(S)-3,5-DHPG

Pricing Availability Delivery Time Qty
Cat.No. 0805 - (S)-3,5-DHPG | C8H9NO4 | CAS No. 162870-29-3
Description: Selective group I mGlu agonist. Active enantiomer of 3,5-DHPG (Cat. No. 0342)
Chemical Name: (S)-3,5-Dihydroxyphenylglycine
Purity: ≥98% (HPLC)
Datasheet
Citations (25)
Literature

Biological Activity

Selective group I mGlu receptor agonist. Also available as part of the Group I mGlu Receptor Tocriset™ and Mixed mGlu Receptor Tocriset™. (RS)-3,5-DHPG (Cat. No. 0342) also available.

Technical Data

M. Wt 183.16
Formula C8H9NO4
Storage Desiccate at -20°C
Purity ≥98% (HPLC)
CAS Number 162870-29-3
PubChem ID 443586
InChI Key HOOWCUZPEFNHDT-ZETCQYMHSA-N
Smiles OC1=CC([C@]([H])(N)C(O)=O)=CC(O)=C1

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

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
phosphate buffered saline 9.16 50
DMSO 3.66 20mM with gentle warming
water 9.16 50

Preparing Stock Solutions

The following data is based on the product molecular weight 183.16. Batch specific molecular weights may vary from batch to batch due to solvent 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 5.46 mL 27.3 mL 54.6 mL
5 mM 1.09 mL 5.46 mL 10.92 mL
10 mM 0.55 mL 2.73 mL 5.46 mL
50 mM 0.11 mL 0.55 mL 1.09 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Schoepp et al (1994) 3,5-Dihydroxyphenylglycine is a highly selective agonist for phosphoinositide-linked metabotropic glutamate receptors in the rat hippocampus. J.Neurochem. 63 769 PMID: 8035201

Sekiyama et al (1996) Structure-activity relationships of new agonists and antagonists of different metabotropic glutamate receptor subtypes. Br.J.Pharmacol. 117 1493 PMID: 8730745

Wisniewski and Car (2002) (S)-3,5-DHPG: a review. CNS Drug Rev. 8 101 PMID: 12070529

Baker et al (1995) Enzymatic resolution and pharmacological activity of the enantiomers of 3,5-dihydroxyphenylglycine, a metabotropic glutamate receptor agonist. Bioorg.Med.Chem.Lett. 5 223 PMID:


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Keywords: (S)-3,5-DHPG, supplier, Selective, group, I, agonists, Active, enantiomer, Group, Receptors, mGlu1, mGlu5, mGluR1, mGluR5, Glutamate, Metabotropic, Glutamate, (Metabotropic), Group, I, Receptors, Tocris Bioscience

25 Citations for (S)-3,5-DHPG

Citations are publications that use Tocris products. Selected citations for (S)-3,5-DHPG include:

Bozdagi et al (2012) Haploinsufficiency of Cyfip1 produces fragile X-like phenotypes in mice. J Neurosci 7 e42422 PMID: 22900020

Taman and Ribeiro (2011) Characterization of a truncated metabotropic glutamate receptor in a primitive metazoan, the parasitic flatworm Schistosoma mansoni. PLoS One 6 e27119 PMID: 22069494

Fu and Pol (2010) Kisspeptin directly excites anorexigenic proopiomelanocortin neurons but inhibits orexigenic neuropeptide Y cells by an indirect synaptic mechanism. J Neurosci 30 10205 PMID: 20668204

Pan et al (2010) Ictal activity induced by group I metabotropic glutamate receptor activation and loss of afterhyperpolarizations. Neuropharmacology 59 86 PMID: 20385148

Filippov et al (2010) The scaffold protein NHERF2 determines the coupling of P2Y1 nucleotide and mGluR5 glutamate receptor to different ion channels in neurons. Mol Pharmacol 30 11068 PMID: 20720114

Westmark and Malter (2007) FMRP mediates mGluR5-dependent translation of amyloid precursor protein. PLoS Biol 5 e52 PMID: 17298186

