Chemistry:Zetekitoxin AB
From HandWiki
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| Names | |
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| IUPAC name
[(3R,5S,6S,11R,12S,14Z,16S,17Z)-14,17-Diamino-19,19-dihydroxy-6-(hydroxymethyl)-10-oxo-3-(sulfooxy)-8-oxa-1,9,13,15,18-pentaazapentacyclo[9.5.2.1~3,16~.0~5,9~.0~12,16~]nonadeca-14,17-dien-13-yl]methyl hydroxycarbamate
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| Other names
ZTX
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
PubChem CID
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| Properties | |
| C16H24N8O12S | |
| Molar mass | 552.47 g·mol−1 |
| Hazards | |
| Main hazards | Extremely toxic |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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11 μg/kg (mice) |
| Related compounds | |
Related compounds
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Saxitoxin Neosaxitoxin Tetrodotoxin |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Zetekitoxin AB (ZTX) is a guanidine alkaloid found in the Panamanian golden frog Atelopus zeteki. It is an extremely potent neurotoxin.
Structure
ZTX is a guanidine alkaloid. It's structurally related to saxitoxin, but with some differences. ZTX has a guanidine core similar to saxitoxin. It contains an isoxazolidine ring, a sulfonate group and a N-hydroxycarbamate group.[2]
Mechanism of action
ZTX is an extremely potent sodium channel blocker. It has been shown to block the voltage-gated sodium channels at picomolar concentrations. It is about 580 times more potent than saxitoxin.[2]
Toxicity
ZTX is an extremely potent neurotoxin. The -1">50 of ZTX in mice is 11 μg/kg.[3]
See also
References
- ↑ Chambers, Michael. "ChemIDplus - 0062996387 - Zetekitoxin AB - Searchable synonyms, formulas, resource links, and other chemical information." (in en). https://chem.nlm.nih.gov/chemidplus/sid/0062996387.
- ↑ 2.0 2.1 Yotsu-Yamashita, M.; Kim, Y. H.; Dudley, S. C.; Choudhary, G.; Pfahnl, A.; Oshima, Y.; Daly, J. W. (22 March 2004). "The structure of zetekitoxin AB, a saxitoxin analog from the Panamanian golden frog Atelopus zeteki: A potent sodium-channel blocker". Proceedings of the National Academy of Sciences 101 (13): 4346–4351. doi:10.1073/pnas.0400368101. PMID 15070720. Bibcode: 2004PNAS..101.4346Y.
- ↑ Brown, George B.; Kim, Yong H.; Küntzel, Heiner; Mosher, Harry S.; Fuhrman, Geraldine J.; Fuhrman, Frederick A. (January 1977). "Chemistry and pharmacology of skin toxins from the frog Atelopus Zeteki (Atelopidtoxin: Zetekitoxin)". Toxicon 15 (2): 115–128. doi:10.1016/0041-0101(77)90030-7. PMID 558664.
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