MAFP
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MedKoo CAT#: 526468

CAS#: 188404-10-6

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

Chemical Structure

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MAFP
CAS# 188404-10-6
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 526468
Name: MAFP
CAS#: 188404-10-6
Chemical Formula: C21H36FO2P
Exact Mass: 370.24
Molecular Weight: 370.489
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 2 weeks
25mg USD 1150 2 weeks
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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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. 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

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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