ArticleJournal of the American Chemical Society2011
Total synthesis of pinnatoxins A and G and revision of the mode of action of pinnatoxin A.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
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.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
36 citing papers in PubMed.
- The Potential and Prospects of Marine Drugs in Intervening Nerve-Tumor Crosstalk.Marine drugs · 2026Review
- Review
- Portimine A maintains bioactivity following exposure to liver microsomes and cell lysates: no evidence for significant metabolic inactivation.Medical oncology (Northwood, London, England) · 2025Article
- The Chemistry of Phytoplankton.Chemical reviews · 2024Review
- The Cyclic Imine Core Common to the Marine Macrocyclic Toxins Is Sufficient to Dictate Nicotinic Acetylcholine Receptor Antagonism.Marine drugs · 2024Article
- Article
- Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters.Journal of the American Chemical Society · 2022Article
- Highly Selective Synthesis of Seven-Membered Azaspiro Compounds by a Rh(I)-Catalyzed Cycloisomerization/Diels-Alder Cascade of 1,5-Bisallenes.The Journal of organic chemistry · 2022Article
- Current Trends and New Challenges in Marine Phycotoxins.Marine drugs · 2022Review
- Collective Total Synthesis of Casbane Diterpenes: One Strategy, Multiple Targets.Angewandte Chemie (International ed. in English) · 2021Article
- Global Diastereoconvergence in the Ireland-Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted α-Amino Acids.Journal of the American Chemical Society · 2020Article
- Article
- Dictating Thermodynamic Control through Tethering: Applications to Stereoselective Bis-Spiroketal Synthesis.Angewandte Chemie (International ed. in English) · 2020Article
- Acute Oral Toxicity of Pinnatoxin G in Mice.Toxins · 2020Article
- Pinnatoxins' Deleterious Effects on Cholinergic Networks: From Experimental Models to Human Health.Marine drugs · 2019Review
- Kabirimine, a New Cyclic Imine from an Okinawan Dinoflagellate.Marine drugs · 2019Article
- Synthetic Pinnatoxins A and G Reversibly Block Mouse Skeletal Neuromuscular Transmission In Vivo and In Vitro.Marine drugs · 2019Article
- Phycotoxins in Marine Shellfish: Origin, Occurrence and Effects on Humans.Marine drugs · 2018Review
- Article
- Cyclic imine toxins from dinoflagellates: a growing family of potent antagonists of the nicotinic acetylcholine receptors.Journal of neurochemistry · 2017Review
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
9 authors.
Funding
Abstract
Pinnatoxins belong to an emerging class of potent marine toxins of the cyclic imine group. Detailed studies of their biological effects have been impeded by unavailability of the complex natural product from natural sources. This work describes the development of a robust, scalable synthetic sequence relying on a convergent strategy that delivered a sufficient amount of the toxin for detailed biological studies and its commercialization for use by other research groups and regulatory agencies. A central transformation in the synthesis is the highly diastereoselective Ireland-Claisen rearrangement of a complex α,α-disubstituted allylic ester based on a unique mode for stereoselective enolization through a chirality match between the substrate and the lithium amide base. With synthetic pinnatoxin A, a detailed study has been performed that provides conclusive evidence for its mode of action as a potent inhibitor of nicotinic acetylcholine receptors selective for the human neuronal α7 subtype. The comprehensive electrophysiological, biochemical, and computational studies support the view that the spiroimine subunit of pinnatoxins is critical for blocking nicotinic acetylcholine receptor subtypes, as evidenced by analyzing the effect of a synthetic analogue of pinnatoxin A containing an open form of the imine ring. Our studies have paved the way for the production of certified standards to be used for mass-spectrometric determination of these toxins in marine matrices and for the development of tests to detect these toxins in contaminated shellfish.
Indexed as
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.