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Chemosensors 2015, 3(2), 36-54; doi:10.3390/chemosensors3020036

Synthesis and Properties of 2'-Deoxyuridine Analogues Bearing Various Azobenzene Derivatives at the C5 Position

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
*
Author to whom correspondence should be addressed.
Academic Editor: Patrick Hrdlicka
Received: 4 September 2014 / Revised: 7 March 2015 / Accepted: 9 March 2015 / Published: 27 March 2015
(This article belongs to the Special Issue Nucleic Acid Probes)
View Full-Text   |   Download PDF [1048 KB, uploaded 27 March 2015]   |  

Abstract

Nucleic acids that change their properties upon photo-irradiation could be powerful materials for molecular sensing with high spatiotemporal resolution. Recently, we reported a photo-isomeric nucleoside bearing azobenzene at the C5 position of 2'-deoxyuridine (dUAz), whose hybridization ability could be reversibly controlled by the appropriate wavelength of light. In this paper, we synthesized and evaluated dUAz analogues that have various para-substitutions on the azobenzene moiety. Spectroscopic measurements and HPLC analyses revealed that the para-substitutions of the azobenzene moiety strongly affect the photo-isomerization ability and thermal stability of the cis-form. The results suggest that proper substitution of the azobenzene moiety can improve the properties of dUAz as a light-responsive nucleic acid probe. View Full-Text
Keywords: azobenzene; nucleoside; nucleic acid probe; oligonucleotide; photochromism azobenzene; nucleoside; nucleic acid probe; oligonucleotide; photochromism
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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. (CC BY 4.0).

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MDPI and ACS Style

Mori, S.; Morihiro, K.; Kasahara, Y.; Tsunoda, S.-I.; Obika, S. Synthesis and Properties of 2'-Deoxyuridine Analogues Bearing Various Azobenzene Derivatives at the C5 Position. Chemosensors 2015, 3, 36-54.

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