Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H21NO6 |
Molecular Weight | 311.3303 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H](\C=C\C=C(\C)[C@H]1CN[C@@H]([C@H]1CC(O)=O)C(O)=O)C(O)=O
InChI
InChIKey=VZFRNCSOCOPNDB-AOKDLOFSSA-N
InChI=1S/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-5,9-11,13,16H,6-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b5-3+,8-4-/t9-,10+,11-,13+/m1/s1
Domoic acid is one of the best-known marine toxins, causative of important neurotoxic alterations. In the year 1987, domoic acid was responsible for four deaths and the illness of more than 100 people after consuming blue mussels (Mytilus edulis) harvested in the Cardigan Bay of Prince Edward Island, Canada. The symptomatology comprised three kinds of signs: gastrointestinal (nausea, vomiting,), cardiovascular (unstable blood pressure and arrhythmias), and neurological signs (disorientation, confusion, hallucinations, coma, and memory impairment). After this event was discovered the domoic acid epileptic. Nearly a year after the amnesic shellfish poisoning event, an 84 years old male survivor re-experienced severe seizures and was diagnosed with temporal lobe epilepsy caused by domoic acid intoxication. This toxin has a high affinity for the glutamate receptors (GluRs) subtypes: alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) and KA receptors. The binding of domoic acid to receptors provokes an increase of calcium (Ca2+) levels, causing the release of Glu to the extracellular space, and the activation of N-methyl-d-aspartate (NMDA) receptors. The histological consequences of these cellular alterations comprise astrocytosis, cytoskeletal disarrangement and, finally, cell death.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18164102 |
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Target ID: CHEMBL2109241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18793656 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Synthesis of a series of aryl kainic acid analogs and evaluation in cells stably expressing the kainate receptor humGluR6. | 1996 Sep 13 |
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Glutathione levels modulate domoic acid induced apoptosis in mouse cerebellar granule cells. | 2007 Dec |
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Domoic acid induces direct DNA damage and apoptosis in Caco-2 cells: recent advances. | 2008 Dec |
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Chemo-enzymatic synthesis of a series of 2,4-syn-functionalized (S)-glutamate analogues: new insight into the structure-activity relation of ionotropic glutamate receptor subtypes 5, 6, and 7. | 2008 Jul 24 |
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Transcriptional responses of xenobiotic metabolizing enzymes, HSP70 and Na+/K+ -ATPase in the liver of rabbitfish (Siganus oramin) intracoelomically injected with amnesic shellfish poisoning toxin. | 2008 Jun |
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Muscarinic receptors prevent oxidative stress-mediated apoptosis induced by domoic acid in mouse cerebellar granule cells. | 2009 Apr |
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DDT exposure of zebrafish embryos enhances seizure susceptibility: relationship to fetal p,p'-DDE burden and domoic acid exposure of California sea lions. | 2009 Jan |
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Gene expression profiles in zebrafish brain after acute exposure to domoic acid at symptomatic and asymptomatic doses. | 2009 Jan |
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Domoic acid induces a long-lasting enhancement of CA1 field responses and impairs tetanus-induced long-term potentiation in rat hippocampal slices. | 2009 Sep |
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Zebrafish seizure model identifies p,p -DDE as the dominant contaminant of fetal California sea lions that accounts for synergistic activity with domoic acid. | 2010 Apr |
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Influences of domoic Acid exposure on cardiac development and the expression of cardiovascular relative genes in zebrafish (Daniorerio) embryos. | 2015 Jun |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26978401
Heart alterations in rats: 2.5 mg/kg
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18164102
In mouse cerebellar granule neurons (CGNs) domoic acid (DomA) induces neuronal cell death, either by apoptosis or by necrosis, depending on its concentration, with apoptotic damage predominating in response to low concentrations (100 nM). DomA-induced apoptosis is due to selective activation of AMPA/kainate receptors, and is mediated by DomA-induced oxidative stress, leading to mitochondrial dysfunction and activation of caspase-3
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BAD BUG BOOK | DA |
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m4736
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34727
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C012301
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DTXSID20274180
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DOMOIC ACID
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5282253
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DB02852
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SUBSTANCE RECORD