Methoxy arachidonyl fluorophosphonate, commonly referred as MAFP, is an irreversible active site-directed
enzyme inhibitor
An enzyme inhibitor is a molecule that binds to an enzyme and blocks its activity. Enzymes are proteins that speed up chemical reactions necessary for life, in which substrate molecules are converted into products. An enzyme facilitates a sp ...
that inhibits nearly all
serine hydrolases and
serine proteases.
It inhibits
phospholipase A2
The enzyme phospholipase A2 (EC 3.1.1.4, PLA2, systematic name phosphatidylcholine 2-acylhydrolase) catalyse the cleavage of fatty acids in position 2 of phospholipids, hydrolyzing the bond between the second fatty acid “tail” and the glyce ...
and
fatty acid amide hydrolase with special potency, displaying
IC50 values in the low-nanomolar range. In addition, it binds to the
CB1 receptor in rat brain membrane preparations (
IC50 = 20 nM),
but does not appear to
agonize or
antagonize the receptor,
though some related derivatives do show cannabinoid-like properties.
[Martin BR, Beletskaya I, Patrick G, Jefferson R, Winckler R, Deutsch DG, Di Marzo V, Dasse O, Mahadevan A, Razdan RK. Cannabinoid properties of methylfluorophosphonate analogs. ''J Pharmacol Exp Ther''. 2000 Sep;294(3):1209-18. ]
See also
*
DIFP
Diisopropyl fluorophosphate (DFP) or Isoflurophate is an oily, colorless liquid with the chemical formula C6H14FO3P. It is used in medicine and as an organophosphorus insecticide. It is stable, but undergoes hydrolysis when subjected to moisture ...
– diisopropyl fluorophosphate, a related inhibitor
*
IDFP – isopropyl dodecylfluorophosphonate, another related inhibitor with selectivity for FAAH and MAGL
*
Activity-based probes
References
Cannabinoids
Phosphonofluoridates
Serine protease inhibitors
Arachidonyl compounds
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