188404-10-6
188404-10-6 structure
- Name: Methyl Arachidonyl Fluorophosphonate
- Chemical Name: MAFP,(5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraenyl-methylesterphosphonofluoridicacid
- CAS Number: 188404-10-6
- Molecular Formula: C21H36FO2P
- Molecular Weight: 370.482
- Catalog: Signaling Pathways Metabolic Enzyme/Protease Phospholipase
- Create Date: 2017-08-19 02:18:44
- Modify Date: 2024-01-09 23:19:43
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MAFP (Methyl Arachidonyl Fluorophosphonate) is an selective, active-site directed and irreversible inhibitor of cPLA2 and iPLA2. MAFP is also a potent irreversible inhibitor of anandamide amidase.
| Name | MAFP,(5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraenyl-methylesterphosphonofluoridicacid |
|---|---|
| Synonyms |
Methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-ylphosphonofluoridate
Methyl (5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraen-1-ylphosphonofluoridate Phosphonofluoridic acid, P-[(5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraen-1-yl]-, methyl ester Methyl Arachidonyl Fluorophosphonate MAPF,Phosphonofluoridic acid,methyl-5Z,8Z,11Z,14Z-eicosatetraenyl ester Phosphonofluoridicacid 5Z,8Z,11Z,14Z-EICOSATETRAENYL-PHOSPHONOFLUORIDIC ACID,METHYL ESTER MAPF METHYLPHOSPHONOFLUORIDIC ACID 5,8,11,14-EICOSATETRAENYL ESTER METHYL-5Z,8Z,11Z,14Z-EICOSATETRAENYL ESTER PHOSPHONOFLUORIDIC ACID METHYL ACETATE MAFP |
| Description | MAFP (Methyl Arachidonyl Fluorophosphonate) is an selective, active-site directed and irreversible inhibitor of cPLA2 and iPLA2. MAFP is also a potent irreversible inhibitor of anandamide amidase. |
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| Related Catalog | |
| Target |
cPLA2, iPLA2[1], Anandamide amidase[2] |
| In Vitro | MAFP inhibits iPLA2, in a concentration-dependent manner with an IC50 of 5 μM after a 5 min preincubation at 40°C in P388D1 cells. cPLA, is a phospholipid hydrolase using the hydroxyl of serine-228 residue as its catalytic nucleophile[1]. MAFP is also an inhibitor of anandamide amidase and as a ligand for the CB1 cannabinoid receptor. MAFP demonstrates selectivity towards anandamide amidase for which it is approximately 3000 and 30000-fold more potent than it is towards chymotrypsin and trypsin, respectively. MAFP displaces [3H]CP-55940 binding to the CB1 cannabinoid receptor with an IC50 of 20 nM vs 40 nM for anandamide[2]. |
| Kinase Assay | MAFP is dissolved and diluted in DMSO. To investigate the reversibility of iPLA 2 inhibition by MAFP, the P388D1 iPLA 2 is first concentrated approximately 10-fold using a Centricon-10 concentrator from Amicon. The concentrated iPLA 2 (20 μL) is then preincubated with either 80 μM MAFP in DMSO or DMSO alone (2 μL) for 5 min at 40°C. A 2 μL aliquot is removed and subsequently diluted 1500-fold into 3 mL of assay mixture containing 100 μM DPPC (200000 cpm per 50 μL assay mixture), 400 μM Triton X-100, 100 mM Hepes (pH 7.5), 5 mM EDTA, 1 mM DTT and 0.8 mM ATP. At the indicated time points, a 50 μL aliquot is removed and the remaining enzyme activity is quantified[1]. |
| Cell Assay | Inhibition of anandamide amidase in cell culture is measured using approximately 1x106 Nl8TG2 intact neuroblastoma cells. Experimental cells are preincubated for 20 min in 1.5 mL medium, consisting of Fl2/DMEM with penicillin, streptomycin, gentamicin, 10% bovine calf serum, plus MAFP (1, 5, 10, 20 nM). Control cells contained no inhibitor. Arachidonoyl is then added and the incubation continued for I hr. The amount of [3H]anandamide in the cells is quantified by liquid scintillation counting of the silica scraped from the appropriate areas of the TLC plate identified by exposure to X-ray film[2]. |
| References |
| Density | 1.0±0.1 g/cm3 |
|---|---|
| Boiling Point | 455.3±34.0 °C at 760 mmHg |
| Molecular Formula | C21H36FO2P |
| Molecular Weight | 370.482 |
| Flash Point | 229.1±25.7 °C |
| Exact Mass | 370.243683 |
| PSA | 36.11000 |
| LogP | 7.44 |
| Vapour Pressure | 0.0±1.1 mmHg at 25°C |
| Index of Refraction | 1.474 |
| Storage condition | 2-8℃ |
| Hazard Codes | F: Flammable;Xi: Irritant; |
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| Risk Phrases | R11 |
| Safety Phrases | 16-26-29-33 |
| RIDADR | UN 1231 3/PG 2 |