Gambierol
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| Category | Mycotoxins |
| Catalog number | BBF-01478 |
| CAS | 146763-62-4 |
| Molecular Weight | 756.96 |
| Molecular Formula | C43H64O11 |
| Purity | 99% |
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Description
It is produced by the strain of Gambierdiscus toxicus. Gambierol is the substance that causes ciguatera poisoning (severe diarrhea, perceptual abnormalities, etc.).
Specification
| Synonyms | (-)-Gambierol |
| IUPAC Name | (1S,3R,5S,7R,10S,11R,13S,15R,17S,20R,22S,24R,26S,27S,29S,31R,33S,35R)-11-[(1Z,3Z)-hepta-1,3,6-trienyl]-29-(3-hydroxypropyl)-3,5,10,24,26-pentamethyl-2,6,12,16,21,25,30,34-octaoxaoctacyclo[18.16.0.03,17.05,15.07,13.022,35.024,33.026,31]hexatriacont-8-ene-10,27-diol |
| Canonical SMILES | CC12CC3C(CC4C(O3)CCC5C(O4)(CC6(C(O5)CC7C(O6)C=CC(C(O7)C=CC=CCC=C)(C)O)C)C)OC1CC8C(O2)(C(CC(O8)CCCO)O)C |
| InChI | InChI=1S/C43H64O11/c1-7-8-9-10-11-14-34-39(2,46)18-17-28-30(49-34)22-36-42(5,52-28)25-41(4)35(51-36)16-15-27-31(53-41)21-29-32(48-27)24-40(3)37(50-29)23-38-43(6,54-40)33(45)20-26(47-38)13-12-19-44/h7,9-11,14,17-18,26-38,44-46H,1,8,12-13,15-16,19-25H2,2-6H3/b10-9-,14-11-/t26-,27+,28+,29+,30-,31-,32-,33-,34+,35-,36+,37-,38+,39-,40+,41+,42-,43-/m0/s1 |
| InChI Key | GKLILONDTZZKRF-IDJCTBPMSA-N |
Properties
| Appearance | Amorphous Solid |
| Boiling Point | 823.7°C at 760 mmHg |
| Density | 1.18 g/cm3 |
Reference Reading
1. Gambierol and n-alkanols inhibit Shaker Kv channel via distinct binding sites outside the K(+) pore
Evelyn Martínez-Morales, Ivan Kopljar, Jon D Rainier, Jan Tytgat, Dirk J Snyders, Alain J Labro Toxicon. 2016 Sep 15;120:57-60. doi: 10.1016/j.toxicon.2016.07.017. Epub 2016 Jul 28.
The marine polycyclic-ether toxin gambierol and 1-butanol (n-alkanol) inhibit Shaker-type Kv channels by interfering with the gating machinery. Competition experiments indicated that both compounds do not share an overlapping binding site but gambierol is able to affect 1-butanol affinity for Shaker through an allosteric effect. Furthermore, the Shaker-P475A mutant, which inverses 1-butanol effect, is inhibited by gambierol with nM affinity. Thus, gambierol and 1-butanol inhibit Shaker-type Kv channels via distinct parts of the gating machinery.
2. Gambierol Potently Increases Evoked Quantal Transmitter Release and Reverses Pre- and Post-Synaptic Blockade at Vertebrate Neuromuscular Junctions
Jordi Molgó, Sébastien Schlumberger, Makoto Sasaki, Haruhiko Fuwa, M Carmen Louzao, Luis M Botana, Denis Servent, Evelyne Benoit Neuroscience. 2020 Jul 15;439:106-116. doi: 10.1016/j.neuroscience.2019.06.024. Epub 2019 Jun 28.
Gambierol is a marine polycyclic ether toxin, first isolated from cultured Gambierdiscus toxicus dinoflagellates collected in French Polynesia. The chemical synthesis of gambierol permitted the analyses of its mode of action which includes the selective inhibition of voltage-gated K+ (KV) channels. In the present study we investigated the action of synthetic gambierol at vertebrate neuromuscular junctions using conventional techniques. Gambierol was studied on neuromuscular junctions in which muscle nicotinic ACh receptors have been blocked with d-tubocurarine (postsynaptic block), or in junctions in which quantal ACh release has been greatly reduced by a low Ca2+-high Mg2+ medium or by botulinum neurotoxin type-A (BoNT/A) (presynaptic block). Results show that nanomolar concentrations of gambierol inhibited the fast K+ current and prolonged the duration of the presynaptic action potential in motor nerve terminals, as revealed by presynaptic focal current recordings, increased stimulus-evoked quantal content in junctions blocked by high Mg2+-low Ca2+ medium, and by BoNT/A, reversed the postsynaptic block produced by d-tubocurarine and increased the transient Ca2+ signals in response to nerve-stimulation (1-10 Hz) in nerve terminals loaded with fluo-3/AM. The results suggest that gambierol, which on equimolar basis is more potent than 3,4-diaminopyridine, can have potential application in pathologies in which it is necessary to antagonize pre- or post-synaptic neuromuscular block, or both. This article is part of a Special Issue entitled: Honoring Ricardo Miledi - outstanding neuroscientist of XX-XXI centuries.
3. Gambierol Blocks a K+ Current Fraction without Affecting Catecholamine Release in Rat Fetal Adrenomedullary Cultured Chromaffin Cells
Evelyne Benoit, Sébastien Schlumberger, Jordi Molgó, Makoto Sasaki, Haruhiko Fuwa, Roland Bournaud Toxins (Basel). 2022 Apr 2;14(4):254. doi: 10.3390/toxins14040254.
Gambierol inhibits voltage-gated K+ (KV) channels in various excitable and non-excitable cells. The purpose of this work was to study the effects of gambierol on single rat fetal (F19-F20) adrenomedullary cultured chromaffin cells. These excitable cells have different types of KV channels and release catecholamines. Perforated whole-cell voltage-clamp recordings revealed that gambierol (100 nM) blocked only a fraction of the total outward K+ current and slowed the kinetics of K+ current activation. The use of selective channel blockers disclosed that gambierol did not affect calcium-activated K+ (KCa) and ATP-sensitive K+ (KATP) channels. The gambierol concentration necessary to inhibit 50% of the K+ current-component sensitive to the polyether (IC50) was 5.8 nM. Simultaneous whole-cell current-clamp and single-cell amperometry recordings revealed that gambierol did not modify the membrane potential following 11s depolarizing current-steps, in both quiescent and active cells displaying repetitive firing of action potentials, and it did not increase the number of exocytotic catecholamine release events, with respect to controls. The subsequent addition of apamin and iberiotoxin, which selectively block the KCa channels, both depolarized the membrane and enhanced by 2.7 and 3.5-fold the exocytotic event frequency in quiescent and active cells, respectively. These results highlight the important modulatory role played by KCa channels in the control of exocytosis from fetal (F19-F20) adrenomedullary chromaffin cells.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
