Zetekitoxin AB
{{Chembox
| Name = Zetekitoxin AB
| ImageFile =Zetekitoxin AB.svg
| IUPACName = [(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
| OtherNames = ZTX
| Section1 = {{Chembox Identifiers
| CASNo = 62996-38-7
| CASNo_Ref = {{cite web |last1=Chambers |first1=Michael |title=ChemIDplus - 0062996387 - Zetekitoxin AB - Searchable synonyms, formulas, resource links, and other chemical information. |url=https://chem.nlm.nih.gov/chemidplus/sid/0062996387 |website=chem.nlm.nih.gov |language=en}}{{Cascite|changed|}}
| 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
| ChemSpiderID = 10207686
| PubChem = 21589240
| ChEMBL = 3617050
| StdInChI=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
| StdInChIKey = BJJIKPMJNDTIHW-FGWFJEOOSA-N
}}
| Section2 = {{Chembox Properties
| C=16|H=24|N=8|O=12|S=1
}}
| Section3 = {{Chembox Hazards
| MainHazards = Extremely toxic
| LD50 = 11 μg/kg (mice)
}}
| Section4 = {{Chembox Related
| OtherCompounds = Saxitoxin
Neosaxitoxin
Tetrodotoxin
}}
}}
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 contains an isoxazolidine ring, a sulfonate group and an N-hydroxycarbamate group.{{cite journal|last1=Yotsu-Yamashita|first1=M.|last2=Kim|first2=Y. H.|last3=Dudley|first3=S. C.|last4=Choudhary|first4=G.|last5=Pfahnl|first5=A.|last6=Oshima|first6=Y.|last7=Daly|first7=J. W.|title=The structure of zetekitoxin AB, a saxitoxin analog from the Panamanian golden frog Atelopus zeteki: A potent sodium-channel blocker|journal=Proceedings of the National Academy of Sciences|date=22 March 2004|volume=101|issue=13|pages=4346–4351|doi=10.1073/pnas.0400368101|pmid=15070720|pmc=384749|bibcode=2004PNAS..101.4346Y|doi-access=free}}
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.
Toxicity
ZTX is an extremely potent neurotoxin. The {{LD50}} of ZTX in mice is 11 μg/kg.{{cite journal|last1=Brown|first1=George B.|last2=Kim|first2=Yong H.|last3=Küntzel|first3=Heiner|last4=Mosher|first4=Harry S.|last5=Fuhrman|first5=Geraldine J.|last6=Fuhrman|first6=Frederick A.|title=Chemistry and pharmacology of skin toxins from the frog Atelopus Zeteki (Atelopidtoxin: Zetekitoxin)|journal=Toxicon|date=January 1977|volume=15|issue=2|pages=115–128|doi=10.1016/0041-0101(77)90030-7|pmid=558664|bibcode=1977Txcn...15..115B }}
See also
References
{{reflist}}
{{Neurotoxins}}
{{Toxins}}
{{Ion channel modulators}}
Category:Voltage-gated sodium channel blockers
Category:Nitrogen heterocycles
Category:Heterocyclic compounds with 5 rings
{{Neurotoxin-stub}}