Next Article in Journal
Catechins and Procyanidins of Ginkgo biloba Show Potent Activities towards the Inhibition of β-Amyloid Peptide Aggregation and Destabilization of Preformed Fibrils
Next Article in Special Issue
Thermodynamics and Kinetics of Guest-Induced Switching between “Basket Handle” Porphyrin Isomers
Previous Article in Journal
Natural Dibenzo-α-Pyrones and Their Bioactivities
Molecules 2014, 19(4), 5109-5118; doi:10.3390/molecules19045109
Communication

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

1
, 1,2,*  and 1,2,*
1 Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan 2 National Institute of Biomedical Innovation (NIBIO), 7-6-8 Saito-Asagi, Osaka 567-0085, Japan
* Authors to whom correspondence should be addressed.
Received: 3 March 2014 / Revised: 15 April 2014 / Accepted: 17 April 2014 / Published: 22 April 2014
(This article belongs to the Special Issue Molecular Switches)
View Full-Text   |   Download PDF [581 KB, uploaded 18 June 2014]   |   Browse Figures

Abstract

A new photoisomeric nucleoside dUAz bearing an azobenzene group at the C5-position of 2'-deoxyuridine was designed and synthesized. Photoisomerization of dUAz in oligodeoxynucleotides can be achieved rapidly and selectively with 365 nm (forward) and 450 nm (backward) irradiation. Thermal denaturation experiments revealed that dUAz 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 dUAz could be a powerful material for reversibly manipulating nucleic acid hybridization with spatiotemporal control.
Keywords: azobenzene; molecular switch; nucleoside; oligonucleotide; photochromism azobenzene; molecular switch; nucleoside; oligonucleotide; photochromism
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


MDPI and ACS Style

Mori, S.; Morihiro, K.; Obika, S. C5-Azobenzene-substituted 2'-Deoxyuridine-containing Oligodeoxynucleotides for Photo-Switching Hybridization. Molecules 2014, 19, 5109-5118.

View more citation formats

Supplement

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert