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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2014
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Materias: | |
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. |
format | Online Article Text |
id | pubmed-6271114 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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