Pteridine Derivatives Modified with a Guanidine for Binding and Sensing an Orphan Guanine in RNA Duplexes

被引：6

作者：

Sato, Yusuke ^{[1
]}

Asami, Takahiro ^{[1
]}

Toriyabe, Yu ^{[1
]}

Sato, Takaya ^{[1
]}

Teramae, Norio ^{[1
]}

Nishizawa, Seiichi ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

CHEMISTRY LETTERS | 2016年 / 45卷 / 08期

关键词：

Fluorescence sensing; RNA-binding ligand; Orphan guanine; SMALL MOLECULES; TARGETING RNA; NUCLEIC-ACIDS; ABASIC SITE; RECOGNITION; DNA; MICRORNA; LIGANDS; AMINOGLYCOSIDES; NUCLEOBASES;

D O I：

10.1246/cl.160425

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report on a fluorescent pteridine derivative modified with a guanidino group for the selective detection of an orphan guanine in RNA duplexes with a dissociation constant of 31 +/- 7 nM (pH 7.0, T = 20 degrees C). The significant effect of the guanidino group attached to the pteridine ring on the binding selectivity and affinity is discussed based on the examination of thermodynamic parameters.

引用

收藏

页码：982 / 984

页数：3

相关论文

共 19 条

[1] Probing the specificity of aminoglycoside ribosomal RNA interactions with designed synthetic analogs [J].

Alper, PB ;

Hendrix, M ;

Sears, P ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (09) :1965-1978

[2] MicroRNAs: Genomics, biogenesis, mechanism, and function (Reprinted from Cell, vol 116, pg 281-297, 2004) [J].

Bartel, David P. .

CELL, 2007, 131 (04) :11-29

[3]

Chaires JB, 1996, ANTI-CANCER DRUG DES, V11, P569

[4] Small Molecule Modifiers of the microRNA and RNA Interference Pathway [J].

Deiters, Alexander .

AAPS JOURNAL, 2010, 12 (01) :51-60

[5] Selectively Guanidinylated Aminoglycosides as Antibiotics [J].

Fair, Richard J. ;

Hensler, Mary E. ;

Thienphrapa, Wdee ;

Dam, Quang N. ;

Nizet, Victor ;

Tor, Yitzhak .

CHEMMEDCHEM, 2012, 7 (07) :1237-1244

[6] Synthesis of 8-Substituted Adenine and Adenosine Libraries and the Binding to pre-miR-29a [J].

Fukuzumi, Takeo ;

Aikawa, Haruo ;

Harada, Yasue ;

Sugai, Ayako ;

Murata, Asako ;

Nakatani, Kazuhiko .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2014, 87 (09) :1013-1015

[7] Rational Design for Cooperative Recognition of Specific Nucleobases Using -Cyclodextrin-Modified DNAs and Fluorescent Ligands on DNA and RNA Scaffolds [J].

Futamura, Akika ;

Uemura, Asuka ;

Imoto, Takeshi ;

Kitamura, Yusuke ;

Matsuura, Hirotaka ;

Wang, Chun-Xia ;

Ichihashi, Toshiki ;

Sato, Yusuke ;

Teramae, Norio ;

Nishizawa, Seiichi ;

Ihara, Toshihiro .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (32) :10526-10535

[8] Recent Advances in Developing Small Molecules Targeting RNA [J].

Guan, Lirui ;

Disney, Matthew D. .

ACS CHEMICAL BIOLOGY, 2012, 7 (01) :73-86

[9] Recognition of Double-Stranded RNA by Guanidine-Modified Peptide Nucleic Acids [J].

Gupta, Pankaj ;

Muse, Oluwatoyosi ;

Rozners, Eriks .

BIOCHEMISTRY, 2012, 51 (01) :63-73

[10] Circulating micro-RNA expression profiles in early stage nonsmall cell lung cancer [J].

Heegaard, Niels H. H. ;

Schetter, Aaron J. ;

Welsh, Judith A. ;

Yoneda, Mitsuhiro ;

Bowman, Elise D. ;

Harris, Curtis C. .

INTERNATIONAL JOURNAL OF CANCER, 2012, 130 (06) :1378-1386