Zetekitoxin AB

Zetekitoxin AB (ZTX) is a guanidine alkaloid found in the Panamanian golden frog Atelopus zeteki. It is an extremely potent neurotoxin.

Zetekitoxin AB

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
CAS Number	62996-38-7[1] N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3617050
ChemSpider	10207686
PubChem CID	21589240
InChI InChI=1S/C16H24N8O12S/c17-11-19-8-9-15(20-12(18)22(9)5-34-13(27)21-30)16(28,29)14(4-23(11)15,36-37(31,32)33)1-7-6(2-25)3-35-24(7)10(8)26/h6-9,25,28-30H,1-5H2,(H2,17,19)(H2,18,20)(H,21,27)(H,31,32,33)/t6-,7-,8+,9-,14+,15-/m0/s1 Key: BJJIKPMJNDTIHW-FGWFJEOOSA-N
SMILES [H]/N=C/1\N2[C@@]34N/C(=N/[H])/N([C@H]3[C@@H](N1)C(=O)N5OC[C@@H]([C@@H]5C[C@@](C2)([C@]4(O)O)OS(=O)(=O)O)CO)COC(=O)NO
Properties
Chemical formula	C16H24N8O12S
Molar mass	552.47 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Extremely toxic
Lethal dose or concentration (LD, LC):
LD50 (median dose)	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

Structure

ZTX is a guanidine alkaloid. It's structurally related to saxitoxin, but with some differences. ZTX contains an isoxazolidine ring, a sulfonate group and an 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 LD₅₀ of ZTX in mice is 11 μg/kg.^[3]

See also

• Tetrodotoxin

References

1. Chambers, Michael. "ChemIDplus - 0062996387 - Zetekitoxin AB - Searchable synonyms, formulas, resource links, and other chemical information". chem.nlm.nih.gov.
2. 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. Bibcode:2004PNAS..101.4346Y. doi:10.1073/pnas.0400368101. PMC 384749. PMID 15070720.
3. 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.