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SML1612

Sigma-Aldrich

2-PMPA

≥98% (HPLC), powder, glutamate carboxypeptidase II inhibitor

Synonyme(s) :

2-(Phosphonomethyl)-pentandioic acid, 2-Phosphonomethyl pentanedioic acid, PMPA

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About This Item

Formule empirique (notation de Hill):
C6H11O7P
Numéro CAS:
173039-10-6
Poids moléculaire :
226.12
Numéro MDL:
MFCD00940167
Code UNSPSC :
12352200
ID de substance PubChem :
329825498
Nomenclature NACRES :
NA.77

product name

2-PMPA, ≥98% (HPLC)

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

H2O: 20 mg/mL, clear

Température de stockage

room temp

Chaîne SMILES 

O=C(O)CCC(C(O)=O)CP(O)(O)=O

InChI

1S/C6H11O7P/c7-5(8)2-1-4(6(9)10)3-14(11,12)13/h4H,1-3H2,(H,7,8)(H,9,10)(H2,11,12,13)

Clé InChI

ISEYJGQFXSTPMQ-UHFFFAOYSA-N

Actions biochimiques/physiologiques

2-(phosphonomethyl)pentanedioic acid (2-PMPA) blocks intravenous cocaine self-administration maintained by low unit doses of cocaine. In addition, it also inhibits cocaine-induced reinstatement of drug-seeking behavior. 2-PMPA reduces blood oxygen-level dependent (BOLD) signals in brain of anesthetized mice.
2-PMPA is a potent (IC50 ~ 1 nM) and selective inhibitor of Glutamate carboxypeptidase II (GCPII), also known as N-acetyl-L-aspartyl-L-glutamate peptidase I (NAALADase I), NAAG peptidase, or prostate-specific membrane antigen (PSMA). 2-PMPA has neuroprotective activity activity. 2-PMPA has been shown to prevent and treat cognitive impairment in the EAE model of multiple sclerosis and to protect against soman-induced neuropathology.
2-PMPA is a potent and selective inhibitor of Glutamate carboxypeptidase II (GCPII).

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Mena Asha Krishnan et al.
Biomaterials science, 9(6), 2295-2312 (2021-02-09)
The current challenge in fluorescence guided surgery (FGS) for prostate cancer (PCa) is in the design of imaging probes with high selectivity, clear visualization of tumour margins, and minimal toxicity. This report aims to design and develop a novel NIR-nanoprobe
Eden Kapcan et al.
Current protocols in chemical biology, 12(4), e88-e88 (2020-12-17)
The emergence of covalent inhibitors and chemoproteomic probes in translational chemical biology research requires the development of robust biophysical and analytical methods to characterize their complex interactions with target biomolecules. Importantly, these methods must efficiently assess target selectivity and accurately
Inhibition of N-acetylated-alpha-Linked-Acidic Dipeptidase (NAALADase) by 2-PMPA Attenuates Cocaine-Induced Relapse in Rats: A NAAG-mGluR2/3-Mediated Mechanism
Xi Z X, et al.
Journal of Neurochemistry, 112(2), 564-564 (2010)
2-PMPA, a NAAG peptidase inhibitor, attenuates magnetic resonance BOLD signals in brain of anesthetized mice
Baslow M H, et al.
Journal of Molecular Neuroscience, 26(1), 1-16 (2005)
Mena Asha Krishnan et al.
Current protocols in chemical biology, 10(4), e50-e50 (2018-09-14)
Present treatment strategies focus on minimizing unwanted toxicity to healthy cells during chemotherapeutic treatment. This is achieved by developing strategies to selectively deliver drugs to malignant cells over-expressing specific protein biomarkers. The drugs are attached via a self-immolative linker to
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