Coumarin–Tetrazine Probes for Bioimaging

  • Author: Chemistry – A European Journal
  • Published Date: 09 September 2020
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH GmbH
thumbnail image: Coumarin–Tetrazine Probes for Bioimaging

Related Societies

The labeling and visualization of biomolecules within living systems are important for the study of complex biological processes. Commonly used strategies for this are based on fluorescent dyes that are attached to enzymes or proteins by a selective chemical click reaction and then observed by fluorescence microscopy. One problem in such experiments is the generation of unspecific signals arising from an excess of the fluorescent probe. Fluorescent probes that only light up upon a specific chemical reaction can solve this problem and allow improved precision in the observation of biological systems.


Milan Vrabel and colleagues, Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague, have systematically studied the fluorogenic properties of a series of coumarin–tetrazine probes (pictured above). These probes produce fluorescent dyes after a reaction with a trans-cyclooctene (TCO) or bicyclononyne (BCN) dienophile. The team prepared a variety of probes starting from a coumarin derivative. They used a reaction sequence that includes an amination to introduce R1, a Suzuki coupling to introduce a (hetero-)aromatic spacer, and a cycloaddition to form the R2-substituted tetrazine unit.


The team found that azetidine or N,N-dimethylpiperazine groups attached to the coumarin scaffold lead to improved fluorescence quantum yield. They identified a probe with an azetidine-substituted coumarin, a pyridyl linker, and a 6-pyrimidine‐substituted tetrazine (pictured on the right) as the most versatile probe with superior labeling efficiency in live cells. The team attributes the probe's good performance to a combination of good reaction kinetics and cell permeability.


 

 

Article Views: 1686

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


Magazine of Chemistry Europe (16 European Chemical Societies)published by Wiley-VCH