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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 SeO2to the corresponding α,β-unsaturated aldehyde and then reduced with NaBH4in 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. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Registro:

Documento: Artículo
Título:“Reduced” Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy
Autor:Nizamov, S.; Sednev, M.V.; Bossi, M.L.; Hebisch, E.; Frauendorf, H.; Lehnart, S.E.; Belov, V.N.; Hell, S.W.
Filiación:Department of NanoBiophotonics, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, Göttingen, 37077, Germany
Laboratorio de Nanoscopias Fotonicas, INQUIMAE-DQIAyQF (FCEyN), Universidad de Buenos Aires & Conicet, Buenos Aires, Argentina
Institute for Organic and Biomolecular Chemistry, Georg-August University, Tammannstrasse 2, Göttingen, 37077, Germany
Heart Research Center Göttingen, Department of Cardiology & Pulmonology, University Medical Center Göttingen, Göttingen, 37077, Germany
Palabras clave:bioconjugation; coumarins; dyes/pigments; fluorescence; STED microscopy; Antibodies; Carboxylation; Fluorescence; Fluorescence microscopy; Phosphorylation; Stimulated emission; Substitution reactions; Antibody conjugate; Bio-conjugation; coumarins; Dyes/pigments; Photophysical properties; Secondary antibodies; STED microscopies; Unsaturated aldehydes; Methanol; coumarin derivative; fluorescent dye; quinoline derivative; chemistry; fluorescence microscopy; phosphorylation; synthesis; Coumarins; Fluorescent Dyes; Microscopy, Fluorescence; Phosphorylation; Quinolines
Año:2016
Volumen:22
Número:33
Página de inicio:11631
Página de fin:11642
DOI: http://dx.doi.org/10.1002/chem.201601252
Título revista:Chemistry - A European Journal
Título revista abreviado:Chem. Eur. J.
ISSN:09476539
CODEN:CEUJE
CAS:Coumarins; Fluorescent Dyes; Quinolines
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09476539_v22_n33_p11631_Nizamov

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Citas:

---------- APA ----------
Nizamov, S., Sednev, M.V., Bossi, M.L., Hebisch, E., Frauendorf, H., Lehnart, S.E., Belov, V.N.,..., Hell, S.W. (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.
http://dx.doi.org/10.1002/chem.201601252
---------- CHICAGO ----------
Nizamov, S., Sednev, M.V., Bossi, M.L., Hebisch, E., Frauendorf, H., Lehnart, S.E., et al. "“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, no. 33 (2016) : 11631-11642.
http://dx.doi.org/10.1002/chem.201601252
---------- MLA ----------
Nizamov, S., Sednev, M.V., Bossi, M.L., Hebisch, E., Frauendorf, H., Lehnart, S.E., et al. "“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, vol. 22, no. 33, 2016, pp. 11631-11642.
http://dx.doi.org/10.1002/chem.201601252
---------- VANCOUVER ----------
Nizamov, S., Sednev, M.V., Bossi, M.L., Hebisch, E., Frauendorf, H., Lehnart, S.E., et al. “Reduced” Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy. Chem. Eur. J. 2016;22(33):11631-11642.
http://dx.doi.org/10.1002/chem.201601252