Luminescence-based colorimetric discrimination of single-nucleotide transversions by the combined use of the derivatives of DOTA-conjugated naphthyridine and its terbium complex

被引:13
作者
Atsumi, Hiroshi [1 ]
Yoshimoto, Keitaro [1 ,2 ,3 ,4 ]
Saito, Shingo [3 ,5 ]
Ohkuma, Moriya [3 ]
Maeda, Mizuo [3 ]
Nagasaki, Yukio [1 ,2 ,4 ,6 ,7 ]
机构
[1] Univ Tsukuba, Grad Sch Pure & Appl Sci, Tsukuba, Ibaraki 3058573, Japan
[2] Univ Tsukuba, Ctr Tsukuba Adv Res Alliance, Tsukuba, Ibaraki 3058577, Japan
[3] RIKEN, Bioengn Lab, Wako, Saitama 3510198, Japan
[4] Univ Tsukuba, Tsukuba Res Ctr Interdisciplinary Mat Sci, Tsukuba, Ibaraki 3058573, Japan
[5] Saitama Univ, Grad Sch Sci & Engn, Sakura Ku, Saitama 3388570, Japan
[6] Univ Tsukuba, Grad Sch Comprehens Human Sci, Masters Sch Med Sci, Tsukuba, Ibaraki 3058573, Japan
[7] NIMS, Int Ctr Mat Nanoarchilecton, Satellite Lab, Tsukuba, Ibaraki 3058573, Japan
关键词
Nucleobase; Fluorescence; Lanthanide energy transfer; Point mutation; DOTA; Terbium; GUANINE-GUANINE MISMATCHES; SITE-CONTAINING DNA; PYRIMIDINE/PURINE TRANSVERSION; FLUORESCENCE DETECTION; ENERGY-TRANSFER; TB3+ COMPLEX; BINDING; RECOGNITION; SEQUENCE; PROBES;
D O I
10.1016/j.tetlet.2009.02.152
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We newly synthesized a nucleobase-binding ligand, ND-DOTA, in which 2-amino-5,7-dimethyl-1,8-naphthyridine (ND) was conjugated with 1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid (DOTA) via an amide linker, and found that its terbium(III) complex (ND-DOTA-Tb) showed green emission based on an energy transfer from the naphthyridine moiety to Tb3+. The blue emission of ND-DOTA was selectively quenched by adding abasic site-containing DNA duplexes that have pyrimidine bases opposite to the abasic site. In contrast, at the same excitation wavelength, ND-DOTA-Tb showed green emission independently of the bases opposite to the abasic site. Thus, a mixed solution of ND-DOTA and ND-DOTA-Tb enabled the luminescence-based colorimetric discrimination of single-nucleotide transversions with the naked eye at a single excitation wavelength. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2177 / 2180
页数:4
相关论文
共 58 条
[1]   Single-mismatch detection using gold-quenched fluorescent oligonucleotides [J].
Dubertret, B ;
Calame, M ;
Libchaber, AJ .
NATURE BIOTECHNOLOGY, 2001, 19 (04) :365-370
[2]   Recognition and reaction of metallointercalators with DNA [J].
Erkkila, KE ;
Odom, DT ;
Barton, JK .
CHEMICAL REVIEWS, 1999, 99 (09) :2777-2795
[3]   Detection of guanine-adenine mismatches by surface plasmon resonance sensor carrying naphthyridine-azaquinolone hybrid on the surface [J].
Hagihara, S ;
Kumasawa, H ;
Goto, Y ;
Hayashi, G ;
Kobori, A ;
Saito, I ;
Nakatani, K .
NUCLEIC ACIDS RESEARCH, 2004, 32 (01) :278-286
[4]   Development of a zinc ion-selective luminescent lanthanide chemosensor for biological applications [J].
Hanaoka, K ;
Kikuchi, K ;
Kojima, H ;
Urano, Y ;
Nagano, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (39) :12470-12476
[5]   Fluorescent 2,7-dialkylamino-[1,8]-naphthyridines: Preparation and spectroscopic properties [J].
Hoock, C ;
Reichert, J ;
Schmidtke, M .
MOLECULES, 1999, 4 (10) :264-271
[6]   Highly selective luminescence determination of terbium at the sub-ppb level with sulfonylcalix[4]arene-p-tetrasulfonate [J].
Horiuchi, T ;
Iki, N ;
Oka, H ;
Miyano, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2002, 75 (12) :2615-2619
[7]  
Hsu TM, 2001, CLIN CHEM, V47, P1373
[8]   Colorimetric SNP analysis using oligonucleotide-modified nanoparticles [J].
Ihara, T ;
Chikaura, Y ;
Tanaka, S ;
Jyo, A .
CHEMICAL COMMUNICATIONS, 2002, (18) :2152-2153
[9]   Photochemical ligation of DNA conjugates through anthracene cyclodimer formation and its fidelity to the template sequences [J].
Ihara, T ;
Fujii, T ;
Mukae, M ;
Kitamura, Y ;
Jyo, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (29) :8880-8881
[10]   Homogeneous DNA-detection based on the non-enzymatic reactions promoted by target DNA [J].
Ihara, Toshihiro ;
Mukae, Motoko .
ANALYTICAL SCIENCES, 2007, 23 (06) :625-629