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SML1612

Sigma-Aldrich

2-PMPA

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H11O7P
CAS Number:
173039-10-6
Molecular Weight:
226.12
MDL number:
MFCD00940167
UNSPSC Code:
12352200
PubChem Substance ID:
329825498
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 20 mg/mL, clear

storage temp.

room temp

SMILES string

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)

InChI key

ISEYJGQFXSTPMQ-UHFFFAOYSA-N

Biochem/physiol Actions

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).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
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
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)
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
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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