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  "Reduced" coumarin dyes with an O-phosphorylated 2,2-dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline fragment: Synthesis, spectra, and STED microscopy.

Nizamov, S., Sednev, M. V., Bossi, M. L., Hebisch, E., Frauendorf, H., Lehnart, S. E., et al. (2016). "Reduced" coumarin dyes with an O-phosphorylated 2,2-dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline fragment: Synthesis, spectra, and STED microscopy. Chemistry - A European Journal, 22(33), 11631-11642. doi:10.1002/chem.201601252.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-002B-2227-4 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-002B-223F-0
Genre: Journal Article

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 Creators:
Nizamov, S.1, Author              
Sednev, M. V.1, Author              
Bossi, M. L.1, Author              
Hebisch, E.1, Author              
Frauendorf, H., Author
Lehnart, S. E., 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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 Abstract: Large Stokes-shift coumarin dyes with an O-phosphorylated 4-(hydroxymethyl)-2,2-dimethyl-1,2,3,4-tetrahydroquinoline fragment emitting in the blue, green, and red regions of the visible spectrum were synthesized. For this purpose, N-substituted and O-protected 1,2-dihydro-7-hydroxy-2,2,4-trimethylquinoline was oxidized with SeO2 to the corresponding α,β-unsaturated aldehyde and then reduced with NaBH4 in a "one-pot" fashion to yield N-substituted and 7-O-protected 4-(hydroxymethyl)-7-hydroxy-2,2-dimethyl-1,2,3,4-tetrahydroquinoline as a common precursor to all the coumarin dyes reported here. The photophysical properties of the new dyes ("reduced coumarins") and 1,2-dihydroquinoline analogues (formal precursors) with a trisubstituted C=C bond were compared. The "reduced coumarins" were found to be more photoresistant and brighter than their 1,2-dihydroquinoline counterparts. Free carboxylate analogues, as well as their antibody conjugates (obtained from N-hydroxysuccinimidyl esters) were also prepared. All studied conjugates with secondary antibodies afforded high specificity and were suitable for fluorescence microscopy. The red-emitting coumarin dye bearing a betaine fragment at the C-3-position showed excellent performance in stimulation emission depletion (STED) microscopy.

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Language(s): eng - English
 Dates: 2016-07-072016-08-08
 Publication Status: Published in print
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 Rev. Method: Peer
 Identifiers: DOI: 10.1002/chem.201601252
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Title: Chemistry - A European Journal
Source Genre: Journal
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Pages: - Volume / Issue: 22 (33) Sequence Number: - Start / End Page: 11631 - 11642 Identifier: -