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  Reversibly photoswitchable fluorescent diarylethenes resistant against photobleaching in aqueous solutions.

Uno, K., Bossi, M. L., Irie, M., Belov, V. N., & Hell, S. W. (2019). Reversibly photoswitchable fluorescent diarylethenes resistant against photobleaching in aqueous solutions. Journal of the American Chemical Society, 141(41), 16471-16478. doi:10.1021/jacs.9b08748.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0005-0A42-6 Version Permalink: http://hdl.handle.net/21.11116/0000-0005-0A46-2
Genre: Journal Article

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Uno, K.1, Author              
Bossi, M. L.1, Author              
Irie, M., Author
Belov, V. N.1, Author              
Hell, S. W.1, Author              
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1Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society, ou_578627              

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 Abstract: Low photostability in aqueous solutions is the main drawback of synthetic photochromic dyes, which limits their switching performance and utility in biology, medicine, and life sciences. Even the most promising photochromes—reversibly photoswitchable diarylethenes (DAEs) with fluorescent “closed” forms—are known to undergo only several tens (typically 20–30) of switching cycles in aqueous solutions. In this work, we introduce water-soluble and highly photostable 1,2-[bis(2-ethyl/2-isobutyl-1-benzothiophene-1,1-dioxide-6-phenyl-3-yl)]perfluorocyclopentenes decorated with four −CONHC(CH2R)3 residues capped with 12 carboxylic acid groups (R = CH2CO2H, O(CH2)2CO2H). Under irradiation with UV (365 nm) and visible light (470 nm), they provide several hundred (for the “rapid” DAEs with isobutyl groups, up to 1000) full switching cycles in aqueous solutions without exclusion of air oxygen (outperforming the photoswitchable and fluorescent protein Dreiklang). The new branching approach based on secondary carboxamides with N-tert-alkyl residues decorated with polar groups may serve as a blueprint for the design of highly fatigue resistant and reversibly photoswitchable fluorescent probes applicable in life sciences as aqueous solutions.

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Language(s): eng - English
 Dates: 2019-09-222019
 Publication Status: Published in print
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 Rev. Method: Peer
 Identifiers: DOI: 10.1021/jacs.9b08748
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Title: Journal of the American Chemical Society
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Pages: - Volume / Issue: 141 (41) Sequence Number: - Start / End Page: 16471 - 16478 Identifier: -