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AB120003

D-AP5, NMDA glutamate site antagonist

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(277 Publications)

D-AP5 (CAS: 79055-68-8)(ab120003) is a competitive NMDA receptor glutamate site antagonist. More active form of DL-AP5. 2-APV,D-APV,D-2-amino-5-phosphonovalerate. MW 197.1.

- Proven performance: cited in over 270 publications
- Available in different sizes to fit your experimental needs
4 Images
Chemical Structure - D-AP5, NMDA glutamate site antagonist (AB120003)
  • Chemical Structure

Lab

Chemical Structure - D-AP5, NMDA glutamate site antagonist (AB120003)

2D chemical structure image of ab120003, D-AP5, NMDA glutamate site antagonist

Functional Studies - D-AP5, NMDA glutamate site antagonist (AB120003)
  • FuncS

PubMed

Functional Studies - D-AP5, NMDA glutamate site antagonist (AB120003)

Representative voltage-clamp recording (Vh= −60 mV, ECl−=+8 mV) of a Purkinje cells response to simulated ischemia and sequential block of glutamate receptors and GABAA receptors.

Image from Brady JD et al., Neuroscience. 2010;168(1):108-17. Fig 3.; doi: 10.1016/j.neuroscience.2010.03.009 with permission from Elsevier.

Functional Studies - D-AP5, NMDA glutamate site antagonist (AB120003)
  • FuncS

PubMed

Functional Studies - D-AP5, NMDA glutamate site antagonist (AB120003)

Averaged Ca2+ transients (500 Hz line scans) evoked by 40 ms voltage step in a dendrite (left) and spine (right) in control (black), D-AP5 (red, 10 µM), after a 10 min washout of D-AP5 (green), and in 5 µM NMDA (blue). Mibefradil (20 µM), nimodipine (20 µM) and TTX (0.5 µM) were present throughout.

Image from Herman MA et al., PLoS One. 2011;6(11):e26501. Fig 2(A).; doi: 10.1371/journal.pone.0026501. Reproduced under the Creative Commons license http://creativecommons.org/licenses/by/4.0/

Cellular Activation - D-AP5, NMDA glutamate site antagonist (AB120003)
  • CellAct

Unknown

Cellular Activation - D-AP5, NMDA glutamate site antagonist (AB120003)

(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 (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.

Image from Barker M et al., Plos One, 7(5), e35955. Fig 1,; doi: 10.1371/journal.pone.0035955

Key facts

CAS number

79055-68-8

Purity

>99%

Form

Solid

form

Molecular weight

197.13 Da

Molecular formula

C<sub>5</sub>H<sub>1</sub><sub>2</sub>NO<sub>5</sub>P

PubChem

135342

Nature

Synthetic

Solubility

Available in multiple formatsab144482: Soluble in 1 ml of water to give specified mM/ml concentration; ab120003: Soluble in water to 100 mM; ab285210: Supplied

Biochemical name

5-Phosphono-D-norvaline

Biological description

Competitive NMDA receptor glutamate site antagonist. More active form of DL-AP5.

Canonical smiles

C(CC(C(=O)O)N)CP(=O)(O)O

Isomeric smiles

C(C[C@H](C(=O)O)N)CP(=O)(O)O

InChi

InChI=1S/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)/t4-/m1/s1

InChiKey

VOROEQBFPPIACJ-SCSAIBSYSA-N

IUPAC Name

(2R)-2-amino-5-phosphonopentanoic acid

Product details

Check out our range of NMDA glutamate antagonist here

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

Supplementary information

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

NMDAR and AMPA receptors have massive implications in neurodegenerative diseases like Alzheimer's and neuropsychiatric disorders such as schizophrenia. Dysregulation in NMDAR function possibly through inadequate blockade by antagonists like D-AP5 or D-APV links to excitotoxicity a condition contributing to neuronal death as seen in Alzheimer's. In schizophrenia altered NMDAR signaling is connected to cognitive dysfunction and both NMDAR and AMPA may serve as therapeutic targets.
Pathways

NMDARs and AMPA receptors integrate into key neural and signaling pathways such as the long-term potentiation pathway which is essential for memory formation. NMDAR activation allows calcium influx necessary for initiating intracellular signaling cascades. The interactions with proteins like CaMKII and synaptic scaffolds like PSD-95 illustrate the role of these receptors in synaptic and protein signaling networks that adjust synaptic strength.

Biological function summary

These glutamate receptor subunits forming part of NMDAR and AMPA receptor complexes modulate synaptic plasticity which underlies learning and memory. NMDARs are tetrameric complexes composed mostly of two GluN1 subunits combined with two region-specific GluN2 (A-D) or GluN3 (A B) subunits creating diversity in function and pharmacological characteristics. The AMPA receptor primarily built of GluA1 through GluA4 subunits contributes to fast excitatory neurotransmission. Together these receptors regulate calcium ion flow into neurons impacting cellular events essential for neural communication and adaptation.

