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MW 336.28 Da, Purity >99%. Potent, selective and competitive AMPA/kainate receptor antagonist. Neuroprotective and anticonvulsant in vivo. Water-soluble form available - please see NBQX disodium salt (ab120046).

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Images

Chemical Structure - NBQX, AMPA / kainate antagonist (AB120045), expandable thumbnail
  • Functional Studies - NBQX, AMPA / kainate antagonist (AB120045), expandable thumbnail
  • Functional Studies - NBQX, AMPA / kainate antagonist (AB120045), expandable thumbnail

Publications

Key facts

CAS number

118876-58-7

Purity

> 99%

Form

Solid

Molecular weight

336.28 Da

Molecular formula

C12H8N4O6S

PubChem identifier

3272524

Nature

Synthetic

Alternative names

Recommended products

MW 336.28 Da, Purity >99%. Potent, selective and competitive AMPA/kainate receptor antagonist. Neuroprotective and anticonvulsant in vivo. Water-soluble form available - please see NBQX disodium salt (ab120046).

Key facts

Purity

> 99%

PubChem identifier

3272524

Solubility

Soluble in DMSO to 100 mM.

Biochemical name

2,3-Dioxo-6-nitro-7-sulfamoylbenzo(f)quinoxaline

Biological description

Potent, selective and competitive AMPA/kainate receptor antagonist. Neuroprotective and anticonvulsant in vivo. Water-soluble form available - please see NBQX disodium salt (ab120046).

Canonical SMILES

C1=CC2=C3C(=CC(=C2C(=C1)S(=O)(=O)N)[N+](=O)[O-])NC(=O)C(=O)N3

InChI

InChI=1S/C12H8N4O6S/c13-23(21,22)8-3-1-2-5-9(8)7(16(19)20)4-6-10(5)15-12(18)11(17)14-6/h1-4H,(H,14,17)(H,15,18)(H2,13,21,22)

InChIKey

UQNAFPHGVPVTAL-UHFFFAOYSA-N

IUPAC name

6-nitro-2,3-dioxo-1,4-dihydrobenzo[f]quinoxaline-7-sulfonamide

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

Glutamate Receptor 1 (AMPA subtype) and its related proteins such as BMPR1A BMPR1B and others like GRIK2/GluK2 and GluA3 function as ionotropic glutamate receptors that mediate excitatory synaptic transmission in the central nervous system. The mass of individual components like GluA3 is approximately 100-110 kDa. These receptors including kainate subtypes are widely expressed in the brain specifically in areas involved in learning and memory such as the hippocampus and the cerebral cortex. AMPA receptors work by allowing the flow of ions particularly sodium and calcium into the cells when glutamate binds to them resulting in neuron depolarization essential for synaptic plasticity and neurotransmission.

Biological function summary

These receptors play an important role in synaptic communication and plasticity influencing processes like learning and memory formation. The GluA3 and GluK2 subunits are integral parts of the receptor complexes that also include other subunits such as GluA4 and GluK5. These receptors dynamically regulate the synaptic strength by their assembly into tetrameric structures determining excitatory synaptic responses. The diversity in subunit composition allows for precise modulation and response to synaptic activity.

Pathways

These receptors participate in key signaling cascades such as the glutamatergic and calcium signaling pathways. They directly interact with other proteins including scaffolding proteins like PSD-95 that link them to downstream effectors in these pathways. In the calcium signaling pathway the opening of these receptors leads to calcium influx which is significant for activating downstream signaling molecules including calmodulin-dependent protein kinases which modulate synaptic strength and plasticity.

Associated diseases and disorders

The dysfunction of these receptors has a strong connection to neurological diseases like epilepsy and neurodegenerative disorders such as Alzheimer's disease. Alterations in receptor function or subunit expression particularly those involving GluA3 and GluK2 have been observed in patients with these conditions. These proteins serve as potential targets for drug development and antagonists such as NBQX are being explored for therapeutic intervention. AMPA receptor dysregulation impacts synaptic stability and plasticity contributing to the disease pathophysiology.

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3 product images

  • Chemical Structure - NBQX, AMPA / kainate antagonist (ab120045), expandable thumbnail

    Chemical Structure - NBQX, AMPA / kainate antagonist (ab120045)

    2D chemical structure image of ab120045, NBQX, AMPA / kainate antagonist

  • Functional Studies - NBQX, AMPA / kainate antagonist (ab120045), expandable thumbnail
    Barker M et al. PLoS One. 2012; 7(5): e35955. 10.1371/journal.pone.0035955 Reproduced under the Creative Commons license http://creativecommons.org/licenses/by/4.0/

    Functional Studies - NBQX, AMPA / kainate antagonist (ab120045)

    A - Photomicrograph of a DCN fusiform cell filled with lucifer yellow (top) and whole cell voltage clamp recording of this fusiform cell while stimulating the LVN (bottom).

    B - Photomicrograph of a DCN granule cell filled with lucifer yellow (top) and whole cell voltage clamp recording of this granule cell while stimulating the LVN (bottom)

    Both cells were held at −68 mV and the LVN was stimulated at 0.3 Hz. Glutamatergic EPSCs are represented in black and are blocked by 50 μm D-AP5 and 10 μm NBQX (ab120045, traces in red). Each trace represents an average of 10–20 single traces. The arrowhead represents the artifact of stimulus that has been removed for clarity. Scale bar: (A) 50 μm, (B) 20 μm

    Credit: Barker M et al. PLoS One. 2012; 7(5): e35955. 10.1371/journal.pone.0035955

  • Functional Studies - NBQX, AMPA / kainate antagonist (ab120045), expandable thumbnail

    Functional Studies - NBQX, AMPA / kainate antagonist (ab120045)

    Anti-MEK1 (phospho S298) antibody [EPR3338] ab96379 staining MEK1 (phospho S298) in SK-N-SH cells treated with NBQX (ab120045), by ICC/IF. Decrease in MEK1 (phospho S298) expression correlates with increased concentration of NBQX, as described in literature.
    The cells were incubated at 37°C for 1h in media containing different concentrations of ab120045 (NBQX) in DMSO, fixed with 4% formaldehyde for 10 minutes at room temperature 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 Anti-MEK1 (phospho S298) antibody [EPR3338] ab96379 (1/100 dilution) was performed overnight at 4°C in PBS containing 1% BSA and 0.1% tween. A DyLight 488 goat anti-rabbit polyclonal antibody (Goat Anti-Rabbit IgG H&L (DyLight® 488) preadsorbed ab96899) at 1/250 dilution was used as the secondary antibody.

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