ArticleProceedings of the National Academy of Sciences of the United States of America2004
The structure of zetekitoxin AB, a saxitoxin analog from the Panamanian golden frog Atelopus zeteki: a potent sodium-channel blocker.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2004. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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31 citing papers in PubMed, 106 citations in OpenAlex.
- Towards a better understanding of the use of probiotics for preventing chytridiomycosis in Panamanian golden frogs.EcoHealth · 2011Trial
- Synthesis of 1,3-Dihydro-2,1-benzisoxazoles by Intramolecular C-N Coupling: Evaluation as an Indane Bioisostere.ACS medicinal chemistry letters · 2026Article
- Mechanistic DFT investigation of the cycloaddition reaction of nitrones with allene-propargyl equilibria toward isoxazoline and isoxazolidine derivatives.Journal of molecular modeling · 2026Article
- The Multifaceted Importance of Amphibians: Ecological, Biomedical, and Socio-Economic Perspectives.Biology · 2026Review
- Ion Channel-Targeting Toxins: Structural Mechanisms of Activation, Inhibition, and Therapeutic Potential.Toxins · 2025Review
- A Fresh Perspective on Cyanobacterial Paralytic Shellfish Poisoning Toxins: History, Methodology, and Toxicology.Marine drugs · 2025Review
- Macrocycles of Saxitoxin: Insights into the Structure of Zetekitoxin AB.Chembiochem : a European journal of chemical biology · 2025Article
- Synthesis of New Isoxazolidine Derivatives Utilizing the Functionality ofMolecules (Basel, Switzerland) · 2024Article
- New 3-(Dibenzyloxyphosphoryl)isoxazolidine Conjugates of N1-Benzylated Quinazoline-2,4-diones as Potential Cytotoxic Agents against Cancer Cell Lines.Molecules (Basel, Switzerland) · 2024Article
- Eco-Metabolomics Applied to the Chemical Ecology of Poison Frogs (Dendrobatoidea).Journal of chemical ecology · 2023Review
- A review of chemical defense in harlequin toads (Bufonidae:Toxicon: X · 2022Review
- Silylpyrrole Oxidation En Route to Saxitoxin Congeners Including 11-Saxitoxinethanoic Acid.The Journal of organic chemistry · 2021Article
- A Convenient Synthesis of (16Molecules (Basel, Switzerland) · 2020Article
- Synthetic Approaches to Zetekitoxin AB, a Potent Voltage-Gated Sodium Channel Inhibitor.Marine drugs · 2019Review
- A Direct C11 Alkylation Strategy on the Saxitoxin Core: A Synthesis of (+)-11-Saxitoxinethanoic Acid.Organic letters · 2019Article
- Natural Voltage-Gated Sodium Channel Ligands: Biosynthesis and Biology.Chembiochem : a European journal of chemical biology · 2019Review
- Divergent Synthesis of Natural Derivatives of (+)-Saxitoxin Including 11-Saxitoxinethanoic Acid.Angewandte Chemie (International ed. in English) · 2019Article
- Mutant cycle analysis with modified saxitoxins reveals specific interactions critical to attaining high-affinity inhibition of hNaV1.7.Proceedings of the National Academy of Sciences of the United States of America · 2016Article
- Article
- Military Importance of Natural Toxins and Their Analogs.Molecules (Basel, Switzerland) · 2016Review
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7 authors at 1 institution in 1 country.
Funding
Abstract
Bufonid anurans of the genus Atelopus contain both steroidal bufadienolides and various guanidinium alkaloids of the tetrodotoxin class. The former inhibit sodium-potassium ATPases, whereas the latter block voltage-dependent sodium channels. The structure of one guanidinium alkaloid, zetekitoxin AB, has remained a mystery for over 30 years. The structure of this alkaloid now has been investigated with a sample of approximately 0.3 mg, purified from extracts obtained decades ago from the Panamanian golden frog Atelopus zeteki. Detailed NMR and mass spectral analyses have provided the structure and relative stereochemistry of zetekitoxin AB and have revealed that it is an analog of saxitoxin. The proposed structure is characterized by richness of heteroatoms (C16H25N8O12S) and contains a unique 1,2-oxazolidine ring-fused lactam, a sulfate ester, and an N-hydroxycarbamate moiety. Zetekitoxin AB proved to be an extremely potent blocker of voltage-dependent sodium channels expressed in Xenopus oocytes. The IC50 values were 280 pM for human heart channels, 6.1 pM for rat brain IIa channels, and 65 pM for rat skeletal muscle channels, thus being roughly 580-, 160-, and 63-fold more potent at these channels than saxitoxin.
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