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

Chemosensors

Shohei Mori²  Kunihiko Morihiro²  Yuuya Kasahara²  Shin-ichi Tsunoda¹  Satoshi Obika² 

[1] National Institute of Biomedical Innovation (NIBIO), 7-6-8 Saito-Asagi, Osaka 567-0085, Japan; E-Mail:;Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan; E-Mails:

关键词: azobenzene;    nucleoside;    nucleic acid probe;    oligonucleotide;    photochromism;   

DOI  :  10.3390/chemosensors3020036

来源: mdpi

【 摘 要 】

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 (dU^Az), whose hybridization ability could be reversibly controlled by the appropriate wavelength of light. In this paper, we synthesized and evaluated dU^Az 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 dU^Az as a light-responsive nucleic acid probe.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.