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DOI: 10.1055/s-0039-1690291
Water-Soluble BODIPY Dyes for Voltage Imaging
Publikationsverlauf
Publikationsdatum:
18. Oktober 2019 (online)
![](https://www.thieme-connect.de/media/synfacts/201911/i_t105_s1_10-1055_s-0039-1690291.gif)
Significance
Previously, water solubility of BODIPY dyes was achieved through direct functionalization of the BODIPY fluorophore. Miller and co-workers report an elegant and versatile solution that does not significantly alter the dye electronics through introduction of a sulfonate on the meso-aromatic ring. These fluorophores are used to generate a series of new VoltageFluor (VF) dyes that enable the recording of action potential dynamics in neurons and cardiomyocytes.
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Comment
The TFA-catalyzed condensation of aldehydes with pyrroles in the synthesis of BODIPY dyes is commonly performed in CH2Cl2 and often reported to be low-yielding. Here, the authors optimized this reaction with their sulfonated aldehyde, which was found to be insoluble in CH2Cl2 and toluene. Comparably good yields were obtained in DMF (e.g. 49% over three steps, see above). Therefore, the reported strategy for water-soluble BODIPY synthesis could be very useful for the wider community.
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![](https://www.thieme-connect.de/media/synfacts/201911/i_t105_s1_10-1055_s-0039-1690291.gif)