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Submit Review(RS)-3,5-DHPG
Description: Selective group I mGlu agonist
Chemical Name: (RS)-3,5-Dihydroxyphenylglycine
Purity: ≥99% (HPLC)
Biological Activity for (RS)-3,5-DHPG
(RS)-3,5-DHPG is a selective group I metabotropic glutamate receptor agonist which activates both mGlu1 and mGlu5. Also reported to be an antagonist at metabotropic glutamate receptors linked to phospholipase D.
S-enantiomer also available.
Technical Data for (RS)-3,5-DHPG
| M. Wt | 183.16 |
| Formula | C8H9NO4 |
| Storage | Desiccate at -20°C |
| Purity | ≥99% (HPLC) |
| CAS Number | 146255-66-5 |
| PubChem ID | 108001 |
| InChI Key | HOOWCUZPEFNHDT-UHFFFAOYSA-N |
| Smiles | NC(C(O)=O)C1=CC(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 (RS)-3,5-DHPG
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 1.83 | 10 |
Preparing Stock Solutions for (RS)-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 |
|---|---|---|---|
| 0.1 mM | 54.6 mL | 272.99 mL | 545.97 mL |
| 0.5 mM | 10.92 mL | 54.6 mL | 109.19 mL |
| 1 mM | 5.46 mL | 27.3 mL | 54.6 mL |
| 5 mM | 1.09 mL | 5.46 mL | 10.92 mL |
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Product Datasheets for (RS)-3,5-DHPG
References for (RS)-3,5-DHPG
References are publications that support the biological activity of the product.
Ito et al (1992) 3,5-Dihydroxyphenylglycine: a potent agonist of metabotropic glutamate receptors. NeuroReport 3 1013 PMID: 1362358
Mistry et al (1998) Regulation of phosphoinositide turnover in neonatal rat cerebral cortex by group I- and II-selective metabotropic glutamate receptor agonists. Br.J.Pharmacol. 123 581 PMID: 9504400
Pellegrini-Giampietro et al (1996) Pharmacological characterization of metabotropic glutamate recpetors coupled to phopholipase D in the rat hippocampus. Br.J.Pharmacol. 118 1035 PMID: 8799579
Palmer et al (1997) The group I mGlu receptor agonist DHPG induces a novel form of LTD in the CA1 region of the hippocampus. Neuropharmacology 36 1517 PMID: 9517422
If you know of a relevant reference for (RS)-3,5-DHPG, please let us know.
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Keywords: (RS)-3,5-DHPG, (RS)-3,5-DHPG supplier, Selective, group, I, mGlur, agonists, Group, Receptors, mGlu1, mGlu5, mGluR1, mGluR5, Glutamate, Metabotropic, 19641-83-9, (Metabotropic), 0342, Tocris Bioscience
68 Citations for (RS)-3,5-DHPG
Citations are publications that use Tocris products. Selected citations for (RS)-3,5-DHPG include:
Sakuragi et al (2013) Involvement of TrkB- and p75(NTR)-signaling pathways in two contrasting forms of long-lasting synaptic plasticity. J Vis Exp 3 3185 PMID: 24212565
Coulon et al (2011) Activity Modes in Thalamocortical Relay Neurons are Modulated by G(q)/G(11) Family G-proteins - Serotonergic and Glutamatergic Signaling. Front Cell Neurosci 4 132 PMID: 21267426
Hays et al (2011) Altered neocortical rhythmic activity states in Fmr1 KO mice are due to enhanced mGluR5 signaling and involve changes in excitatory circuitry. J Neurosci 31 14223 PMID: 21976507
Chai et al (2017) Neural Circuit-Specialized Astrocytes: Transcriptomic, Proteomic, Morphological, and Functional Evidence. Neuron 95 531 PMID: 28712653
Levenga et al (2017) AKT isoforms have distinct hippocampal expression and roles in synaptic plasticity. Elife 6 PMID: 29173281
Takano et al (2014) Rapid manifestation of reactive astrogliosis in acute hippocampal brain slices. Glia 62 78 PMID: 24272704
Lee et al (2014) Long-term depression-inducing stimuli promote cleavage of the synaptic adhesion molecule NGL-3 through NMDA receptors, matrix metalloproteinases and presenilin/γ-secretase. Philos Trans R Soc Lond B Biol Sci 369 20130158 PMID: 24298159
