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K0250

Sigma-Aldrich

Kainic acid monohydrate

≥99% (TLC), powder, ionotropic glutamate receptor (kainate class) agonist

Synonym(e):

Digenin, Kainate, 2-Carboxy-3-carboxymethyl-4-isopropenylpyrrolidine

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About This Item

Empirische Formel (Hill-System):
C10H15NO4 · H2O
CAS-Nummer:
Molekulargewicht:
231.25
MDL-Nummer:
UNSPSC-Code:
12352106
PubChem Substanz-ID:
NACRES:
NA.77

product name

Kainic acid monohydrate, ≥99% (TLC)

Qualitätsniveau

Assay

≥99% (TLC)

Form

powder

Verunreinigungen

Glutamate, free

Löslichkeit

H2O: soluble

Lagertemp.

2-8°C

SMILES String

O.CC(=C)[C@H]1CN[C@@H]([C@H]1CC(O)=O)C(O)=O

InChI

1S/C10H15NO4.H2O/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13;/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15);1H2/t6-,7+,9-;/m0./s1

InChIKey

FZNZRJRSYLQHLT-SLGZUKMRSA-N

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Allgemeine Beschreibung

Kainic acid monohydrate serves as an agonist for kainate-class ionotropic glutamate receptors, initiating seizures and neurodegeneration in live organisms. It is employed to induce experimental epilepsy in rodents and to explore the mechanisms underlying excitation-induced neuronal apoptosis.

Anwendung

Kainic acid (KA) has been used:
  • tostudy mechanisms of excitation-induced apoptosis and epilepsy.
  • to hamper themitochondrial function ()
  • used to induce c-fosexpression in the mice′s brains, specifically targeting the dorsal hippocampus.()

Biochem./physiol. Wirkung

Kainic acid monohydrate disrupts mitochondrial function by inducing the release of lactate dehydrogenase (LDH) and reducing 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyl tetrazolium bromide (MTT). It also triggers the generation of lipid peroxides, which are key mediators in initiating and regulating inflammation and oxidative stress.
Kainic acid monohydrate is an agonist at the kainate class of ionotropic glutamate receptors, which induces seizures and neurodegeneration in vivo and is used to induce experimental epilepsy in rodents and study the mechanisms of excitation-induced neuronal apoptosis.

Leistungsmerkmale und Vorteile

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Excitatory Amino Acid Transporters and Glutamate Receptors (Ion Channel Family) pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Angaben zur Herstellung

Dissolve in 1-2 drops of 1N NaOH then bring to volume with water or aqueous buffer. Can be stored 1-2 days refrigerated.

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Preisangaben

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

Xing-Mei Zhang et al.
Current neuropharmacology, 9(2), 388-398 (2011-12-02)
Glutamate excitotoxicity contributes to a variety of disorders in the central nervous system, which is triggered primarily by excessive Ca(2+) influx arising from overstimulation of glutamate receptors, followed by disintegration of the endoplasmic reticulum (ER) membrane and ER stress, the
Xin Zhang et al.
Scientific reports, 9(1), 4518-4518 (2019-03-16)
Epilepsy is a multi-etiological brain dysfunction syndrome. Hippocampal neuronal damage induced by seizures may be one of the causes leading to cognitive impairment, but the underlying mechanism remains to be further elucidated. The kainic acid (KA) model of temporal lobe
Lily M Y Yu et al.
eNeuro, 3(1) (2016-03-30)
Epilepsy is a neurological disorder defined by the presence of seizure activity, manifest both behaviorally and as abnormal activity in neuronal networks. An established model to study the disorder in rodents is the systemic injection of kainic acid, an excitatory
I Ferrer et al.
Acta neuropathologica, 99(3), 245-256 (2000-02-09)
Caspases play crucial roles in the inflammatory response and in the cell pathway leading to apoptosis. Caspase 1 (ICE), 2 (Nedd2), 3 (CPP32), 6 (Mch2) and 8 (Mch5, FLICE) expression was examined using immunohistochemistry in the brains of rats and
J T Coyle
Ciba Foundation symposium, 126, 186-203 (1987-01-01)
Kainic acid, an acidic pyrolidine isolated from the seaweed Digenea simplex, is the most potent of the commonly used exogenous excitotoxins. The neurotoxic threshold of kainic acid is nearly two magnitudes lower than that of the other receptor-specific agonists, N-methyl-D-aspartic

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