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Molecules 2014, 19(4), 5109-5118; doi:10.3390/molecules19045109

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

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)
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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 (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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

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