Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 16, Pages 4047-4051Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201805900
Keywords
biotechnology; diselenolane; protein delivery; ring tension; streptavidin
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Funding
- University of Geneva
- Swiss National Centre of Competence in Research (NCCR) Chemical Biology
- NCCR Molecular Systems Engineering
- Swiss NSF
- JSPS Overseas research fellowship
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Cyclic oligochalcogenides are emerging as powerful tools to penetrate cells. With disulfide ring tension maximized, selenium chemistry had to be explored next to enhance speed and selectivity of dynamic covalent exchange on the way into the cytosol. We show that diseleno lipoic acid (DiSeL) delivers a variety of relevant substrates. DiSeL-driven uptake of artificial metalloenzymes enables bioorthogonal fluorophore uncaging within cells. Binding of a bicyclic peptide, phalloidin, to actin fibers evinces targeted delivery to the cytosol. Automated tracking of diffusive compared to directed motility and immobility localizes 79 % of protein-coated quantum dots (QDs) in the cytosol, with little endosomal capture (0.06 %). These results suggest that diselenolanes might act as molecular walkers along disulfide tracks in locally denatured membrane proteins, surrounded by adaptive micellar membrane defects. Miniscule and versatile, DiSeL tags are also readily available, stable, soluble, and non-toxic.
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