Janez ;
Wagenknecht, Hans-Achim .
TETRAHEDRON, 2007, 63 (17) :3434-3439
[43]   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
[44]  
MAYOR M, 2003, NANOELECTRONICS INFO, P501
[45]   Electrical rectification by a molecule: The advent of unimolecular electronic devices [J].
Metzger, RM .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (11) :950-957
[46]   Molecular rectification: why is it so rare? [J].
Mujica, V ;
Ratner, MA ;
Nitzan, A .
CHEMICAL PHYSICS, 2002, 281 (2-3) :147-150
[47]   Helical pyrene-array along the outside of duplex RNA [J].
Nakamura, M ;
Ohtoshi, Y ;
Yamana, K .
CHEMICAL COMMUNICATIONS, 2005, (41) :5163-5165
[48]   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-+
[49]   Pyrene aromatic arrays on RNA duplexes as helical templates [J].
Nakamura, Mitsunobu ;
Shimomura, Yukinori ;
Ohtoshi, Yukinori ;
Sasa, Kazuhiro ;
Hayashi, Haruhisa ;
Nakano, Hidehiko ;
Yamana, Kazushige .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (12) :1945-1951
[50]   Fluorescent nucleotide base analogs as probes of nucleic acid structure, dynamics and interactions [J].
Rist, MJ ;
Marino, JP .
CURRENT ORGANIC CHEMISTRY, 2002, 6 (09) :775-793