Pyrene aromatic arrays on RNA duplexes as helical templates

被引：53

作者：

Nakamura, Mitsunobu ^{[1
]}

Shimomura, Yukinori ^{[1
]}

Ohtoshi, Yukinori ^{[1
]}

Sasa, Kazuhiro ^{[1
]}

Hayashi, Haruhisa ^{[1
]}

Nakano, Hidehiko ^{[1
]}

Yamana, Kazushige ^{[1
]}

机构：

[1] Univ Hyogo, Grad Sch Engn, Dept Chem & Mat Sci, Himeji, Hyogo 6712201, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2007年 / 5卷 / 12期

关键词：

D O I：

10.1039/b705933g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

RNA oligomers having multiple (2 to 4) pyrenylmethyl substituents at the 2'-O-sugar residues were synthesized. UV-melting studies showed that the pyrene-modified RNAs could form duplexes with complementary RNA sequences without loss of thermal stability. Absorption, fluorescence, and circular dichroism (CD) spectra revealed that the incorporated pyrenes projected toward the outside of A-form RNA duplexes and assembled in helical aromatic arrays along the minor grooves of the RNA duplexes. Results of computer simulations agreed with the assembled structures of the pyrenes. The helical pyrene arrays exhibited remarkably strong excimer fluorescence, which was dependent on the sequence contexts of RNA duplexes.

引用

页码：1945 / 1951

页数：7

共 31 条

[1] DNA-dye conjugates for controllable H* aggregation [J].

Asanuma, H ;

Shirasuka, K ;

Takarada, T ;

Kashida, H ;

Komiyama, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (08) :2217-2223

[2] DNA as a supramolecular scaffold for the helical arrangement of a stack of 1-ethynylpyrene chromophores [J].

Barbaric, Janez ;

Wagenknecht, Hans-Achim .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) :2088-2090

[3] Metal-intercalator-mediated self-association and one-dimensional aggregation in the structure of the excised major DNA adduct of a platinum-acridine agent [J].

Baruah, H ;

Day, CS ;

Wright, MW ;

Bierbach, U .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (14) :4492-4493

[4]

Berova, 2000, CIRCULAR DICHROISM P, P337

[5] CHARGE-TRANSFER QUENCHING OF SINGLET EXCITED COMPLEXES [J].

CALDWELL, RA ;

CREED, D ;

DEMARCO, DC ;

MELTON, LA ;

OHTA, H ;

WINE, PH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (07) :2369-2377

[6] Enzymatic synthesis of fluorescent oligomers assembled on a DNA backbone [J].

Cho, YJ ;

Kool, ET .

CHEMBIOCHEM, 2006, 7 (04) :669-672

[7] A 2ND GENERATION FORCE-FIELD FOR THE SIMULATION OF PROTEINS, NUCLEIC-ACIDS, AND ORGANIC-MOLECULES [J].

CORNELL, WD ;

CIEPLAK, P ;

BAYLY, CI ;

GOULD, IR ;

MERZ, KM ;

FERGUSON, DM ;

SPELLMEYER, DC ;

FOX, T ;

CALDWELL, JW ;

KOLLMAN, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (19) :5179-5197

[8] Effect of PNA backbone modifications on cyanine dye binding to PNA-DNA duplexes investigated by optical spectroscopy and molecular dynamics simulations [J].

Dilek, I ;

Madrid, M ;

Singh, R ;

Urrea, CP ;

Armitage, BA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3339-3345

[9]

ENHART EM, 2006, ANGEW CHEM INT EDIT, V45, P3372

[10] Ultrafast excited-state dynamics of DNA fluorescent intercalators:: New insight into the fluorescence enhancement mechanism [J].

Fuerstenberg, Alexandre ;

Julliard, Marc D. ;

Deligeorgiev, Todor G. ;

Gadjev, Nikolai I. ;

Vasilev, Aleksey A. ;

Vauthey, Eric .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) :7661-7669

← 1 2 3 4 →