Methoxy arachidonyl fluorophosphonate
Names
Preferred IUPAC name
Methyl [(5Z ,8Z ,11Z ,14Z )-icosa-5,8,11,14-tetraen-1-yl]phosphonofluoridate
Other names
MAFP
Identifiers
ChEMBL
ChemSpider
EC Number
InChI=1S/C21H36FO2P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(22,23)24-2/h7-8,10-11,13-14,16-17H,3-6,9,12,15,18-21H2,1-2H3/b8-7-,11-10-,14-13-,17-16-
Y Key: KWKZCGMJGHHOKJ-ZKWNWVNESA-N
Y
FP(=O)(OC)CCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Properties
C21 H36 FO2 P
Molar mass
370.5
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Methoxy arachidonyl fluorophosphonate , commonly referred as MAFP , is an irreversible active site-directed enzyme inhibitor that inhibits nearly all serine hydrolases and serine proteases .[ 1] It inhibits phospholipase A2 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),[ 2] but does not appear to agonize or antagonize the receptor,[ 3] though some related derivatives do show cannabinoid-like properties.[ 4]
^ Hoover HS, Blankman JL, Niessen S, Cravatt BF (July 2008). "Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling" . Bioorg. Med. Chem. Lett . 18 (22): 5838–41. doi :10.1016/j.bmcl.2008.06.091 . PMC 2634297 . PMID 18657971 .
^ Deutsch DG, Omeir R, Arreaza G, Salehani D, Prestwich GD, Huang Z, Howlett A (1997). "Methyl arachidonyl fluorophosphonate: a potent irreversible inhibitor of anandamide amidase". Biochem. Pharmacol . 53 (3): 255–60. doi :10.1016/s0006-2952(96)00830-1 . PMID 9065728 .
^ Savinainen JR, Saario SM, Niemi R, Järvinen T, Laitinen JT (2003). "An optimized approach to study endocannabinoid signaling: evidence against constitutive activity of rat brain adenosine A1 and cannabinoid CB1 receptors" . Br. J. Pharmacol . 140 (8): 1451–9. doi :10.1038/sj.bjp.0705577 . PMC 1574161 . PMID 14623770 .
^ 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. PMID 10945879