Methoxy_arachidonyl_fluorophosphonate
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
ChEMBL
ChemSpider
EC Number
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
FP(=O)(OC)CCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Properties
C21 H36 FO2 P
Molar mass
370.5
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
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
^ 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 .
^ 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 .
^ 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 .
^ 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
Receptor (ligands )
DP (D2 ) Tooltip Prostaglandin D2 receptor
DP1 Tooltip Prostaglandin D2 receptor 1 DP2 Tooltip Prostaglandin D2 receptor 2
EP (E2 ) Tooltip Prostaglandin E2 receptor
EP1 Tooltip Prostaglandin EP1 receptor
Antagonists: AH-6809
ONO-8130
SC-19220
SC-51089
SC-51322
EP2 Tooltip Prostaglandin EP2 receptor
Antagonists: AH-6809
PF-04418948
TG 4-155
EP3 Tooltip Prostaglandin EP3 receptor EP4 Tooltip Prostaglandin EP4 receptor
Antagonists: Grapiprant
GW-627368
L-161982
ONO-AE3-208
Unsorted
FP (F2α ) Tooltip Prostaglandin F receptor IP (I2 ) Tooltip Prostacyclin receptor TP (TXA2 ) Tooltip Thromboxane receptor Unsorted
Arbaprostil
Ataprost
Ciprostene
Clinprost
Cobiprostone
Delprostenate
Deprostil
Dimoxaprost
Doxaprost
Ecraprost
Eganoprost
Enisoprost
Eptaloprost
Esuberaprost
Etiproston
Fenprostalene
Flunoprost
Froxiprost
Lanproston
Limaprost
Luprostiol
Meteneprost
Mexiprostil
Naxaprostene
Nileprost
Nocloprost
Ornoprostil
Oxoprostol
Penprostene
Pimilprost
Piriprost
Posaraprost
Prostalene
Rioprostil
Rivenprost
Rosaprostol
Spiriprostil
Tiaprost
Tilsuprost
Tiprostanide
Trimoprostil
Viprostol
Enzyme (inhibitors )
COX (PTGS )PGD2 S Tooltip Prostaglandin D synthase PGES Tooltip Prostaglandin E synthase HQL-79
PGFS Tooltip Prostaglandin F synthase PGI2 S Tooltip Prostacyclin synthase TXAS Tooltip Thromboxane A synthase
Others
Receptor (ligands )
BLT Tooltip Leukotriene B4 receptor
BLT1 Tooltip Leukotriene B4 receptor 1
Antagonists: 20-Carboxy-LTB4
Amelubant
CGS-23131 (LY-223982)
CGS-25019C
CP-105696
CP-195543
Etalocib
LY-293111
Moxilubant
ONO-4057
RG-14893
RP-69698
SB-209247
SC-53228
Ticolubant
U-75302
ZK-158252
BLT2 Tooltip Leukotriene B4 receptor 2
Antagonists: CP-195543
LY-255283
ZK-158252
CysLT Tooltip Cysteinyl leukotriene receptor
CysLT1 Tooltip Cysteinyl leukotriene receptor 1
Antagonists: Ablukast
BAYu9773
BAYu9916
BAYx7195
Cinalukast
FPL-55712
ICI-198615
Iralukast
LY-170680
Masilukast
MK-571
Montelukast
ONO-1078
Pobilukast
Pranlukast
Ritolukast
SKF-104353
SR-2640
Sulukast
Tipelukast
Tomelukast
Verlukast
Zafirlukast
ZD-3523
CysLT2 Tooltip Cysteinyl leukotriene receptor 2
Antagonists: BAYu9773
BAYu9916
CysLTE Tooltip Cysteinyl leukotriene receptor E
Enzyme (inhibitors )
5-LOX Tooltip Arachidonate 5-lipoxygenase
FLAP Tooltip Arachidonate 5-lipoxygenase-activating protein inhibitors: AM-103
AM-679
BAYx1005
MK-591
MK-886
12-LOX Tooltip Arachidonate 12-lipoxygenase 15-LOX Tooltip Arachidonate 15-lipoxygenase LTA4 H Tooltip Leukotriene A4 hydrolase LTB4 H Tooltip Leukotriene B4 ω-hydroxylase LTC4 S Tooltip Leukotriene C4 synthase LTC4 H Tooltip Leukotriene C4 hydrolase LTD4 Tooltip Leukotriene D4 hydrolase
Others
Receptor (ligands )
CB1 Tooltip Cannabinoid receptor type 1
Agonists(abridged,full list ) Inverse agonists Antagonists
CB2 Tooltip Cannabinoid receptor type 2
Agonists
2-AG
2-AGE (noladin ether)
3,3'-Diindolylmethane
4-O-Methylhonokiol
α-Amyrin · β-Amyrin
A-796,260
A-834,735
A-836,339
AM-1172
AM-1221
AM-1235
AM-1241
AM-2232
Anandamide
AZ-11713908
Cannabinol
Caryophyllene
CB-13
CBS-0550
CP 55,940
GW-405,833 (L-768,242)
GW-842,166X
HU-308
JTE 7-31
JWH-007
JWH-015
JWH-018
JWH-73
JWH-133
L-759,633
L-759,656
Lenabasum (anabasum)
Magnolol
MDA-19
Nabitan
NADA
Olorinab (APD-371)
PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
THC (dronabinol)
THCV
Tetrahydromagnolol
Virodhamine
Antagonists
NAGly (GPR18 )
GPR55
GPR119
Transporter (modulators )
eCBTs Tooltip Endocannabinoid transporter
Enzyme (modulators )
FAAH Tooltip Fatty acid amide hydrolase MAGL ABHD6
Inhibitors: JZP-169
JZP-430
KT182
KT185
KT195
KT203
LEI-106
ML294
ML295
ML296
UCM710
WWL-70
ABHD12
Others
Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
ARN-272 (FAAH-like anandamide transporter inhibitor)
The article is a derivative under the Creative Commons Attribution-ShareAlike License .
A link to the original article can be found here and attribution parties here
By using this site, you agree to the Terms of Use . Gpedia ® is a registered trademark of the Cyberajah Pty Ltd