Efficient RNA-targeting by the introduction of aromatic stacking in the duplex major groove via 5-(1-phenyl-1,2,3-triazol-4-yl)-2′-deoxyuridines

被引：37

作者：

Andersen, Nicolai Krog ^{[2
]}

Chandak, Navneet ^{[1
]}

Brulikova, Lucie ^{[2
]}

Kumar, Pawan ^{[1
]}

Jensen, Michael Dalager ^{[2
]}

Jensen, Frank ^{[3
]}

Sharma, Pawan K. ^{[1
]}

Nielsen, Poul ^{[2
]}

机构：

[1] Kurukshetra Univ, Dept Chem, Kurukshetra 136119, Haryana, India

[2] Univ So Denmark, Dept Chem & Phys, Nucle Acid Ctr, DK-5230 Odense M, Denmark

[3] Aarhus Univ, Dept Chem, DK-8000 Aarhus, Denmark

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2010年 / 18卷 / 13期

基金：

新加坡国家研究基金会;

关键词：

Oligonucleotides; pi-pi-Stacking; Click chemistry; RNA-targeting; NUCLEIC-ACID NANOTECHNOLOGY; ANTISENSE GENE INHIBITION; CLICK CHEMISTRY; TERMINAL ALKYNES; FORCE-FIELD; OLIGONUCLEOTIDES; AZIDES; OLIGODEOXYNUCLEOTIDES; PROTEINS; ANALOGS;

D O I：

10.1016/j.bmc.2010.05.019

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Three pyrimidine nucleosides with differently substituted phenyltriazoles attached to the 5-position were prepared by Cu(I)-assisted azide-alkyne cycloadditions (CuAAC) and incorporated into oligonucleotides. Efficient pi-pi-stacking between two or more phenyltriazoles in the major groove was found to increase the thermal stability of a DNA: RNA duplex significantly. The best stacking, and most stable duplex, was obtained by a sulfonamide substituted derivative. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4702 / 4710

页数：9

共 28 条

[1] Rapid synthesis of aryl azides from aryl halides under mild conditions [J].

Andersen, J ;

Madsen, U ;

Björkling, F ;

Liang, XF .

SYNLETT, 2005, (14) :2209-2213

[2]

[Anonymous], MACROMODEL VERS 9 1

[3]

[Anonymous], GAUSSIAN 03

[4] Detection of S-phase cell cycle progression using 5-ethynyl-2′-deoxyuridine incorporation with click chemistry an alternative to using 5-bromo-2′-deoxyuridine antibodies [J].

Buck, Suzanne B. ;

Bradford, Jolene ;

Gee, Kyle R. ;

Agnew, Brian J. ;

Clarke, Scott T. ;

Salic, Adrian .

BIOTECHNIQUES, 2008, 44 (07) :927-929

[5] Directed DNA metallization [J].

Burley, GA ;

Gierlich, J ;

Mofid, MR ;

Nir, H ;

Tal, S ;

Eichen, Y ;

Carell, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1398-1399

[6] Preparation of N-aryl compounds by amino acid-promoted Ullmann-type coupling reactions [J].

Cai, Q ;

Zhu, W ;

Zhang, H ;

Zhang, YD ;

Ma, DW .

SYNTHESIS-STUTTGART, 2005, (03) :496-499

[7] AN INTERNAL COORDINATE MONTE-CARLO METHOD FOR SEARCHING CONFORMATIONAL SPACE [J].

CHANG, G ;

GUIDA, WC ;

STILL, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4379-4386

[8] Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA [J].

Gierlich, Johannes ;

Burley, Glenn A. ;

Gramlich, Philipp M. E. ;

Hammond, David M. ;

Carell, Thomas .

ORGANIC LETTERS, 2006, 8 (17) :3639-3642

[9] Antisense gene inhibition by C-5-substituted deoxyuridine-containing oligodeoxynucleotides [J].

Gutierrez, AJ ;

Matteucci, MD ;

Grant, D ;

Matsumura, S ;

Wagner, RW ;

Froehler, BC .

BIOCHEMISTRY, 1997, 36 (04) :743-748

[10] 5-HETEROARYL-2'-DEOXYURIDINE ANALOGS - SYNTHESIS AND INCORPORATION INTO HIGH-AFFINITY OLIGONUCLEOTIDES [J].

GUTIERREZ, AJ ;

TERHORST, TJ ;

MATTEUCCI, MD ;

FROEHLER, BC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5540-5544

← 1 2 3 →