Iliff et al (2013) Impaired activity-dependent FMRP translation and enhanced mGluR-dependent LTD in Fragile X premutation mice. Hum Mol Genet 22 1180 PMID: 23250915
Chen and Shen (2013) Modulation of mGluR-dependent MAP1B translation and AMPA receptor endocytosis by microRNA miR-146a-5p. J Neurosci 33 9013 PMID: 23699512
Xu et al (2013) Simultaneous monitoring of presynaptic transmitter release and postsynaptic receptor trafficking reveals an enhancement of presynaptic activity in metabotropic glutamate receptor-mediated long-term depression. J Neurosci 33 5867 PMID: 23536098
Wang et al (2009) Converging signal on ERK1/2 activity regulates group I mGluR-mediated Arc transcription. J Neurosci 460 36 PMID: 19446601
Citri et al (2009) N-MthD.-aspartate receptor- and metabotropic glutamate receptor-dependent long-term depression are differentially regulated by the ubiquitin-proteasome system. J Neurosci 30 1443 PMID: 19821836
Kim et al (2008) Aberrant early-phase ERK inactivation impedes neuronal function in fragile X syndrome. J Neurosci 105 4429 PMID: 18332424
Zhang et al (2008) The tyrosine phosphatase STEP mediates AMPA receptor endocytosis after metabotropic glutamate receptor stimulation. J Neurosci 28 10561 PMID: 18923032
Marchaland et al (2008) Fast subplasma membrane Ca2+ transients control exo-endocytosis of synaptic-like microvesicles in astrocytes. J Neurosci 28 9122 PMID: 18784293
Thompson and Perkel (2011) Endocannabinoids mediate synaptic plasticity at glutamatergic synapses on spiny neurons within a basal ganglia nucleus necessary for song learning. J Neurophysiol 105 1159 PMID: 21177997
Xi (2017) Metabotropic glutamate receptor 5 mediates the suppressive effect of 6-OHDA-induced model of Parkinson's disease on liver cancer. Pharmacol Res 121 145 PMID: 28455267
Schmidt et al (2015) Group I metabotropic glutamate receptor-mediated activation of PKC gamma in the nucleus accumbens core promotes the reinstatement of cocaine seeking. Addict Biol 20 285 PMID: 24506432
Patel et al (2009) Mobilization of calcium from intracellular stores facilitates somatodendritic DA release. J Neurosci 29 6568 PMID: 19458227
Bagayogo and Dreyfus (2009) Regulated release of BDNF by cortical oligodendrocytes is mediated through metabotropic glutamate receptors and the PLC pathway. ASN Neuro 1 PMID: 19570026
Wang et al (2017) Striatopallidal dysfunction underlies repetitive behavior in Shank3-deficient model of autism. J Clin Invest 127 1978 PMID: 28414301
Nonobe et al (2016) Application of surface plasmon resonance imaging to monitoring G protein-coupled receptor signaling and its modulation in a heterologous expression system. BMC Biotechnol 16 36 PMID: 27068216
Zhong et al (2015) BDNF interacts with endocannabinoids to regulate cocaine-induced synaptic plasticity in mouse midbrain DA neurons. Sci Rep 35 4469 PMID: 25762688
Hasegawa et al (2015) Dendritic spine dynamics leading to spine elimination after repeated inductions of LTD. J Neurosci 5 7707 PMID: 25573377
Choi et al (2015) PDE-4 inhibition rescues aberrant synaptic plasticity in Drosophila and mouse models of fragile X syndrome. Proc Natl Acad Sci U S A 35 396 PMID: 25568131
Ramiro-Cortés (2013) Long lasting protein synthesis- and activity-dependent spine shrinkage and elimination after synaptic depression. PLoS One 8 e71155 PMID: 23951097
Pasquale and Sherman (2013) A modulatory effect of the feedback from higher visual areas to V1 in the mouse. J Neurophysiol 109 2618 PMID: 23446698
Oh et al (2013) Synapse-specific and size-dependent mechanisms of spine structural plasticity accompanying synaptic weakening. Proc Natl Acad Sci U S A 110 E305 PMID: 23269840
Sherkhane and Kapfhammer (2013) The plasma membrane Ca2+-ATPase2 (PMCA2) is involved in the regulation of Purkinje cell dendritic growth in cerebellar organotypic slice cultures. J Neurosci 2013 321685 PMID: 24288624
