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(RS)-PPG

Potent, selective mGlu8 agonist CAS# 120667-15-4

(RS)-PPG

Catalog No. BCC6975----Order now to get a substantial discount!

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Chemical structure

(RS)-PPG

3D structure

Chemical Properties of (RS)-PPG

Cas No. 120667-15-4 SDF Download SDF
PubChem ID 4545574 Appearance Powder
Formula C8H10NO5P M.Wt 231.14
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 100 mM in 1eq. NaOH
Chemical Name 2-amino-2-(4-phosphonophenyl)acetic acid
SMILES C1=CC(=CC=C1C(C(=O)O)N)P(=O)(O)O
Standard InChIKey JRQRKFDFHAPMGQ-UHFFFAOYSA-N
Standard InChI InChI=1S/C8H10NO5P/c9-7(8(10)11)5-1-3-6(4-2-5)15(12,13)14/h1-4,7H,9H2,(H,10,11)(H2,12,13,14)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of (RS)-PPG

DescriptionA potent and selective group III metabotropic glutamate receptor agonist, with approximately 25-fold preference for hmGlu8; anticonvulsant and neuroprotective in vivo. Also available as part of the Group III mGlu Receptor.

(RS)-PPG Dilution Calculator

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(RS)-PPG Molarity Calculator

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Preparing Stock Solutions of (RS)-PPG

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.3264 mL 21.6319 mL 43.2638 mL 86.5276 mL 108.1596 mL
5 mM 0.8653 mL 4.3264 mL 8.6528 mL 17.3055 mL 21.6319 mL
10 mM 0.4326 mL 2.1632 mL 4.3264 mL 8.6528 mL 10.816 mL
50 mM 0.0865 mL 0.4326 mL 0.8653 mL 1.7306 mL 2.1632 mL
100 mM 0.0433 mL 0.2163 mL 0.4326 mL 0.8653 mL 1.0816 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on (RS)-PPG

(R,S)-4-phosphonophenylglycine, a potent and selective group III metabotropic glutamate receptor agonist, is anticonvulsive and neuroprotective in vivo.[Pubmed:10336568]

J Pharmacol Exp Ther. 1999 Jun;289(3):1678-87.

Group III metabotropic glutamate receptors (mGluRs) are thought to modulate neurotoxicity of excitatory amino acids, via mechanisms of presynaptic inhibition, such as regulation of neurotransmitter release. Here, we describe (R,S)-4-phosphonophenylglycine (PPG) as a novel, potent, and selective agonist for group III mGluRs. In recombinant cell lines expressing the human receptors hmGluR4a, hmGluR6, hmGluR7b, or hmGluR8a, EC50 values for (R,S)-PPG of 5.2 +/- 0.7 microM, 4.7 +/- 0.9 microM, 185 +/- 42 microM, and 0.2 +/- 0.1 microM, respectively, were measured. The compound showed EC50 and IC50 values of >/=200 microM at group I and II hmGluRs and was inactive at cloned human N-methyl-D-aspartate, alpha-amino-3-hydroxy-5-methyl-isoxazole-4-propionate, and kainate receptors (>300 microM). On the other hand, it showed micromolar affinity for a Ca2+/Cl--dependent L-glutamate binding site in rat brain, similar to other phosphono-substituted amino acids like L-2-amino-4-phosphonobutyrate. In cultured cortical neurons, (R, S)-PPG provided protection against a toxic pulse of N-methyl-D-aspartate (EC50 = 12 microM), which was reversed by the group III mGluR antagonist (R,S)-alpha-methylserine-O-phosphate but not by the group II antagonist (2S)-alpha-ethylglutamate. Moreover, (R,S)-PPG protected against N-methyl-D-aspartate- and quinolinic acid-induced striatal lesions in rats and was anticonvulsive in the maximal electroshock model in mice. In contrast to the group III mGluR agonists L-2-amino-4-phosphonobutyrate and L-serine-O-phosphate, (R,S)-PPG showed no proconvulsive effects (2200 nmol i.c.v.). These data provide novel in vivo evidence for group III mGluRs as attractive targets for neuroprotective and anticonvulsive therapy. Also, (R,S)-PPG represents an attractive tool to analyze the roles of group III mGluRs in nervous system physiology and pathology.

Exploration of phenyl-spaced 2-amino-(5-9)-phosphonoalkanoic acids as competitive N-methyl-D-aspartic acid antagonists.[Pubmed:2544728]

J Med Chem. 1989 Jul;32(7):1580-90.

To investigate the preferred spatial relationship of the distal phosphonic acid to the alpha-amino acid group of the established competitive N-methyl-D-aspartic acid (NMDA) antagonists APH (1) and APV (2), we have prepared a series of ortho-, meta-, and para-substituted (phosphonoalkyl)phenylglycine and -phenylalanine derivatives. With use of a [3H]CPP receptor binding assay, significant binding activity was observed to be critically dependent on both the position of substitution and length of alkyl spacing groups. Two compounds, 4-(phosphonomethyl)-phenylglycine (6, PD 129635) and 3-(phosphonomethyl)phenylalanine (15, PD 130527), displayed receptor-binding affinity comparable to that of APH. Like APH, these compounds were also effective in antagonizing both the proconvulsant and lethal action of NMDA-administered retrobulbar in the mouse. Data are also provided which compare directly the binding efficacy of these compounds against that disclosed recently for the related NMDA antagonist 18 (NPC 451). A preliminary comparison of the structures showing good receptor-binding affinity and in vivo antagonist activity suggests that the NMDA receptor prefers a "folded" rather than "extended" conformation.

Description

(RS)-PPG is a potent and selective agonist for group III mGluRs. The EC50s of 5.2 μM, 4.7 μM, 185 μM, and 0.2 μM for hmGluR4a, hmGluR6, hmGluR7b, and hmGluR8a, respectively. Anticonvulsive and neuroprotective activity.

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