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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
  • 62996-38-7[1] N
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL3617050
ChemSpider
  • 10207686
  • 21589240
  • 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
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):
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).

Structure edit

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 edit

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 edit

ZTX is an extremely potent neurotoxin. The LD50 of ZTX in mice is 11 μg/kg.[3]

See also edit

References edit

  1. ^ Chambers, Michael. "ChemIDplus - 0062996387 - Zetekitoxin AB - Searchable synonyms, formulas, resource links, and other chemical information". chem.nlm.nih.gov.
  2. ^ 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.
  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.

zetekitoxin, guanidine, alkaloid, found, panamanian, golden, frog, atelopus, zeteki, extremely, potent, neurotoxin, names, iupac, name, diamino, dihydroxy, hydroxymethyl, sulfooxy, pentaazapentacyclo, nonadeca, dien, methyl, hydroxycarbamate, other, names, ide. 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 s1Key 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 C 16H 24N 8O 12S 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 mg kg mice Related compounds Related compounds SaxitoxinNeosaxitoxinTetrodotoxin Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Structure 2 Mechanism of action 3 Toxicity 4 See also 5 ReferencesStructure editZTX 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 editZTX 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 editZTX is an extremely potent neurotoxin The LD50 of ZTX in mice is 11 mg kg 3 See also editTetrodotoxinReferences edit 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 Kuntzel 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 nbsp This neurotoxin article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Zetekitoxin AB amp oldid 1224332411, wikipedia, wiki, book, books, library,

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