Methoxy arachidonyl fluorophosphonate

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]

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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 201-185-2
PubChem CID
InChI
  • 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
SMILES
  • FP(=O)(OC)CCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Properties
Chemical formula
 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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Infobox references

See also
  • DIFP - diisopropyl fluorophosphate, a related inhibitor
  • IDFP - isopropyl dodecylfluorophosphonate, another related inhibitor with selectivity for FAAH and MAGL
  • Activity based probes

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. Cannabinoid properties of methylfluorophosphonate analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):1209-18. PMID 10945879


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