“Reduced” Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy
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-trimethylqu...
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todo:paper_09476539_v22_n33_p11631_Nizamov2023-10-03T15:49:30Z “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. Hell, S.W. 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 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 Fil:Bossi, M.L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_09476539_v22_n33_p11631_Nizamov |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Nizamov, S. Sednev, M.V. Bossi, M.L. Hebisch, E. Frauendorf, H. Lehnart, S.E. Belov, V.N. Hell, S.W. “Reduced” Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy |
| topic_facet |
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 |
| description |
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 |
| format |
JOUR |
| author |
Nizamov, S. Sednev, M.V. Bossi, M.L. Hebisch, E. Frauendorf, H. Lehnart, S.E. Belov, V.N. Hell, S.W. |
| author_facet |
Nizamov, S. Sednev, M.V. Bossi, M.L. Hebisch, E. Frauendorf, H. Lehnart, S.E. Belov, V.N. Hell, S.W. |
| author_sort |
Nizamov, S. |
| title |
“Reduced” Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy |
| title_short |
“Reduced” Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy |
| title_full |
“Reduced” Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy |
| title_fullStr |
“Reduced” Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy |
| title_full_unstemmed |
“Reduced” Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy |
| title_sort |
“reduced” coumarin dyes with an o-phosphorylated 2,2-dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline fragment: synthesis, spectra, and sted microscopy |
| url |
http://hdl.handle.net/20.500.12110/paper_09476539_v22_n33_p11631_Nizamov |
| work_keys_str_mv |
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