4,9-Anhydrotetrodotoxin - CAS 13072-89-4
Category: Inhibitor
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Molecular Formula:
C11H15N3O7
Molecular Weight:
301.25
COA:
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Targets:
Sodium Channel
Description:
4,9-Anhydrotetrodotoxin is a derivative of tetrodotoxin, which is a potent neurotoxin and can be isolated from pufferfish. It is also a selective and potent Nav1.6 channel blocker with IC50 value of 7.8 nM. It selectively blocks inward sodium current through Nav1.6 voltage-activated sodium channels. It may be a useful compound for treating diseases related to the voltage-gated sodium channel α subunit Nav1.6.
Purity:
≥98% by HPLC
Synonyms:
(4S,5aS,6S,8R,9S,10S,11S,11aR,12R)-2-amino-1,4,5a,6,8,9,10,11-octahydro-9-(hydroxymethyl)-6,10-Epoxy-4,8,11a-metheno-11aH-oxocino[4,3-f][1,3,5]oxadiazepine-6,9,11-triol; (4β,9β)-4,9-Dideoxy-4,9-epoxy-tetrodotoxin; Anhydro-tetrodotoxin; Anhydroepitetrodotoxin; 4,9-anhydro-TTX
MSDS:
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InChIKey:
STNXQECXKDMLJK-SBAGGNPESA-N
InChI:
InChI=1S/C11H15N3O7/c12-8-13-6-2-4-9(17,1-15)5-3(16)10(2,14-8)7(19-6)11(18,20-4)21-5/h2-7,15-18H,1H2,(H3,12,13,14)/t2-,3-,4-,5+,6+,7+,9+,10+,11+/m1/s1
Canonical SMILES:
C(C1(C2C3C4N=C(NC35C(C1OC(C5O4)(O2)O)O)N)O)O
1.Further report of the occurrence of tetrodotoxin in Atelopus species (family: Bufonidae).
Mebs D;Yotsu-Yamashita M;Yasumoto T;Lötters S;Schlüter A Toxicon. 1995 Feb;33(2):246-9.
In alcoholic extracts from museum samples of the toads Atelopus subornatus and A. peruensis tetrodotoxin and its analogues, 4-epitetrodotoxin and 4,9-anhydrotetrodotoxin were detected by fluorometric HPLC analysis, extending the list of amphibians containing this toxin. However, the toxin was not detected in samples of Melanophryniscus stelzneri, Dendrophryniscus minutus and Oreophrynella sp.
2.Accumulation of tetrodotoxin and 4,9-anhydrotetrodotoxin in cultured juvenile kusafugu Fugu niphobles by dietary administration of natural toxic komonfugu Fugu poecilonotus liver.
Kono M;Matsui T;Furukawa K;Yotsu-Yamashita M;Yamamori K Toxicon. 2008 Jun 1;51(7):1269-73. doi: 10.1016/j.toxicon.2008.02.017. Epub 2008 Mar 2.
Non-toxic cultured juvenile kusafugu Fugu niphobles were fed with a diet containing highly toxic natural komonfugu Fugu poecilonotus liver until the 30th day (8.0 microg of TTX and 3.7 microg of 4,9-anhydroTTX/fish/day), and then fed with a non-toxic diet until the 240th day. During the 30-240th day, five or six fish were periodically sampled six times, and the contents of TTX and 4,9-anhydroTTX in each tissue were determined. The total TTX and 4,9-anhydroTTX accumulated in all tissues tested was not significantly changed during the experimental period, both being kept at 70% of administrated doses. However, in the liver, the TTX content accounted to be 120 microg (50% of administrated) on the 30th day, and then it gradually decreased to 50 microg until the 240th day, while 4,9-anhydroTTX content was kept at approximately 40 microg (40% of administrated) during all the experimental periods. In contrast to the liver, in the skin, TTX and 4,9-anhydroTTX were 40 and 5 microg, respectively, on the 30th day, and then gradually increased to 80 and 24 microg, respectively, until the 240th day. In the intestine, TTX and 4,9-anhydroTTX contents were kept at 25 and 12 microg, respectively, during all the experimental periods.
3.Total Synthesis of (-)-Tetrodotoxin and 11-norTTX-6(R)-ol.
Maehara T;Motoyama K;Toma T;Yokoshima S;Fukuyama T Angew Chem Int Ed Engl. 2017 Feb 1;56(6):1549-1552. doi: 10.1002/anie.201611574. Epub 2017 Jan 11.
The enantioselective total synthesis of (-)-tetrodotoxin [(-)-TTX] and 4,9-anhydrotetrodotoxin, which are selective blockers of voltage-gated sodium channels, was accomplished from the commercially available p-benzoquinone. This synthesis was based on efficient stereocontrol of the six contiguous stereogenic centers on the core cyclohexane ring through Ogasawara's method, [3,3]-sigmatropic rearrangement of an allylic cyanate, and intramolecular 1,3-dipolar cycloaddition of a nitrile oxide. Our synthetic route was applied to the synthesis of the tetrodotoxin congeners 11-norTTX-6(R)-ol and 4,9-anhydro-11-norTTX-6(R)-ol through late-stage modification of the common intermediate. Neutral deprotection at the final step enabled easy purification of tetrodotoxin and 11-norTTX-6(R)-ol without competing dehydration to their 4,9-anhydro forms.
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CAS 13072-89-4 4,9-Anhydrotetrodotoxin

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