Methyl Arachidonyl Fluorophosphonate

Modify Date: 2024-01-09 23:19:43

Methyl Arachidonyl Fluorophosphonate structure	Common Name	Methyl Arachidonyl Fluorophosphonate
	CAS Number	188404-10-6	Molecular Weight	370.482
	Density	1.0±0.1 g/cm3	Boiling Point	455.3±34.0 °C at 760 mmHg
	Molecular Formula	C₂₁H₃₆FO₂P	Melting Point	N/A
	MSDS	USA	Flash Point	229.1±25.7 °C

Use of Methyl Arachidonyl Fluorophosphonate

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
Synonym	More Synonyms

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.
Related Catalog	Signaling Pathways >> Metabolic Enzyme/Protease >> Phospholipase Research Areas >> Neurological Disease Research Areas >> Cardiovascular Disease Research Areas >> Metabolic Disease
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	[1]. Lio YC, et al. Irreversible inhibition of Ca(2+)-independent phospholipase A2 by methyl arachidonyl fluorophosphonate. Biochim Biophys Acta. 1996 Jul 12;1302(1):55-60. [2]. Deutsch DG, et al. Methyl arachidonyl fluorophosphonate: a potent irreversible inhibitor of anandamide amidase. Biochem Pharmacol. 1997 Feb 7;53(3):255-60.

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;
Risk Phrases	R11
Safety Phrases	16-26-29-33
RIDADR	UN 1231 3/PG 2

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

DC Chemicals Limited
China
Product Name: MAFP
Price: $Inquiry/100mg $Inquiry/250mg $Inquiry/500mg
Purity: 98.0%
Stocking Period: 3 Day
Contact: Tony Cao

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Methyl Arachidonyl Fluorophosphonate

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