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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

Methyl Arachidonyl Fluorophosphonate

Cayman Chemical Item Number 70660

MAFP (CAS 188404-10-6)

Methyl Arachidonyl Fluorophosphonate (CAS 188404-10-6)

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Description

Methyl arachidonyl fluorophosphonate (MAFP) is a selective, active-site directed, irreversible inhibitor of cPLA2 and iPLA2.1,2,3 It inhibits A23187-induced arachidonic acid release from human platelets with an IC50 value of 0.6 µM.1 The IC50 value for inhibition of iPLA2 from P388D1 cells is 0.5 µM.2 MAFP is a potent inhibitor of fatty acid amide hydrolase, exhibiting an IC50 value of 2.5 nM. MAFP also binds to the CB1 receptor in rat brain membrane preparations. The IC50 values for MAFP and arachidonyl ethanolamide in this assay are 20 and 40 nM, respectively.4

1 Huang, Z., Liu, S., Street, I., et al. Methyl arachidonyl fluorophosphonate, a potent irreversible cPLA2 inhibitor, blocks the mobilization of arachidonic acid in human platelets and neutrophils. Mediators Inflamm 3 307-308 (1994).

2 Lio, Y., Reynolds, L.J., Balsinde, J., et al. Irreversible inhibition of Ca2+-independent phospholipase A2 by methyl arachidonyl fluorophosphonate. Biochim Biophys Acta 1302 55-60 (1996).

3 Balsinde, J., and Dennis, E.A. Distinct roles in signal transduction for each of the phospholipase A2 enzymes present in P388D1 macrophages. J Biol Chem 271 6758-6765 (1996).

4 Deutsch, D.G., Omeir, R., Arreaza, G., et al. Methyl arachidonyl fluorophosphonate: A potent irreversible inhibitor of anandamide amidase. Biochem Pharmacol 53 255-260 (1997).

Synonyms
  • MAFP
Formal Name 5Z,​8Z,​11Z,​14Z-​eicosatetraenyl-​phosphonofluoridic acid,​ methyl ester
CAS Number 188404-10-6
Molecular Formula C21H36FO2P
Formula Weight 370.5
Formulation A solution in methyl acetate
Purity >98%
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCP(F)​(OC)​=O

Background Reading

Balsinde, J., and Dennis, E.A. Distinct roles in signal transduction for each of the phospholipase A2 enzymes present in P388D1 macrophages. J Biol Chem 271 6758-6765 (1996).

Huang, Z., Liu, S., Street, I., et al. Methyl arachidonyl fluorophosphonate, a potent irreversible cPLA2 inhibitor, blocks the mobilization of arachidonic acid in human platelets and neutrophils. Mediators Inflamm 3 307-308 (1994).

Lio, Y., Reynolds, L.J., Balsinde, J., et al. Irreversible inhibition of Ca2+-independent phospholipase A2 by methyl arachidonyl fluorophosphonate. Biochim Biophys Acta 1302 55-60 (1996).

Deutsch, D.G., Omeir, R., Arreaza, G., et al. Methyl arachidonyl fluorophosphonate: A potent irreversible inhibitor of anandamide amidase. Biochem Pharmacol 53 255-260 (1997).

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Methyl Arachidonyl Fluorophosphonate is available in the following screening library:

Size Price Quantity Subtotal
1 mg $21.00 $0.00
5 mg $95.00 $0.00
10 mg $168.00 $0.00
50 mg $735.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-12. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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