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Chem Asian J. 2014 Dec;9(12):3344-58. doi: 10.1002/asia.201402758. Epub 2014 Sep 18.

Modification of nucleic acids by azobenzene derivatives and their applications in biotechnology and nanotechnology.

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College of Food Science and Engineering, Ocean University of China, Nucleic Acids Chemistry and Biotechnology Laboratory, No. 5 Yushan Road, Shinan-qu, Qingdao City (China), Fax: (+81)‚ÄČ532-82031086.


Azobenzene has been widely used as a photoregulator due to its reversible photoisomerization, large structural change between E and Z isomers, high photoisomerization yield, and high chemical stability. On the other hand, some azobenzene derivatives can be used as universal quenchers for many fluorophores. Nucleic acid is a good candidate to be modified because it is not only the template of gene expression but also widely used for building well-organized nanostructures and nanodevices. Because the size and polarity distribution of the azobenzene molecule is similar to a nucleobase pair, the introduction of azobenzene into nucleic acids has been shown to be an ingenious molecular design for constructing light-switching biosystems or light-driven nanomachines. Here we review recent advances in azobenzene-modified nucleic acids and their applications for artificial regulation of gene expression and enzymatic reactions, construction of photoresponsive nanostructures and nanodevices, molecular beacons, as well as obtaining structural information using the introduced azobenzene as an internal probe. In particular, nucleic acids bearing multiple azobenzenes can be used as a novel artificial nanomaterial with merits of high sequence specificity, regular duplex structure, and high photoregulation efficiency. The combination of functional groups with biomolecules may further advance the development of chemical biotechnology and biomolecular engineering.


DNA nanotechnology; azobenzene; nucleic acids; photoregulation; probes

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