The N-Methyl-D-Aspartate Receptor (NMDAR) subunits such as NMDAR2A NMDAR2B GluN2C NMDAR1 GluN2D NR3A and NR3B are key components of glutamate receptors also including the AMPA subtype Glutamate Receptor 1. These receptors are ionotropic and mediate synaptic transmission in the central nervous system. They are expressed in the brain particularly in regions such as the hippocampus and cortex. NMDAR1 also known as GluN1 serves as an obligatory subunit required for functional receptor assembly. The mass of NMDAR subunits varies; for example the GluN1 subunit has an approximate mass of 120 kDa.

Product protocols

Publications (277)

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

Communications biology 7:1707 PubMed39730868

2024

Dexmedetomidine accelerates photoentrainment and affects sleep structure through the activation of SCN neurons.

Applications

Unspecified application

Species

Unspecified reactive species

Ying Zhang,Wei Wang,Jiaxin Li,Dongmei Zhao,Yue Shu,Xinlu Jia,Yibo Wang,Xinqi Cheng,Liecheng Wang,Juan Cheng

Molecular brain 17:78 PubMed39511688

2024

Transcriptomic and de novo proteomic analyses of organotypic entorhino-hippocampal tissue cultures reveal changes in metabolic and signaling regulators in TTX-induced synaptic plasticity.

Applications

Unspecified application

Species

Unspecified reactive species

Maximilian Lenz,Paul Turko,Pia Kruse,Amelie Eichler,Zhuo Angel Chen,Juri Rappsilber,Imre Vida,Andreas Vlachos

Advanced science (Weinheim, Baden-Wurttemberg, Germany) 11:e2410927 PubMed39435757

2024

Enriched Environment Reduces Seizure Susceptibility via Entorhinal Cortex Circuit Augmented Adult Neurogenesis.

Applications

Unspecified application

Species

Unspecified reactive species

Zhongxia Li,Liying Chen,Fan Fei,Wenqi Wang,Lin Yang,Yu Wang,Heming Cheng,Yingwei Xu,Cenglin Xu,Shuang Wang,Yan Gu,Feng Han,Zhong Chen,Yi Wang

Neurochemical research 49:2926-2939 PubMed39078522

2024

Dexmedetomidine Promotes NREM Sleep by Depressing Oxytocin Neurons in the Paraventricular Nucleus in Mice.

Applications

Unspecified application

Species

Unspecified reactive species

Ying Zhang,Jiaxin Li,Yan Li,Wei Wang,Daming Wang,Junli Ding,Licheng Wang,Juan Cheng

iScience 27:110145 PubMed38952682

2024

Layer specific regulation of critical period timing and maturation of mouse visual cortex by endocannabinoids.

Applications

Unspecified application

Species

Unspecified reactive species

Taisuke Yoneda,Katsuro Kameyama,Takahiro Gotou,Keiko Terata,Masahiro Takagi,Yumiko Yoshimura,Kenji Sakimura,Masanobu Kano,Yoshio Hata

Nature communications 15:5095 PubMed38876987

2024

Scanless two-photon voltage imaging.

Applications

Unspecified application

Species

Unspecified reactive species

Ruth R Sims,Imane Bendifallah,Christiane Grimm,Aysha S Mohamed Lafirdeen,Soledad Domínguez,Chung Yuen Chan,Xiaoyu Lu,Benoît C Forget,François St-Pierre,Eirini Papagiakoumou,Valentina Emiliani

The Journal of neuroscience : the official journal of the Society for Neuroscience 44: PubMed38839301

2024

Phospholipid Scramblase 1 Controls Efficient Neurotransmission and Synaptic Vesicle Retrieval at Cerebellar Synapses.

Applications

Unspecified application

Species

Unspecified reactive species

Margherita Caputo,Daniela Ivanova,Sylvette Chasserot-Golaz,Frédéric Doussau,Anne-Marie Haeberlé,Cathy Royer,Sebahat Ozkan,Jason Ecard,Nicolas Vitale,Michael A Cousin,Petra Tóth,Stéphane Gasman,Stéphane Ory

Cell reports methods 3:100544 PubMed37671014

2023

Functional imaging-guided cell selection for evolving genetically encoded fluorescent indicators.

Applications

Unspecified application

Species

Unspecified reactive species

Chang Lin,Lihao Liu,Peng Zou

Molecular therapy. Methods & clinical development 30:1-13 PubMed37324975

2023

Starburst amacrine cells amplify optogenetic visual restoration through gap junctions.

Applications

Unspecified application

Species

Unspecified reactive species

Yusaku Katada,Hiromitsu Kunimi,Naho Serizawa,Deokho Lee,Kenta Kobayashi,Kazuno Negishi,Hideyuki Okano,Kenji F Tanaka,Kazuo Tsubota,Toshihide Kurihara

Frontiers in molecular neuroscience 16:1148219 PubMed37122623

2023

Denervated mouse CA1 pyramidal neurons express homeostatic synaptic plasticity following entorhinal cortex lesion.

Applications

Unspecified application

Species

Unspecified reactive species

Maximilian Lenz,Amelie Eichler,Pia Kruse,Phyllis Stöhr,Dimitrios Kleidonas,Christos Galanis,Han Lu,Andreas Vlachos
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