Diselenolane-Mediated Cellular Uptake: Efficient Cytosolic Delivery of Probes, Peptides, Proteins, Artificial Metalloenzymes and Protein-Coated Quantum Dots

Chemistry : a European Journal
Eline BartolamiStefan Matile

Abstract

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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Citations

Jun 7, 2019·Angewandte Chemie·Yangyang ChengStefan Matile
Oct 12, 2019·Chembiochem : a European Journal of Chemical Biology·Quentin LaurentStefan Matile
Jul 8, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tomoki Himiyama, Yasunori Okamoto
Oct 14, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Dandan SuSébastien Ulrich
Sep 26, 2020·Chembiochem : a European Journal of Chemical Biology·Rémi MartinentStefan Matile
Jan 19, 2021·Journal of Peptide Science : an Official Publication of the European Peptide Society·Bastian BeckerHarald Kolmar
Jan 6, 2021·Topics in Current Chemistry·Sueden O SouzaGoreti Pereira
Feb 1, 2020·Materials Chemistry Frontiers·Yan ZhangOlof Ramström
Sep 2, 2021·JACS Au·Quentin LaurentStefan Matile

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