Inherently Emissive Puromycin Analogues for Live Cell Labelling

Puromycin derivatives containing an emissive thieno[3,4‐d]‐pyrimidine core, modified with azetidine and 3,3‐difluoroazetidine as Me2N surrogates, exhibit translation inhibition and bactericidal activity similar to the natural antibiotic. The analogues are capable of cellular puromycylation of nascen...

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Bibliographic Details
Published in:Angewandte Chemie 2023-06, Vol.135 (23), p.n/a
Main Authors: Hadidi, Kaivin, Steinbuch, Kfir B., Dozier, Lara E., Patrick, Gentry N., Tor, Yitzhak
Format: Article
Language:English
Subjects:
Antibiotics
Bactericidal activity
Chemistry
Emissivity
Fluorescence
Heterocycles
Hippocampus
Labeling
Labelling
Modified Nucleosides
Peptides
Puromycin
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Summary:Puromycin derivatives containing an emissive thieno[3,4‐d]‐pyrimidine core, modified with azetidine and 3,3‐difluoroazetidine as Me2N surrogates, exhibit translation inhibition and bactericidal activity similar to the natural antibiotic. The analogues are capable of cellular puromycylation of nascent peptides, generating emissive products without any follow‐up chemistry. The 3,3‐difluoroazetidine‐containing analogue is shown to fluorescently label newly translated peptides and be visualized in both live and fixed HEK293T cells and rat hippocampal neurons. Inherently emissive puromycin analogues can fluorescently tag newly synthesized proteins in live‐cells without the need for further chemical treatments.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202216784