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

Article Article scientifique Article Diselenolane‐Mediated Cellular Uptake: Efficient Cytosolic Delivery of Probes, Peptides, Proteins, Artificial Metalloenzymes and Protein‐Coated Quantum Dots eng 2019 author Bartolami Eline 849247 author Basagiannis Dimitris 884836 author Zong Lili 848484 author Martinent Rémi 885155 author Okamoto Yasunori author Laurent Quentin François Antoine 893791 author Ward Thomas R. author Gonzalez Gaitan Marcos 645929 author Sakai Naomi 0000-0002-9460-1944 131140 author Matile Stefan 0000-0002-8537-8349 129654 4047-4051 10.1002/chem.201805900 0947-6539 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. Dewey 540 36 Département de chimie organique 141 39 Département de biochimie 144 false 765 Groupe Gonzalez Gaitan 761 Groupe Matile Chemistry - A European Journal 25 16 56edbcaa-8c08-4cb3-8480-6167a691f35c Article (Published version) Restricted Bartolami_et_al-2019-Chemistry_-_A_European_Journal.pdf 1186461 application/pdf 3eaeca90-b9bb-4dbb-b1e7-126f27785f1a Article (Accepted version) Public 299.pdf 8956727 application/pdf Restricted 2020-02-19 openAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique Faculté des sciences / Section de chimie et biochimie / Département de biochimie

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Morphogen gradient scaling by recycling of intracellular Dpp	Nature	2021	752	565
Diselenolane‐Mediated Cellular Uptake: Efficient Cytosolic Delivery of Probes, Peptides, Proteins, Artificial Metalloenzymes and Protein‐Coated Quantum Dots	Chemistry - A European Journal	2019	556	402

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