Xu et al (2007) Calpain-mediated mGluR1alpha truncation: a key step in excitotoxicity. Neuron 53 399 PMID: 17270736

Fukunaga et al (2007) Potent and specific action of the mGlu1 antagonists YM-298198 and JNJ16259685 on synaptic transmission in rat cerebellar slices. Br J Pharmacol 151 870 PMID: 17502847

Nakamoto et al (2007) Fragile X mental retardation protein deficiency leads to excessive mGluR5-dependent internalization of AMPA receptors. Proc Natl Acad Sci U S A 104 15537 PMID: 17881561

Ruangkittisakul et al (2006) High sensitivity to neuromodulator-activated signaling pathways at physiological [K+] of confocally imaged respiratory center neurons in on-line-calibrated newborn rat brainstem slices. J Neurosci 26 11870 PMID: 17108160

El-Kouhen et al (2006) Blockade of mGluR1 receptor results in analgesia and disruption of motor and cognitive performances: effects of A-841720, a novel non-competitive mGluR1 receptor antagonist. Br J Pharmacol 149 761 PMID: 17016515

Kuang et al (2006) Ancestral reconstruction of the ligand-binding pocket of Family C G protein-coupled receptors. J Neurosci 103 14050 PMID: 16966606

Jacob et al (2005) Signaling microdomains regulate inositol 1,4,5-trisphosphate-mediated intracellular calcium transients in cultured neurons. Proc Natl Acad Sci U S A 25 2853 PMID: 15772345

Jung et al (2005) Stimulation of endocannabinoid formation in brain slice cultures through activation of group I metabotropic glutamate receptors. Proc Natl Acad Sci U S A 68 1196 PMID: 16051747

Cai et al (2004) Activity-dependent expression of inositol 1,4,5-trisphosphate receptor type 1 in hippocampal neurons. PLoS One 279 23691 PMID: 15016804

Paladini et al (2003) Dopamine controls the firing pattern of dopamine neurons via a network feedback mechanism. Sci Rep 100 2866 PMID: 12604788

Tang and Alger (2015) Homer protein-metabotropic glutamate receptor binding regulates endocannabinoid signaling and affects hyperexcitability in a mouse model of fragile X syndrome. J Neurosci 35 3938 PMID: 25740522

Tang et al (2015) Stimulation-evoked Ca2+ signals in astrocytic processes at hippocampal CA3-CA1 synapses of adult mice are modulated by glutamate and ATP. J Neurosci 35 3016 PMID: 25698739

Ifrim et al (2015) Single-Molecule Imaging of PSD-95 mRNA Translation in Dendrites and Its Dysregulation in a Mouse Model of Fragile X Syndrome. PLoS One 35 7116 PMID: 25948262

Henderson et al (2015) A Low Affinity GCaMP3 Variant (GCaMPer) for Imaging the Endoplasmic Reticulum Calcium Store. J Neurosci 10 e0139273 PMID: 26451944

Aguilar-Valles et al (2015) Inhibition of Group I Metabotropic Glutamate Receptors Reverses Autistic-Like Phenotypes Caused by Deficiency of the Translation Repressor eIF4E Binding Protein 2. Neuropharmacology 35 11125 PMID: 26245973

Pollard et al (2014) Modulation of neuronal microcircuit activities within the medial prefrontal cortex by mGluR5 positive allosteric modulator. J Psychopharmacol 28 935 PMID: 25031220

Careaga et al (2014) Group I metabotropic glutamate receptor mediated dynamic immune dysfunction in children with fragile X syndrome. J Neuroinflammation 11 110 PMID: 24942544

McQuail et al (2013) Hippocampal Gαq/11 but not Gαo-coupled receptors are altered in aging. PLoS One 70 63 PMID: 23347951

Kuribayashi et al (2013) The role of metabotropic glutamate receptor 5 on the stromal cell-derived factor-1/CXCR4 system in oral cancer. J Biol Chem 8 e80773 PMID: 24236200


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