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AB120066

Dihydrokainic acid, EAAT2 (GLT-1) inhibitor

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(13 Publications)

MW 215.25 Da. Selective, non-transportable inhibitor of glutamate transporter EAAT2 (GLT-1) (Ki = 23 μM). 130-fold selective over EAAT1 and EAAT3 (Ki > 3 mM).

View Alternative Names

EA6, EAA1_HUMAN, EAA2_HUMAN, EAA3_HUMAN, EAAC 1, EAAT2, Excitatory amino acid transporter 1, Excitatory amino acid transporter 2, Excitatory amino acid transporter 3, Excitatory amino-acid carrier 1, Excitotoxic amino acid transporter 2, FLJ25094, GLAST, GLAST-1, GLT-1, GLUTAMATE TRANSPORTER, HIGH-AFFINITY, Glial high affinity glutamate transporter, Glutamate aspartate transporter II, Glutamate transporter 1, Glutamate/aspartate transporter II, High affinity neuronal glutamate transporter, MEAAC 1, Neuronal and epithelial glutamate transporter, REAAC 1, SLC1A1, SOLUTE CARRIER FAMILY 1 (NEURONAL/EPITHELIAL HIGH AFFINITY GLUTAMATE TRANSPORTER), MEMBER 1, Slc1 a1, Slc1a 1, Slc1a2, Slc1a3, Sodium dependent glutamate aspartate transporter 2, Sodium dependent glutamate/aspartate transporter, Sodium-dependent glutamate/aspartate transporter 1, Sodium-dependent glutamate/aspartate transporter 2, Sodium-dependent glutamate/aspartate transporter 3, Solute carrier family 1 (glial high affinity glutamate transporter) member 3, Solute carrier family 1 (neuronal / epithelial high affinity glutamate transporter, system Xag), member 1, Solute carrier family 1 glial high affinity glutamate transporter member 2, Solute carrier family 1 member 1, Solute carrier family 1 member 2, Solute carrier family 1 member 3, glutamate/aspartate transporter, high affinity, sodium-dependent, solute carrier family 1 (glial high affinity glutamate transporter), member 2

1 Images
Chemical Structure - Dihydrokainic acid, EAAT2 (GLT-1) inhibitor (AB120066)
  • Chemical Structure

Lab

Chemical Structure - Dihydrokainic acid, EAAT2 (GLT-1) inhibitor (AB120066)

2D chemical structure image of ab120066, Dihydrokainic acid, EAAT2 (GLT-1) inhibitor

Key facts

CAS number

52497-36-6

Form

Solid

form

Molecular weight

215.25 Da

Molecular formula

C<sub>1</sub><sub>0</sub>H<sub>1</sub><sub>7</sub>NO<sub>4</sub>

PubChem

107883

Nature

Synthetic

Solubility

Soluble in water to 25 mM

Biochemical name

Dihydrokainic acid

Biological description

Selective, non-transportable inhibitor of glutamate transporter EAAT2 (GLT-1) (Ki = 23 μM). 130-fold selective over EAAT1 and EAAT3 (Ki > 3 mM).

Canonical smiles

CC(C)C1CNC(C1CC(=O)O)C(=O)O

Isomeric smiles

CC(C)[C@H]1CN[C@@H]([C@H]1CC(=O)O)C(=O)O

InChi

InChI=1S/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

InChiKey

JQPDCKOQOOQUSC-OOZYFLPDSA-N

IUPAC Name

(2S,3S,4R)-3-(carboxymethyl)-4-propan-2-ylpyrrolidine-2-carboxylic acid

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Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
+4°C
Appropriate long-term storage conditions
+4°C
Storage information
Store under desiccating conditions|The product can be stored for up to 12 months
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Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

The excitatory amino acid transporters EAAT3 EAAT1 and EAAT2 also known as GLT-1 are integral membrane proteins responsible for regulating the synaptic concentration of glutamate in the central nervous system. EAAT3 is alternately known as SLC1A1. These transporters include a mass approximately 50 to 62 kDa are primarily expressed in neurons and glial cells. EAAT1 often referred to as GLAST is primarily in astrocytes whereas EAAT2 or GLT-1 is mainly in astrocytes and some neurons. The effective function of these transporters is important for preventing excitotoxicity a condition that occurs when excessive synaptic glutamate overstimulates cells.
Biological function summary

Excitatory amino acid transporters modulate synaptic transmission by taking up extracellular glutamate converting it to a less reactive form inside the cell. By clearing glutamate from synapses they ensure proper neuronal communication and prevent overstimulation that could damage neurons. EAAT2 representing the major glutamate transporter in the hippocampus and cortex contributes to more than 90% of glutamate uptake. The transporters exist in functional complexes with other proteins including scaffolding and signaling proteins which enhance neuronal ion balance and signal transduction.

Pathways

Excitatory amino acid transporters integrate into the glutamatergic neurotransmission system and work within glutamate-glutamine cycling. These systems are vital in brain regions responsible for learning and memory. In this context EAAT2 interacts with postsynaptic density proteins such as PSD-95 and forms a complex that links with ionotropic glutamate receptors which play a role in synaptic plasticity and long-term potentiation. Furthermore EAAT transporters cooperate with other amino acid transporters that partake in metabolism and neurotransmitter cycling.