Kapfhammer and Gugger (2012) The analysis of purkinje cell dendritic morphology in organotypic slice cultures. J Neurosci NULL PMID: 22473312
Hoffman et al (2010) Control of cannabinoid CB1 receptor function on glutamate axon terminals by endogenous adenosine acting at A1 receptors. J Neurosci 30 545 PMID: 20071517
Citri et al (2010) Calcium binding to PICK1 is essential for the intracellular retention of AMPA receptors underlying long-term depression. J Neurosci 30 16437 PMID: 21147983
Glitsch (2010) Activation of native TRPC3 cation channels by phospholipase D. FASEB J 24 318 PMID: 19741172
Romei et al (2016) Colocalization of neurotransmitter transporters on the plasma membrane of the same nerve terminal may reflect cotransmission. Brain Research Bulletin 127 100 PMID: 27565422
Guo et al (2016) Selective Disruption of Metabotropic Glutamate Receptor 5-Homer Interactions Mimics Phenotypes of Fragile X Syndrome in Mice. J Neurosci 36 2131 PMID: 26888925
Sethna et al (2016) Calmodulin activity regulates group I metabotropic glutamate receptor-mediated signal transduction and synaptic depression. J Neurosci Res 94 401 PMID: 26864654
Rojas et al (2013) Activation of group I metabotropic glutamate receptors potentiates heteromeric kainate receptors. Mol Pharmacol 83 106 PMID: 23066089
Lin et al (2016) Neuronal splicing regulator RBFOX3(NeuN) regulates adult hippocampal neurogenesis and synaptogenesis PLoS One 11 e0164164 PMID: 27701470
Wall et al (2018) The Temporal Dynamics of Arc Expression Regulate Cognitive Flexibility. Neuron 98 1124 PMID: 29861284
Lim et al (2018) Neuronal Activity-Dependent Activation of Astroglial Calcineurin in Mouse Primary Hippocampal Cultures. Int J Mol Sci 19 PMID: 30274399
Yasuda et al (2018) Drebrin Isoforms Critically Regulate NMDAR- and mGluR-Dependent LTD Induction. Front Cell Neurosci 12 330 PMID: 30349460
Vergassola et al (2018) Presynaptic mGlu1 Receptors Control GABAB Receptors in an Antagonist-Like Manner in Mouse Cortical GABAergic and Glutamatergic Nerve Endings. Front Mol Neurosci 11 324 PMID: 30279647
Crock et al (2012) Central amygdala metabotropic glutamate receptor 5 in the modulation of visceral pain. Eur J Neurosci 32 14217 PMID: 23055491
Zhong et al (2012) MeCP2 phosphorylation is required for modulating synaptic scaling through mGluR5. Stem Cell Reports 32 12841 PMID: 22973007
Bateup et al (2011) Loss of Tsc1 in vivo impairs hippocampal mGluR-LTD and increases excitatory synaptic function. Neurosci Lett 31 8862 PMID: 21677170
Kim et al (2010) Group II metabotropic glutamate receptor stimulation triggers production and release of Alzheimer's amyloid(β)42 from isolated intact nerve terminals. J Neurosci 30 3870 PMID: 20237257
Schapitz et al (2010) Neuroligin 1 is dynamically exchanged at postsynaptic sites. J Neurosci 30 12733 PMID: 20861378
Kolber et al (2010) Activation of metabotropic glutamate receptor 5 in the amygdala modulates pain-like behavior. Sci Rep 30 8203 PMID: 20554871
Keuren-Jensen and Cline (2006) Visual experience regulates metabotropic glutamate receptor-mediated plasticity of AMPA receptor synaptic transmission by homer1a induction. J Neurosci 26 7575 PMID: 16855085
Etkin et al (2006) A role in learning for SRF: deletion in the adult forebrain disrupts LTD and the formation of an immediate memory of a novel context. Neuron 50 127 PMID: 16600861
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
Hsieh et al (2006) AMPAR removal underlies Abeta-induced synaptic depression and dendritic spine loss. Neuron 52 831 PMID: 17145504
Muddashetty et al (2007) Dysregulated metabotropic glutamate receptor-dependent translation of AMPA receptor and postsynaptic density-95 mRNAs at synapses in a mouse model of fragile X syndrome. J Neurosci 27 5338 PMID: 17507556
