1. Metabolic Enzyme/Protease
  2. Phospholipase
  3. MAFP

MAFP (Synonyms: Methyl Arachidonyl Fluorophosphonate)

Cat. No.: HY-103334 Purity: >98.0%
Handling Instructions

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.

For research use only. We do not sell to patients.

MAFP Chemical Structure

MAFP Chemical Structure

CAS No. : 188404-10-6

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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.

IC50 & 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].

Molecular Weight

370.48

Formula

C₂₁H₃₆FO₂P

CAS No.

188404-10-6

SMILES

CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCP(OC)(F)=O

Shipping

Room temperature in continental US; may vary elsewhere

Storage
Powder -20°C 3 years
In solvent -80°C 6 months
  -20°C 1 month
Solvent & Solubility
In Vitro: 

Methyl Acetate : ≥ 10 mg/mL (26.99 mM)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions
Concentration Solvent Mass 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
*Please refer to the solubility information to select the appropriate solvent.
References
Kinase Assay
[1]

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].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Assay
[2]

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].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

References

Purity: >98.0%

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MAFP
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