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MW 258.05 Da, Purity >99%. Potent NMDA receptor glycine site antagonist. Water soluble form available - see (ab120254).

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Images

Chemical Structure - 5,7-Dichlorokynurenic acid, NMDA receptor glycine site antagonist (AB120023), expandable thumbnail
  • Functional Studies - 5,7-Dichlorokynurenic acid, NMDA receptor glycine site antagonist (AB120023), expandable thumbnail

Publications

Key facts

CAS number

131123-76-7

Purity

> 99%

Form

Solid

Molecular weight

258.05 Da

Molecular formula

C10H5Cl2NO3

PubChem identifier

1779

Nature

Synthetic

Alternative names

Recommended products

MW 258.05 Da, Purity >99%. Potent NMDA receptor glycine site antagonist. Water soluble form available - see (ab120254).

Key facts

Purity

> 99%

PubChem identifier

1779

Solubility

Soluble in 1 eq. NaOH to 50 mM.

Biochemical name

5,7-Dichlorokynurenic acid

Biological description

Potent NMDA receptor glycine site antagonist. Water soluble form available - see (ab120254).

Canonical SMILES

C1=C(C=C(C2=C1NC(=CC2=O)C(=O)O)Cl)Cl

InChI

InChI=1S/C10H5Cl2NO3/c11-4-1-5(12)9-6(2-4)13-7(10(15)16)3-8(9)14/h1-3H,(H,13,14)(H,15,16)

InChIKey

BGKFPRIGXAVYNX-UHFFFAOYSA-N

IUPAC name

5,7-dichloro-4-oxo-1H-quinoline-2-carboxylic acid

Storage

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

Supplementary info

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

Activity summary

The target 'Glutamate Receptor' also known by its subtypes like NMDAR2A NMDAR2B GluN2C NMDAR1 and others serves as an essential component in synaptic transmission in the central nervous system. These receptors are ionotropic meaning they form ion channels and are known for binding to the neurotransmitter glutamate. The GluN2 subunits including GluN2A GluN2B GluN2C and GluN2D contribute to the heteromeric complexes of NMDAR (N-methyl-D-aspartate receptors) which have a role in excitatory neurotransmission. The mass of these receptors varies with their subunits generally within the range of 105-180 kDa. They are expressed widely in the brain with each subtype showing distinct patterns of expression in regions like the hippocampus cortex and cerebellum.

Biological function summary

These glutamate receptors play a pivotal role in synaptic plasticity which underpins learning and memory. Within synaptic complexes NMDARs form associations with scaffolding proteins and signal transduction molecules facilitating cellular responses to activity. The AMPA-type glutamate receptors including Glutamate Receptor 1 (GluA1) and Glutamate Receptor 3 (GluA3) collaborate with NMDARs in synaptic transmission by controlling the fast component of excitatory postsynaptic currents. These interactions enable the receptors to modulate synaptic strength and contribute to the maintenance of neural circuits.

Pathways

These ionotropic glutamate receptors function prominently within the glutamatergic signaling pathway and the calcium signaling pathway. The NMDARs are known to influence calcium influx pivotal for downstream activation of signaling cascades such as CaMKII and MAPK. Related proteins like PSD-95 form complexes with NMDARs mediating cellular responses important for signal transduction. These pathways highlight glutamate receptors' roles in pre- and post-synaptic cellular responses affecting numerous downstream effects that influence neural plasticity and survival.

Associated diseases and disorders

Disruptions in the function of these glutamate receptors are associated with neurodegenerative diseases and psychiatric disorders. For instance NMDAR malfunction links to Alzheimer's disease due to its involvement in synaptic failure and resultant cognitive deficits. Dysfunctional glutamatergic signaling also connects to schizophrenia where altered NMDAR activity affects neurotransmission and can contribute to symptoms. Proteins like GluA1 also interact in these contexts impacting synaptic plasticity further and potentially exacerbating disease progression through maladaptive synaptic changes.

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2 product images

  • Chemical Structure - 5,7-Dichlorokynurenic acid, NMDA receptor glycine site antagonist (ab120023), expandable thumbnail

    Chemical Structure - 5,7-Dichlorokynurenic acid, NMDA receptor glycine site antagonist (ab120023)

    2D chemical structure image of ab120023, 5,7-Dichlorokynurenic acid, NMDA receptor glycine site antagonist

  • Functional Studies - 5,7-Dichlorokynurenic acid, NMDA receptor glycine site antagonist (ab120023), expandable thumbnail

    Functional Studies - 5,7-Dichlorokynurenic acid, NMDA receptor glycine site antagonist (ab120023)

    ab12416 staining cGMP in SKNSH cells treated with 5,7-Dichlorokynurenic acid (ab120023), by ICC/IF. Decrease in cGMP expression correlates with increased concentration of 5,7-Dichlorokynurenic acid, as described in literature.
    The cells were incubated at 37°C for 20 minutes in media containing different concentrations of ab120023 (5,7-Dichlorokynurenic acid) in DMSO. Some samples where then further incubated with 15 µM NMDA (NMDA, excitotoxic amino acid ab120052) for 5 minutes and all samples were fixed with 100% methanol for 5 minutes at -20°C and blocked with PBS containing 10% goat serum, 0.3 M glycine, 1% BSA and 0.1% tween for 2h at room temperature. Staining of the treated cells with ab12416 (5 µg/ml) was performed overnight at 4°C in PBS containing 1% BSA and 0.1% tween. A DyLight 488 anti-rabbit polyclonal antibody (Goat Anti-Rabbit IgG H&L (DyLight® 488) preadsorbed ab96899) at 1/250 dilution was used as the secondary antibody. Nuclei were counterstained with DAPI and are shown in blue.

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