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K0250

Sigma-Aldrich

Kainic acid monohydrate

≥99% (TLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H15NO4 · H2O
CAS Number:
58002-62-3
Molecular Weight:
231.25
MDL number:
MFCD00150833
UNSPSC Code:
12352106
PubChem Substance ID:
24277985
NACRES:
NA.77

Quality Level

100

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

Gene Information

human ... GRIA1(2890) , GRIA2(2891) , GRIA4(2893) , GRIK1(2897) , GRIK2(2898) , GRIK3(2899) , GRIK4(2900) , GRIK5(2901) , SLC1A1(6505) , SLC1A2(6506) , SLC1A3(6507)
mouse ... Gria1(14799)
rat ... Gria1(50592) , Grik1(29559) , Grik4(24406) , Grin2a(24409)

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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.

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flash_point_c

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Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Qun Wang et al.
Molecular neurobiology, 31(1-3), 3-16 (2005-06-15)
Neuronal excitation involving the excitatory glutamate receptors is recognized as an important underlying mechanism in neurodegenerative disorders. Excitation resulting from stimulation of the ionotropic glutamate receptors is known to cause the increase in intracellular calcium and trigger calcium-dependent pathways that
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
M Nakai et al.
Journal of neurochemistry, 74(2), 647-658 (2000-01-26)
The present study evaluated whether nuclear factor-kappaB (NF-kappaB) activation contributes to the apoptotic-like death of striatal neurons induced by kainic acid (KA) receptor stimulation. Intrastriatally infused KA (1.25-5.0 nmol) produced substantial neuronal loss as indicated by an 8-73% decrease in
Seena S Mathew et al.
Neuropharmacology, 55(1), 106-116 (2008-05-30)
We examined the mechanisms of kainate (KA) induced modulation of GABA release in rat prefrontal cortex. Pharmacologically isolated IPSCs were recorded from visually identified layer II/III pyramidal cells using whole-cell patch clamp techniques. KA produced an increase in evoked IPSC
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
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