Basic information Safety Supplier Related
ChemicalBook >  Product Catalog >  Biochemical Engineering >  Amino Acids and proteins >  KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE

KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE

Basic information Safety Supplier Related

KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE Basic information

Product Name:
KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE
Synonyms:
  • 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE
  • 2-CARBOXYL-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE MONOHYDRATE
  • [2S-(2A,3BETA,4BETA)]-2-CAROXY-4-(1-METHYLETHENYL)-3-PYRROLIDINEACETIC ACID, MONOHYDRATE
  • (2S,3S,4S)-2-CARBOXY-4-ISOPROPENYL-3-PYRROLIDINEACETIC ACID
  • KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE
  • (-)-KAINIC ACID, MONOHYDRATE
  • KAINIC ACID MONOHYDRATE
  • KAINIC ACID MONOHYDRATE, ISOLATED FROM D
CAS:
58002-62-3
MF:
C10H17NO5
MW:
231.25
Product Categories:
  • Miscellaneous
  • Glutamate
Mol File:
58002-62-3.mol
More
Less

KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE Chemical Properties

Melting point:
250-252°C
RTECS 
UX9665250
storage temp. 
2-8°C
solubility 
H2O: >10 mg/mL
form 
solid
color 
white
biological source
Digenea simplex
Water Solubility 
H2O: soluble
Sensitive 
Light Sensitive
InChI
InChI=1/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-;/s3
InChIKey
FZNZRJRSYLQHLT-JMDCRQGXNA-N
SMILES
C([C@@H]1[C@H](NC[C@@H]1C(=C)C)C(=O)O)C(=O)O.O |&1:1,2,5,r|
More
Less

Safety Information

Safety Statements 
22-24/25
WGK Germany 
3
F 
10
TSCA 
No

MSDS

More
Less

KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE Usage And Synthesis

Description

(−)-(α)-Kainic acid is a cyclic analog of L-glutamate originally isolated from D. simplex that has neuroexcitatory activities. It binds to the homomeric kainate receptors GluK1, GluK2, GluK3, GluK4, and GluK5 (Kis = 75.9, 12.7, 32.8, 4.7, and 15 nM, respectively). (−)-(α)-Kainic acid (5 mM) induces calcium influx and membrane depolarization, as well as glutamate release, in rat brain synaptosomes. It induces chromatin condensation and nuclear membrane fragmentation, markers of apoptosis, in primary neonatal cerebellar granule neurons when used at a concentration of 100 μM. Intracerebroventricular administration of (−)-(α)-kainic acid induces convulsive behavior in rats (ED50 = 0.51 nmol/animal) and induces seizures in mice with a 50% convulsive dose (CD50) value of 0.39 nmol/animal. It has been commonly used to induce seizures in rodents.

Uses

Kainic acid is used to study mechanisms of excitation-induced apoptosis and epilepsy.

Uses

Kainic acid monohydrate has been used:

  • As a convulsant to induce epileptogenesis and epilepsy in mice.
  • To stimulate in vitro excitotoxic trauma in spiral ganglion neurons on inner hair cells.
  • To induce seizures in rat model.
  • To induce status epilepticus in adult male Wistar rats.

General Description

Kainic acid is an agonist for kainate-class ionotropic glutamate receptors. Kainate receptors directly gate ion channels and are generally excitatory. Excess stimulation by Kainic acid induces neurocytosis (apoptosis) and epileptic seizures.

Biochem/physiol Actions

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.

in vivo

Kainic acid can be used to create epilepsy models and can be administered systemically, into the hippocampus, or amygdala, and is reproducible in various species. The systemic Kainic acid model closely mimics the manifestations of human temporal lobe epilepsy. When injected at a dose of 5 nM into the neostriatum, substantia nigra, or cerebellum, over half of the Kainic acid disappears from the injection site and brain within 0.5 hours, with radioactivity detected in other brain regions at concentrations lower than 7 pmol/mg[3][4][6].

Induction of epilepsy model[5]
Background
Kainic acid, an analog of L-glutamate and an ionotropic KA receptor agonist, can damage hippocampal pyramidal neurons.
Specific Modeling Methods
Mice: C57BL/6J ? male ? 7 weeks old ? 22 g body weight
Administration: 10 μg in 5 μL ? i.c.v.
Note
(1) The right lateral brain ventricle is localized with a stereotactic instrument.
(2) After the operation, skin was sutured, and keep the mice under a warming place until they wake up.
(3) 48 hours after lateral ventricle injection, the mice are anaesthetized using Isoflurane and then sequentially intracardially perfused with saline and PFA (4%, 30 mL). Rapidly remove The mouse brain processed for paraffin embedding or frozen sections.
Modeling Indicators
Electroencephalogram (EEG) recording: Had higher local maximal amplitude and reduced spike frequency compared to the control group.
Histology analysis: Showed Triangulated pyknotic nuclei and cytoplasmic shrinkage in the hippocampal neuron, and induced neuronal loss.
Correlated Product(s): /
Opposite Product(s): Sitagliptin (HY-13749)

Animal Model:8 weeks, 200-250 g male adult Wistar rats[1]
Dosage:5 mg/kg
Administration:I.p.; hourly at least 3 h until status epilepticus
Result:Induced seizures in rats.

References

[1] NAREDLA KESAVA REDDY  Srivari C. Total Synthesis of (?)-α-Kainic acid via Chirality Transfer through Ireland–Claisen Rearrangement[J]. The Journal of Organic Chemistry, 2013, 78 7: 3355-3360. DOI: 10.1021/jo400001t
[2] EMANUELLE SAGOT. 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[J]. Journal of Medicinal Chemistry, 2008, 51 14: 4093-4103. DOI: 10.1021/jm800092x
[3] ANNA PASTUSZKO  M. E  David F Wilson. Effects of Kainic Acid in Rat Brain Synaptosomes: The Involvement of Calcium[J]. Journal of Neurochemistry, 1984, 43 3: 747-754. DOI: 10.1111/j.1471-4159.1984.tb12796.x
[4] N.A SIMONIAN . Kainic acid induces apoptosis in neurons[J]. Neuroscience, 1996, 75 4: Pages 1047-1055. DOI: 10.1016/0306-4522(96)00326-0
[5] CHRISTIAN CHIAMULERA. Domoic Acid Toxicity in Rats and Mice after Intracerebroventricular Administration: Comparison with Excitatory Amino Acid Agonists[J]. Basic & Clinical Pharmacology & Toxicology, 1992, 70 2: 115-120. DOI: 10.1111/j.1600-0773.1992.tb00439.x
[6] QUN WANG. Kainic acid-mediated excitotoxicity as a model for neurodegeneration.[J]. Molecular Neurobiology, 2005, 31 1-3: 3-16. DOI: 10.1385/mn:31:1-3:003
[7] HELENA DOMIN . Neuroprotective potential of mGluR5 antagonist MTEP: effects on kainate-induced excitotoxicity in the rat hippocampus[J]. Pharmacological Reports, 2010, 62 6: Pages 1051-1061. DOI: 10.1016/s1734-1140(10)70367-4

KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINESupplier

Hangzhou Milestone Pharmtech Co., Ltd. Gold
Tel
0571-82896630 18969958410
Email
sales_hz@milestonepharmtech.com
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Email
3bsc@sina.com
Ascent Scientific
Tel
4401179829988
Email
customerservice@ascentscientific.co.uk
Syntechem Co.,Ltd
Tel
Email
info@syntechem.com
ShangHai YuanYe Biotechnology Co., Ltd.
Tel
021-61312847 13636370518
Email
shyysw007@163.com
More
Less

KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE(58002-62-3)Related Product Information