Jan and Westbrook (2007) Disynaptic amplification of metabotropic glutamate receptor 1 responses in the olfactory bulb. J Neurosci 27 132 PMID: 17202480
Ziskin et al (2007) Vesicular release of glutamate from unmyelinated axons in white matter. Proc Natl Acad Sci U S A 10 321 PMID: 17293857
Rancillac et al (2006) Glutamatergic Control of Microvascular Tone by Distinct GABA Neurons in the Cerebellum. J Neurosci 26 6997 PMID: 16807329
Li et al (2007) The different roles of cyclinD1-CDK4 in STP and mGluR-LTD during the postnatal development in mice hippocampus area CA1. BMC Dev Biol 7 57 PMID: 17535444
Brager and Johnston (2007) Plasticity of intrinsic excitability during long-term depression is mediated through mGluR-dependent changes in I(h) in hippocampal CA1 pyramidal neurons. J Neurosci 27 13926 PMID: 18094230
Chiu and Castillo (2008) Input-specific plasticity at excitatory synapses mediated by endocannabinoids in the dentate gyrus. Neuropharmacology 54 68 PMID: 17706254
Grueter et al (2008) In vivo metabotropic glutamate receptor 5 (mGluR5) antagonism prevents cocaine-induced disruption of postsynaptically maintained mGluR5-dependent long-term depression. J Neurosci 28 9261 PMID: 18784306
Dai et al (2008) A crucial role for cAMP and protein kinase A in D1 DA receptor regulated intracellular calcium transients. Neurosignals 16 112 PMID: 18253052
McElligott (2008) Alpha1-adrenergic receptor-induced heterosynaptic long-term depression in the bed nucleus of the stria terminalis is disrupted in mouse models of affective disorders. Neuropsychopharmacology 33 2313 PMID: 18046308
Job and Eberwine (2001) Identification of sites for exponential translation in living dendrites. Proc Natl Acad Sci U S A 98 13037 PMID: 11606784
Nishi et al (2003) Metabotropic mGlu5 receptors regulate adenosine A2A receptor signaling. J Neurosci 100 1322 PMID: 12538871
Collard et al (2002) Neutrophil-derived glutamate regulates vascular endothelial barrier function. J Biol Chem 277 14801 PMID: 11847215
Huber et al (2002) Altered synaptic plasticity in a mouse model of fragile X mental retardation. Proc Natl Acad Sci U S A 99 7746 PMID: 12032354
Calò et al (2005) Interactions between ephrin-B and metabotropic glutamate 1 receptors in brain tissue and cultured neurons. J Neurosci 25 2245 PMID: 15745950
Gallagher et al (2004) Extracellular signal-regulated protein kinase activation is required for metabotropic glutamate receptor-dependent long-term depression in hippocampal area CA1. Neural Plast 24 4859 PMID: 15152046
Do you know of a great paper that uses (RS)-3,5-DHPG from Tocris? Please let us know.
Reviews for (RS)-3,5-DHPG
Average Rating: 4.5 (Based on 2 Reviews.)
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Test of potential modulation of 5HT-1B receptor effects.
By
Sergiy Sylantyev on 12/10/2023
Assay Type: In Vitro
Species: Mouse
Cell Line/Tissue: Arcuate nucleus
(RS)-3,5-DHPG was used to test a (potential) impact of metabotropic glutamate receptors on the effect of 5HT-1B receptors on neurotransmitter vesicle release in interneuronal synapse. Picture: membrane capacitance fluctuation of living neuron after series of electrical stimuli delivered to acute neural tissue. Left: control. Right: activation of metabotropic glutamate receptors (with 1 μM CHPG, 1 μM (RS)-3,5-DHPG and 1 μM AMN 082), GABA-B receptors and ACh receptors does not show a significant effect. Grey traces: individual recordings; red: averaged trace.
Using (RS)-3,5-DHPG in slice ephys recordings.
By
Estela Correa on 12/06/2023
Assay Type: Ex Vivo
Species: Mouse
I used (RS)-3,5-DHPG (Cat. No. 0342) in slice ephys recordings. Worked as expected.
Dissolved in MilliQ H2O, and used at a concentration of 0.1 mM.
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