2023
DOI: 10.1002/hlca.202300020
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Tetrel‐Centered Exchange Cascades to Decouple Inhibition and Induction of Thiol‐Mediated Uptake: Introducing Cell‐Penetrating Thiolactones, Focus on Reversible Michael Acceptor Dimers

Abstract: This study adds thiolactones to the collection of cascade exchangers (CAXs) and reports with dynamic covalent Michael acceptor dimers the first CAXs that rather inhibit than enable thiol‐mediated uptake. The superior performance of dimers compared to monomeric Michael acceptors as inhibitors might suggest that top inhibitors move along thiol/ate arrays without losing covalent contact, while cell penetrators exchange along disulfide arrays. This decoupling of inhibition and induction of thiol‐mediated uptake is… Show more

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Cited by 7 publications
(17 citation statements)
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“…(B) Similar IC 50 comparison for MDA-MB-231 cell motility on fibronectin (symbols as in Figure J). Uptake data from refs , , . (C–F) Fluorescence microscopy images of (C, D) wild-type and (E, F) INT β 1 siRNA knockdown HK cells incubated with (C, E) immunofluorescence integrin probe (red) and (D, F) 17 (green) (yellow, blue: Hoechst 33342, nuclei; scale bars, 30 μm).…”
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“…(B) Similar IC 50 comparison for MDA-MB-231 cell motility on fibronectin (symbols as in Figure J). Uptake data from refs , , . (C–F) Fluorescence microscopy images of (C, D) wild-type and (E, F) INT β 1 siRNA knockdown HK cells incubated with (C, E) immunofluorescence integrin probe (red) and (D, F) 17 (green) (yellow, blue: Hoechst 33342, nuclei; scale bars, 30 μm).…”
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confidence: 99%
“…This decrease matched the formal wound healing times to close a 1 mm scratch (17 h against 40 h). Because it was important to avoid misinterpretation of cell death as motility inhibition, CAXs and controls 1 – 12 were reconfirmed , as nontoxic under the experimental conditions (Figure S3).…”
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