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Substituting deuterium for hydrogen improves fluorescent properties of dyes

Isotope effects slow processes that destabilize and dim dyes

by Celia Henry Arnaud
May 7, 2021 | A version of this story appeared in Volume 99, Issue 17


Superresolution cell images using undeuterated (top) and deuterated (bottom) rhodamine dyes as fluorescent labels.
Credit: JACS Au
Deuterated rhodamine dyes (bottom) fluoresce brighter and longer than undeuterated ones (top). Shown here are labeled Golgi apparatus in yeast cells at 0 min. After 3 min, the undeuterated dyes no longer fluoresce, but the deuterated ones are still visible.

Fluorescence microscopy is a powerful tool for biological research. Researchers would like brighter, more stable fluorophores that enable longer imaging experiments. Rhodamine dyes are particularly bright and stable, and they can be tuned by incorporating various substituents into their structure. But even rhodamines have room for improvement. A team led by Luke D. Lavis of the Howard Hughes Medical Institute’s Janelia Research Campus has upped rhodamines’ game by making a simple switch—replacing hydrogen atoms with their more massive chemical twin, deuterium (JACS Au 2021, DOI: 10.1021/jacsau.1c00006). Instead of deuterating the xanthene core, the researchers deuterated the alkylamino substituents. The deuteration improved the brightness and stability of the dyes without causing unwanted shifts in their fluorescence spectra. The improvements result from isotope effects that slow processes that destabilize and dim the dyes. For cellular imaging, the dyes enabled experiments with longer duration and higher signal. In addition, the researchers showed that deuteration improves the properties of other classes of fluorophores, which suggests that it could be a general approach for improving fluorescent labels.


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