Jump to content

Methoxy arachidonyl fluorophosphonate

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by 85.151.137.164 (talk) at 09:21, 2 November 2016. The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Methoxy arachidonyl fluorophosphonate
Names
IUPAC name
methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14- tetraenylphosphonofluoridate
Other names
MAFP
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • 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- checkY
    Key: KWKZCGMJGHHOKJ-ZKWNWVNESA-N checkY
  • InChI=1/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-
    Key: KWKZCGMJGHHOKJ-ZKWNWVNEBX
  • 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).
checkY verify (what is checkY☒N ?)

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]

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.


Stub icon

This biochemistry article is a stub. You can help Wikipedia by expanding it.

Stub icon

This enzyme-related article is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Methoxy_arachidonyl_fluorophosphonate&oldid=747424800"