Methoxy arachidonyl fluorophosphonate
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| Names | |
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| Preferred IUPAC name
Methyl [(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yl]phosphonofluoridate | |
| Other names
MAFP
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| Identifiers | |
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3D model (JSmol)
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PubChem CID
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| 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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Template:Chembox Footer/trackingTemplate:Short description
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
- DIFP – diisopropyl fluorophosphate, a related inhibitor
- IDFP – isopropyl dodecylfluorophosphonate, another related inhibitor with selectivity for FAAH and MAGL
- Activity-based probes
References
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- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
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