52497-36-6 Usage
Description
(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID, also known as Dihydrokainic acid (DHK), is a compound that acts as an inhibitor of excitatory amino acid transporter 2 (EAAT2). It is selective for EAAT2 over EAAT1 and EAAT3, with a Ki value of 23 μM for glutamate uptake by COS cells expressing EAAT2. DHK has been studied for its potential effects on various neurological and psychiatric conditions due to its ability to modulate glutamate and serotonin levels, as well as its impact on the expression of c-Fos in the dorsal raphe nucleus.
Uses
Used in Pharmaceutical Industry:
Dihydrokainic acid is used as a glutamate transporter (GLT-1) inhibitor in the glutamate uptake assay of astrocytes and glial cells. It is particularly relevant for research and development in the field of neuroscience, as it may be used as a GLT-1 inhibitor in the Lateral habenula (LHb), which is a region of the brain involved in various cognitive and emotional processes.
Used in Antidepressant Research:
DHK has demonstrated antidepressant-like behavior in the forced swim test in rats, reducing the time spent immobile. This effect is blocked by the AMPA receptor antagonist NBQX and the serotonin (5-HT) receptor subtype 5-HT1A antagonist WAY-100635, suggesting that DHK may have potential applications in the development of novel antidepressant therapies.
Used in Behavioral and Cognitive Research:
DHK has been shown to increase glutamate and serotonin levels, as well as the expression of c-Fos in the dorsal raphe nucleus, which is involved in the regulation of mood and stress responses. Additionally, DHK has been found to impair memory acquisition, consolidation, and retrieval in mice in the novel object recognition test, indicating its potential use in studying the underlying mechanisms of cognitive and emotional disorders.
Used in Neuroprotective Research:
The ability of DHK to modulate glutamate levels may also have implications for its use in neuroprotective research, as excessive glutamate release and excitotoxicity are implicated in various neurodegenerative diseases such as Alzheimer's, Parkinson's, and Huntington's disease. Further investigation into the neuroprotective potential of DHK could lead to the development of novel therapeutic strategies for these conditions.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 52497-36-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,4,9 and 7 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 52497-36:
(7*5)+(6*2)+(5*4)+(4*9)+(3*7)+(2*3)+(1*6)=136
136 % 10 = 6
So 52497-36-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H17NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h5-7,9,11H,3-4H2,1-2H3,(H,12,13)(H,14,15)/t6-,7+,9-/m0/s1
52497-36-6Relevant articles and documents
Stereocontrolled syntheses of kainoid amino acids from 7-azabicyclo[2.2.1] heptadienes using tandem radical addition-homoallylic radical rearrangement
Hodgson, David M.,Hachisu, Shuji,Andrews, Mark D.
, p. 8866 - 8876 (2007/10/03)
N-Boc syn-7-(2-hydroxyethyl)-4-(alkyl or aryl)sulfonyl-2-azabicyclo[2.2.1] hept-5-enes serve as precursors in syntheses of the neuroexcitants 3-(carboxymethyl)pyrrolidine-2,4-dicarboxylic acid 43, α-kainic acid 12, α-isokainic acid 14, and α-dihydroalloka
