Potent group II/III mGlu receptor antagonist, with approximately 20-fold selectivity for group III over group II (IC₅₀ values of 2.2 and 46.2 nM respectively). A much less potent antagonist at group I receptors in neonatal rat cortical slices (K_B = 0.65 ± 0.07 nM).

Technical Data

M. Wt	271.21
Formula	C₁₁H₁₄NO₅P
Storage	Store at RT
Purity	≥98% (HPLC)
CAS Number	183364-82-1
PubChem ID	2878
InChi Key	IGODGTDUQSMDQU-UHFFFAOYSA-N
Smiles	NC(C2CC2)(C(O)=O)C1=CC=C(P(O)(O)=O)C=C1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
Solubility	1eq. NaOH	27.12	100

Preparing Stock Solutions

The following data is based on the product molecular weight 271.21.

Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	3.69 mL	18.44 mL	36.87 mL
5 mM	0.74 mL	3.69 mL	7.37 mL
10 mM	0.37 mL	1.84 mL	3.69 mL
50 mM	0.07 mL	0.37 mL	0.74 mL

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References

References are publications that support the biological activity of the product.

Jane Potent antagonists at the L-AP4- and (1S, 3S)-ACPD-sensitive presynaptic metabotropic glutamate receptors in the neonatal rat spinal cord. Neuropharmacology 1996 PMID: 9121605
Toms The effects of (RS)-α-cyclopropyl-4-phosphonophenylglycine ((RS)-CPPG), a potent and selective metabotropic glutamate receptor antagonist. BrJ.Pharmacol. 1996 PMID: 8922731
Kemp α-Methyl-3-phosphonophenylglycine and α-cyclopropyl-4-phosphonophenylglycine are potent antagonists at mGluRs negatively coupled to adenylyl cyclase. Br.J.Pharmacol.

Citations (21)

Showing 1 - 10 of 21 citations Showing All

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Citations are publications that use Bio-Techne products. Selected citations for CPPG include:

Hellmer et al. (2018) A group I metabotropic glutamate receptor controls synaptic gain between rods and rod bipolar cells in the mouse retina. Physiol Rep. 6:e13885
PMID: 30338673
Dornier (2017) Glutaminolysis drives membrane trafficking to promote invasiveness of breast cancer cells. Nat Commun. 8(1):2255
PMID: 29269878
Tassin et al. (2016) Phasic and Tonic mGlu7 Receptor Activity Modulates the Thalamocortical Network. Front Neural Circuits. 10:31
PMID: 27199672
Spampinato et al. (2015) Glial metabotropic glutamate receptor-4 increases maturation and survival of oligodendrocytes. Neurotox Res. 8:462
PMID: 25642169
Nieus et al. (2014) Regulation of output spike patterns by phasic inhibition in cerebellar granule cells. Front Cell Neurosci. 8:246
PMID: 25202237
Bennett et al. (2014) Examination of VLC-PUFA-deficient photoreceptor terminals. J Neurosci. 55:4063
PMID: 24764063
Domin et al. (2014) Group III mGlu receptor agonist, ACPT-I, exerts potential neuroprotective effects in vitro and in vivo. Proc Natl Acad Sci U S A. 26:99
PMID: 24402869
De-May and Ali (2013) Cell type-specific regulation of inhibition via cannabinoid type 1 receptors in rat neocortex. J Neurophysiol. 109:216
PMID: 23054605
He et al. (2012) Increased Kv1 channel expression may contribute to decreased sIPSC frequency following chronic inhibition of NR2B-containing NMDAR. Neuropsychopharmacology. 37:1338
PMID: 22218089
Ichinose and Lukasiewicz (2012) The mode of retinal presynaptic inhibition switches with light intensity. J Neurosci. 32:4360
PMID: 22457487
Cassé et al. (2012) Glutamate controls tPA recycling by astrocytes, which in turn influences glutamatergic signals. J Neurosci. 32:5186
PMID: 22496564
Broadstock et al. (2012) Antiparkinsonian potential of targeting group III metabotropic glutamate receptor subtypes in the rodent substantia nigra pars reticulata. Br J Pharmacol. 165:1034
PMID: 21627638
Ali (2011) CB1 modulation of temporally distinct synaptic facilitation among local circuit interneurons mediated by N-type calcium channels in CA1. J Neurophysiol. 105:1051
PMID: 21123660
Zhang et al. (2010) RGS7 and -11 complexes accelerate the ON-bipolar cell light response. Invest Ophthalmol Vis Sci. 51:1121
PMID: 19797214
Balakrishnan et al. (2009) Slow glycinergic transmission mediated by transmitter pooling. Nat Neurosci. 12:286
PMID: 19198604
Rancillac et al. (2006) Glutamatergic Control of Microvascular Tone by Distinct GABA Neurons in the Cerebellum. J Neurosci. 26:6997
PMID: 16807329
Jiang et al. (2006) Activation of group III metabotropic glutamate receptors attenuates rotenone toxicity on DArgic neurons through a microtubule-dependent mechanism. J Neurosci. 26:4318
PMID: 16624952
Newman (2005) Calcium increases in retinal glial cells evoked by light-induced neuronal activity. Front Cell Neurosci. 25:5502
PMID: 15944378
Mathiesen et al. (2003) Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP. Br J Pharmacol. 138:1026
PMID: 12684257
Nishi et al. (2003) Metabotropic mGlu5 receptors regulate adenosine A2A receptor signaling. Invest Ophthalmol Vis Sci. 100:1322
PMID: 12538871
Collard et al. (2002) Neutrophil-derived glutamate regulates vascular endothelial barrier function. J Biol Chem. 277:14801
PMID: 11847215

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Customer Reviews (2)

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Used in inhibitor cocktail

Name: Anonymous

Species: Rat

Assay Type: In Vitro

Cell Line/Tissue: Retinal rod bipolar cells

Retinal dissections were performed in HEPES-buffered extracellular solution containing glutamate inhibitor cocktail - 600 umol/L

PMID: 30338673
Use of CPPG as a blocker of mGluRs group III

Name: Anonymous

Species: Rat

Assay Type: In Vitro

Cell Line/Tissue: Cerebellum

CPPG (5 microM) was used for pharmacological isolation of GABA-A receptor activity in nucleated membrane patches. Being added to perfusion solution, CPPG blocked contaminating receptor activity in a recorded response, thus revealing clear GABA-ergic single-channel openings. Figure: single-channel openings of GABA-A receptors in a membrane patch after application of CPPG.

Compound should be sonicated when dissolving.

PMID: 30042389

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CPPG

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Biological Activity