| Identification | Back Directory | [Name]
(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID | [CAS]
52497-36-6 | [Synonyms]
DHK
DIHYDROKAINIC ACID
2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid
(2S,3S,4R)-3-(carboxymethyl)-4-isopropyl-proline
(2S,3R,4R)-2-Carboxy-4-iospropyl-3-pyrrolidineacetic acid
(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID
3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethyl)-, (2S,3S,4R)-
(2S,3S,4R)-3-(Carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid
(2S,3S,4R)-3-(carboxymethyl)-4-propan-2-yl-2-pyrrolidinecarboxylic acid
(2S,3S,4R)-3-(carboxymethyl)-4-propan-2-yl-pyrrolidine-2-carboxylic acid | [Molecular Formula]
C10H17NO4 | [MDL Number]
MFCD03412037 | [MOL File]
52497-36-6.mol | [Molecular Weight]
215.25 |
| Chemical Properties | Back Directory | [Melting point ]
285 °C (decomp) | [Boiling point ]
416.6±30.0 °C(Predicted) | [density ]
1.187±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
H2O: >10 mg/mL | [form ]
solid | [pka]
2.11±0.60(Predicted) | [color ]
White | [Water Solubility ]
Soluble to 25 mM in water |
| Hazard Information | Back Directory | [Description]
Dihydrokainic acid (DHK) is an inhibitor of excitatory amino acid transporter 2 (EAAT2; Ki = 23 μM for glutamate uptake by COS cells expressing EAAT2). It is selective for EEAT2 over EAAT1 and EAAT3 (Ki = >3 mM for both). DHK microinfusion (5 nmol) into the rat infralimbic cortex reduces the time spent immobile in the forced swim test, indicating antidepressant-like behavior, an effect that is blocked by the AMPA receptor antagonist NBQX and the serotonin (5-HT) receptor subtype 5-HT1A antagonist WAY-100635 . It also increases glutamate and serotonin levels and the expression of c-Fos in the dorsal raphe nucleus. In contrast, DHK microinjection (6.25 nmol) into the rat prefrontal cortex (PFC) increases the latency to drink sucrose in a sucrose intake test, indicating anhedonia-like behavior. It also impairs memory acquisition, consolidation, and retrieval in mice in the novel object recognition test. | [Uses]
Dihydrokainic acid has been used as a glutamate transporter (GLT-1) inhibitor in the glutamate uptake assay of astrocytes and glial cells. It may be used as a GLT-1 inhibitor in Lateral habenula (LHb). | [Definition]
ChEBI: Dihydrokainic acid is a dicarboxylic acid. It is functionally related to a kainic acid. | [Biological Activity]
EAAT2(GLT1)-selective non-transportable inhibitor of L-glutamate and L-aspartate uptake (K i = 23 μ M). 130-fold selective over EAAT1 and EAAT3 (K i > 3 mM). Also available as part of the Excitatory Amino Acid Transporter Inhibitor Tocriset™ . | [Biochem/physiol Actions]
Dihydrokainic favors neuronal cell death. It modulates anxiety and depression behaviors. | [storage]
Room temperature | [References]
[1] J. ARRIZA. Functional comparisons of three glutamate transporter subtypes cloned from human motor cortex[J]. Journal of Neuroscience, 1994, 42 1: 5559-5569. DOI: 10.1523/jneurosci.14-09-05559.1994
[2] J GASULL-CAMóS. Glial GLT-1 blockade in infralimbic cortex as a new strategy to evoke rapid antidepressant-like effects in rats[J]. Translational Psychiatry, 2017, 7 2: e1038-e1038. DOI: 10.1038/tp.2017.7
[3] JúLIA GASULL-CAMóS . Serotonergic mechanisms involved in antidepressant-like responses evoked by GLT-1 blockade in rat infralimbic cortex[J]. Neuropharmacology, 2018, 139: Pages 41-51. DOI: 10.1016/j.neuropharm.2018.06.029
[4] CATHERINE S JOHN. Blockade of Astrocytic Glutamate Uptake in the Prefrontal Cortex Induces Anhedonia[J]. Neuropsychopharmacology, 2012, 37 11: 2467-2475. DOI: 10.1038/npp.2012.105
[5] SHAO-WEN TIAN . Glutamate transporter GLT1 inhibitor dihydrokainic acid impairs novel object recognition memory performance in mice[J]. Physiology & Behavior, 2019, 199: Pages 28-32. DOI: 10.1016/j.physbeh.2018.10.019 |
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Sigma-Aldrich
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Energy Chemical
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http://www.energy-chemical.com |
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