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Zetekitoxin AB

Zetekitoxin AB
Zetekitoxin AB.svg
Names
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
Other names
ZTX
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
Properties
C16H24N8O12S
Molar mass 552.47 g·mol−1
Hazards
Main hazards Extremely toxic
Lethal dose or concentration (LD, LC):
11 μg/kg (mice)
Related compounds
Related compounds
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's 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.[1]

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.[1]

Toxicity

ZTX is an extremely potent neurotoxin. The LD50 of ZTX in mice is 11 μg/kg.[2]

See also

References

  1. ^ a b 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. PMC 384749. PMID 15070720.
  2. ^ 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.