C5-Azobenzene-substituted 2'-Deoxyuridine-containing Oligodeoxynucleotides for Photo-Switching Hybridization

A new photoisomeric nucleoside dU(Az) bearing an azobenzene group at the C5-position of 2'-deoxyuridine was designed and synthesized. Photoisomerization of dU(Az) in oligodeoxynucleotides can be achieved rapidly and selectively with 365 nm (forward) and 450 nm (backward) irradiation. Thermal de...

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Detalles Bibliográficos
Autores principales: Mori, Shohei, Morihiro, Kunihiko, Obika, Satoshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271114/
https://www.ncbi.nlm.nih.gov/pubmed/24759071
http://dx.doi.org/10.3390/molecules19045109
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author Mori, Shohei
Morihiro, Kunihiko
Obika, Satoshi
author_facet Mori, Shohei
Morihiro, Kunihiko
Obika, Satoshi
author_sort Mori, Shohei
collection PubMed
description A new photoisomeric nucleoside dU(Az) bearing an azobenzene group at the C5-position of 2'-deoxyuridine was designed and synthesized. Photoisomerization of dU(Az) in oligodeoxynucleotides can be achieved rapidly and selectively with 365 nm (forward) and 450 nm (backward) irradiation. Thermal denaturation experiments revealed that dU(Az) stabilized the duplex in the cis-form and destabilized it in the trans-form with mismatch discrimination ability comparable to thymidine. These results indicate that dU(Az) could be a powerful material for reversibly manipulating nucleic acid hybridization with spatiotemporal control.
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spelling pubmed-62711142019-01-02 C5-Azobenzene-substituted 2'-Deoxyuridine-containing Oligodeoxynucleotides for Photo-Switching Hybridization Mori, Shohei Morihiro, Kunihiko Obika, Satoshi Molecules Communication A new photoisomeric nucleoside dU(Az) bearing an azobenzene group at the C5-position of 2'-deoxyuridine was designed and synthesized. Photoisomerization of dU(Az) in oligodeoxynucleotides can be achieved rapidly and selectively with 365 nm (forward) and 450 nm (backward) irradiation. Thermal denaturation experiments revealed that dU(Az) stabilized the duplex in the cis-form and destabilized it in the trans-form with mismatch discrimination ability comparable to thymidine. These results indicate that dU(Az) could be a powerful material for reversibly manipulating nucleic acid hybridization with spatiotemporal control. MDPI 2014-04-22 /pmc/articles/PMC6271114/ /pubmed/24759071 http://dx.doi.org/10.3390/molecules19045109 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Communication
Mori, Shohei
Morihiro, Kunihiko
Obika, Satoshi
C5-Azobenzene-substituted 2'-Deoxyuridine-containing Oligodeoxynucleotides for Photo-Switching Hybridization
title C5-Azobenzene-substituted 2'-Deoxyuridine-containing Oligodeoxynucleotides for Photo-Switching Hybridization
title_full C5-Azobenzene-substituted 2'-Deoxyuridine-containing Oligodeoxynucleotides for Photo-Switching Hybridization
title_fullStr C5-Azobenzene-substituted 2'-Deoxyuridine-containing Oligodeoxynucleotides for Photo-Switching Hybridization
title_full_unstemmed C5-Azobenzene-substituted 2'-Deoxyuridine-containing Oligodeoxynucleotides for Photo-Switching Hybridization
title_short C5-Azobenzene-substituted 2'-Deoxyuridine-containing Oligodeoxynucleotides for Photo-Switching Hybridization
title_sort c5-azobenzene-substituted 2'-deoxyuridine-containing oligodeoxynucleotides for photo-switching hybridization
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271114/
https://www.ncbi.nlm.nih.gov/pubmed/24759071
http://dx.doi.org/10.3390/molecules19045109
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AT obikasatoshi c5azobenzenesubstituted2deoxyuridinecontainingoligodeoxynucleotidesforphotoswitchinghybridization

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