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MedKoo Cat#: 526468 | Name: MAFP
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

MAFP is an irreversible inhibitor of Ca(2+)-independent phospholipase A2 (iPLA2).

Chemical Structure

MAFP
MAFP
CAS#188404-10-6

Theoretical Analysis

MedKoo Cat#: 526468

Name: MAFP

CAS#: 188404-10-6

Chemical Formula: C21H36FO2P

Exact Mass: 370.2437

Molecular Weight: 370.49

Elemental Analysis: C, 68.08; H, 9.79; F, 5.13; O, 8.64; P, 8.36

Price and Availability

Size Price Availability Quantity
10mg USD 585.00 2 weeks
25mg USD 1,150.00 2 weeks
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Related CAS #
No Data
Synonym
MAFP
IUPAC/Chemical Name
5Z,8Z,11Z,14Z-eicosatetraenyl-phosphonofluoridic acid, methyl ester
InChi Key
CIUOPCICGWBRIH-ZKWNWVNESA-N
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(2)24-25(22)23/h7-8,10-11,13-14,16-17,21,25H,3-6,9,12,15,18-20H2,1-2H3/b8-7-,11-10-,14-13-,17-16-
SMILES Code
O=P(F)OC(C)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
Appearance
Colorless to light yellow liquid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
MAFP (Methyl Arachidonyl Fluorophosphonate) is an selective, active-site directed and irreversible inhibitor of cPLA2 and iPLA2.
In vitro activity:
Conversely, the irreversible inhibitor of cytosolic phospholipase As, methyl-arachidonoyl-fluoro-phosphonate (MAFP), covalently inhibited the amidohydrolase. MAFP was active at concentrations 10(3) times lower than those reported for phospholipase A2 inhibition, and is the most potent anandamide amidohydrolase inhibitor so far described (IC50 = 1-3 nM). Reference: Biochem Biophys Res Commun. 1997 Feb 3;231(1):82-8. https://pubmed.ncbi.nlm.nih.gov/9070224/
In vivo activity:
In the current study, methyl arachidonyl fluorophosphonate (MAFP), an arachidonyl binding site directed phosphonylation reagent, was tested as an inhibitor of anandamide amidase and as a ligand for the CB1 cannabinoid receptor. MAFP was 800 times more potent than Arach-CF3 and phenylmethylsulfonyl fluoride (PMSF) as an amidase inhibitor in rat brain homogenates. Reference: Biochem Pharmacol. 1997 Feb 7;53(3):255-60. https://pubmed.ncbi.nlm.nih.gov/9065728/
Solvent mg/mL mM
Solubility
DMF 3.0 8.10
DMSO 3.0 8.10
Ethanol 3.5 9.45
Ethanol:PBS (pH 7.2) (1:1) 0.5 1.35
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 370.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. De Petrocellis L, Melck D, Ueda N, Maurelli S, Kurahashi Y, Yamamoto S, Marino G, Di Marzo V. Novel inhibitors of brain, neuronal, and basophilic anandamide amidohydrolase. Biochem Biophys Res Commun. 1997 Feb 3;231(1):82-8. doi: 10.1006/bbrc.1997.6000. PMID: 9070224. 2. Lio YC, Reynolds LJ, Balsinde J, Dennis EA. Irreversible inhibition of Ca(2+)-independent phospholipase A2 by methyl arachidonyl fluorophosphonate. Biochim Biophys Acta. 1996 Jul 12;1302(1):55-60. doi: 10.1016/0005-2760(96)00002-1. PMID: 8695655. 3. Fernando SR, Pertwee RG. Evidence that methyl arachidonyl fluorophosphonate is an irreversible cannabinoid receptor antagonist. Br J Pharmacol. 1997 Aug;121(8):1716-20. doi: 10.1038/sj.bjp.0701303. PMID: 9283708; PMCID: PMC1564861. 4. Deutsch DG, Omeir R, Arreaza G, Salehani D, Prestwich GD, Huang Z, Howlett A. Methyl arachidonyl fluorophosphonate: a potent irreversible inhibitor of anandamide amidase. Biochem Pharmacol. 1997 Feb 7;53(3):255-60. doi: 10.1016/s0006-2952(96)00830-1. PMID: 9065728.
In vitro protocol:
1. De Petrocellis L, Melck D, Ueda N, Maurelli S, Kurahashi Y, Yamamoto S, Marino G, Di Marzo V. Novel inhibitors of brain, neuronal, and basophilic anandamide amidohydrolase. Biochem Biophys Res Commun. 1997 Feb 3;231(1):82-8. doi: 10.1006/bbrc.1997.6000. PMID: 9070224. 2. Lio YC, Reynolds LJ, Balsinde J, Dennis EA. Irreversible inhibition of Ca(2+)-independent phospholipase A2 by methyl arachidonyl fluorophosphonate. Biochim Biophys Acta. 1996 Jul 12;1302(1):55-60. doi: 10.1016/0005-2760(96)00002-1. PMID: 8695655.
In vivo protocol:
1. Fernando SR, Pertwee RG. Evidence that methyl arachidonyl fluorophosphonate is an irreversible cannabinoid receptor antagonist. Br J Pharmacol. 1997 Aug;121(8):1716-20. doi: 10.1038/sj.bjp.0701303. PMID: 9283708; PMCID: PMC1564861. 2. Deutsch DG, Omeir R, Arreaza G, Salehani D, Prestwich GD, Huang Z, Howlett A. Methyl arachidonyl fluorophosphonate: a potent irreversible inhibitor of anandamide amidase. Biochem Pharmacol. 1997 Feb 7;53(3):255-60. doi: 10.1016/s0006-2952(96)00830-1. PMID: 9065728.
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