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Nucleic acid-specific photoactivation of oligodeoxyribonucleotides labeled with deuterated dihydro-N,N,N',N'-tetramethylrhodamine using green light.

作者信息

Schikora Margot, Dutta Subrata, Mokhir Andriy

机构信息

Department of Chemistry and Pharmacy, Organic Chemistry II, Friedrich-Alexander-University of Erlangen-Nuremberg, Henkestr. 42, 91054, Erlangen, Germany.

出版信息

Histochem Cell Biol. 2014 Jul;142(1):103-11. doi: 10.1007/s00418-014-1187-0. Epub 2014 Feb 5.


DOI:10.1007/s00418-014-1187-0
PMID:24496596
Abstract

We developed a simple protocol for high-yielding synthesis of conjugates of a deuterated dihydro-N,N,N',N'-tetramethylrhodamine (F*) with oligodeoxyribonucleotides and a 2'-OMe RNA (a representative nuclease-resistant, chemically modified oligonucleotide) using easily accessible starting materials including NaBD4 and conjugates of oligonucleotides with N,N,N',N'-tetramethylrhodamine (F). These compounds were found to be stable in air and insensitive to light at 525, 635 and 650 nm, whereas slow activation occurs upon their exposure to 470 nm light. However, at the conditions of the templated reaction, in the presence of a target nucleic acid and a photocatalyst based on the eosin structure, the F* is oxidized forming fluorescent F. This reaction is >30-fold faster than the background reaction in the absence of the template. Moreover, the presence of a single mismatch in the target nucleic acid slows down the templated reaction by eightfold. These activatable dyes can potentially find applications as nucleic acid-specific probes for super-resolution imaging in live cells.

摘要

相似文献

[1]
Nucleic acid-specific photoactivation of oligodeoxyribonucleotides labeled with deuterated dihydro-N,N,N',N'-tetramethylrhodamine using green light.

Histochem Cell Biol. 2014-7

[2]
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[6]
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[7]
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[8]
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[10]
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引用本文的文献

[1]
DNA-Dye-Conjugates: Conformations and Spectra of Fluorescence Probes.

PLoS One. 2016-7-28

[2]
The Histochemistry and Cell Biology pandect: the year 2014 in review.

Histochem Cell Biol. 2015-4

[3]
In this special issue.

Histochem Cell Biol. 2014-7

本文引用的文献

[1]
Fluorogenic, catalytic, photochemical reaction for amplified detection of nucleic acids.

Bioconjug Chem. 2013-9-3

[2]
Detection of miRNA in live cells by using templated RuII-catalyzed unmasking of a fluorophore.

Chemistry. 2013-4-30

[3]
Photoreductive uncaging of fluorophore in response to protein oligomers by templated reaction in vitro and in cellulo.

J Am Chem Soc. 2012-11-30

[4]
Hybridization and reaction-based fluorogenic nucleic acid probes.

Chem Commun (Camb). 2012-10-7

[5]
Light-controlled tools.

Angew Chem Int Ed Engl. 2012-7-24

[6]
Live-cell super-resolution imaging with synthetic fluorophores.

Annu Rev Phys Chem. 2012

[7]
Nucleic acid templated uncaging of fluorophores using Ru-catalyzed photoreduction with visible light.

Org Lett. 2011-12-29

[8]
Far-field nanoscopy with reversible chemical reactions.

Angew Chem Int Ed Engl. 2011-3-21

[9]
1,9-Dialkoxyanthracene as a (1)O2-sensitive linker.

J Am Chem Soc. 2011-2-23

[10]
An autocatalytic chromogenic and fluorogenic photochemical reaction controlled by nucleic acids.

Chem Commun (Camb). 2010-11-22

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