Methoxy arachidonyl fluorophosphonate

Last updated
Methoxy arachidonyl fluorophosphonate
Mafp.png
Names
Preferred IUPAC name
Methyl [(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yl]phosphonofluoridate
Other names
MAFP
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 201-185-2
PubChem CID
  • 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- Yes check.svgY
    Key: KWKZCGMJGHHOKJ-ZKWNWVNESA-N Yes check.svgY
  • FP(=O)(OC)CCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Properties
C21H36FO2P
Molar mass 370.5
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

See also

References

  1. 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.
  2. 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.
  3. 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.
  4. Martin BR, Beletskaya I, Patrick G, Jefferson R, Winckler R, Deutsch DG, Di Marzo V, Dasse O, Mahadevan A, Razdan RK (Sep 2000). "Cannabinoid properties of methylfluorophosphonate analogs". J Pharmacol Exp Ther. 294 (3): 1209–18. PMID   10945879.