A Versatile Route to Red-Emitting Carbopyronine Dyes for Optical Microscopy and Nanoscopy
Biological microscopy favors photostable fluorescent markers with large fluorescence quantum yields, low dark triplet state population, good biocompatibility and absorption and emission maxima in the near-infrared, where cellular autofluorescence is minimized. In the present study, carbopyronines ab...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2010
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| _version_ | 1797051343746105344 |
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| author | Kolmakov, K Belov, V Wurm, C Harke, B Leutenegger, M Eggeling, C Hell, S |
| author_facet | Kolmakov, K Belov, V Wurm, C Harke, B Leutenegger, M Eggeling, C Hell, S |
| author_sort | Kolmakov, K |
| collection | OXFORD |
| description | Biological microscopy favors photostable fluorescent markers with large fluorescence quantum yields, low dark triplet state population, good biocompatibility and absorption and emission maxima in the near-infrared, where cellular autofluorescence is minimized. In the present study, carbopyronines absorbing around 640 nm and emitting at around 660 nm, with a low intersystem crossing rate (kisc ≈ 0.5×106 s-1) and excellent properties for cellular imaging were synthesized. A general synthetic route to carbopyronines with functional groups variable in the final steps of the synthesis or in the resulting fluorescent dye is presented. Possessing two 2-me-thoxyethyl groups, the parent dye is soluble in water and most organic solvents. Demethylation of the dye or its precursors is straightforward, clean, and furnishes compounds with one or two 2-hydroxyethyl groups, which can be used for further transformations. Modifications in the linker-containing carboxy group are also possible. A multistep synthesis of the dye starting from a simple precursor and utilizing a single temporary protective group is described. The presented approach may be further applied to the design of caged carbopyronines. © 2010 Wiley-VCH Verlag GmbH and Co. KGaA, Weinheim. |
| first_indexed | 2024-03-06T18:18:10Z |
| format | Journal article |
| id | oxford-uuid:055a39a1-0ba7-42db-8a7d-1ece84863226 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T18:18:10Z |
| publishDate | 2010 |
| record_format | dspace |
| spelling | oxford-uuid:055a39a1-0ba7-42db-8a7d-1ece848632262022-03-26T08:56:39ZA Versatile Route to Red-Emitting Carbopyronine Dyes for Optical Microscopy and NanoscopyJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:055a39a1-0ba7-42db-8a7d-1ece84863226EnglishSymplectic Elements at Oxford2010Kolmakov, KBelov, VWurm, CHarke, BLeutenegger, MEggeling, CHell, SBiological microscopy favors photostable fluorescent markers with large fluorescence quantum yields, low dark triplet state population, good biocompatibility and absorption and emission maxima in the near-infrared, where cellular autofluorescence is minimized. In the present study, carbopyronines absorbing around 640 nm and emitting at around 660 nm, with a low intersystem crossing rate (kisc ≈ 0.5×106 s-1) and excellent properties for cellular imaging were synthesized. A general synthetic route to carbopyronines with functional groups variable in the final steps of the synthesis or in the resulting fluorescent dye is presented. Possessing two 2-me-thoxyethyl groups, the parent dye is soluble in water and most organic solvents. Demethylation of the dye or its precursors is straightforward, clean, and furnishes compounds with one or two 2-hydroxyethyl groups, which can be used for further transformations. Modifications in the linker-containing carboxy group are also possible. A multistep synthesis of the dye starting from a simple precursor and utilizing a single temporary protective group is described. The presented approach may be further applied to the design of caged carbopyronines. © 2010 Wiley-VCH Verlag GmbH and Co. KGaA, Weinheim. |
| spellingShingle | Kolmakov, K Belov, V Wurm, C Harke, B Leutenegger, M Eggeling, C Hell, S A Versatile Route to Red-Emitting Carbopyronine Dyes for Optical Microscopy and Nanoscopy |
| title | A Versatile Route to Red-Emitting Carbopyronine Dyes for Optical Microscopy and Nanoscopy |
| title_full | A Versatile Route to Red-Emitting Carbopyronine Dyes for Optical Microscopy and Nanoscopy |
| title_fullStr | A Versatile Route to Red-Emitting Carbopyronine Dyes for Optical Microscopy and Nanoscopy |
| title_full_unstemmed | A Versatile Route to Red-Emitting Carbopyronine Dyes for Optical Microscopy and Nanoscopy |
| title_short | A Versatile Route to Red-Emitting Carbopyronine Dyes for Optical Microscopy and Nanoscopy |
| title_sort | versatile route to red emitting carbopyronine dyes for optical microscopy and nanoscopy |
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