ArticleACS central science2017
Epidithiodiketopiperazines: Strain-Promoted Thiol-Mediated Cellular Uptake at the Highest Tension.
Article in ACS central science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
37 citing papers in PubMed, 94 citations in OpenAlex.
- Traceless trimethyl-lock translators for thiol-mediated uptake of native proteins as covalent constructs.Chemical science · 2026Article
- Cell surface thiol-disulfide regulation in cancer: Mechanisms, implications, and theranostic strategies.Redox biology · 2026Review
- Ketoboronate as a Minimal Covalent-Reversible Tag for Targeted Lysosomal Degradation of Extracellular and Membrane Proteins.Journal of the American Chemical Society · 2025Article
- Thiol-mediated uptake of phosphorothioate liposomes, visualized with fluorescent flippers.Chemical science · 2025Article
- Medical and Nonmedical Applications of Synthetic Transmembrane Anion Transporters.Chemical reviews · 2025Review
- Total Synthesis of (±)-3-Thiaglutamate.Tetrahedron letters · 2024Article
- Trivalent Disulfide Unit-Masked System Efficiently Delivers Large Oligonucleotide.Molecules (Basel, Switzerland) · 2024Article
- Trigonometric Bundling Disulfide Unit Starship Synergizes More Effectively to Promote Cellular Uptake.International journal of molecular sciences · 2024Article
- Total Synthesis and Stereochemical Assignment of Enteropeptin A.Journal of the American Chemical Society · 2024Article
- Inclusive Pattern Generation Protocols to Decode Thiol-Mediated Uptake.ACS central science · 2024Article
- FluorogenicJACS Au · 2023Article
- Fluorescent Probes for Mammalian Thioredoxin Reductase: Mechanistic Analysis, Construction Strategies, and Future Perspectives.Biosensors · 2023Review
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- Dynamic Covalent Michael Acceptors to Penetrate Cells: Thiol-Mediated Uptake with Tetrel-Centered Exchange Cascades, Assisted by Halogen-Bonding Switches.Angewandte Chemie (International ed. in English) · 2022Article
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- Article
- Cyclic Thiosulfonates for Thiol-Mediated Uptake: Cascade Exchangers, Transporters, Inhibitors.JACS Au · 2022Article
- Cyclic 5-membered disulfides are not selective substrates of thioredoxin reductase, but are opened nonspecifically.Nature communications · 2022Article
- Stereodivergent Chirality Transfer by Noncovalent Control of Disulfide Bonds.Journal of the American Chemical Society · 2022Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The disulfide dihedral angle in epidithiodiketopiperazines (ETPs) is near 0°. Application of this highest possible ring tension to strain-promoted thiol-mediated uptake results in efficient delivery to the cytosol and nucleus. Compared to the previous best asparagusic acid (AspA), ring-opening disulfide exchange with ETPs occurs more efficiently even with nonactivated thiols, and the resulting thiols exchange rapidly with nonactivated disulfides. ETP-mediated cellular uptake is more than 20 times more efficient compared to AspA, occurs without endosomal capture, depends on temperature, and is "unstoppable" by inhibitors of endocytosis and conventional thiol-mediated uptake, including siRNA against the transferrin receptor. These results suggest that ETP-mediated uptake not only maximizes delivery to the cytosol and nucleus but also opens the door to a new multitarget hopping mode of action.
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.