Methoxy arachidonyl fluorophosphonate: Difference between revisions

Methoxy arachidonyl fluorophosphonate
Names
	IUPAC name methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14- tetraenylphosphonofluoridate
	Other names MAFP
Identifiers
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL113262 ;
ChemSpider	8604682 ;
PubChem CID	10429254;
	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- Key: KWKZCGMJGHHOKJ-ZKWNWVNESA-N ; 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;
	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). verify (what is ?) Infobox references

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Methyl 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]

References

^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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. 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.

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[pmid18657971-1] 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[pmid9065728-2] 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. PMID 9065728.

[pmid14623770-3] 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.

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-'''Methoxy arachidonyl fluorophosphonate''', commonly referred as '''MAFP''', is an irreversible active site-directed [[enzyme inhibitor]] that inhibits nearly all [[serine hydrolase]]s and [[serine protease]]s.<ref name="pmid18657971">{{cite journal |author=Hoover HS, Blankman JL, Niessen S, Cravatt BF |title=Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling |journal=Bioorg. Med. Chem. Lett. |volume= 18|issue= 22|pages= 5838–41|date=July 2008 |pmid=18657971 |doi=10.1016/j.bmcl.2008.06.091 |url= |pmc=2634297}}</ref>  It inhibits [[phospholipase A2]] and [[fatty acid amide hydrolase]] with special potency, displaying [[IC50|IC<sub>50</sub>]] values in the low-nanomolar range. In addition, it binds to the [[cannabinoid receptor type 1|CB<sub>1</sub> receptor]] in rat brain membrane preparations ([[IC50|IC<sub>50</sub>]] = 20 nM),<ref name="pmid9065728">{{cite journal | vauthors = Deutsch DG, Omeir R, Arreaza G, Salehani D, Prestwich GD, Huang Z, Howlett A | title = Methyl arachidonyl fluorophosphonate: a potent irreversible inhibitor of anandamide amidase | journal = Biochem. Pharmacol. | volume = 53 | issue = 3 | pages = 255–60 | year = 1997 | pmid = 9065728 | doi = | url = }}</ref> but does not appear to [[agonist|agonize]] or [[receptor antagonist|antagonize]] the receptor.<ref name="pmid14623770">{{cite journal | vauthors = Savinainen JR, Saario SM, Niemi R, Järvinen T, Laitinen JT | title = An optimized approach to study endocannabinoid signaling: evidence against constitutive activity of rat brain adenosine A1 and cannabinoid CB1 receptors | journal = Br. J. Pharmacol. | volume = 140 | issue = 8 | pages = 1451–9 | year = 2003 | pmid = 14623770 | pmc = 1574161 | doi = 10.1038/sj.bjp.0705577 | url = }}</ref>
+'''Methyl arachidonyl fluorophosphonate''', commonly referred as '''MAFP''', is an irreversible active site-directed [[enzyme inhibitor]] that inhibits nearly all [[serine hydrolase]]s and [[serine protease]]s.<ref name="pmid18657971">{{cite journal |author=Hoover HS, Blankman JL, Niessen S, Cravatt BF |title=Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling |journal=Bioorg. Med. Chem. Lett. |volume= 18|issue= 22|pages= 5838–41|date=July 2008 |pmid=18657971 |doi=10.1016/j.bmcl.2008.06.091 |url= |pmc=2634297}}</ref>  It inhibits [[phospholipase A2]] and [[fatty acid amide hydrolase]] with special potency, displaying [[IC50|IC<sub>50</sub>]] values in the low-nanomolar range. In addition, it binds to the [[cannabinoid receptor type 1|CB<sub>1</sub> receptor]] in rat brain membrane preparations ([[IC50|IC<sub>50</sub>]] = 20 nM),<ref name="pmid9065728">{{cite journal | vauthors = Deutsch DG, Omeir R, Arreaza G, Salehani D, Prestwich GD, Huang Z, Howlett A | title = Methyl arachidonyl fluorophosphonate: a potent irreversible inhibitor of anandamide amidase | journal = Biochem. Pharmacol. | volume = 53 | issue = 3 | pages = 255–60 | year = 1997 | pmid = 9065728 | doi = | url = }}</ref> but does not appear to [[agonist|agonize]] or [[receptor antagonist|antagonize]] the receptor.<ref name="pmid14623770">{{cite journal | vauthors = Savinainen JR, Saario SM, Niemi R, Järvinen T, Laitinen JT | title = An optimized approach to study endocannabinoid signaling: evidence against constitutive activity of rat brain adenosine A1 and cannabinoid CB1 receptors | journal = Br. J. Pharmacol. | volume = 140 | issue = 8 | pages = 1451–9 | year = 2003 | pmid = 14623770 | pmc = 1574161 | doi = 10.1038/sj.bjp.0705577 | url = }}</ref>
 ==See also==