ArticleACS central science2016
Synthesis and Sulfur Electrophilicity of the Nuphar Thiaspirane Pharmacophore.
Article in ACS central science, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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Who cites it
9 citing papers in PubMed, 22 citations in OpenAlex.
- Multimodal Acridine Photocatalysis Enables Direct Access to Thiols from Carboxylic Acids and Elemental Sulfur.ACS catalysis · 2024Article
- Inhibition of Cysteine Proteases by 6,6'-Dihydroxythiobinupharidine (DTBN) fromMolecules (Basel, Switzerland) · 2021Article
- 6,6'-Dihydroxythiobinupharidine (DTBN) Purified fromMolecules (Basel, Switzerland) · 2021Article
- Natural Product Synthesis through the Lens of Informatics.Accounts of chemical research · 2021Review
- Nuphar lutea Extracts Exhibit Anti-Viral Activity against the Measles Virus.Molecules (Basel, Switzerland) · 2020Article
- Nuphar alkaloids induce very rapid apoptosis through a novel caspase-dependent but BAX/BAK-independent pathway.Cell biology and toxicology · 2019Article
- General, Mild, and Selective Method for Desaturation of Aliphatic Amines.Journal of the American Chemical Society · 2018Article
- Total Synthesis of Unsymmetrically Oxidized Nuphar Thioalkaloids via Copper-Catalyzed Thiolane Assembly.Journal of the American Chemical Society · 2017Article
- Nuphar Dimers: Crouching Sulfur, Hidden Reactivity.ACS central science · 2016Article
Corrections and comments
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Authors and funding
8 authors at 1 institution in 1 country.
Funding
Abstract
We describe a general method to synthesize the iminium tetrahydrothiophene embedded in the dimeric Nuphar alkaloids. In contrast to prior studies, the sulfur atom of the thiaspirane pharmacophore is shown to be electrophilic. This α-thioether reacts with thiophenol or glutathione at ambient temperature to cleave the C-S bond and form a disulfide. Rates of conversion are proportional to the corresponding ammonium ion pK a and exhibit half-lives less than 5 h at a 5 mM concentration of thiol. A simple thiophane analogue of the Nuphar dimers causes apoptosis at single-digit micromolar concentration and labels reactive cysteines at similar levels as the unsaturated iminium "warhead". Our experiments combined with prior observations suggest the sulfur of the Nuphar dimers can react as an electrophile in cellular environments and that sulfur-triggered retrodimerization can occur in the cell.
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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.