Structure via PubChem · Public domain (PubChem)
maitotoxin
Sign in to saveAlso known as MTX
Maitotoxin (MTX) is an extremely potent toxin produced by Gambierdiscus toxicus, a dinoflagellate species. Maitotoxin has been shown to be more than one hundred thousand times as potent as the nerve agent VX. Maitotoxin is so potent that it has been demonstrated that an intraperitoneal injection of 130 ng/kg was lethal in mice. Maitotoxin was named from the ciguateric fish Ctenochaetus striatus—called "maito" in Tahiti—from which maitotoxin was isolated for the first time. It was later shown that maitotoxin is actually produced by the dinoflagellate Gambierdiscus toxicus.
Chemical data
- Formula
- C164H256Na2O68S2
- Molecular weight
- 3425.9 g/mol
- SMILES
- C[C@H](CC[C@@H]([C@@H]([C@H](C)C[C@H](C(=C)/C(=C/CO)/C)O)O)OS(=O)(=O)[O-])[C@H]([C@@H](C)[C@H]1[C@@H]([C@@H]([C@H]2[C@H](O1)[C@@H](C[C@]3([C@H](O2)C[C@H]4[C@H](O3)C[C@]5([C@H](O4)[C@H]([C@H]6[C@H](O5)C[C@H]([C@H](O6)[C@@H]([C@H](C[C@H]7[C@@H]([C@@H]([C@H]8[C@H](O7)C[C@H]9[C@H](O8)C[C@H]1[C@H](O9)[C@H]([C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)[C@H]1[C@@H]([C@H]([C@H]2[C@@H](O1)C[C@H]([C@@H](O2)[C@@H](C[C@H](C[C@H]1[C@@H]([C@H]([C@H]2[C@@H](O1)C[C@H]([C@@H](O2)[C@H]1[C@@H](C[C@]2([C@H](O1)[C@@H]([C@]1([C@H](O2)C[C@]2([C@H](O1)CC[C@]1([C@H](O2)C[C@]2([C@H](O1)C[C@H]1[C@H](O2)CC[C@H](O1)[C@]1([C@@H](C[C@H]2[C@](O1)(C[C@H]1[C@](O2)(CC[C@]2([C@H](O1)C[C@H]1[C@](O2)(C[C@H]2[C@H](O1)C/C=C\[C@H]1[C@H](O2)C[C@H]2[C@](O1)(C[C@]1([C@H](O2)C[C@H]2[C@](O1)(CC[C@H](O2)[C@H]([C@@H](C[C@@H](C)[C@@H](C)CC=C)O)O)C)C)C)C)C)C)C)O)C)C)C)C)C)O)C)O)O)O)O)O)O)O)O)O)O)O)O)O)OS(=O)(=O)[O-])O)O)O)O)C)C)O)O)O)O.[Na+].[Na+]
- InChIKey
- NWQUHAJRFNRIIU-DVGFTKJRSA-L
- Polar surface area
- 1010 Ų
- H-bond donors
- 28
- H-bond acceptors
- 68
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 3424.584
Show 4 more facts
- Commons category
- Maitotoxin
- chemical formula
- C₁₆₄H₂₅₆Na₂O₆₈S₂
- median lethal dose (LD50)
- 50
- subject has role
- toxin
Sources (1)
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Mechanism of toxicity
- Molecular structure
- Biosynthesis
- Total synthesis
- See also
- References
- Further reading
Maitotoxin (MTX) is an extremely potent toxin produced by Gambierdiscus toxicus, a dinoflagellate species. Maitotoxin has been shown to be more than one hundred thousand times as potent as the nerve agent VX. Maitotoxin is so potent that it has been demonstrated that an intraperitoneal injection of 130 ng/kg was lethal in mice. Maitotoxin was named from the ciguateric fish Ctenochaetus striatus—called "maito" in Tahiti—from which maitotoxin was isolated for the first time. It was later shown that maitotoxin is actually produced by the dinoflagellate Gambierdiscus toxicus.
== Mechanism of toxicity == Maitotoxin activates calcium channels, leading to an increase in levels of cytosolic Ca2+ ions. The exact molecular target of maitotoxin is unknown, but it has been suggested that maitotoxin binds to the plasma membrane Ca2+ ATPase (PMCA) and turns it into an ion channel, similar to how palytoxin turns the Na+/K+-ATPase into a sodium channel. Ultimately, a necroptosis cascade is activated, resulting in membrane blebbing and eventually cell lysis. The toxicity of maitotoxin in mice is the highest for nonprotein toxins: the is 50 ng/kg.
Excerpted from Wikipedia’s “maitotoxin” article, available under the CC BY-SA 4.0 licence.