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Highly Activatable and Environment-Insensitive Optical Highlighters for Selective Spatiotemporal Imaging of Target Proteins

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† ‡ Graduate School of Pharmaceutical Sciences and Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
§ Departments of Biochemistry and Molecular Biology, Faculty of Sciences, Geneva University, 30 Quai Ernest-Ansermet, 1211 Geneva, Switzerland
*To whom correspondence should be addressed. E-mail: [email protected]
Cite this: J. Am. Chem. Soc. 2012, 134, 27, 11153–11160
Publication Date (Web):June 13, 2012
Copyright © 2012 American Chemical Society

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    Optical highlighters are photoactivatable fluorescent molecules that exhibit pronounced changes in their spectral properties in response to irradiation with light of a specific wavelength and intensity. Here, we present a novel design strategy for a new class of caged BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) fluorophores, based on the use of photoremovable protecting groups (PRPGs) with high reduction potentials that serve as both a photosensitive unit and a fluorescence quencher via photoinduced electron transfer (PeT). 2,6-Dinitrobenzyl (DNB)-caged BODIPY was efficiently photoactivated, with activation ratios exceeding 600-fold in aqueous solutions. We then combined this photoactivatable fluorophore with a SNAP (mutant of O6-alkylguanine DNA alkyltransferase) ligand to obtain a small-molecule-based optical highlighter for visualization of protein dynamics, using the well-established SNAP tag technology. As proof of concept, we demonstrate spatiotemporal imaging of the fusion protein of epidermal growth factor receptor (EGFR) with SNAP tag in living cells. We also demonstrate highlighting of cells of interest in live zebrafish embryos, using the fusion protein of histone 2A with SNAP tag.

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    Experimental conditions; supplementary methods for chemical synthesis and characterization of compounds; supplementary experiments and data; Figures S1–S15; Table S1; supplementary movies 1–3; complete ref 26. This material is available free of charge via the Internet at

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