| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
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| 50mg |
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| Other Sizes |
| Targets |
mGluR 1 mGluR 5
Group I metabotropic glutamate receptors (mGluR1 and mGluR5); phosphoserine phosphatase. |
|---|---|
| ln Vitro |
In primary neurons, DL-AP3 (10 µM, 6 hours) reduces damage (cell viability) caused by oxygen glucose deprivation (OGD) [1]. In primary neurons, OGD-induced decreases in p-Akt1 levels and increases in cytochrome C are restored by DL-AP3 (10 µM, 6 hours) [1]. Rat brain phosphoserine phosphatase activity is inhibited by DL-AP3 (1-100 µM), with an IC50 of 187 µM and a Ki of 77 µM[2]. In slices of Fmr1 KO mice, DL-AP3 (10 μM, 10min) plus SKF81297 (5 μM) significantly increased long-term potentiation (LTP) [3].
DL-AP3 antagonizes mGluR1α and mGluR5 responses in a competitive manner, with an IC50 of approximately 2.1 mM for mGluR1α. It inhibits rat brain phosphoserine phosphatase activity with an IC50 of 187 µM and a Ki of 77 µM. These activities confirm its role as a group I mGluR antagonist and a phosphatase inhibitor. |
| ln Vivo |
For five weeks, DL-AP3 (4 mg/kg, ip) and SKF81297 (1 mg/kg, ip) together decreased the hyperactivity phenotype in Fmr1 KO mice[3]. The development of visceral pain symptoms and neuroendocrinological alterations in plasma in sheep is inhibited by DL-AP3 (4.0-12.0 mg/animal, icv infusion, 100 μL)[4].
In slices from Fmr1 knockout mice, DL-AP3 has been used to characterize the role of mGluR signaling. As a competitive antagonist, its in vivo effects are primarily related to the inhibition of group I mGluR-mediated synaptic transmission, which can modulate various physiological and pathological processes in the central nervous system. |
| Enzyme Assay |
In vitro receptor binding assays are performed using membrane preparations from cells expressing mGluR1 or mGluR5. The binding affinity of DL-AP3 is determined by its ability to displace a specific radiolabeled agonist or antagonist. Functional antagonism is confirmed by demonstrating that the compound can shift the dose-response curve of a standard agonist (e.g., glutamate) to the right in a concentration-dependent manner.
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| Cell Assay |
Cell Viability Assay[1]
Cell Types: Primary neurons with oxygen-glucose deprivation (OGD) treatment Tested Concentrations: 10 µM Incubation Duration: 24 h or 72 h Experimental Results: Attenuated the inhibitory effect of OGD on neuronal viability. Western Blot Analysis[1] Cell Types: Primary neurons with oxygen-glucose deprivation (OGD) treatment Tested Concentrations: 10 µM Incubation Duration: 6 h Experimental Results: Increased the diminished levels of p-Akt1, and diminished the increase of cytochrome C. Cells expressing recombinant mGluR1 or mGluR5 are exposed to an agonist in the presence of varying concentrations of DL-AP3. The inhibition of agonist-induced intracellular signaling, such as calcium mobilization or PI hydrolysis, is measured to quantify the antagonistic activity. The competitive nature of the antagonism is established by assessing the reversal of inhibition at high agonist concentrations. |
| Animal Protocol |
Animal/Disease Models: Fmr1 KO mice[3]
Doses: 4 mg/kg with SKF81297 (1 mg/kg) Route of Administration: ip, for 5 weeks. Experimental Results: decreased the distance traveled by Fmr1 KO mice (open-field test). decreased the swim latency on the final day in the Fmr1 KO mice (Morris Water Maze test). Animal/Disease Models: Sheep with visceral pain evoked by colonic distension (CD)[4] Doses: 4.0-12.0 mg/animal Route of Administration: icv infusion, 100 μL Experimental Results: diminished intensity from appearance of clinical signs of visceral pain caused by CD test. Diminished the increase of plasma cortisol, E, NE and DA concentrations caused by visceral pain provoked by CD episode. In vivo studies typically involve systemic administration of DL-AP3 in rodent models to investigate the role of group I mGluRs in behaviors and pathologies. For example, it can be administered via intracerebroventricular (i.c.v.) or systemic injection to assess its effects on seizure susceptibility, pain sensitivity, or cognitive function. Dosing regimens are usually determined based on preliminary dose-response studies. |
| ADME/Pharmacokinetics |
No detailed pharmacokinetic data are publicly available for DL-AP3. As a small, polar molecule, it is likely to have limited oral bioavailability and blood-brain barrier penetration. For such research compounds, PK parameters are typically evaluated in rodents following parenteral administration to guide in vivo study design.
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| Toxicity/Toxicokinetics |
No specific toxicity data are publicly available for DL-AP3. As a research chemical, standard safety precautions should be followed. Its toxicity profile is expected to be related to its pharmacological activity, potentially affecting glutamatergic transmission and causing CNS-related side effects at high doses.
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| References |
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| Additional Infomation |
2-Amino-3-phosphonopropionic acid is a non-protein α-amino acid, a derivative of alanine, in which a hydrogen atom of the terminal methyl group is replaced by a dihydroxy(oxidized)-λ(5)-phosphonoyl group. It is a metabolic glutamate receptor antagonist and a human metabolite. It is a non-protein α-amino acid, belonging to the phosphonate class, and is a derivative of alanine. 1-Aminopropion-2-one-3-phosphate is a metabolite found in or produced by Escherichia coli (K12 strain, MG1655 strain).
DL-AP3 is a classic tool compound for studying group I mGluRs, particularly mGluR1 and mGluR5. Its ability to inhibit phosphoserine phosphatase adds another dimension to its utility. It is not approved for clinical use and is exclusively employed in preclinical research to understand the pathophysiology of conditions like Fragile X syndrome, pain, and addiction. |
| Molecular Formula |
C3H8NO5P
|
|---|---|
| Molecular Weight |
169.07
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| Exact Mass |
169.014
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| CAS # |
5652-28-8
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| PubChem CID |
3857
|
| Appearance |
White to off-white solid powder
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| Density |
1.8±0.1 g/cm3
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| Boiling Point |
481.6±55.0 °C at 760 mmHg
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| Flash Point |
245.1±31.5 °C
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| Vapour Pressure |
0.0±2.6 mmHg at 25°C
|
| Index of Refraction |
1.559
|
| LogP |
-2.29
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
10
|
| Complexity |
174
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| Defined Atom Stereocenter Count |
0
|
| SMILES |
C(C(C(=O)O)N)P(=O)(O)O
|
| InChi Key |
LBTABPSJONFLPO-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)
|
| Chemical Name |
2-amino-3-phosphonopropanoic acid
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| 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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O: 5 mg/mL (29.57 mM)
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.9147 mL | 29.5735 mL | 59.1471 mL | |
| 5 mM | 1.1829 mL | 5.9147 mL | 11.8294 mL | |
| 10 mM | 0.5915 mL | 2.9574 mL | 5.9147 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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