From Wikipedia, the free encyclopedia
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
ChEMBL
ChemSpider
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
[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
C 16 H 24 N 8 O 12 S
Molar mass
552.47 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
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).
Chemical compound
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.
[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
References
^ Chambers, Michael.
"ChemIDplus - 0062996387 - Zetekitoxin AB - Searchable synonyms, formulas, resource links, and other chemical information" . chem.nlm.nih.gov .
^
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.
Bibcode :
2004PNAS..101.4346Y .
doi :
10.1073/pnas.0400368101 .
PMC
384749 .
PMID
15070720 .
^ 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 .
Calcium
VDCCs Tooltip Voltage-dependent calcium channels
Potassium
VGKCs Tooltip Voltage-gated potassium channels
IRKs Tooltip Inwardly rectifying potassium channel
KCa Tooltip Calcium-activated potassium channel
K2Ps Tooltip Tandem pore domain potassium channel
Sodium
VGSCs Tooltip Voltage-gated sodium channels
ENaC Tooltip Epithelial sodium channel
ASICs Tooltip Acid-sensing ion channel
Chloride
CaCCs Tooltip Calcium-activated chloride channel
CFTR Tooltip Cystic fibrosis transmembrane conductance regulator
Unsorted
Others
TRPs Tooltip Transient receptor potential channels
LGICs Tooltip Ligand gated ion channels