Malfunctions in these transporters associate with neurological conditions such as epilepsy and amyotrophic lateral sclerosis (ALS). Reduced activity or expression of EAAT2 has been observed in patients with ALS leading to elevated glutamate levels and subsequent neurodegeneration. In epilepsy altered EAAT2 function can result in disrupted neuronal excitability heightening seizure susceptibility. Understanding these connections highlights the potential for developing GLT-1 inhibitor drugs that can modulate glutamate activity aimed at such neurological disorders.
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Product protocols

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Publications (13)

Recent publications for all applications. Explore the full list and refine your search

The Journal of clinical investigation 133: PubMed37104042

2023

Postoperative risk of IDH-mutant glioma-associated seizures and their potential management with IDH-mutant inhibitors.

Applications

Unspecified application

Species

Unspecified reactive species

Michael R Drumm,Wenxia Wang,Thomas K Sears,Kirsten Bell-Burdett,Rodrigo Javier,Kristen Y Cotton,Brynna Webb,Kayla Byrne,Dusten Unruh,Vineeth Thirunavu,Jordain Walshon,Alicia Steffens,Kathleen McCortney,Rimas V Lukas,Joanna J Phillips,Esraa Mohamed,John D Finan,Lucas Santana-Santos,Amy B Heimberger,Colin K Franz,Jonathan Kurz,Jessica W Templer,Geoffrey T Swanson,Craig Horbinski

Glia 71:1197-1216 PubMed36617748

2023

Yes-associated protein regulates glutamate homeostasis through promoting the expression of excitatory amino acid transporter-2 in astrocytes via β-catenin signaling.

Applications

Unspecified application

Species

Unspecified reactive species

Xingxing Xu,Jiaojiao Wang,Siyu Du,Xiya Shen,Jiashu Lian,Jian Zhou,Mianxian Wang,Wenjin Feng,Zhaoting Lv,Junzhe Zhu,Lingting Jin,Huankun Sun,Lihao Wu,Xiaoning Wang,Haoyu Qiu,Wei Wang,Honglin Teng,Ying Wang,Zhihui Huang

The European journal of neuroscience 57:217-232 PubMed36440503

2022

Repeated sevoflurane exposures inhibit neurogenesis by inducing the upregulation of glutamate transporter 1 in astrocytes.

Applications

Unspecified application

Species

Unspecified reactive species

Fanli Kong,Yao Zhang,Tingting Wang,Liang Zhong,Chun Feng,Yuanyuan Wu

Nature neuroscience 20:393-395 PubMed28135241

2017

[F]FDG PET signal is driven by astroglial glutamate transport.

Applications

Unspecified application

Species

Unspecified reactive species

Eduardo R Zimmer,Maxime J Parent,Débora G Souza,Antoine Leuzy,Clotilde Lecrux,Hyoung-Ihl Kim,Serge Gauthier,Luc Pellerin,Edith Hamel,Pedro Rosa-Neto

The Journal of neuroscience : the official journal of the Society for Neuroscience 36:10404-10415 PubMed27707974

2016

Glutamate Clearance Is Locally Modulated by Presynaptic Neuronal Activity in the Cerebral Cortex.

Applications

Unspecified application

Species

Unspecified reactive species

Moritz Armbruster,Elizabeth Hanson,Chris G Dulla

Journal of neurophysiology 113:3634-45 PubMed25855696

2015

Different pools of glutamate receptors mediate sensitivity to ambient glutamate in the cochlear nucleus.

Applications

Unspecified application

Species

Unspecified reactive species

Yang Yang,Matthew A Xu-Friedman

The Journal of physiology 592:2813-27 PubMed24835172

2014

A functional coupling between extrasynaptic NMDA receptors and A-type K+ channels under astrocyte control regulates hypothalamic neurosecretory neuronal activity.

Applications

Unspecified application

Species

Unspecified reactive species

Krishna Naskar,Javier E Stern

Neuroscience 258:374-84 PubMed24300109

2013

Primary cultures of rat cortical microglia treated with nicotine increases in the expression of excitatory amino acid transporter 1 (GLAST) via the activation of the α7 nicotinic acetylcholine receptor.

Applications

Unspecified application

Species

Unspecified reactive species

N Morioka,M Tokuhara,Y Nakamura,Y Idenoshita,S Harano,F F Zhang,K Hisaoka-Nakashima,Y Nakata

Journal of neurophysiology 110:368-77 PubMed23615553

2013

pH modulation of glial glutamate transporters regulates synaptic transmission in the nucleus of the solitary tract.

Applications

Unspecified application

Species

Unspecified reactive species

Rafiq Huda,Donald R McCrimmon,Marco Martina

The Journal of neuroscience : the official journal of the Society for Neuroscience 33:631-40 PubMed23303942

2013

Astrocytes modulate a postsynaptic NMDA-GABAA-receptor crosstalk in hypothalamic neurosecretory neurons.

Applications

Unspecified application

Species

Unspecified reactive species

Evgeniy S Potapenko,Vinicia C Biancardi,Yiqiang Zhou,Javier E Stern
View all publications
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