ArticleChemical science2018
Diselenolane-mediated cellular uptake.
Article in Chemical science, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 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
19 citing papers in PubMed, 60 citations in OpenAlex.
- Ketoboronate as a Minimal Covalent-Reversible Tag for Targeted Lysosomal Degradation of Extracellular and Membrane Proteins.Journal of the American Chemical Society · 2025Article
- Dimensional control of DNA nanostructures enhances cellular uptake and guides tissue-regenerative responses.Journal of nanobiotechnology · 2025Article
- Medical and Nonmedical Applications of Synthetic Transmembrane Anion Transporters.Chemical reviews · 2025Review
- Inclusive Pattern Generation Protocols to Decode Thiol-Mediated Uptake.ACS central science · 2024Article
- Fluorescent Probes for Mammalian Thioredoxin Reductase: Mechanistic Analysis, Construction Strategies, and Future Perspectives.Biosensors · 2023Review
- An Orthogonal Dynamic Covalent Chemistry Tool for Ring-Opening Polymerization of Cyclic Oligochalcogenides on Detachable Helical Peptide Templates.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- 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
- Dithiolane quartets: thiol-mediated uptake enables cytosolic delivery in deep tissue.Chemical science · 2021Article
- Thiol-Mediated Uptake.JACS Au · 2021Review
- Small changes in the length of diselenide bond-containing linkages exert great influences on the antitumor activity of docetaxel homodimeric prodrug nanoassemblies.Asian journal of pharmaceutical sciences · 2021Article
- Strategies to expand peptide functionality through hybridisation with a small molecule component.RSC chemical biology · 2021Review
- Inhibitors of thiol-mediated uptake.Chemical science · 2020Article
- Article
- Cell-Penetrating Streptavidin: A General Tool for Bifunctional Delivery with Spatiotemporal Control, Mediated by Transport Systems Such as Adaptive Benzopolysulfane Networks.Journal of the American Chemical Society · 2020Article
- Combination of chemotherapy and oxidative stress to enhance cancer cell apoptosis.Chemical science · 2020Article
- Dynamic Covalent Polymers for Biomedical Applications.Materials chemistry frontiers · 2020Article
- Automated high-content imaging for cellular uptake, from the Schmuck cation to the latest cyclic oligochalcogenides.Beilstein journal of organic chemistry · 2020Article
- Cell-Penetrating Dynamic-Covalent Benzopolysulfane Networks.Angewandte Chemie (International ed. in English) · 2019Article
Corrections and comments
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Authors and funding
8 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The emerging power of thiol-mediated uptake with strained disulfides called for a move from sulfur to selenium. We report that according to results with fluorescent model substrates, cellular uptake with 1,2-diselenolanes exceeds uptake with 1,2-dithiolanes and epidithiodiketopiperazines with regard to efficiency as well as intracellular localization. The diselenide analog of lipoic acid performs best. This 1,2-diselenolane delivers fluorophores efficiently to the cytosol of HeLa Kyoto cells, without detectable endosomal capture as with 1,2-dithiolanes or dominant escape into the nucleus as with epidithiodiketopiperazines. Diselenolane-mediated cytosolic delivery is non-toxic (MTT assay), sensitive to temperature but insensitive to inhibitors of endocytosis (chlorpromazine, methyl-β-cyclodextrin, wortmannin, cytochalasin B) and conventional thiol-mediated uptake (Ellman's reagent), and to serum. Selenophilicity, the extreme CSeSeC dihedral angle of 0° and the high but different acidity of primary and secondary selenols might all contribute to uptake. Thiol-exchange affinity chromatography is introduced as operational mimic of thiol-mediated uptake that provides, in combination with rate enhancement of DTT oxidation, direct experimental evidence for existence and nature of the involved selenosulfides.
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.