Oligonucleotides containing new fluorescent 1-phenylethynylpyrene and 9,10-bis(phenylethynyl)anthracene uridine-2'-carbamates: synthesis and properties

被引：34

作者：

Dioubankova, NN ^{[1
]}

Malakhov, AD ^{[1
]}

Shenkarev, ZO ^{[1
]}

Korshun, VA ^{[1
]}

机构：

[1] Russian Acad Sci, Shemyakin Ovchinnikov Inst Bioorgan Chem, Moscow 117997, Russia

来源：

TETRAHEDRON | 2004年 / 60卷 / 21期

基金：

俄罗斯基础研究基金会;

关键词：

modified oligonucleotides; polycyclic aromatic hydrocarbons; fluorescence; duplex stability;

D O I：

10.1016/j.tet.2004.03.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of two novel fluorescent uridine-2'-carbamate phosphoramidites is described. The reagents carrying fluorescent polyaromatic hydrocarbons 1-phenylethynylpyrene (PEPy) or 9,10-bis(phenylethynyl)anthracene (BPEA) are suitable for oligonucleotide synthesis. Prepared oligonucleotide conjugates show strong dye emissions at 401 and 485 nm, but low FRET rate when located in the oligonucleotide duplex. The dyes show considerable compensation of the usual carbamate duplex destabilization. The possible explanation of both effects is binding of PEPy and BPEA to the minor groove of the DNA duplex. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4617 / 4626

页数：10

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