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Key Documents

K0250

Sigma-Aldrich

Kainic acid monohydrate

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

Synonyma:

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

Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen


About This Item

Empirický vzorec (Hillův zápis):
C10H15NO4 · H2O
Číslo CAS:
Molekulová hmotnost:
231.25
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77

product name

Kainic acid monohydrate, ≥99% (TLC)

assay

≥99% (TLC)

form

powder

impurities

Glutamate, free

solubility

H2O: soluble

storage temp.

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

InChI key

FZNZRJRSYLQHLT-SLGZUKMRSA-N

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General description

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.

Application

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 Actions

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.

Features and Benefits

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.

Preparation Note

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

related product

Č. produktu
Popis
Stanovení ceny

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Osvědčení o analýze (COA)

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Navštívit knihovnu dokumentů

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
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
Fudong Liu et al.
Stroke, 40(5), 1842-1848 (2009-03-07)
Over the past 5 years, experimental data have emerged that ischemia-induced cell death pathways may differ in males and females. Cell death in males is triggered by poly(ADP-ribose) polymerase activation and nuclear translocation of apoptosis-inducing factor. We have previously shown
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
D Schmitz et al.
Proceedings of the National Academy of Sciences of the United States of America, 98(20), 11003-11008 (2001-09-27)
Hippocampal mossy fibers, which are the axons of dentate granule cells, form powerful excitatory synapses onto the proximal dendrites of CA3 pyramidal cells. It has long been known that high-affinity binding sites for kainate, a glutamate receptor agonist, are present

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