Synthesis of a far-red photoactivatable silicon-containing rhodamine for super-resolution microscopy.

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Angewandte Chemie (International ed. in English). 2015 Dec 11;55(5):1723-7. doi: 10.1002/anie.201509649

Synthesis of a far-red photoactivatable silicon-containing rhodamine for super-resolution microscopy. Hess LabLavis Lab

Grimm JB, Klein T, Kopek BG, Shtengel G, Hess HF, Sauer M, Lavis LD

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Abstract

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 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.

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Synthesis of a far-red photoactivatable silicon-containing rhodamine for super-resolution microscopy.

Abstract

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