"Reduced" Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-( hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy

2016 | journal article; research paper. A publication with affiliation to the University of Göttingen.

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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.   & Belov, V. N.  et al.​ (2016) 
Chemistry - A European Journal22(33) pp. 11631​-11642​.​ DOI: https://doi.org/10.1002/chem.201601252 

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Authors
Nizamov, Shamil; Sednev, Maksim V. ; Bossi, Mariano L. ; Hebisch, Elke; Frauendorf, Holm ; Lehnart, Stephan E. ; Belov, Vladimir N. ; Hell, Stefan W. 
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 a, alpha,beta-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-dihydroqui-noline 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.
Issue Date
2016
Journal
Chemistry - A European Journal 
Project
SFB 1002: Modulatorische Einheiten bei Herzinsuffizienz 
SFB 1002 | A05: Molekulares Imaging von kardialen Calcium-Freisetzungsdomänen 
SFB 1002 | C02: RhoGTPasen und ihre Bedeutung für die Last-abhängige Myokardfibrose 
Working Group
RG Hell 
RG Lehnart (Cellular Biophysics and Translational Cardiology Section) 
External URL
https://sfb1002.med.uni-goettingen.de/production/literature/publications/148
ISSN
0947-6539; 1521-3765
Language
English

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