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  Phosphorylated 3-heteroarylcoumarins and their use in fluorescence microscopy and nanoscopy.

Nizamov, S., Willig, K. I., Sednev, M. V., Belov, V. N., & Hell, S. W. (2012). Phosphorylated 3-heteroarylcoumarins and their use in fluorescence microscopy and nanoscopy. Chemistry-A European Journal, 18(51), 16339-16348. doi:10.1002/chem.201202382.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-000E-7080-1 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0027-C7DA-6
Genre: Journal Article

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 Creators:
Nizamov, S., Author
Willig, K. I.1, Author              
Sednev, M. V.1, Author              
Belov, V. N.1, Author              
Hell, S. W.1, Author              
Affiliations:
1Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society, ou_578627              

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Free keywords: Bioconjugation; coumarins; dyes/pigments; fluorescence; synthetic methods
 Abstract: Photostable and bright fluorescent dyes with large Stokes shifts are widely used as markers in far-field optical microscopy, but the variety of useful dyes is limited. The present study introduces new 3-heteroaryl coumarins decorated with a primary phosphate group (OP(O)(OH)2) attached to C-4 in 2,2,4-trimethyl-1,2-dihydroquinoline fragment fused with the coumarin fluorophore. The general synthetic route is based on the Suzuki reaction of 3-bromocoumarines with hetarylboronic acids followed by oxidation of the methyl group at the C[DOUBLE BOND]C bond with SeO2 (to an aldehyde), reduction with NaBH4 (to an alcohol), and conversion into a primary phosphate. The 4 position in the coumarin system may be unsubstituted or bear a methyl group. Phosphorylated coumarins were found to have high fluorescence quantum yields in the free state and after conjugation with proteins (in aqueous buffers). In super-resolution light microscopy with stimulated emission depletion (STED), the new coumarin dyes provide an optical resolution of 40–60 nm with a low background signal. Due to their large Stokes shifts and high photostability, phosphorylated coumarins enable to combine multilabel imaging (using one detector and several excitation sources) with diffraction unlimited optical resolution.

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Language(s): eng - English
 Dates: 2012-10-302012-12-14
 Publication Status: Published in print
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 Rev. Method: Peer
 Identifiers: DOI: 10.1002/chem.201202382
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Title: Chemistry-A European Journal
Source Genre: Journal
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Pages: - Volume / Issue: 18 (51) Sequence Number: - Start / End Page: 16339 - 16348 Identifier: -