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Submit Review(S)-3,5-DHPG
Description: Selective group I mGlu agonist; active enantiomer of 3,5-DHPG (Cat. No. 0342)
Chemical Name: (S)-3,5-Dihydroxyphenylglycine
Purity: ≥98% (HPLC)
Biological Activity for (S)-3,5-DHPG
(S)-3,5-DHPG is a selective group I mGlu receptor agonist. (S)-3,5-DHPG regulates the expression of microRNAs in mouse cerebral cortex in vivo. (S)-3,5-DHPG induces a profound depression of synaptic dopamine release in mouse cortico-striatal cells in vitro, and anxiety-like behavior in vivo in mice.
Racemate also available.
Technical Data for (S)-3,5-DHPG
| 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.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for (S)-3,5-DHPG
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 9.16 | 50 |
Preparing Stock Solutions for (S)-3,5-DHPG
The following data is based on the product molecular weight 183.16. 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 |
|---|---|---|---|
| 0.5 mM | 10.92 mL | 54.6 mL | 109.19 mL |
| 2.5 mM | 2.18 mL | 10.92 mL | 21.84 mL |
| 5 mM | 1.09 mL | 5.46 mL | 10.92 mL |
| 25 mM | 0.22 mL | 1.09 mL | 2.18 mL |
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Product Datasheets for (S)-3,5-DHPG
References for (S)-3,5-DHPG
References are publications that support the biological activity of the product.
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
Lusardi et al (2012) Effect of (S)-3,5-DHPG on microRNA expression in mouse brain. Exp.Neurol. 235 497 PMID: 22309833
Mercuri et al (2021) Long-term depression of striatal DA release induced by mGluRs via sustained hyperactivity of local cholinergic interneurons. Front Cell Neurosci. 15 798464 PMID: 34924961
If you know of a relevant reference for (S)-3,5-DHPG, please let us know.
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Keywords: (S)-3,5-DHPG, (S)-3,5-DHPG supplier, Selective, group, I, agonists, Active, enantiomer, Group, Receptors, mGlu1, mGlu5, mGluR1, mGluR5, Glutamate, Metabotropic, (Metabotropic), 0805, Tocris Bioscience
40 Citations for (S)-3,5-DHPG
Citations are publications that use Tocris products. Selected citations for (S)-3,5-DHPG include:
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
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
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
Hashimotodani et al (2017) LTP at Hilar Mossy Cell-Dentate Granule Cell Synapses Modulates Dentate Gyrus Output by Increasing Excitation/Inhibition Balance. Neuron 95 928 PMID: 28817805
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
Mercuri et al (2021) Long-term depression of striatal DA release induced by mGluRs via sustained hyperactivity of local cholinergic interneurons. Front Cell Neurosci. 15 798464 PMID: 34924961
Musella (2017) A novel crosstalk within the endocannabinoid system controls GABA transmission in the striatum. Sci Rep 7 7363 PMID: 28779174
Zhao et al (2011) Dual regulation of fragile X mental retardation protein by group I metabotropic glutamate receptors controls translation-dependent epileptogenesis in the hippocampus. J Neurosci 31 725 PMID: 21228181
Peterfi et al (2012) Endocannabinoid-mediated long-term depression of afferent excitatory synapses in hippocampal pyramidal cells and GABAergic interneurons. J Neurosci 32 14448 PMID: 23055515
Gregg et al (2012) Activation of type 5 metabotropic glutamate receptors and diacylglycerol lipase-α initiates 2-arachidonoylglycerol formation and endocannabinoid-mediated analgesia. J Neurosci 32 9457 PMID: 22787031
Paul et al (2019) Differential Regulation of Syngap1 Translation by FMRP Modulates eEF2 Mediated Response on NMDAR Activity. Front Mol Neurosci 12 97 PMID: 31143100
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
Lusardi et al (2012) Effect of (S)-3,5-DHPG on microRNA expression in mouse brain. Exp.Neurol. 235 497 PMID: 22309833
Govindaiah (2018) Group I metabotropic glutamate receptors generate two types of intrinsic membrane oscillations in hippocampal oriens/alveus interneurons. Neuropharmacology 139 150 PMID: 29964095
Zhao (2014) BDNF-endocannabinoid interactions at neocortical inhibitory synapses require phospholipase C signaling. J Neurophysiol 111 1008 PMID: 24335212
Fairless et al (2013) Membrane potential measurements of isolated neurons using a voltage-sensitive dye. PLoS One 8 e58260 PMID: 23516458
Pallo et al (2016) Mechanisms of tau and Aβ-induced excitotoxicity. Brain Res 1634 119 PMID: 26731336
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
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
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
Morel et al (2018) JIP1-Mediated JNK Activation Negatively Regulates Synaptic Plasticity and Spatial Memory. J Neurosci 38 3708 PMID: 29540552
Bozdagi et al (2012) Haploinsufficiency of Cyfip1 produces fragile X-like phenotypes in mice. J Neurosci 7 e42422 PMID: 22900020
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
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
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
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
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
Kuang et al (2006) Ancestral reconstruction of the ligand-binding pocket of Family C G protein-coupled receptors. J Neurosci 103 14050 PMID: 16966606
Wu et al (2004) Group I metabotropic glutamate receptor activation produces a direct excitation of identified septohippocampal cholinergic neurons. J Neurophysiol 92 1216 PMID: 15044519
Paladini et al (2003) DA controls the firing pattern of DA neurons via a network feedback mechanism. Sci Rep 100 2866 PMID: 12604788
Do you know of a great paper that uses (S)-3,5-DHPG from Tocris? Please let us know.
Reviews for (S)-3,5-DHPG
Average Rating: 5 (Based on 2 Reviews.)
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Used in inhibitor cocktail.
By
Anonymous on 12/03/2019
Assay Type: In Vitro
Species: Rat
Cell Line/Tissue: Retinal rod bipolar cells
Retinal dissections were performed in HEPES-buffered extracellular solution containing glutamate inhibitor cocktail 100 umol/L
No issues.
By
Talia James on 01/08/2018
Assay Type: Ex Vivo
Species: Mouse
Cell Line/Tissue: C57BL/6
Used this compound to induce Group I mGluR-dependent LTD in acute brain slices from the mouse hippocampus at a concentration of 50μM. Reliably induces LTD to 50-80% of baseline.
Pay close attention to enantiomer. Some report that R,S-DHPG is not as effective at inducing LTD as S-DHPG alone, which is something I will anecdotally corroborate.
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