A new phosphoramidite enables orthogonal double labelling to form combination oligonucleotide probes

被引:3
作者
Bai, Chunsen [1 ]
Klimkowski, Piotr [1 ]
Jin, Cheng [1 ]
Kuchlyan, Jagannath [1 ]
El-Sagheer, Afaf H. [1 ,2 ]
Brown, Tom [1 ]
机构
[1] Univ Oxford, Dept Chem, 12 Mansfield Rd, Oxford OX1 3TA, England
[2] Suez Univ, Fac Petr & Min Engn, Dept Sci & Math, Chem Branch, Suez 43721, Egypt
关键词
DYE THIAZOLE ORANGE; HYBEACON(TM) PROBES; FIT-PROBES; DNA; HYBRIDIZATION;
D O I
10.1039/d2ob01899c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oligonucleotides labelled with thiazole orange intercalator and a reporter dye on the same thymine base have been synthesized. The key phosphoramidite (AP-C3 dT) contains an alkyne and amine, enabling dual orthogonal labelling of the nucleobase. Multiple monomers can be added to produce heavily functionalised oligonucleotides. In their DNA and 2 '-OMe RNA formats these combination probes display high duplex stability and fluorescence when bound to complementary DNA and RNA.
引用
收藏
页码:8618 / 8622
页数:5
相关论文
共 31 条
[1]   Fluorescent Color Readout of DNA Hybridization with Thiazole Orange as an Artificial DNA Base [J].
Berndl, Sina ;
Wagenknecht, Hans-Achim .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (13) :2418-2421
[2]   Designed thiazole orange nucleotides for the synthesis of single labelled oligonucleotides that fluoresce upon matched hybridization [J].
Bethge, Lucas ;
Singh, Ishwar ;
Seitz, Oliver .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (10) :2439-2448
[3]   Dual recognition of double-stranded DNA by 2′-aminoethoxy-modified oligonucleotides:: The solution structure of an intramolecular triplex obtained by NMR spectroscopy [J].
Blommers, MJJ ;
Natt, F ;
Jahnke, W ;
Cuenoud, B .
BIOCHEMISTRY, 1998, 37 (51) :17714-17725
[4]   Illumina universal bead arrays [J].
Fan, Jian-Bing ;
Gunderson, Kevin L. ;
Bibikova, Marina ;
Yeakley, Joanne M. ;
Chen, Jing ;
Wickham Garcia, Eliza ;
Lebruska, Lori L. ;
Laurent, Marc ;
Shen, Richard ;
Barker, David .
DNA MICROARRAYS PART A: ARRAY PLATFORMS AND WET-BENCH PROTOCOLS, 2006, 410 :57-+
[5]   A bright FIT-PNA hybridization probe for the hybridization state specific analysis of a C → U RNA edit via FRET in a binary system [J].
Fang, Ge-min ;
Chamiolo, Jasmine ;
Kankowski, Svenja ;
Hoevelmann, Felix ;
Friedrich, Dhana ;
Loewer, Alexander ;
Meier, Jochen C. ;
Seitz, Oliver .
CHEMICAL SCIENCE, 2018, 9 (21) :4794-4800
[6]   Efficient Nucleic Acid Detection by Templated Reductive Quencher Release [J].
Franzini, Raphael M. ;
Kool, Eric T. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (44) :16021-+
[7]   HyBeacon™ probes:: a new tool for DNA sequence detection and allele discrimination [J].
French, DJ ;
Archard, CL ;
Brown, T ;
McDowell, DG .
MOLECULAR AND CELLULAR PROBES, 2001, 15 (06) :363-374
[8]   Ultra-rapid DNA analysis using HyBeacon™ probes and direct PCR amplification from saliva [J].
French, DJ ;
Archard, CL ;
Andersen, MT ;
McDowell, DG .
MOLECULAR AND CELLULAR PROBES, 2002, 16 (05) :319-326
[9]   Sequence dependence of fluorescence emission and quenching of doubly thiazole orange labeled DNA: Effective design of a hybridization-sensitive probe [J].
Ikeda, Shuji ;
Kubota, Takeshi ;
Kino, Katsuhito ;
Okamoto, Akimitsu .
BIOCONJUGATE CHEMISTRY, 2008, 19 (08) :1719-1725
[10]   Divergent and linear solid-phase synthesis of PNA containing thiazole orange as artificial base [J].
Jarikote, DV ;
Köhler, O ;
Socher, E ;
Seitz, O .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (15) :3187-3195