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)
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-TextKeywords:
azobenzene; nucleoside; nucleic acid probe; oligonucleotide; photochromism
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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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