| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| 5mg |
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| 50mg | |||
| Other Sizes |
| Targets |
mGlu1a (EC50 = 3.4 ± 0.9 μM in functional Ca2+ assay; Ki = 0.9 ± 0.01 μM in [3H]quisqualate binding assay)[1]
mGlu5a (EC50 = 2.0 ± 0.4 μM in functional Ca2+ assay; Ki = 3.9 ± 1 μM in [3H]quisqualate binding assay)[1] |
|---|---|
| ln Vitro |
(S)-3,5-DHPG displaces the putative group I mGlu binding site, the high-affinity squilinic acid site, specifically [1].
DHPG inhibited [3H]quisqualate binding to rat mGlu1a receptors with Ki = 0.9 ± 0.01 μM (Hill coefficient 0.76 ± 0.0008) and to rat mGlu5a receptors with Ki = 3.9 ± 1 μM (Hill coefficient 0.6 ± 0.1) in membrane preparations from transiently transfected HEK-293 cells.[1] In functional [Ca2+]i measurements using FLIPR, DHPG acted as an agonist on mGlu1a with EC50 = 3.4 ± 0.9 μM and on mGlu5a with EC50 = 2.0 ± 0.4 μM. The correlation coefficient between binding Ki and functional EC50 was 0.94 for mGlu1a and 0.86 for mGlu5a.[1] In rat brain sections, 1 mM DHPG reduced [3H]quisqualate (10 nM) binding to approximately 10% of total in the cerebellar molecular layer and to 30% in cerebral cortex, indicating its ability to displace group I receptor binding. The combination of 30 μM kainate and 1 mM DHPG further reduced binding to 8% in cerebellum and 14% in cortex.[1] |
| ln Vivo |
(S)-3,5-DHPG (icv; 0.01, 0.1, and 1.0 nmol/5 μL) shows anti-anxiety effect and enhances consolidation and recovery in male Wistar hypoxic rats weighing 160–180 g[2].
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| Enzyme Assay |
[3H]Quisqualate binding assay to mGlu1a and mGlu5a membranes: HEK-293 cells transiently transfected with rat mGlu1a or mGlu5a receptors were harvested, washed, and frozen. Membranes were prepared by homogenization in 20 mM HEPES-NaOH, 10 mM EDTA (pH 7.4), centrifuged at 48,000g for 30 min, then washed and resuspended in 20 mM HEPES-NaOH, 0.1 mM EDTA (pH 7.4). For binding, 25 μg membrane protein was incubated with 10 nM [3H]quisqualate in 20 mM HEPES-NaOH, 2 mM MgCl2, 2 mM CaCl2 (pH 7.4) for 1 h at room temperature. Nonspecific binding was defined with 1 mM glutamate. Inhibition experiments used at least six concentrations of DHPG. The reaction was terminated by filtration onto GF/C filters, washed three times with cold buffer, and radioactivity measured by liquid scintillation. IC50 values were converted to Ki using the Cheng-Prusoff equation.[1]
In vitro binding to rat brain sections: Parasagittal cryostat sections (12 μm) of rat brain were preincubated in 50 mM Tris-HCl (pH 7.4) plus 10 mM EDTA for 10 min at 22°C, then in assay buffer alone for 10 min. Sections were incubated with 10 nM [3H]quisqualate in assay buffer with 2 mM MgCl2 and 2 mM CaCl2 for 60 min at 22°C, followed by three washes (2×15 s + 30 s) at 4°C. To determine group I-specific binding, 30 μM kainate was included to block ionotropic receptors. DHPG at 1 mM was used to displace binding. Sections were exposed to tritium-sensitive imaging plates for 4 days and analyzed by phosphorimager.[1] |
| Cell Assay |
Intracellular calcium ([Ca2+]i) measurement (FLIPR assay): HEK-293 cells expressing rat mGlu1a or mGlu5a receptors were loaded with fluo-3 acetoxymethyl ester for 1 hour and washed four times with assay buffer (DMEM with Hanks' salt and 20 mM HEPES). [Ca2+]i measurements were performed using a fluorometric imaging plate reader (FLIPR) at room temperature. For agonist potency determination, cells were exposed to increasing concentrations of DHPG, and the response was normalized to the maximal stimulatory effect induced by 10 μM glutamate. For antagonist studies (not directly for DHPG), antagonists were applied 3 min before agonist (2 μM glutamate) for 4 min. EC50 values were calculated from concentration-response curves.[1]
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| References |
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| Additional Infomation |
(S)-3,5-Dihydroxyphenylglycine is a glycine derivative, a compound in which the 3- and 5-positions of the benzene ring of L-α-phenylglycine are substituted with hydroxyl groups. It belongs to the resorcinol class of compounds and is a non-protein-derived L-α-amino acid. Functionally, it is related to L-α-phenylglycine. It is a zwitterion tautomer of (S)-3,5-dihydroxyphenylglycine.
DHPG is a weak group I-selective agonist (S)-3,5-dihydroxyphenylglycine. It is often used as a pharmacological tool to discriminate group I metabotropic glutamate receptors from ionotropic receptors. In this study, DHPG was shown to completely displace [3H]quisqualate binding from group I receptors in rat brain sections, and its binding affinity correlated well with functional activity. The compound was inactive on ionotropic receptors under the conditions used. No information on ADME, toxicity, or in vivo effects is provided in this paper.[1] |
| Molecular Formula |
C8H11NO5
|
|---|---|
| Molecular Weight |
201.17
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| Exact Mass |
183.053
|
| CAS # |
162870-29-3
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| Related CAS # |
DHPG;146255-66-5
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| PubChem CID |
443586
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
|
| Boiling Point |
448.8±33.0 °C at 760 mmHg
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| Flash Point |
225.2±25.4 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
|
| Index of Refraction |
1.680
|
| LogP |
-0.52
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
13
|
| Complexity |
187
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
C1=C(C=C(C=C1O)O)[C@@H](C(=O)O)N
|
| InChi Key |
HOOWCUZPEFNHDT-ZETCQYMHSA-N
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| InChi Code |
InChI=1S/C8H9NO4/c9-7(8(12)13)4-1-5(10)3-6(11)2-4/h1-3,7,10-11H,9H2,(H,12,13)/t7-/m0/s1
|
| Chemical Name |
(2S)-2-amino-2-(3,5-dihydroxyphenyl)acetic acid
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| Synonyms |
Dihydroxyphenylglycine DHPG J516.528H
|
| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~545.97 mM)
H2O : ~25 mg/mL (~136.49 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.65 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.65 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (13.65 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.9709 mL | 24.8546 mL | 49.7092 mL | |
| 5 mM | 0.9942 mL | 4.9709 mL | 9.9418 mL | |
| 10 mM | 0.4971 mL | 2.4855 mL | 4.9709 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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