| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| 25mg |
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| 50mg | |||
| Other Sizes |
Purity: ≥98%
| Targets |
MAFP targets multiple enzymes: cPLA2 (IC50 = 5 µM), iPLA2 (IC50 = 0.5 µM), and FAAH (IC50 = 2.5 nM). It is a selective and irreversible inhibitor of PLA2 and FAAH. The compound also binds to the CB1 receptor in rat brain membrane preparations. As an irreversible inhibitor, MAFP covalently modifies the active site of its target enzymes, leading to sustained inhibition.
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| ln Vitro |
MAFP inhibits iPLA2 in P388D1 cells via concentration suspension, with an IC50 of 5 μM, following 5 minutes of pre-buffering at 40°C. Serine residue 228 serves as the catalytic nucleophile in the phospholipid-buffered enzyme known as cPLA [1]. Additionally, MAFP ligand for the CB1 cannabinoid receptor and a stand-in for arachidonic acid amidase. MAFP works around 3000 and 30000 times better than chymotrypsin and trypsin, respectively, and shows selectivity for arachidonic acid amide amidase. The binding of [3H]CP-55940 to the CB1 cannabinoid receptor is replaced by MAFP, which has an IC50 of 20 nM as opposed to 40 nM for anandamide[2].
In vitro, MAFP potently inhibits iPLA2 with half-maximal inhibition observed at 0.5 µM after a 5-minute preincubation at 40°C. The inhibition is not reversed upon extensive dilution, confirming irreversible binding. Preincubation of iPLA2 with MAFP results in linear, time-dependent inactivation of enzyme activity. MAFP does not inhibit arachidonoyl-CoA synthetase, CoA-dependent acyltransferase, or CoA-independent transacylase activities, indicating selectivity for PLA2 enzymes. |
| ln Vivo |
No specific in vivo activity data is publicly available for MAFP. As a research compound, its in vivo efficacy has not been extensively characterized. The compound's irreversible inhibition of PLA2 and FAAH suggests potential applications in studying inflammatory and endocannabinoid pathways, but further studies are needed.
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| Enzyme Assay |
In cell-free enzymatic assays, MAFP's activity is evaluated by measuring its inhibition of PLA2 or FAAH enzyme activity. The enzyme is incubated with a fluorescent or radiolabeled substrate in the presence of varying concentrations of MAFP. The inhibition of substrate hydrolysis is measured, and the IC50 is calculated from the concentration-response curve. The irreversible nature of inhibition is confirmed by dilution experiments.
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| Cell Assay |
In vitro cell-based experiments with MAFP typically involve culturing cells and treating them with the compound to inhibit PLA2 or FAAH activity. The inhibition of arachidonic acid release (for PLA2 inhibition) or anandamide hydrolysis (for FAAH inhibition) is measured. The compound's effects on downstream signaling pathways and inflammatory responses can also be assessed.
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| Animal Protocol |
No specific in vivo animal protocols are publicly available for MAFP. If in vivo studies were to be conducted, typical protocols might involve animal models of inflammation or pain, where the compound would be administered, and inflammatory markers or pain responses would be measured.
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| ADME/Pharmacokinetics |
No detailed pharmacokinetic data is publicly available for MAFP. As a reactive, irreversible inhibitor, its pharmacokinetic properties would be complex due to its covalent binding to target enzymes. The compound has a molecular formula of C21H36FO2P and a molecular weight of 370.5.
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| Toxicity/Toxicokinetics |
No specific toxicity data is publicly available for MAFP. As an irreversible inhibitor of serine hydrolases, its use requires caution due to potential off-target effects. The compound is for research use only and is not intended for human therapeutic applications.
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| References | |
| Additional Infomation |
Methyl Arachidonyl fluorophosphonate is a phosphonate. Methoxyarachidonic fluorophosphonate (MAFP) is an irreversible, site-directed enzyme inhibitor that inhibits almost all serine hydrolases and serine proteases. Its inhibitory effect on phospholipase A2 and fatty acid amide hydrolases is particularly significant, with IC50 values in the low nanomolar range. See also: Methyl Arachidonyl fluorophosphonate (note moved to).
MAFP has a molecular formula of C21H36FO2P and a molecular weight of 370.5. It is also known as Methyl Arachidonyl Fluorophosphonate. The compound is a selective and irreversible inhibitor of cPLA2 (IC50 = 5 µM), iPLA2 (IC50 = 0.5 µM), and FAAH (IC50 = 2.5 nM). It also binds to the CB1 receptor. MAFP is used as a research tool for studying phospholipase and FAAH biology. |
| Molecular Formula |
C21H36FO2P
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|---|---|
| Molecular Weight |
370.48200
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| Exact Mass |
370.243
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| CAS # |
188404-10-6
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| PubChem CID |
10429254
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| Appearance |
Light yellow to yellow liquid
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
455.3±34.0 °C at 760 mmHg
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| Flash Point |
229.1±25.7 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.474
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| LogP |
7.44
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
16
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| Heavy Atom Count |
25
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| Complexity |
453
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCP(OC)(F)=O
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| InChi Key |
KWKZCGMJGHHOKJ-ZKWNWVNESA-N
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| InChi Code |
InChI=1S/C21H36FO2P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(22,23)24-2/h7-8,10-11,13-14,16-17H,3-6,9,12,15,18-21H2,1-2H3/b8-7-,11-10-,14-13-,17-16-
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| Chemical Name |
(5Z,8Z,11Z,14Z)-1-[fluoro(methoxy)phosphoryl]icosa-5,8,11,14-tetraene
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
DMSO : ≥ 100 mg/mL (~269.92 mM)
Methyl Acetate :≥ 10 mg/mL (~26.99 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 | 2.6992 mL | 13.4960 mL | 26.9920 mL | |
| 5 mM | 0.5398 mL | 2.6992 mL | 5.3984 mL | |
| 10 mM | 0.2699 mL | 1.3496 mL | 2.6992 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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