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Description: Potent group I mGlu antagonist
Chemical Name: N-Phenyl-7-(hydroxyimino)cyclopropa[b]chromen-1a-carboxamide
Purity: ≥98% (HPLC)
Biological Activity for PHCCC
PHCCC is a group I metabotropic glutamate receptor antagonist (IC50 ~ 3 μM); 67 times more potent than (S)-4-carboxyphenylglycine (Cat. No. 0323). Also a positive allosteric modulator for mGlu4a; potentiates L-AP4-mediated inhibition of striatopallidal synaptic transmission in vitro. Displays antiParkinsonian effects in rats in vivo.
Licensing Information
Sold for research purposes under license from Suntory Ltd.
Compound Libraries for PHCCC
PHCCC is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.
Technical Data for PHCCC
| M. Wt | 294.31 |
| Formula | C17H14N2O3 |
| Storage | Store at RT |
| Purity | ≥98% (HPLC) |
| CAS Number | 179068-02-1 |
| PubChem ID | 5866327 |
| InChI Key | FPXPIEZPAXSELW-CYVLTUHYSA-N |
| Smiles | O=C(NC4=CC=CC=C4)C3(C2C3)OC1=CC=CC=C1/C2=N/O |
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 Data for PHCCC
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 29.43 | 100 |
Preparing Stock Solutions for PHCCC
The following data is based on the product molecular weight 294.31. 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.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 3.4 mL | 16.99 mL | 33.98 mL |
| 5 mM | 0.68 mL | 3.4 mL | 6.8 mL |
| 10 mM | 0.34 mL | 1.7 mL | 3.4 mL |
| 50 mM | 0.07 mL | 0.34 mL | 0.68 mL |
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Product Datasheets for PHCCC
References for PHCCC
References are publications that support the biological activity of the product.
Mao and Wang (2001) Selective activation of group I metabotropic glutamate receptors upregulates preprodynorphin, substance P and preproenkephalin mRNA expression in rat dorsal striatum. Synapse 39 82 PMID: 11071713
Marino et al (2003) Allosteric modulation of group III metabotropic glutamate receptor 4: a potential approach to Parkinson's disease treatment. Proc.Natl.Acad.Sci.USA 100 13668 PMID: 14593202
Annoura et al (1996) A novel class of antagonists for metabotropic glutamate receptors, 7-(hydroxyimino)cyclopropa[b]chromen-1a-carboxylates. Bioorg.Med.Chem.Lett. 6 763
Flor et al (2002) Positive allosteric modulators of metabotropic glutamate receptor subtype 4: pharmacological and molecular characterization. Neuropharmacology 43 286 Abstr.No. 47
If you know of a relevant reference for PHCCC, please let us know.
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Keywords: PHCCC, PHCCC supplier, Potent, group, I, mGlur, antagonists, Group, Receptors, mGlu1, mGlu5, Glutamate, Metabotropic, mGlu4, (Metabotropic), 1027, Tocris Bioscience
8 Citations for PHCCC
Citations are publications that use Tocris products. Selected citations for PHCCC include:
Jones et al (2011) Discovery, synthesis, and structure-activity relationship development of a series of N-4-(2,5-dioxopyrrolidin-1-yl)phenylpicolinamides (VU0400195, ML182): characterization of a novel positive allosteric modulator of the metabotropic glutamate receptor 4 ( J Med Chem 54 7639 PMID: 21966889
Foong (2009) mGluR(1) Receptors Contribute to Non-Purinergic Slow Excitatory Transmission to Submucosal VIP Neurons of Guinea-Pig Ileum. Front Neurosci 3 46 PMID: 20582273
Spampinato et al (2015) Glial metabotropic glutamate receptor-4 increases maturation and survival of oligodendrocytes. Biol Psychiatry 8 462 PMID: 25642169
Volpi et al (2016) Allosteric modulation of metabotropic glutamate receptor 4 activates IDO1-dependent, immunoregulatory signaling in dendritic cells. Neuropharmacology 102 59 PMID: 26522434
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
Hemstapat et al (2006) A novel class of positive allosteric modulators of metabotropic glutamate receptor subtype 1 interact with a site distinct from that of negative allosteric modulators. Mol Pharmacol 70 616 PMID: 16645124
Niswender et al (2008) Discovery, characterization, and antiparkinsonian effect of novel positive allosteric modulators of metabotropic glutamate receptor 4. Mol Pharmacol 74 1345 PMID: 18664603
Collard et al (2002) Neutrophil-derived glutamate regulates vascular endothelial barrier function. J Biol Chem 277 14801 PMID: 11847215
Do you know of a great paper that uses PHCCC from Tocris? Please let us know.
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Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
*Please note that Tocris will only send literature to established scientific business / institute addresses.
Metabotropic Glutamate Receptors Scientific Review
Written by Francine Acher, this review discusses the pharmacology and therapeutic potential of mGlu receptors, and the compounds acting upon them; compounds available from Tocris are listed.
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