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Synthesis of a far-red photoactivatable silicon-containing rhodamine for super-resolution microscopy
Please always quote using this URN: urn:nbn:de:bvb:20-opus-191069
- The rhodamine system is a flexible framework for building small‐molecule fluorescent probes. Changing N‐substitution patterns and replacing the xanthene oxygen with a dimethylsilicon moiety can shift the absorption and fluorescence emission maxima of rhodamine dyes to longer wavelengths. Acylation of the rhodamine nitrogen atoms forces the molecule to adopt a nonfluorescent lactone form, providing a convenient method to make fluorogenic compounds. Herein, we take advantage of all of these structural manipulations and describe a novelThe rhodamine system is a flexible framework for building small‐molecule fluorescent probes. Changing N‐substitution patterns and replacing the xanthene oxygen with a dimethylsilicon moiety can shift the absorption and fluorescence emission maxima of rhodamine dyes to longer wavelengths. Acylation of the rhodamine nitrogen atoms forces the molecule to adopt a nonfluorescent lactone form, providing a convenient method to make fluorogenic compounds. Herein, we take advantage of all of these structural manipulations and describe a novel photoactivatable fluorophore based on a Si‐containing analogue of Q‐rhodamine. This probe is the first example of a “caged” Si‐rhodamine, exhibits higher photon counts compared to established localization microscopy dyes, and is sufficiently red‐shifted to allow multicolor imaging. The dye is a useful label for super‐resolution imaging and constitutes a new scaffold for far‐red fluorogenic molecules.…
Author: | Jonathan B. Grimm, Teresa Klein, Benjamin G. Kopek, Gleb Shtengel, Harald F. Hess, Markus Sauer, Luke D. Lavis |
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URN: | urn:nbn:de:bvb:20-opus-191069 |
Document Type: | Journal article |
Faculties: | Fakultät für Biologie / Theodor-Boveri-Institut für Biowissenschaften |
Language: | English |
Parent Title (English): | Angewandte Chemie International Edition |
Year of Completion: | 2016 |
Volume: | 55 |
Issue: | 5 |
Pagenumber: | 1723-1727 |
Source: | Angewandte Chemie International Edition (2016) 55:5, S. 1723-1727. https://doi.org/10.1002/anie.201509649 |
DOI: | https://doi.org/10.1002/anie.201509649 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 57 Biowissenschaften; Biologie / 570 Biowissenschaften; Biologie |
Tag: | Si-rhodamine; fluorophore; microscopy; photoactivation; super-resolution imaging |
Release Date: | 2021/02/15 |
Licence (German): | CC BY-NC: Creative-Commons-Lizenz: Namensnennung, Nicht kommerziell 4.0 International |