Photoswitches for Biomolecules

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This article was published as part of the
Downloaded by Shanghai Jiaotong University on 03 December 2011 Published on 12 April 2011 on http://pubs.rsc.org | doi:10.1039/C1CS15023E

Small molecules in biology themed issue
Guest editors Ali Tavassoli, Andrew D. Hamilton and David R. Spring

Please take a look at the issue 8 2011 table of contents to access other reviews in this themed issue

Chem Soc Rev
Cite this: Chem. Soc. Rev., 2011, 40, 4422–4437 www.rsc.org/csr

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CRITICAL REVIEW

Azobenzene photoswitches for biomoleculesw
Andrew A. Beharry and G. Andrew Woolley*
Downloaded by Shanghai Jiaotong University on 03 December 2011 Published on 12 April 2011 on http://pubs.rsc.org | doi:10.1039/C1CS15023E

Received 22nd January 2011 DOI: 10.1039/c1cs15023e The photoisomerization of azobenzene has been known for almost 75 years but only recently has this process been widely applied to biological systems. The central challenge of how to productively couple the isomerization process to a large functional change in a biomolecule has been met in a number of instances and it appears that effective photocontrol of a large variety of biomolecules may be possible. This critical review summarizes key properties of azobenzene that enable its use as a photoswitch in biological systems and describes strategies for using azobenzene photoswitches to drive functional changes in peptides, proteins, nucleic acids, lipids, and carbohydrates (192 references). Genetic approaches that act in vivo (e.g. gene knockouts) often lack temporal precision (i.e. they eliminate the function of the biomolecule at all times and places). Small molecules (e.g. enzyme inhibitors) can permit greater temporal control but may suffer from a lack of target specificity. An ideal approach for probing the role of a specific biomolecule in its native environment is one that can permit spatial and temporal control of that molecule uniquely on a time frame and spatial scale comparable to, or better than, that which occurs naturally. Light can be controlled with high temporal and spatial precision so that if a particular molecule can be made light sensitive, this would achieve precise spatiotemporal control. A variety of approaches have been taken to chemically modifying a biomolecule in a manner aimed at endowing it with light-controlled function. There are a number of requirements that such chemical modifications must meet. First the

Introduction
Cellular events are mediated by complex biochemical pathways involving a network of biomolecules that communicate in a temporally and spatially well-defined fashion. For example, a certain protein may function near the cell membrane during a particular growth stage of the cell and participate in a specific set of interactions whereas the same biomolecule may participate in a different set of interactions at some other time and place. The spatiotemporal details of a biomolecule’s function are lost if the system is purified into components and often this complexity is difficult to reconstitute in vitro. Department of Chemistry, University of Toronto, 80 St. George St. Toronto, ON M5S 3H6, Canada. E-mail: awoolley@chem.utoronto.ca; Fax: +1 416-978-8775; Tel: +1 416-978-0675 w Part of the themed issue on small molecules in biology.

Andrew A. Beharry

Andrew A. Beharry received his Honours BSc Degree in Chemistry (minor in biology) from York University with a focus on physical and biological chemistry. In 2007 he joined G. Andrew Woolley’s lab at the University of Toronto as a PhD candidate student. His current research involves the design and characterization of new azobenzene photoswitches suitable for cellular applications, as well as their ability to reversibly alter protein function.

G. Andrew (Drew) Woolley was born in Edinburgh, Scotland but at a young age he moved to Toronto, Canada. He attended the University of...
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